Hi, I’m Jeremy, I’m glad you’re here.

No matter what you create, I’m guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.

So do I. And so does everyone doing creative work.

This is the Creative Wilderness.

Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.

If you’re building something that matters, but aren’t quite sure how to take the next step forward, I’d be honoured to have you join us.

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    When In Doubt, Follow the Winding Road

    Last weekend, my partner Kelly and I took a weekend road trip through Italy and were plotting a course to Turin from Lucca, a charming old walled city near Florence.

    Consulting the map, we opted for what appeared to be the coastal route, which snaked along the coast to Genoa before heading North to Turin.

    We imagined the route passing through numerous quaint seaside Italian towns, one of which we might stop in for coffee, another for lunch, another still for an afternoon stroll and croissant.

    The idyllic road trip itinerary in other words.

    Filled with excitement, we locked the route into Google Maps and hit the road.

    It didn’t take long to realize, however, that our excitement had been misplaced. Because barely 30 minutes into the drive, our route directed us onto a massive 8-lane tollway.

    The highway was impressive in its own right and promised a smooth and efficient trip back to Turin.

    But that efficiency was not without its cost.

    In our case, that cost was the seaside towns and coastline we had imagined ourselves spending the day winding through.

    My heart sinking, I asked Kelly to see if there was any other route we could take.

    It turns out, there was just one, perhaps the polar opposite of the route we were currently on.

    The Trade-Offs of Efficiency

    The alternative route consisted of a tiny, one-lane road filled with seemingly infinite switchbacks that would add three hours to our trip.

    And yet, one look at the squiggly line the road cut into the map told me this was the road we were looking for.

    If there’s one thing I’ve learned in years of traveling by foot, by bike, and by car it’s that the winding road is always the one you want.

    No, it’s never as efficient as the alternatives, and yes, it takes you much more time, effort, and even stress to get to your destination.

    You need to leave earlier, stay on the road longer, and there are always more than a few hair-raising moments passing opposing vehicles while winding up narrow roads with no guard rail between the pavement and a precipitous drop.

    Despite the obvious downsides, I’ve yet to take a winding road that wasn’t worth it.

    Because what these roads lack in efficiency, they make up for (and more) in discovery, awe, and invigoration.

    This is as true when charting a weekend road trip as it is in charting our creative lives and careers.

    The Winding Road to Original Work

    In our work, we tend to perpetually strive for the most efficient route to our end destination.

    And we don’t have to look far to find them.

    We can merge onto the highway and join the stream of traffic following the latest trends, committing fully to whatever content, formats, and platforms are hot in the moment.

    Done skillfully, we can make a good career of this.

    But the toll is steep.

    It requires us to give up much of our originality, creating generic, often commoditized work for which there is proven demand, forgoing our creative instincts, curiosity, and fulfillment in exchange for efficiency and predictability.

    Not that there’s much creative inspiration to be found on the highway in the first place.

    What’s more, in seeking out the most efficient route through our lives we forget that the only true end destination to which we are hurtling is death.

    Surely we’d rather take a more scenic—if at times challenging—route there?

    The Destination Is Not the Point

    That winding road will be full of switchbacks, wrong turns, and dead ends.

    We’ll deal with more than a few hair-raising near-misses, landslides blocking a previously navigable road, and time when we’re so far off the map our GPS loses signal and we’re left to find our way forward through instinct, hunch, and experimentation.

    And yet it’s undeniable that this route is infinitely enthralling, invigorating, and life-affirming.

    It’s also the type of road with the best chance of leading us somewhere interesting.

    When traveling this road we don’t always know what the end destination will be.

    But then again, on winding roads, the destination is rarely the point.

    And in fact, ending up somewhere entirely other than where you imagine when you left might just be the greatest gift the road could give you.


    Explore how to navigate a creative life that matters

    This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

    A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

    Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

    It’s something I’m proud to create and I’d be honoured to share it with you.


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        10 Unconventional (+ 1 Cliche But True) Lessons I Learned Publishing 100 Issues of My Newsletter

        Just over two years ago, on April 12, 2020, I sent out the first issue of this newsletter.

        I’d attempted to write several newsletters in the past, but they had always fizzled after a few months at most.

        Something about this one felt different however, and now, 100 issues later, it seems that hunch was true.

        Over those 100 issues the newsletter has nearly tripled in size, almost all of that growth coming in the past 12 months, and I’ve learned a lot about creating and growing creative projects like newsletters.

        And while a lot of what I’ve learned corresponds with the standard advice you can find all over Twitter, for this milestone issue, I wanted to share 10 of the more unconventional learnings I’ve had about growing creative projects, several of which fly in the face of standard audience building advice.

        Let’s jump in.

        1 // Feed Yourself First

        We’re often told to serve our audience above all else.

        But in my experience, creative projects have a much higher chance of succeeding when the act of creating them gets us something personally, before anyone else ever interacts with them.

        Ironically (or maybe not), this was the topic of the very first issue of this newsletter, which I titled, Focus on What Fuels You.

        Feeding yourself first is about structuring your projects in a way that first & foremost scratches an itch you have. Then finding a way to adapt & package it in a way that overlaps with an existing audience’s interests & desires.

        This isn’t to say that every project that scratches one of your own itches will have an opportunity to build an audience around it. You need both project-market and project-creator fits to be successful.

        But in my experience, it’s easier to find an audience for a project that feeds you than the other way around.

        2 // Pay Attention to Signals of Progress

        Almost any creative project is going to take several years to grow a significant audience around. But if your work has the potential for growth, you should be getting at least small bits of positive feedback fairly quickly.

        Five issues in, I received my first email response from a reader (shoutout to Jason Perrier!) about how they resonated with the issue.

        That email encouraged me to lean further into what I was doing, and since then, I’ve received at least 1 similar email almost every week.

        If you’re getting your work in front of even a small number of your ideal audience members and you’re not getting any positive reinforcement, it’s a sign you need to make some tweaks.

        And if you’re not regularly getting it in front of even a small number of your ideal audience… well you need to start there.

        3 // The First Version Won’t be the Final Version

        We all want to launch our projects as their fully realized & perfected versions.

        But most of the time, we, ourselves don’t know what they’ll morph into once we launch them. Better to get a first draft out and then iterate on it from there, a process I call Thinking in Drafts which I covered in Issue 27.

        I wrote the first 56 issues of my newsletter under what was essentially a placeholder name, The Listen Up Newsletter.

        I named it with a vaguely audio-related name before I ever wrote the first issue and wholeheartedly believed I was going to be writing about podcasting… which never ended up happening even one time.

        It was only after those 56 issues over more than a year that I started to see the through-line in the newsletter & rebranded to the more aligned Creative Wayfinding Newsletter.

        If you’re creating a long-term body of work like a newsletter or podcast, you should expect it to go through significant shifts over its lifecycle, none of which you can predict before you start.

        Understanding this reduces the pressure you put on the first (or current) iteration to be perfect.

        Ship it & then have the faith to keep moving through the fog and follow where it leads you.

        4 // Being Unable to Describe What You do Might Mean You’re Onto Something

        I often feel sheepish that after 100 issues of my newsletter, I still can’t really describe what it’s about.

        But recently, I’ve discovered that this is a common trait of successful creators’ platforms.

        The reason, I think is that successful creative platforms are often a blend of ideas that haven’t been paired before. This is what makes them novel and interesting. But it also makes it hard to develop messaging around them because the vocabulary doesn’t yet exist.

        Creating that vocabulary is a huge part of our job as creators.

        5 // The Things that Work Best Don’t Always Make Sense

        We all love frameworks, templates & archetypes that promise to shortcut our way to success.

        But the things that work best usually don’t fit neatly into the existing boxes. And they often break all the rules you’re supposed to follow.

        My audience is almost entirely made up of podcast creators, many of whom receieve the newsletter after having signed up for one of my podcast-related offerings.

        My newsletter, however, has almost nothing to do with podcasting and is about finding your way as a creator of any kind.

        This goes against a lot of marketing advice.

        There’s a significant disconnect between my top of funnel (podcasting), middle of funnel (Creative Wayfinding) & paid offerings (podcasting).

        And yet, based on anecdotal feedback from customers and subscribers, I have a suspicion that this franken-funnel somehow works better than if all my content was tightly aligned around podcasting.

        I think there’s a reason…

        A highly aligned funnel probably would do a better job converting cold traffic into one-time sales.

        But my current creative platform allows people to really get to know a much deeper more nuanced version of me without feeling like I’m just buttering them up to make a pitch (which I’m not).

        In the short term, this is likely a less financially successful strategy. But the long-term upside is huge.

        For one, it leads to more perfect-fit customers & clients who buy into my philosophy around creative work which leads to better outcomes for everyone involved.

        It also moves my product offerings away from being commodities which can be easily compared to other products designed to help people achieve similar outcomes. I’ve heard time and time again from PMA students that the biggest reason they enrolled was because of me.

        I don’t know that that would have happened if I was more focused with outcome-oriented, purely instructional podcast content.

        Most important of all, however, this approach leads to friends, partnerships, collaborators & deep personal connections that I have a hard time believing would have come from a super-specific, topic-aligned funnel.

        I regularly get comments from readers along the lines of, “I found Jeremy through his podcast content, but actually stuck around for his ideas around creative work which I don’t get anywhere else.”

        Comments like this are a sign to me that I’m on the right track to building the kind of creative platform I aspire to. One that is nuanced, real, and human.

        There’s no way I could have (or would have) planned this strategy in advance, but somehow I stumbled on to it, and it works.

        6 // Track the Right Metrics

        We all want to see our subscriber counts go up.

        But total subscribers/views/downloads/etc aren’t a great way to measure the true impact of quality of our work. Plus, by measuring the wrong thing we’re likely to optimize for it, which is a big mistake.

        While I certainly track my subscriber count, my North Star metric has always been reader responses.

        These responses, to me, are a signal of resonance, which is the target I’m aiming at with each issue.

        With every issue, I hope to get at least 2-3 meaningful emails from subscribers who resonated with the article. When I don’t get any, I have a closer look at why that might be.

        I also use the Reactions feature from Sparkloop (which you can see below this essay) and track how many responses I get for each issue using the scale:

        👍 Above Average
        👊 Average
        👎 Below Average

        Each issue averages between 5-10 total reactions. Any more or less than that is an interesting data point to look into.

        7 // Know Why You’re Doing It

        Hand in hand with tracking the right metrics is knowing why you’re creating the project in the first place.

        Chances are, it’s not all about audience growth (although that might certainly be one reason). Remembering the true purpose of the project will help keep you on track & avoid distractions.

        This newsletter’s primary purpose for me has always been as a sandbox to:

        • Hash out ideas that later find their way into other parts of my work
        • Experiment with marketing strategies & tactics
        • Hone my writing
        • Get to know myself better

        Reminding myself regularly of the non-audience-growth-related outcomes helps me avoid feeling frustrated when growth is slow as the project is still achieving its other purposes.

        It also keeps me focused on creating work that’s aligned with my internal compass rather than trying to guess what other people want.

        8 // Release the Handbrake

        Last year I took a writing course from The DO Lectures.

        In one lesson, David, the instructor, said something I haven’t been able to shake:

        “You don’t need to find your voice. You already have it, you just need to release the handbrake.”

        Since starting my newsletter, I’ve consistently discovered that the more I release the handbrake & lean into the ideas, quirks & traits that make me unique, the more my work resonates.

        This runs counter to a lot of entrepreneurial advice, however.

        One of the first rules of building a company is building it so that it can run just as well without you.

        But perhaps the first rule of creative work is that the work should seek to fully reflect & embody you as the creator.

        Release the handbrake & remove the barriers to resonance.

        9 // Define & Reinforce Structure

        Creatives are notorious for hating the idea of structure & constraints.

        But the more structure you build into your work the easier it is to create while also providing a frame around which to explore your topic w/ more depth & clarity.

        Structure for me started with defining the general format of the newsletter:

        1. Welcome
        2. Announcement
        3. Community Shoutouts
        4. Feature Essay
        5. 5 Currated Links
        6. Twitter Feature
        7. Sign Off
        8. Gratitude/Wins/Excitement

        After implementing this structure, it immediately made the newsletter easier to put together each week.

        And after my first structural experiment, I decided to take it further by bringing more structure to the 5 Things You Might Dig section of curated links.

        As you might have noticed, those links now fall into one of five consistent buckets:

        1. Thought
        2. Tool
        3. Tactic
        4. Podcasting Resource
        5. Wildcard

        Much like more structure made it easier to put together the newsletter as a whole, more strucuture around the links made it easier to source & curate links for each issue while also reinforcing the “brand” of the newsletter by bringing more consistency to the offering.

        So far, every time I’ve added more structure, the newsletter has gotten better & creating it has become easier & faster.

        Chances are, structure will have the same effect on your work.

        10 // You Can’t Do it Alone (Cliche but True)

        Find your people who will inspire, motivate & support you.

        It’s a long road to building a life around meaningful creative work and you’re going to need all the help you can get.

        We all need a steady supply of inspiration, motivation, support, accountability and commiseration in order to keep moving forward with our creative work. There is a long list of people who’ve played one or more of those roles for me and this newsletter whom I referenced in Issue #47 about Acknowledgments & Accompaniment.

        In my experience, perhaps more important early on than finding your audience is finding what I call your Creator Cohort, the group of people at roughly the same stage as you, with whom you’ll “grow up” together.

        These people will not only help you gain clarity on your audience but also on how you, your work, and your voice fit into the larger conversation taking place in your space.

        11 // You’re Not Going to Figure Out What the Hell You’re Doing for a While. And That’s Fine.

        Big ideas rarely come fully formed.

        In fact, they often take years of steady, persistent excavation.

        But the real purpose of a creative practice isn’t to grow now. It’s to slowly and persistently chip away and excavate the big ideas that will lead to bigger things in the future.

        I’ve been creating in one form or another for over a decade.

        But I’ve got at least 4 more decades of creative work yet to come.

        I’m at the beginning, just finding my feet. My best work is so far off in the future I can’t even imagine it yet, let alone see it on the horizon.

        The same is true for you.

        This work is not for the faint of heart.

        It will wear (if not outright beat) you down.

        It will make you deeply question your self and your worth.

        It will disappoint and frustrate and shatter you more times than you feel you can bear.

        It takes a special kind of person to not only put up with all that, but choose to walk further into the Creative Wilderness without a map, following only the subtle tug of your internal compass and the belief that there’s something out there for you.

        If you’re here, I think you’re probably that type of special person.

        And I’m honoured to be navigating the wilderness alongside you.

        Here’s to the next 100 🍻


        Explore how to navigate a creative life that matters

        This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

        A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

        Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

        It’s something I’m proud to create and I’d be honoured to share it with you.


          Rethinking Your Big Break

          We spend so much time thinking about The Big Break.

          We love to ask and hear about the moment things changed for the creators we aspire to be like.

          And we spend more time than we might like to admit anticipating, fretting, and wondering about whether this will be the post or episode or newsletter or launch that blows up and puts our name on the map.

          Of course, as creators, we’re already well aware that every overnight success is built on years of unheralded work.

          But maybe we’ve already put in those years of unheralded work and feel we’re due.

          Maybe we are.

          Maybe we’re not.

          Regardless, it’s worth reconsidering our conception of The Big Break.

          Because the singular moment of success we often associate with it is simply an Echo Effect, a result of an earlier action now reflecting back to us.

          Which means that what we think of as The Big Break isn’t actually The Big Break at all. It’s simply the echo of it.

          So what is the real Big Break, then?

          Maybe it’s the point at which we break with the mindsets, beliefs, and actions we’ve relied on so far and set out on a new path.

          Maybe it’s the point at which we stop relying on others to guide our work and rely on our inner compass instead.

          Maybe it’s not a point of arrival but of beginning.

          Which means that our Big Break is within our power to make whenever we’re ready.


          Explore how to navigate a creative life that matters

          This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

          A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

          Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

          It’s something I’m proud to create and I’d be honoured to share it with you.


            Creative Success is an Echo

            An echo can’t exist without a gap in time between its source and return.

            In fact, it’s kind of central to its definition.

            The delay of a clap in a small room may be just a few almost imperceptible milliseconds.

            The call and response of a shout across a mountain valley may near a second.

            And a radio ping sent out across the galaxy might take years to make its way home.

            Creative success is an echo as well.

            The delayed result set in motion by an earlier broadcast.

            Depending on the scale of our aspirations and the environment into which we are projecting them, the time it takes the echoing results of our efforts to return will vary.

            As will the strength of signal required to reach its destination and then make its way back to us without dissipating.

            In a way, it’s a comforting thought.

            All the work we’ve broadcast, all the noise we’ve made… out there, somewhere, hurtling through space, waiting to collide with something against which to bounce back.

            Or perhaps it already has.

            And the echo of previous work is at this very moment making its way back to us.


            Explore how to navigate a creative life that matters

            This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

            A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

            Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

            It’s something I’m proud to create and I’d be honoured to share it with you.


              The Sketchbook Approach to Successful Creative Projects

              A couple years ago I started experimenting with hand lettering as a hobby.

              It’s been a while since I’ve practiced, but recently I’ve found myself picking up and flipping through books on various types of lettering, sketching≤ and drawing while browsing bookshops.

              As I’ve been thinking about revisiting and expanding on the hobby, I’ve also been thinking about how we might incorporate some of the practices and lessons from sketching into the rest of our creative work.

              Every Masterpiece Starts with a Pencil

              The first thing I bought when I first got into lettering was a set of coloured felt-tip calligraphy markers, the core tools of lettering and calligraphy.

              The second thing I bought, however, was a set of pencils and a good eraser and it was with these that every piece got its start, long before the markers were uncapped.

              Using the pencil, I would ever so lightly sketch out the rough outline piece in order to ensure the letters were spaced consistently and that the final image would fit onto the page. Invariably, this would take several attempts to get right, requiring me to erase multiple sketches before finally landing on the one that was ready to be reinforced and brought to life.

              Penciling In Your Creative Projects

              This step of sketching out our work applies to our creative careers as well.

              We’re usually unaware we’re doing it, however, which can cause problems and frustrations down the road.

              At this point in our lives and creative careers, most of us have worked in a series of different niches, platforms, mediums, products, businesses, and maybe even careers before ultimately moving on from many if not most of them.

              Each of these can be thought of as a sketch of the life we were aspiring toward at the time.

              In many cases, what causes us to move on from one of these endeavours is that as we’re sketching out an image, we realize it isn’t going to fit on the page we have in front of us – ie. the container that is our life, or more specifically, the life we want.

              Maybe the sketch extends beyond the time we have available, maybe the finances don’t work, maybe completing this image means giving up or compromising on another one.

              Or maybe we just don’t enjoy it all that much.

              Whatever the reason, we decide that this sketch isn’t the one we want to commit to long-term and so we erase it and start again.

              This process of sketching, erasing, and then re-sketching, in order to establish the outline of the image we want to bring to life, is a natural and necessary part of the process of building our creative lives.

              Frustration arises, however, when we fail to understand this and we think that we’re supposed to get the image outlined correctly the first or second, or third (or tenth) time through.

              Further complicating things for ourselves is that we often get seduced by an exciting new idea and jump in with both feet, starting to draw in the fine details of one part of the picture we have in our mind before first finishing the outline.

              As a result, we often find ourselves committing a substantial amount of time and effort to a project… only to unexpectedly run out of space with the image only half-finished.

              This is an outcome that could have been avoided if we would have taken the time upfront to roughly sketch out the image we have in our minds and see how (and if) it could fit onto the canvas we have available to us.

              This means scoping out our personal projects much like we would for a client.

              The excitement of a new idea can quickly be tempered by the realities of what it will take of us in terms of time, energy, capital, and stress to see it through.

              And while it might seem counterintuitive, this is exactly what we want.

              The ideas that have the greatest chance of success are those for which we’re able to maintain our initial excitement even after we’re aware of all the time, costs, and sacrifices that will be required to bring them to life.

              It will likely take us a number of attempts before we land on an outline that meets this criteria and fits squarely within the boundaries of the page we have laid out for it. But taking the time upfront to get the general outline right before committing to the details can save us a lot in the way of frustration, sunk costs, and difficult decisions in the future.

              Once the rough outline has been established, it’s time to refine it.

              The Outline is Just a Guide

              If you’ve ever sketched anything out before (especially if you, like me, are an amateur), you know that it’s incredibly hard to create a clean-looking image with a single stroke of your pencil.

              After just one pass, the outline is full of subtle (and not so subtle) wobbles, the lines aren’t quite straight and the corners aren’t quite smooth.

              There’s a tendency at this stage, when the sketch looks incomplete if not outright ugly, to give up and walk away, insisting that we’re just not capable of drawing.

              But if we persist, and go back over our rough outline for subsequent passes, something interesting begins to happen.

              While the first stroke of the pencil didn’t give us much in the way of anything that could be considered “art”, what it did give us was a guide and a reference point to which we can now anchor our future reinforcements of the general visual concept.

              In overlaying subsequent strokes with the pencil, sticking to and reinforcing the guide line in some places, deviating from and correcting it in others, the dominant lines become straighter, the curves become smoother and the wobbles disappear.

              What’s more, the image begins to take on depth and nuance as pressure gradients begin to appear, creating the impression of light and shadows.

              With every reinforcement, the original outline recedes further into the background, either by being buried beneath subsequent layers of graphite or by being overshadowed by the bolder, darker correction lines that now draw the eye away from it.

              The lesson for us as creators is that the point of the first draft is not to look anything like the final image.

              The goal of the first draft of any of our work–be that a blog post, podcast, product offering, or even business–is to simply provide a guide for future reinforcement and correction.

              The initial outline we create will never look as good as someone else who’s been adding to their sketch for years, adding layer over layer of corrections and reinforcements to their image.

              The only way we can expect our sketches to achieve the same level of clarity and depth is to keep sketching.

              There are no shortcuts here.

              Sure, once you’ve developed into a skilled sketch artist capable of weaving magic with your pencil you may be capable of creating a clean and compelling image with a single stroke of your pencil. But achieving that level of skill takes years of dedicated practice.

              Until then, the best option we as creators have available is to sketch and erase and sketch again until we land on a rough outline that fits into the space we have for it.

              And then refine it, stroke by stroke by stroke.

              Using this method, we don’t need to be master sketch artists to create a clear, compelling image.

              We simply need to be persistent, and willing to continue sketching until the image on the page matches the image in our heads.


              Explore how to navigate a creative life that matters

              This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

              A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

              Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

              It’s something I’m proud to create and I’d be honoured to share it with you.


                You Should Know This By Now

                I don’t know where we pick it up,
                But somewhere, somehow we get the idea that we’re supposed to “know”.
                We think we’re supposed to know all sorts of things.
                We think we’re supposed to know where we’re going
                And how to get there.
                We think we’re supposed to know what we want
                And how to get it.
                We think we’re supposed to know what we’re doing
                And why.
                We think we’re supposed to know who we are
                And our place in the world.
                We think we’re supposed to know what our purpose is
                And how to fulfill it.
                We think that by age 27 or 37 or 47 or 97 we’re supposed to have figured it all out.
                But this couldn’t be further from the truth.


                The truth is we’re never supposed to know
                But to discover.
                And this discovery has no end.
                Discovery is our life’s work.
                We know so little about the world and all that makes it up
                And as little about ourselves.
                But there’s beauty in the not knowing.
                Not knowing creates the potential for surprise
                For wonder
                And for awe.
                Not knowing is our default
                Our natural resting position.
                We come into the world knowing nothing.
                And the wisest, most studied of us will leave it
                Understanding no more than an infinitesimally small fraction of the knowable
                Not to mention all that for now, and possibly forever remains
                Entirely incomprehensible and unknowable.
                The idea that we might truly know anything is a wonder in itself.


                No matter how much or how little you feel you know,
                You’ve already exceeded the expectations of what you’re supposed to know.
                You’re where you’re supposed to be
                When you’re supposed to be there
                With the knowledge you’re supposed to have.
                What you do with that circumstance is up to you.
                There’s no right or wrong answer.
                But a good place to start is with yourself.
                To get to know yourself better than you currently do.
                The knowledge you seek is within you
                If you’re willing to excavate it.
                Knowledge about purpose
                About direction
                About place.
                Start there.


                Explore how to navigate a creative life that matters

                This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                It’s something I’m proud to create and I’d be honoured to share it with you.


                  Top Shelf Blindspots: How to Spot the Big Opportunities Hiding In Plain Sight

                  My partner, Kelly, was frantic that she’d lost her credit card.

                  She’d already searched her wallet, purse, backpack, and jacket–all the usual suspects turning up nothing–when she remembered her jeans. They’d been removed and tossed onto the top shelf of the closet in favour of sweat pants almost the moment we arrived home from lunch, where she had last used the missing card.

                  As I pulled them down off the shelf, a card slipped from the pocket and skittered across the ground.

                  Success!

                  As the card settled, however, we realized it was not the credit card, but her driver’s license. The pockets of the jeans were otherwise empty.

                  Having thoroughly examined seemingly every nook, cranny, and surface in our home, we prepared to head out and retrace our steps of the day, already resigned to the fact that our search was likely to be unsuccessful.

                  As we headed for the door, however, I couldn’t shake a nagging feeling.

                  Following the hunch, I returned to the closet and reached up to the top shelf where the jeans had been resting.

                  The shelf was juuuuuust a few inches above eye level, so while I could see most of the contents of the shelf–even the 3-inch high ironing board that was folded and stored there–I couldn’t see the shelf’s actual surface.

                  I reached up and ran my hands over the shelf.

                  Nothing.

                  Damn.

                  Then I reached further and felt my way across the ironing board.

                  Almost immediately, my fingers brushed up against what could only be the missing card. I pulled it down, elated at having solved the mystery.

                  Not only had I solved the mystery, however.

                  In finding the bank card where and how I did, I’d stumbled onto an important type of blind spot that not only keeps us from seeing lost credit cards, but also many of the biggest opportunities available to us in our creative work.

                  The Direction of Our Gaze Determines the Opportunities We See

                  We tend to navigate the world with our eyes aimed either at or below our own eye level.

                  When it comes to moving through our physical surroundings, this makes sense, as it keeps us from getting tripped up on the many obstacles we encounter on a daily basis.

                  Unfortunately, however, we often maintain this downward-looking perspective with us when navigating the world of opportunities and ideas.

                  This severely limits our potential.

                  The ideas and opportunities at or below our eye level are those we are already equal to. Should we choose to pursue them, we’d be capable of achieving them with our existing skillset, resources, and network. In other words, they don’t require much–if anything–in the way of stretching ourselves.

                  That’s not to say there’s anything inherently wrong with these easily accessible opportunities.

                  In fact, we’d be foolish not to pick much of the low-hanging fruit that surrounds us.

                  The problem is that the opportunities and ideas at or below our eye level are likely the same opportunities and ideas almost everyone around us is also staring at.

                  Which makes differentiating ourselves and our work difficult.

                  This near-ubiquitous focus on the easily visible, however, also presents us with an opportunity.

                  Because if we’re willing to embrace some uncertainty and stretch ourselves just a little, we can choose to raise our gaze and reach into a whole world of opportunities and ideas that have been largely ignored or avoided by our competitors.

                  The challenge, however, is that despite them sitting right in front of us, we often can’t see them.

                  Two Reasons We Miss Opportunities

                  While some of the opportunities above our line of sight are firmly out of our (current) reach, many, like Kelly’s credit card sitting out in the open on the shelf are close enough to touch.

                  Despite the relative accessibility of these ideas and opportunities, however, we’re prevented from reaching for them for one of two reasons.

                  1. Lack of Certainty

                  In many cases, we can clearly see the opportunities sitting on the shelf above our head.

                  We’re often kept from reaching for and pulling them down, however, by our lack of certainty about what else might be hiding on the shelf.

                  Perhaps our lizard brain calls to mind images of snakes and spiders and other unseen threats hiding beyond our line of sight, ready to strike the moment we reach our hand up.

                  Or perhaps we simply can’t imagine these opportunities being that easy to access. And so instead of seizing them immediately, we sit and ponder and second guess ourselves.

                  2. Misplaced Certainty

                  In many cases, however, as with Kelly’s missing card, we’re kept from reaching for opportunities on the shelves above our heads simply because we’ve convinced ourselves the shelves are empty.

                  The reason for our certainty is what I think of as Top Shelf Blindspots.

                  These blindspots exist in the thin slivers of space that are blocked from our view when looking toward a surface slightly above our head.

                  These blindspots are accompanied by a healthy dose of irony.

                  When looking up at a shelf well above our heads we’re fully aware that we can’t see most of its contents.

                  But the closer to eye level the shelf is, the more of its contents we can see. And when the 99% of the shelf space we can see appears to be empty, our brains fill in the remaining 1% of a gap in our perception and we become certain that the shelf is entirely empty.

                  caption for image

                  It doesn’t take much of a height difference to conceal opportunities of incredible value, either.

                  A shelf just half an inch above eye level provides enough of a Top Shelf Blindspot to hide a credit card… or perhaps a gold ingot, or stacks of $100 bills, or countless other objects of value.

                  In fact, while we spend most of our time chasing the big, obvious opportunities and ideas, I’d argue that many if not most of the truly impactful ones are much more modest in their size and packaging.

                  If we’re going to spot and take advantage of the opportunities existing in our Top Shelf Blindspots, then, we often need someone with a little more height who can clearly see the contents on the shelf for what they are to give us a nudge to reach out and take hold of the opportunities in front of us.

                  A few days after the incident with the credit card, this is what my friend (and CW reader) Alina helped me do.

                  Others Can See What We Can’t

                  We were walking to a coffee shop for a co-working session, catching each other up on our weeks.

                  I had made some solid progress and was feeling pretty good about my updates, especially at having turned down an opportunity that, while excellent, felt like a distraction from what I felt I needed to be focusing on.

                  I expected Alina to be proud of my judgment and boundary setting.

                  After a pregnant pause, she responded instead with, “I just want to shake you right now.”

                  Over the next 10 minutes, she proceeded to school me on all of the many opportunities lying out in the open, above my eye level but within easy reach, which I was currently missing… And had potentially just turned down.

                  I was dumbfounded.

                  Over the next few days, I spent a lot of time thinking about the opportunities Alina had outlined.

                  But I probably spent more time thinking about what had kept me from seeing the opportunities in the first place.

                  What was it exactly that had been blocking my view?

                  Understanding The Shelf

                  If we imagine opportunities above our eye level to be resting on one or more progressively higher shelves which block our view of the opportunities resting on them, it helps to know what the shelves are made of.

                  The ideas and opportunities Alina had opened my eyes to involved taking my existing skills, knowledge, and products and applying them to a new audience.

                  The audience in question, however, was one with which I had almost no network, no knowledge of their specific problems or workflows, and almost no working experience.

                  These three traits: A lack of connections, lack of specific (or even general) knowledge, and lack of experience almost always form the basic frame of the shelves. But without being filled in, these frames don’t do much in the way of blocking our view.

                  Unfortunately for us, we ourselves are more than willing to fill in those frames with a thick layer of our own assumptions.

                  In my case, I had been well aware that this alternative audience for my work existed. I’d even done some limited work with some members of this group in the past, albeit in a slightly different capacity.

                  I assumed that my past clients were the outliers, however.

                  I assumed that to work with the vast majority of this audience I would need specialized skills and knowledge beyond what I already possessed.

                  I assumed I would need connections to insiders that would be difficult or impossible to get.

                  But the assumptions didn’t stop there.

                  I assumed I wouldn’t enjoy working with them, and that the expectations would be more than I could meet, and that the effort of accessing this audience wouldn’t be worth the return.

                  Perhaps most of all, I assumed I would surely be found out as an impostor.

                  When you think about it, what is Impostor Syndrome, but a series of assumptions we make about the expectations of others and how we measure up?

                  Stacked together, these assumptions had built up a thick, opaque shelf, completely obscuring my view of the opportunities lying out in the open on the other side of them.

                  Until at least, someone with a little more height, and a little more perspective came along and gave me the boost I needed to help me see clearly the opportunities waiting for me to reach out and take them.

                  So What to Do with This?

                  The first and most important step is to acknowledge that Top Shelf Blindspots exist.

                  This means being aware that in most cases, the most meaningful, impactful (and potentially lucrative) opportunities are lying out in the open, often just above our eye level, waiting to be picked up.

                  To see them, we need to access some height and its accompanying perspective.

                  To do this, we have two options.

                  The first is to wait to grow ourselves.

                  While our physical height may be limited by our genetics, there’s no limit to our metaphorical potential for growth and the perspective that comes with it.

                  But this growth can take years.

                  What’s more, growth and the accompanying perspective related to one topic, niche or industry often doesn’t transfer over to other aspects of our lives.

                  And growth of any kind isn’t guaranteed.

                  This means that if we’re serious about filling in our Top Shelf Blindspots and take advantage of the opportunities hiding in them, we can’t rely on ourselves.

                  Instead, we need to make a habit of seeking out people in spaces related to and adjacent to ours who are taller than us. People like Alina who can give us a boost and point out all the opportunities they see lying out in the open but which are currently blocked from our view.

                  While we have no way of knowing exactly where our Top Shelf Blindspots exist, we can be sure that we are surrounded by them.

                  Knowing this, we can choose to grope around, hoping our fingers randomly land on some opportunity or another.

                  Or, we can choose to surround ourselves with people who have the height and perspective to guide us to those opportunities we can’t see, but which are lying out in the open, just waiting for us to grab them.


                  Explore how to navigate a creative life that matters

                  This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                  A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                  Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                  It’s something I’m proud to create and I’d be honoured to share it with you.


                    Your Creative Workload Is Dangerously Precarious (Here’s How to Fix It)

                    Earlier this week I was walking from the living room to the kitchen to put away a few groceries I’d just picked up.

                    Between the fingers of my right hand were wedged two glass bottles, one kombucha, the other, juice. My left hand had a hold on my jacket and a rather large, round block of cheese, with a bag of apples tucked in the crook of my arm.

                    Halfway to the kitchen, one of the bottles begin to slip between my fingers, followed closely by the other.

                    As the bottles wobbled and slid, I instinctively dropped my jacket and the block of cheese from my one hand and just managed to regain control of both of the bottles, as well as the apples before they crashed to the floor.

                    Disaster (read: sticky, spiky mess) averted.

                    The incident got me thinking, however, about how often we get ourselves into trouble in our creative lives by first loading ourselves up with more than we can carry, and then, trying to maintain control of it all when one piece begins to slip.

                    More Options Aren’t Always Better

                    I think most of us are aware that we’re carrying more than we can sustain control over.

                    The challenge is we’re confronted with a daily barrage of new tools, tactics, and ideas promising to deliver the results we’re chasing. Seduced by the promise of a quick and easy win, we pick them up without thinking about how they’ll affect the balance of the load we’re already carrying.

                    And so on top of our client work or day job, we decide to start a podcast… and then a newsletter… followed by a YouTube channel… all while trying to stay active on TikTok, Instagram, and Twitter as well.

                    Instead of stacking these new additions carefully to form a broad and sturdy foundation, however, we simply stack them on top of each other, forming an ever more precarious tower.

                    Part of the reason we continue to add to our load is that it feels as though there’s nothing we can afford to drop.

                    Our default response when any strategy fails to deliver the results we were promised is not to reduce our load and bring more focus to fewer activities, but to add more on.

                    We think that by diversifying our options we’re increasing our chances of success when in reality, we’re increasing our chances of catastrophe.

                    Part of the potential for catastrophe is rooted in the unsustainable workload we’ve loaded onto ourselves.

                    More subtly, but perhaps more significantly, however, is the way that each new addition to the load we’re carrying further removes our focus away from the activities that really move the needle.

                    If we want to avoid catastrophe, and build a healthy, sustainable creative workload, our task, then, is twofold:

                    1. Reduce the amount we’re carrying overall.
                    2. Reconfigure the types of tasks and projects we take on into a more resilient, balanced workload that prioritizes the activities that actually matter.

                    The first step is to take stock of what we’re already carrying and identify those tasks that matter.

                    3 Types of Activities that Make Up Your Workload

                    Part of the challenge of reconfiguring our workload is that with our arms stacked high, we’re unable to see where exactly we’re going and which of our many activities are helping us get there.

                    It feels as though if we were to drop any of our current activities–even if only for a while–we’d risk losing all our progress and having to start from scratch.

                    But while we might think nothing we’re currently carrying is capable of surviving being dropped, this is rarely the case.

                    In fact, if we take an objective look at everything we’re balancing, we find that our different activities fall into 3 distinct categories, only one of which is truly fragile.

                    1. Droppable Activities

                    Like my jacket and the block of cheese, there are always at least a few activities we’re carrying can be dropped without any consequence whatsoever.

                    Sure they might gather a little dust during their time on the floor. But besides that, they can be picked up again when we’ve regained our balance and, after a quick brush off, be none the worse for wear.

                    When our workload is feeling precarious and we’re feeling our grip start to slip, these activities and projects should be dropped immediately in order to maintain control of other more fragile items.

                    For me, this category includes things like my Scrappy Podcasting Newsletter, Quick Podcast Tips series on Twitter, general social media engagement, partner & collaborator outreach, podcast guesting, and more.

                    2. Bruiseable Activities

                    Bruiseable activities are more like the bag of apples, which if dropped, risk some bruising, but will remain otherwise edible.

                    Dropping a Bruiseable task is likely to result in a setback. For that reason, we’d rather not drop them, and if we do need to, they shouldn’t be neglected for long. With that said, the damage of a fall is unlikely to be catastrophic and can typically be recovered from.

                    My Bruiseable activities include the Creative Wayfinding Newsletter, the Elements of Podcast Growth workshop series, my general health (which most commonly suffers to some extent around launches), and relationships with friends and family.

                    3. Breakable Activities

                    Finally, we have the Breakable activities, which, like the glass bottles will not only shatter when dropped (perhaps with no way to put back together) but may cause a significant mess for us or others to clean up.

                    Activities may be considered Breakable because of their complexity, a reliance on timing, and much more.

                    Perhaps more commonly, however, they may be fragile because a failure in one of these activities would undermine the trust you’ve built with your audience, clients, partners, or other stakeholders.

                    The activities I classify as Breakable for myself are Podcast Marketing Academy, my Client Work, and my relationship with Kelly.

                    The full picture of my activities looks like this:

                    As in the graphic, we should be aiming for a pyramid-shaped distribution of activities, with a small number of Breakable activities on top, supported by a larger number of Bruiseable and Droppable activities beneath it.

                    The idea is that should we begin to lose our grip, we have enough bandwidth to guarantee control over at least the Breakable activities, if not some of the Bruiseable activities as well.

                    What we want to avoid at all costs is the inverse of this triangle.

                    Carrying a high number of Breakable activities puts us in a precarious position, where the slightest slip immediately jeopardizes our entire load.

                    The Benefits of a Balanced Creative Workload

                    Taking a more intentional approach to the allocation of the activities that make up our workload helps us in a few important ways.

                    First, knowing which categories our various projects fall into in advance helps us make quicker decisions about where to direct our time and attention when something begins to slip.

                    Second, understanding that many of our activities can survive a fall lowers the pressure when things are still firmly within our control, knowing we don’t need to keep them all perfectly balanced. This further helps us maintain our control over everything we’re carrying.

                    Finally, we’re able to be more intentional about the activities we’re balancing.

                    This might mean reducing our allocation of Breakable activities down to a small number that we’ll be able to maintain control of even when the going gets rocky. It also allows us to assess new activities before picking them up in the first place.

                    The more Breakable activities we’re carrying, the more likely we are to cause a mess, after all.

                    Over time, a more balanced creative workload allows us to spend less energy simply holding on to everything we’re carrying and more energy actually doing creative work that matters.

                    To us, and hopefully, to others.


                    Explore how to navigate a creative life that matters

                    This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                    A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                    Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                    It’s something I’m proud to create and I’d be honoured to share it with you.


                      How Your Identity As A Creator Will Elevate or Undermine You

                      Last week I shared this post outlining the advantages that come with embracing the mentality of an underdog.

                      I got a number of great messages in response from people who resonated strongly with the sentiment. That didn’t surprise me, as I think most of us here identify as underdogs, struggling for attention amid much larger, better-funded, better-staffed companies, publications, and creators.

                      What did surprise me, however, was one email I got from a long-time reader and PMA alumni, Kelle Sparta, in which she–point by point by point–flatly refuted my encouragement of embracing the underdog mentality.

                      What surprised me even more, however, was that I found myself agreeing wholeheartedly with every point she made.

                      While there are certainly benefits to embracing the mentality of the underdog–it takes a certain level of defiance and even audacity to create change with our creative work after all–Kelle’s email shed light on some of the problems associated with holding onto the underdog mentality too tightly and for too long.

                      So today, I want to share Kelle’s letter along with some further reflections on the identities we choose to adopt and put to work for us.

                      Kelle’s Letter

                      As someone who works with people on their identity, I am fluent in identity issues.

                      Here’s the problem with identifying as an underdog.

                      You are beginning from the assumption of you being “less than”.

                      You see the entire world as your enemy that you have to overcome.

                      You are assumed to be the loser and you have to overcome this assumption.

                      While people may root for you, they will bet on the other guy – giving him all the resources.

                      You are living in a state of lack all the time, fighting for scraps.

                      This sets up an assumption that you must fight for everything so that when things do come easily, you reject or distrust them. When help is offered, you turn it down.

                      There is an inherent assumption that you have to beat someone much bigger and stronger than you to be taken seriously.

                      The odds are always against you. (If they weren’t, you wouldn’t be the underdog.)

                      You’re constantly fighting for your place in the world. And this leaves you no space to be vulnerable and held, no place to be cared for.

                      Because this is your identity, you will always magnetize to you people to serve in the role of your Goliath.

                      This identity is a dominant/dominated roleplay with you always trying to be on top. This isn’t an evolved identity because to overcome and become the oppressor still leaves a winner and loser.

                      This is a Young Warrior identity.

                      Instead, consider the Spiritual Warrior identity where the only thing/person the overcome is yourself.

                      Where you start from believing in your right to take up space in your own life.

                      Where you are in competition with no one.

                      Where the only person you need to be better than is your former self – and even that isn’t required.

                      Where you are calm and in tune with yourself and the world around you.

                      Where you have no natural predators.

                      Where you are not choosing a winner and loser, but everyone gets to win.

                      Where there is always enough and you can manifest more whenever you need it.

                      Where you can share your true self and know that while you may be making yourself vulnerable, there are safe places in which to do that and that no one can hurt you without your permission.

                      There are energies associated with the identity you pick.

                      Choose wisely.

                      Mind Your Identity

                      I was immediately struck by the distinction between what Kelle described as the Young Warrior identity of the underdog and the Spiritual Warrior she describes in the second half.

                      The underdog can be a valuable identity to own early on in our creative careers. We can use it to help us prove our worth and skill (to ourselves as much as others) and to build up confidence.

                      But it’s always meant to be a way station en route to a more mature, evolved identity.

                      The underdog is scrappy, daring, and resourceful, all traits that are needed–perhaps in abundance–early on.

                      But while these traits may remain useful throughout our lives, as we mature as people and creators, we should aspire to rely more on our perspective, wisdom, and belief in the abundance of opportunities.

                      Personally, I feel myself currently existing somewhere between these two identities.

                      I’ve relied on (and benefited from) the underdog mentality to start and grow a successful creative business. But six years in, I’m beginning to realize the limits of just how far this mentality can take me.

                      For one, fighting for everything is exhausting and unsustainable.

                      As I’ve approached these limits, however, I’ve also begun to experience the benefits of (reluctantly at times) adopting the more ease- and abundance-focused mindset of Kelle’s Spiritual Warrior.

                      One of the great lessons for me of the past year is that the biggest gains we stand to make as creators come through self-understanding and mastery.

                      By looking inward instead of outward.

                      Doing so gives helps us understand the environments, projects, and commitments in which we thrive and those in which we don’t. This allows us to put ourselves in positions where success will come more naturally.

                      Similarly, self-awareness allows us to recognize that when we’re not getting the results we’re wanting, chances are, we ourselves are complicit in the problem.

                      This understanding then gives us the power to shift our posture, and thus our results.

                      Shift Your Stance to Shift Your Results

                      As I’ve become more self-assured in myself, my work, and the unique place it occupies in the world, opportunities have started to show up with surprising consistency, and of a scale beyond what I would have imagined a couple years ago.

                      Whereas I used to feel like I had to claw and fight for every scrap of progress, in relaxing my approach, things are flowing more easily with less effort.

                      On the one hand, there’s no doubt that my work is simply better now, both when it comes to this newsletter as well as my work in podcasting. With that in mind, perhaps it’s not surprising that more opportunities are showing up now.

                      But my stance around my work has also shifted significantly.

                      Whereas I used to be defensive and protective of my work, forever looking over my shoulder that someone was going to come along and steal my ideas or do a better job of executing on the same concept, I no longer worry about that.

                      I’ve realized that as long as I keep my gaze directed forward, and continue to put one foot in front of the other, there’s no possible threat of competition.

                      I’m walking my own path, and everyone else is walking theirs.

                      No one else can create in the way I do because they haven’t walked the same path to get here.

                      The only way to guarantee failure is to try and walk the same path as someone else.

                      An underdog mentality might be empowering (and even necessary) during a certain phase of our life cycle as creators.

                      But it pales in comparison to the more mature, evolved identity of standing tall, confident that we’re doing the work that no one else could possibly create. The work that will go uncreated if we choose not to pursue it.

                      Embodying this identity isn’t easy, however.

                      As an underdog, it’s hard to let go of the feeling that we always need to be working just to keep our heads above water, let alone get ahead.

                      The idea of competition is so ingrained into our culture that it’s hard to entertain, let alone embrace the idea that competition is optional, and that all we need to do is choose to approach our work that way.

                      Like so much of creative work, this process takes time.

                      In the meantime, I still believe there are distinct advantages to adopting and embracing the underdog mentality, especially when we’re first starting out.

                      But I also now believe that holding on to the identity for too long will keep us stuck.

                      So embrace the mentality of the underdog fully and fiercely for as long as it serves you.

                      But know that a time will come when that mentality that has served you well for so long will become a burden.

                      And when it does, don’t be afraid to shed it as you step into the new, more mature, more complete, more fully-formed version of yourself.


                      Explore how to navigate a creative life that matters

                      This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                      A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                      Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                      It’s something I’m proud to create and I’d be honoured to share it with you.


                        Stop Squeezing Your Ideas to Death (Do this Instead)

                        Too often, I think, we misunderstand what we’re holding when it comes to our ideas.

                        We treat them as difficult nuts to be cracked, subjecting them to pressure, heat, and force as we attempt to get through the hard outer casing to access the interior.

                        Rather than unlocking creative sustenance, however, more often than not, this approach ends up squeezing our ideas to death.

                        It’s understandable why we do this.

                        When it feels like everyone we look up to is succeeding now, we feel pressure to keep up.

                        And so we then take that pressure and direct it onto our ideas, attempting to accelerate their growth.

                        But herein lies the problem.

                        The value of a nut is not in the small amount of short-term sustenance it can supply as food, but in its long-term potential as a seed.

                        And seeds must be handled very differently from nuts if we want to unlock that potential.

                        So too must our ideas.

                        Like anything in their infancy, ideas–even our very best, most promising ones–implode under pressure.

                        We don’t expect a single sapling to bear enough fruit to feed us.

                        In fact, most trees will take years of nurturing before they bear any fruit at all.

                        And while the timelines may be different, the expectations should be the same around our ideas.

                        Ideas, like seeds, must be given time and space to germinate, sprout, and anchor themselves firmly in fertile soil.

                        Most of all, they must be nurtured.

                        I think we forget that.

                        That nurturing might take months.

                        It might take years.

                        For some, particularly big ideas, it might take decades.

                        But with some patience and some support, in due time, our ideas will grow the strength and stability to support incredible growth and production.

                        Until then, however, our job is not to squeeze everything we can from them before they’re ready to bear the pressure.

                        But to focus on nurturing, providing a safe space for the idea to take root and develop.


                        Explore how to navigate a creative life that matters

                        This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                        A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                        Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                        It’s something I’m proud to create and I’d be honoured to share it with you.


                          The Campfire Approach to Audience Building

                          If you’ve ever built a campfire, you know that to build up the fire successfully, you need to follow a specific, systematic process.

                          Regardless of what style of fire-builder you are (personally, I’m a log cabin-er), the process is always the same and can be summarized as follows.

                          1. Gather the materials you’ll need including tinder, kindling, medium and larger logs, and a match.
                          2. Build a frame using your kindling.
                          3. Fill that frame with tinder, perhaps paper or wood shavings.
                          4. Light the tinder. Supply additional oxygen if needed.
                          5. As the fire spreads to the frame, add progressively larger kindling as the existing frame burns up.
                          6. Continue this process, over time adding larger pieces of wood as the size of the fire grows to support them.

                          In a way, the process is nothing short of magical.

                          While it would be impossible to light even a medium-sized piece of wood with a single match, by following this process, you can fairly quickly build up a fire capable of lighting and consuming whole, uncut logs.

                          When it comes to starting a fire, this process might seem obvious.

                          But it turns out that building a relationship with an audience follows a near-identical process. And yet so often we try to skip steps, attempting to set fire to the whole log without first building up the base.

                          Much like we can follow this systematic, repeatable process to consistently light fires, so too can we follow the same process to consistently grow our audiences.

                          Defining Your End Goal

                          Before we go any further, let’s take a moment to talk over what we’re actually trying to build.

                          When we think about “building an audience” around our creative work, we might first think about the size of our email list, or our podcast, YouTube or website analytics, or perhaps even our customer or client list.

                          But these are all by-products.

                          What we’re really looking to build is relationships.

                          While our audiences are small, these relationships might be reciprocal, meaning we personally know each of the people who follows and engages with us.

                          As we grow, however, these relationships will be increasingly asymmetrical, meaning we don’t know our individual audience members nearly as well as they know us.

                          Regardless of which stage we’re at, however, our goal is to always focus on relationship building, which, in the case of our metaphor is the fire itself.

                          The bigger and hotter the fire we’re able to build with our audience, the more heat we receive back from it in the form of positive benefits.

                          But before we get to the point of having a fire blazing in front of us, we have to gather the raw materials.

                          Gathering Raw Materials

                          The raw materials for fire building are fairly straightforward and can be summarized as follows:

                          • Oxygen – The existing desires, motivations, and frustrations of our audience. If we build something for which there is no desire (ie. oxygen supply) our fire will not burn.
                          • Fuel – This is the work we feed to our audience and it exists in multiple forms. Much like we can’t dive in and ask personal questions requiring vulnerability with any type of new relationship, we must build up the level of trust and intimacy with our audiences over time by feeding them different types of fuel.
                            • Tinder – Content that requires a negligible investment of time and attention. This might include social engagement and community participation, snackable ultra-short-form content, and in some cases, simply a very well-written sales page.
                            • Kindling – This is our medium- to long-form content including newsletters, blogs, podcasts, etc. This content requires more of an investment from our audience members and they must warm up to a certain level before they’re likely to consume this type of content.
                            • Logs – These are our high commitment offerings that require a more serious investment of time, attention, and/or money from our audiences. These might include live events, courses, paid products, and more. While there is always the potential for these logs to burn when presented to our ideal audience members, they require a great deal of heat before they’re actually capable of catching flame.
                          • Spark – Finally, we have the spark, the concentrated burst of energy that, when directed towards the right materials, will set them alight. The spark is an idea or perspective that reacts with the hopes, desires, and/or frustrations of our audience and is triggered by the friction between where/who they are now, and where/who they want to be. If we want to spark a fire, we need to be keenly aware of this tension our audience holds within themselves.

                          Choosing Your Fire’s Location

                          With our materials assembled, we’re ready to assemble them and start the fire.

                          But before we do, there are a few considerations regarding the placement of our fire.

                          At the end of the day, the materials that will start, sustain, and grow our fires are naturally occurring but may be more prevalent in one area than another.

                          This means we need to be mindful of where we choose to set them up initially.

                          1. A Ready Supply of Oxygen

                          Of most importance is oxygen, or the existing desires, frustrations, and motivations of our target audience.

                          Countless businesses, newsletters, and podcasts have failed because the content on offer attempted to address a need or interest that didn’t really exist for the audience.

                          There’s no guarantee that anyone else will share your interests, or be willing to spend time or money on the problem you can help them solve. This is one of the painful truths of creative work that we all need to come to terms with, especially when what we’re creating just isn’t landing.

                          No oxygen. No fire.

                          2. An Abundant Source of Fuel

                          Starting and maintaining a fire in a location without an easy supply of wood isn’t the best idea if we’re looking to sustain that fire over time.

                          The same holds true for starting a creative endeavour in a niche or on a topic that doesn’t naturally inspire new and interesting ideas in us.

                          Much like an abundance of easily accessible trees makes it easier to keep a fire going, a topic, niche, or industry that is constantly sparking interesting ideas and conversations makes it easier to create quality fuel to feed into our own creative fires.

                          I’ve started many creative projects in the past for which coming up with fresh, interesting ideas was like banging my head against a wall.

                          Before starting the projects, I’d come up with 10 or 15 potential content ideas, but once I made my way through those, I would find myself stuck. At this point, I would struggle to come up with ideas, start missing my publishing due date, be unhappy with the content I did create, and ultimately shut down the projects.

                          The best bet is to focus your creative work on a topic or idea you can’t help but think about all the time.

                          For many of us, this big idea might not be immediately obvious and will require some digging to get to. But once we find it, we can be sure we’ll have a steady supply of high-quality fuel to feed our fire as it grows.

                          3. Room to Grow

                          An abundance of both oxygen and fuel will allow us to start and build a red-hot fire. But without room to grow and spread, its potential will be limited.

                          In practice, a lack of room to grow might result in a project with a small but extremely dedicated fan base. And for some people and some projects, this is enough.

                          If you’re looking to sell a $10k service, for example, you likely don’t need all that many people to resonate with what you do in order to make a fantastic living doing it.

                          Many of us, however, require a larger number of people to resonate with our creative work in order for it to be financially viable.

                          This is where having room to grow comes in.

                          At its core, this means choosing a topic, niche, or industry where there are enough potential customers, clients, or audience members for you to build a sustainable business from your work*.

                          Let’s do some quick and simple math to see what this looks like in the wild.

                          Let’s say you sell a $100 course and would one day love to be making $100k per year.

                          With this product and goal, you would need to sell 1,000 courses per year. This means you need to choose a market that has room for you to grow into finding 1,000 new customers each and every year.

                          But that’s not quite the whole story.

                          Keep in mind that not everyone in your audience is going to buy your course from you. In fact, a fairly standard conversion benchmark for an online course is around 2.5%.

                          With that in mind, in order to get those 1,000 new customers per year, you actually need to grow your overall audience by 40,000(!!!) people each and every year (1,000 is 2.5% of 40,000).

                          From there, you have to think about what percentage of people in your niche or industry will ultimately resonate with you and your content? It certainly won’t be everyone.

                          Even if you’re able to capture 10% of your niche, that means that to meet your goals the niche needs to consist of at least 400,000 people.

                          Of course, this is an extreme example.

                          As a creator, you might have a series of products you offer allowing you to sell to the same audience multiple times. Or you may create offerings that are much more expensive, requiring a smaller audience in order to make a sustainable living off your creative work.

                          And yet, the principal is worth remembering.

                          Too often creators choose an area to start their fire that limits its ability to grow from the outset by choosing a topic or niche for which there is simply no room to grow into.

                          In these cases, even if there is an abundance of fuel and oxygen, the fire may be incapable of spreading far enough in order to sustain you financially as a creator.

                          Assuming you’ve chosen a spot with sufficient fuel, oxygen, and room to grow, however, it’s time to light the fire.

                          * If you really want to nerd out about this stuff, you can read more about concepts like Total Addressable Market (TAM), Serviceable Addressable Market (SAM), and Serviceable Obtainable Market (SOM) here.

                          Lighting the Fire

                          Much like there are many ways to light a campfire (matches, rubbing two sticks together, and blowtorches come to mind), there are many ways to light the fire between us and each of our individual audience members.

                          Some of these methods require more effort than others, however.

                          We talked before about how the spark in our scenario is an idea or perspective that reacts with the hopes, desires, and/or frustrations of our audience and is triggered by the friction between where/who they are now, and where/who they want to be.

                          This means that first and foremost, we as creators need to be aware of that friction, and of those hopes, desires, and frustrations.

                          Then, we need to regularly share our ideas related to those topics publicly.

                          Like starting a fire with flint and tinder, however, we need to be intentional about directing the sparks we’re sending off into the midst of the tinder–which is the most likely thing to catch flame.

                          In practice, this means first embedding ourselves in a receptive community before sharing our ideas that have the potential to spark connection.

                          When we take this approach of embedding ourselves in a receptive community, we find that fires are much easier to start. This is because we’re no longer attempting a cold start but are instead simply stoking the tinder that is already lying around smoldering.

                          In these cases, someone who has already been warmed up in an adjacent fire may make the leap directly to consuming our kindling or even logs.

                          This is why it’s so valuable to find and engage regularly in the broader community surrounding your topic rather than attempting to build your fire in isolation.

                          It’s also worth noting that we don’t always need to be the ones to start the fire in the first place.

                          One of the most effective methods of starting the fire between us and our audiences is by tapping into an existing fire that someone else has already taken the care to create.

                          Practices like podcast guesting, guest blogging, collaborations, partner workshops, and more all have the effect of taking a hot burning log from one fire and transplanting it to a new collection of fuel and tinder waiting to be lit.

                          These tactics allow us to quickly build up a hotter and more stable fire than we would be able to on our own.

                          Building & Maintaining the Fire

                          Regardless of the method, we choose to light our fire, new fires require nurturing and shelter.

                          Small fires are easily extinguished by gusts of wind and lack of anything but the exact right size of fuel.

                          This means that early on, we might need to light and relight the fire several times before it really takes, and then must constantly feed the fire a steady supply of just the right fuel, oxygen, and attention while shielding it from the wind.

                          During this phase of the fire, much of our effort goes toward fleeting, temporary results.

                          While frustrating, this is the way building a fire works.

                          While our big picture goal is to build up a large, blazing fire that can immediately engulf whole logs, we need to take some intermediary steps to get there.

                          This might mean:

                          • Chopping down our large, in-depth content and offerings into small, easily-consumable chunks…even though we’d rather people just consume the original.
                          • Or engaging regularly in other people’s communities related to our topic…even though we really want people to join the one we’ve established.
                          • Or doing unscalable activities like creating a custom welcome Loom video for each new social media follower… even though we’d rather just send a scalable automated message.

                          Much like tossing a whole log on a fledgling fire will smother it entirely, so too will offering our fledgling audience members only large, in-depth, content that requires more time and trust than they’ve built up with us so far.

                          If we want to deepen that trust and build the fire, we have to meet each audience where they’re at and offer them a steady supply of fuel appropriate to what they can consume at that moment.

                          Over time the fire will grow stronger. As it does, it will become capable not only of consuming larger sources of fuel but also of sustaining itself without our constant attention.

                          Continue to build the fire and soon it will begin to naturally throw off sparks, each of which has the potential to help the fire jump and spread as our people talk about our work.

                          Build the fire long enough and we create a searing bed of embers that are capable of retaining heat for an incredible amount of time.

                          The embers are our superfans.

                          They’re the people who’ve been with us the longest, have consumed every form of fuel we could feed them, and are capable of smoldering for years even without the regular addition of new fuel. When new fuel is finally presented, however, often all it takes is a simple stoking for the flames to jump back to life.

                          Not every fire we start will develop into a bed of embers, but this is ultimately the most powerful form of fire we can hope to build.

                          It also takes the most time and attention.

                          While a grass fire might light easily and spread far and fast, there’s little retained heat once it burns through the landscape and may fizzle out when it reaches a tree line filled with fuel it’s not hot enough to consume.

                          Create a focused fire, however, and nurture, feed, and attend to it carefully for years at a time, and it will grow to become capable of consuming whole anything you present to it.


                          Explore how to navigate a creative life that matters

                          This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                          A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                          Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                          It’s something I’m proud to create and I’d be honoured to share it with you.


                            Creative Wayfinding For Ambitious Optimists.

                            How to Boost Your Creative Output by Taking Advantage of Interstitial Opportunities

                            The other day, I found myself stuck in a long, slow line at the grocery store.

                            There was only one checkout lane open and the cashier seemed to be working through some problem with the customer currently at the head of the line.

                            With a handful of people still ahead of me, I instinctively reached for my phone and began to browse.

                            First I scanned the news headlines, then checked for anything new on my hockey team, the Edmonton Oilers before opening up my newsletter feed to chip away at the hundreds of unread newsletter issues sitting in my inbox.

                            After a few minutes of scrolling, I glanced up to check the line and saw that every single other person in the line also had their phone, skimming through their content of choice.

                            Of course, this observation is far from groundbreaking.

                            If anything, the fact that we immediately reach for our devices to fill even the tiniest amount of empty space in our lives with content of one form or another is the assumed default.

                            In fact, if you’re like me, and you choose to fill the space with newsletters and articles about marketing, creativity, and business, this habit feels downright productive. When we find ourselves stuck in these in-between moments of waiting, what else could we possibly do that would be a better use of our time?

                            But herein lies the problem.

                            Because how do we really know what the best use of our time is?

                            It’s easy to look to content consumption as a productive task because (at least when we’re consuming a certain type of content) we are keenly aware of the learning it delivers.

                            We read an article or listen to a podcast and learn a new tactic, discover a new tool, or shift our thinking in some way. These are all valuable outcomes, perhaps even necessary for the continued inspiration and progression of our creative work.

                            But what if their easily observable value causes us to overemphasize their importance at the expense of other potentially more important uses of our time as creators?

                            Because while consumption is certainly an important element of creative work, in order to connect the dots and make sense of what we’ve consumed we need to leave empty space for integration.

                            Interstitial Opportunities

                            The interplay between consumption and integration is the engine that drives all creative work.

                            They are yin and yang and it’s impossible to do successful creative work without each of them.

                            Without consumption, there are no new ideas for our creative brains to connect and meld together.

                            But without time to allow these ideas to integrate and percolate, we never end up with actual novel ideas with which to do anything with… which is kind of the foundation of any kind of creative work.

                            The process of integration and connection is almost entirely subconscious, but in order for this process to occur, our brains require periods of slack where they’re not actively engaged in working on a problem or consuming content.

                            In other words, like standing in line at a grocery store is a perfect opportunity for this process to take place.

                            I like to think of these small moments as Interstitial Opportunities, the small moments of limbo where we’re stuck in between tasks, waiting, with nothing “productive” to do.

                            Of course, at first glance it might not seem as though we could get much creative thinking done in these brief interstitials.

                            And yet, these small moments of slack and boredom and ennui are exactly the moments when we stand to make the greatest creative breakthroughs, an idea that has been backed up by research.

                            With little to occupy our subconscious minds, they naturally seek to fill the void by going to work on a problem we’ve been puzzling over or connecting the dots between ideas and experiences.

                            In addition, with our conscious minds undistracted by tasks or consumption, we’re more open to noticing the connections being formed behind the scenes.

                            You likely experience this regularly.

                            How often do you have new ideas in the shower or while out for a walk, or while diving after all?

                            Despite this we spend so much time, either actively or unconsciously crowding out these opportunities for enlightenment by filling them with content and distraction.

                            Creative work certainly requires inspiration.

                            And building a creative business requires guidance and education.

                            But I’d argue that most of us have an overwhelming surplus of tools, tactics and strategies occupying our mental space already.

                            What we’re lacking are novel big ideas to which we can apply those resources.

                            If you’re like me, you imagine your big ideas being born of the hours-long creative brainstorming sessions you’ll surely one day have the time and bandwidth available to schedule regularly

                            And yet, if we’re honest with ourselves, we know that day will never come.

                            In a world with so few big unbroken swaths of time then, making better use of many small moments of slack in our schedules might just be a creative superpower.

                            The next time you’re stuck in line, or sitting down to eat lunch, or faced with an unexpected delay and you feel the compulsion to reach for your phone, stop.

                            Notice it.

                            Push back on it.

                            Recognize the interstitial as an opportunity.

                            And instead of filling it, simply sit.

                            Allow yourself to be bored.

                            Allow your mind to wander.

                            Make space for ideas to fill.

                            Or not.

                            The ideas might not show up the first or the second or the fifth time.

                            But nature abhors a vacuum.

                            And if you keep making space, it’s only a matter of time before it will be filled.


                            Explore how to navigate a creative life that matters

                            This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                            A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                            Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                            It’s something I’m proud to create and I’d be honoured to share it with you.


                              10 Unconventional (+ 1 Cliche But True) Lessons I Learned Publishing 100 Issues of My Newsletter

                              Just over two years ago, on April 12, 2020, I sent out the first issue of this newsletter.

                              I’d attempted to write several newsletters in the past, but they had always fizzled after a few months at most.

                              Something about this one felt different however, and now, 100 issues later, it seems that hunch was true.

                              Over those 100 issues the newsletter has nearly tripled in size, almost all of that growth coming in the past 12 months, and I’ve learned a lot about creating and growing creative projects like newsletters.

                              And while a lot of what I’ve learned corresponds with the standard advice you can find all over Twitter, for this milestone issue, I wanted to share 10 of the more unconventional learnings I’ve had about growing creative projects, several of which fly in the face of standard audience building advice.

                              Let’s jump in.

                              1 // Feed Yourself First

                              We’re often told to serve our audience above all else.

                              But in my experience, creative projects have a much higher chance of succeeding when the act of creating them gets us something personally, before anyone else ever interacts with them.

                              Ironically (or maybe not), this was the topic of the very first issue of this newsletter, which I titled, Focus on What Fuels You.

                              Feeding yourself first is about structuring your projects in a way that first & foremost scratches an itch you have. Then finding a way to adapt & package it in a way that overlaps with an existing audience’s interests & desires.

                              This isn’t to say that every project that scratches one of your own itches will have an opportunity to build an audience around it. You need both project-market and project-creator fits to be successful.

                              But in my experience, it’s easier to find an audience for a project that feeds you than the other way around.

                              2 // Pay Attention to Signals of Progress

                              Almost any creative project is going to take several years to grow a significant audience around. But if your work has the potential for growth, you should be getting at least small bits of positive feedback fairly quickly.

                              Five issues in, I received my first email response from a reader (shoutout to Jason Perrier!) about how they resonated with the issue.

                              That email encouraged me to lean further into what I was doing, and since then, I’ve received at least 1 similar email almost every week.

                              If you’re getting your work in front of even a small number of your ideal audience members and you’re not getting any positive reinforcement, it’s a sign you need to make some tweaks.

                              And if you’re not regularly getting it in front of even a small number of your ideal audience… well you need to start there.

                              3 // The First Version Won’t be the Final Version

                              We all want to launch our projects as their fully realized & perfected versions.

                              But most of the time, we, ourselves don’t know what they’ll morph into once we launch them. Better to get a first draft out and then iterate on it from there, a process I call Thinking in Drafts which I covered in Issue 27.

                              I wrote the first 56 issues of my newsletter under what was essentially a placeholder name, The Listen Up Newsletter.

                              I named it with a vaguely audio-related name before I ever wrote the first issue and wholeheartedly believed I was going to be writing about podcasting… which never ended up happening even one time.

                              It was only after those 56 issues over more than a year that I started to see the through-line in the newsletter & rebranded to the more aligned Creative Wayfinding Newsletter.

                              If you’re creating a long-term body of work like a newsletter or podcast, you should expect it to go through significant shifts over its lifecycle, none of which you can predict before you start.

                              Understanding this reduces the pressure you put on the first (or current) iteration to be perfect.

                              Ship it & then have the faith to keep moving through the fog and follow where it leads you.

                              4 // Being Unable to Describe What You do Might Mean You’re Onto Something

                              I often feel sheepish that after 100 issues of my newsletter, I still can’t really describe what it’s about.

                              But recently, I’ve discovered that this is a common trait of successful creators’ platforms.

                              The reason, I think is that successful creative platforms are often a blend of ideas that haven’t been paired before. This is what makes them novel and interesting. But it also makes it hard to develop messaging around them because the vocabulary doesn’t yet exist.

                              Creating that vocabulary is a huge part of our job as creators.

                              5 // The Things that Work Best Don’t Always Make Sense

                              We all love frameworks, templates & archetypes that promise to shortcut our way to success.

                              But the things that work best usually don’t fit neatly into the existing boxes. And they often break all the rules you’re supposed to follow.

                              My audience is almost entirely made up of podcast creators, many of whom receieve the newsletter after having signed up for one of my podcast-related offerings.

                              My newsletter, however, has almost nothing to do with podcasting and is about finding your way as a creator of any kind.

                              This goes against a lot of marketing advice.

                              There’s a significant disconnect between my top of funnel (podcasting), middle of funnel (Creative Wayfinding) & paid offerings (podcasting).

                              And yet, based on anecdotal feedback from customers and subscribers, I have a suspicion that this franken-funnel somehow works better than if all my content was tightly aligned around podcasting.

                              I think there’s a reason…

                              A highly aligned funnel probably would do a better job converting cold traffic into one-time sales.

                              But my current creative platform allows people to really get to know a much deeper more nuanced version of me without feeling like I’m just buttering them up to make a pitch (which I’m not).

                              In the short term, this is likely a less financially successful strategy. But the long-term upside is huge.

                              For one, it leads to more perfect-fit customers & clients who buy into my philosophy around creative work which leads to better outcomes for everyone involved.

                              It also moves my product offerings away from being commodities which can be easily compared to other products designed to help people achieve similar outcomes. I’ve heard time and time again from PMA students that the biggest reason they enrolled was because of me.

                              I don’t know that that would have happened if I was more focused with outcome-oriented, purely instructional podcast content.

                              Most important of all, however, this approach leads to friends, partnerships, collaborators & deep personal connections that I have a hard time believing would have come from a super-specific, topic-aligned funnel.

                              I regularly get comments from readers along the lines of, “I found Jeremy through his podcast content, but actually stuck around for his ideas around creative work which I don’t get anywhere else.”

                              Comments like this are a sign to me that I’m on the right track to building the kind of creative platform I aspire to. One that is nuanced, real, and human.

                              There’s no way I could have (or would have) planned this strategy in advance, but somehow I stumbled on to it, and it works.

                              6 // Track the Right Metrics

                              We all want to see our subscriber counts go up.

                              But total subscribers/views/downloads/etc aren’t a great way to measure the true impact of quality of our work. Plus, by measuring the wrong thing we’re likely to optimize for it, which is a big mistake.

                              While I certainly track my subscriber count, my North Star metric has always been reader responses.

                              These responses, to me, are a signal of resonance, which is the target I’m aiming at with each issue.

                              With every issue, I hope to get at least 2-3 meaningful emails from subscribers who resonated with the article. When I don’t get any, I have a closer look at why that might be.

                              I also use the Reactions feature from Sparkloop (which you can see below this essay) and track how many responses I get for each issue using the scale:

                              👍 Above Average
                              👊 Average
                              👎 Below Average

                              Each issue averages between 5-10 total reactions. Any more or less than that is an interesting data point to look into.

                              7 // Know Why You’re Doing It

                              Hand in hand with tracking the right metrics is knowing why you’re creating the project in the first place.

                              Chances are, it’s not all about audience growth (although that might certainly be one reason). Remembering the true purpose of the project will help keep you on track & avoid distractions.

                              This newsletter’s primary purpose for me has always been as a sandbox to:

                              • Hash out ideas that later find their way into other parts of my work
                              • Experiment with marketing strategies & tactics
                              • Hone my writing
                              • Get to know myself better

                              Reminding myself regularly of the non-audience-growth-related outcomes helps me avoid feeling frustrated when growth is slow as the project is still achieving its other purposes.

                              It also keeps me focused on creating work that’s aligned with my internal compass rather than trying to guess what other people want.

                              8 // Release the Handbrake

                              Last year I took a writing course from The DO Lectures.

                              In one lesson, David, the instructor, said something I haven’t been able to shake:

                              “You don’t need to find your voice. You already have it, you just need to release the handbrake.”

                              Since starting my newsletter, I’ve consistently discovered that the more I release the handbrake & lean into the ideas, quirks & traits that make me unique, the more my work resonates.

                              This runs counter to a lot of entrepreneurial advice, however.

                              One of the first rules of building a company is building it so that it can run just as well without you.

                              But perhaps the first rule of creative work is that the work should seek to fully reflect & embody you as the creator.

                              Release the handbrake & remove the barriers to resonance.

                              9 // Define & Reinforce Structure

                              Creatives are notorious for hating the idea of structure & constraints.

                              But the more structure you build into your work the easier it is to create while also providing a frame around which to explore your topic w/ more depth & clarity.

                              Structure for me started with defining the general format of the newsletter:

                              1. Welcome
                              2. Announcement
                              3. Community Shoutouts
                              4. Feature Essay
                              5. 5 Currated Links
                              6. Twitter Feature
                              7. Sign Off
                              8. Gratitude/Wins/Excitement

                              After implementing this structure, it immediately made the newsletter easier to put together each week.

                              And after my first structural experiment, I decided to take it further by bringing more structure to the 5 Things You Might Dig section of curated links.

                              As you might have noticed, those links now fall into one of five consistent buckets:

                              1. Thought
                              2. Tool
                              3. Tactic
                              4. Podcasting Resource
                              5. Wildcard

                              Much like more structure made it easier to put together the newsletter as a whole, more strucuture around the links made it easier to source & curate links for each issue while also reinforcing the “brand” of the newsletter by bringing more consistency to the offering.

                              So far, every time I’ve added more structure, the newsletter has gotten better & creating it has become easier & faster.

                              Chances are, structure will have the same effect on your work.

                              10 // You Can’t Do it Alone (Cliche but True)

                              Find your people who will inspire, motivate & support you.

                              It’s a long road to building a life around meaningful creative work and you’re going to need all the help you can get.

                              We all need a steady supply of inspiration, motivation, support, accountability and commiseration in order to keep moving forward with our creative work. There is a long list of people who’ve played one or more of those roles for me and this newsletter whom I referenced in Issue #47 about Acknowledgments & Accompaniment.

                              In my experience, perhaps more important early on than finding your audience is finding what I call your Creator Cohort, the group of people at roughly the same stage as you, with whom you’ll “grow up” together.

                              These people will not only help you gain clarity on your audience but also on how you, your work, and your voice fit into the larger conversation taking place in your space.

                              11 // You’re Not Going to Figure Out What the Hell You’re Doing for a While. And That’s Fine.

                              Big ideas rarely come fully formed.

                              In fact, they often take years of steady, persistent excavation.

                              But the real purpose of a creative practice isn’t to grow now. It’s to slowly and persistently chip away and excavate the big ideas that will lead to bigger things in the future.

                              I’ve been creating in one form or another for over a decade.

                              But I’ve got at least 4 more decades of creative work yet to come.

                              I’m at the beginning, just finding my feet. My best work is so far off in the future I can’t even imagine it yet, let alone see it on the horizon.

                              The same is true for you.

                              This work is not for the faint of heart.

                              It will wear (if not outright beat) you down.

                              It will make you deeply question your self and your worth.

                              It will disappoint and frustrate and shatter you more times than you feel you can bear.

                              It takes a special kind of person to not only put up with all that, but choose to walk further into the Creative Wilderness without a map, following only the subtle tug of your internal compass and the belief that there’s something out there for you.

                              If you’re here, I think you’re probably that type of special person.

                              And I’m honoured to be navigating the wilderness alongside you.

                              Here’s to the next 100 🍻


                              Explore how to navigate a creative life that matters

                              This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                              A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                              Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                              It’s something I’m proud to create and I’d be honoured to share it with you.


                                Rethinking Your Big Break

                                We spend so much time thinking about The Big Break.

                                We love to ask and hear about the moment things changed for the creators we aspire to be like.

                                And we spend more time than we might like to admit anticipating, fretting, and wondering about whether this will be the post or episode or newsletter or launch that blows up and puts our name on the map.

                                Of course, as creators, we’re already well aware that every overnight success is built on years of unheralded work.

                                But maybe we’ve already put in those years of unheralded work and feel we’re due.

                                Maybe we are.

                                Maybe we’re not.

                                Regardless, it’s worth reconsidering our conception of The Big Break.

                                Because the singular moment of success we often associate with it is simply an Echo Effect, a result of an earlier action now reflecting back to us.

                                Which means that what we think of as The Big Break isn’t actually The Big Break at all. It’s simply the echo of it.

                                So what is the real Big Break, then?

                                Maybe it’s the point at which we break with the mindsets, beliefs, and actions we’ve relied on so far and set out on a new path.

                                Maybe it’s the point at which we stop relying on others to guide our work and rely on our inner compass instead.

                                Maybe it’s not a point of arrival but of beginning.

                                Which means that our Big Break is within our power to make whenever we’re ready.


                                Explore how to navigate a creative life that matters

                                This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                                A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                                Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                                It’s something I’m proud to create and I’d be honoured to share it with you.


                                  Creative Success is an Echo

                                  An echo can’t exist without a gap in time between its source and return.

                                  In fact, it’s kind of central to its definition.

                                  The delay of a clap in a small room may be just a few almost imperceptible milliseconds.

                                  The call and response of a shout across a mountain valley may near a second.

                                  And a radio ping sent out across the galaxy might take years to make its way home.

                                  Creative success is an echo as well.

                                  The delayed result set in motion by an earlier broadcast.

                                  Depending on the scale of our aspirations and the environment into which we are projecting them, the time it takes the echoing results of our efforts to return will vary.

                                  As will the strength of signal required to reach its destination and then make its way back to us without dissipating.

                                  In a way, it’s a comforting thought.

                                  All the work we’ve broadcast, all the noise we’ve made… out there, somewhere, hurtling through space, waiting to collide with something against which to bounce back.

                                  Or perhaps it already has.

                                  And the echo of previous work is at this very moment making its way back to us.


                                  Explore how to navigate a creative life that matters

                                  This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                                  A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                                  Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                                  It’s something I’m proud to create and I’d be honoured to share it with you.


                                    The Sketchbook Approach to Successful Creative Projects

                                    A couple years ago I started experimenting with hand lettering as a hobby.

                                    It’s been a while since I’ve practiced, but recently I’ve found myself picking up and flipping through books on various types of lettering, sketching≤ and drawing while browsing bookshops.

                                    As I’ve been thinking about revisiting and expanding on the hobby, I’ve also been thinking about how we might incorporate some of the practices and lessons from sketching into the rest of our creative work.

                                    Every Masterpiece Starts with a Pencil

                                    The first thing I bought when I first got into lettering was a set of coloured felt-tip calligraphy markers, the core tools of lettering and calligraphy.

                                    The second thing I bought, however, was a set of pencils and a good eraser and it was with these that every piece got its start, long before the markers were uncapped.

                                    Using the pencil, I would ever so lightly sketch out the rough outline piece in order to ensure the letters were spaced consistently and that the final image would fit onto the page. Invariably, this would take several attempts to get right, requiring me to erase multiple sketches before finally landing on the one that was ready to be reinforced and brought to life.

                                    Penciling In Your Creative Projects

                                    This step of sketching out our work applies to our creative careers as well.

                                    We’re usually unaware we’re doing it, however, which can cause problems and frustrations down the road.

                                    At this point in our lives and creative careers, most of us have worked in a series of different niches, platforms, mediums, products, businesses, and maybe even careers before ultimately moving on from many if not most of them.

                                    Each of these can be thought of as a sketch of the life we were aspiring toward at the time.

                                    In many cases, what causes us to move on from one of these endeavours is that as we’re sketching out an image, we realize it isn’t going to fit on the page we have in front of us – ie. the container that is our life, or more specifically, the life we want.

                                    Maybe the sketch extends beyond the time we have available, maybe the finances don’t work, maybe completing this image means giving up or compromising on another one.

                                    Or maybe we just don’t enjoy it all that much.

                                    Whatever the reason, we decide that this sketch isn’t the one we want to commit to long-term and so we erase it and start again.

                                    This process of sketching, erasing, and then re-sketching, in order to establish the outline of the image we want to bring to life, is a natural and necessary part of the process of building our creative lives.

                                    Frustration arises, however, when we fail to understand this and we think that we’re supposed to get the image outlined correctly the first or second, or third (or tenth) time through.

                                    Further complicating things for ourselves is that we often get seduced by an exciting new idea and jump in with both feet, starting to draw in the fine details of one part of the picture we have in our mind before first finishing the outline.

                                    As a result, we often find ourselves committing a substantial amount of time and effort to a project… only to unexpectedly run out of space with the image only half-finished.

                                    This is an outcome that could have been avoided if we would have taken the time upfront to roughly sketch out the image we have in our minds and see how (and if) it could fit onto the canvas we have available to us.

                                    This means scoping out our personal projects much like we would for a client.

                                    The excitement of a new idea can quickly be tempered by the realities of what it will take of us in terms of time, energy, capital, and stress to see it through.

                                    And while it might seem counterintuitive, this is exactly what we want.

                                    The ideas that have the greatest chance of success are those for which we’re able to maintain our initial excitement even after we’re aware of all the time, costs, and sacrifices that will be required to bring them to life.

                                    It will likely take us a number of attempts before we land on an outline that meets this criteria and fits squarely within the boundaries of the page we have laid out for it. But taking the time upfront to get the general outline right before committing to the details can save us a lot in the way of frustration, sunk costs, and difficult decisions in the future.

                                    Once the rough outline has been established, it’s time to refine it.

                                    The Outline is Just a Guide

                                    If you’ve ever sketched anything out before (especially if you, like me, are an amateur), you know that it’s incredibly hard to create a clean-looking image with a single stroke of your pencil.

                                    After just one pass, the outline is full of subtle (and not so subtle) wobbles, the lines aren’t quite straight and the corners aren’t quite smooth.

                                    There’s a tendency at this stage, when the sketch looks incomplete if not outright ugly, to give up and walk away, insisting that we’re just not capable of drawing.

                                    But if we persist, and go back over our rough outline for subsequent passes, something interesting begins to happen.

                                    While the first stroke of the pencil didn’t give us much in the way of anything that could be considered “art”, what it did give us was a guide and a reference point to which we can now anchor our future reinforcements of the general visual concept.

                                    In overlaying subsequent strokes with the pencil, sticking to and reinforcing the guide line in some places, deviating from and correcting it in others, the dominant lines become straighter, the curves become smoother and the wobbles disappear.

                                    What’s more, the image begins to take on depth and nuance as pressure gradients begin to appear, creating the impression of light and shadows.

                                    With every reinforcement, the original outline recedes further into the background, either by being buried beneath subsequent layers of graphite or by being overshadowed by the bolder, darker correction lines that now draw the eye away from it.

                                    The lesson for us as creators is that the point of the first draft is not to look anything like the final image.

                                    The goal of the first draft of any of our work–be that a blog post, podcast, product offering, or even business–is to simply provide a guide for future reinforcement and correction.

                                    The initial outline we create will never look as good as someone else who’s been adding to their sketch for years, adding layer over layer of corrections and reinforcements to their image.

                                    The only way we can expect our sketches to achieve the same level of clarity and depth is to keep sketching.

                                    There are no shortcuts here.

                                    Sure, once you’ve developed into a skilled sketch artist capable of weaving magic with your pencil you may be capable of creating a clean and compelling image with a single stroke of your pencil. But achieving that level of skill takes years of dedicated practice.

                                    Until then, the best option we as creators have available is to sketch and erase and sketch again until we land on a rough outline that fits into the space we have for it.

                                    And then refine it, stroke by stroke by stroke.

                                    Using this method, we don’t need to be master sketch artists to create a clear, compelling image.

                                    We simply need to be persistent, and willing to continue sketching until the image on the page matches the image in our heads.


                                    Explore how to navigate a creative life that matters

                                    This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                                    A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                                    Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                                    It’s something I’m proud to create and I’d be honoured to share it with you.


                                      You Should Know This By Now

                                      I don’t know where we pick it up,
                                      But somewhere, somehow we get the idea that we’re supposed to “know”.
                                      We think we’re supposed to know all sorts of things.
                                      We think we’re supposed to know where we’re going
                                      And how to get there.
                                      We think we’re supposed to know what we want
                                      And how to get it.
                                      We think we’re supposed to know what we’re doing
                                      And why.
                                      We think we’re supposed to know who we are
                                      And our place in the world.
                                      We think we’re supposed to know what our purpose is
                                      And how to fulfill it.
                                      We think that by age 27 or 37 or 47 or 97 we’re supposed to have figured it all out.
                                      But this couldn’t be further from the truth.


                                      The truth is we’re never supposed to know
                                      But to discover.
                                      And this discovery has no end.
                                      Discovery is our life’s work.
                                      We know so little about the world and all that makes it up
                                      And as little about ourselves.
                                      But there’s beauty in the not knowing.
                                      Not knowing creates the potential for surprise
                                      For wonder
                                      And for awe.
                                      Not knowing is our default
                                      Our natural resting position.
                                      We come into the world knowing nothing.
                                      And the wisest, most studied of us will leave it
                                      Understanding no more than an infinitesimally small fraction of the knowable
                                      Not to mention all that for now, and possibly forever remains
                                      Entirely incomprehensible and unknowable.
                                      The idea that we might truly know anything is a wonder in itself.


                                      No matter how much or how little you feel you know,
                                      You’ve already exceeded the expectations of what you’re supposed to know.
                                      You’re where you’re supposed to be
                                      When you’re supposed to be there
                                      With the knowledge you’re supposed to have.
                                      What you do with that circumstance is up to you.
                                      There’s no right or wrong answer.
                                      But a good place to start is with yourself.
                                      To get to know yourself better than you currently do.
                                      The knowledge you seek is within you
                                      If you’re willing to excavate it.
                                      Knowledge about purpose
                                      About direction
                                      About place.
                                      Start there.


                                      Explore how to navigate a creative life that matters

                                      This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                                      A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                                      Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                                      It’s something I’m proud to create and I’d be honoured to share it with you.


                                        Top Shelf Blindspots: How to Spot the Big Opportunities Hiding In Plain Sight

                                        My partner, Kelly, was frantic that she’d lost her credit card.

                                        She’d already searched her wallet, purse, backpack, and jacket–all the usual suspects turning up nothing–when she remembered her jeans. They’d been removed and tossed onto the top shelf of the closet in favour of sweat pants almost the moment we arrived home from lunch, where she had last used the missing card.

                                        As I pulled them down off the shelf, a card slipped from the pocket and skittered across the ground.

                                        Success!

                                        As the card settled, however, we realized it was not the credit card, but her driver’s license. The pockets of the jeans were otherwise empty.

                                        Having thoroughly examined seemingly every nook, cranny, and surface in our home, we prepared to head out and retrace our steps of the day, already resigned to the fact that our search was likely to be unsuccessful.

                                        As we headed for the door, however, I couldn’t shake a nagging feeling.

                                        Following the hunch, I returned to the closet and reached up to the top shelf where the jeans had been resting.

                                        The shelf was juuuuuust a few inches above eye level, so while I could see most of the contents of the shelf–even the 3-inch high ironing board that was folded and stored there–I couldn’t see the shelf’s actual surface.

                                        I reached up and ran my hands over the shelf.

                                        Nothing.

                                        Damn.

                                        Then I reached further and felt my way across the ironing board.

                                        Almost immediately, my fingers brushed up against what could only be the missing card. I pulled it down, elated at having solved the mystery.

                                        Not only had I solved the mystery, however.

                                        In finding the bank card where and how I did, I’d stumbled onto an important type of blind spot that not only keeps us from seeing lost credit cards, but also many of the biggest opportunities available to us in our creative work.

                                        The Direction of Our Gaze Determines the Opportunities We See

                                        We tend to navigate the world with our eyes aimed either at or below our own eye level.

                                        When it comes to moving through our physical surroundings, this makes sense, as it keeps us from getting tripped up on the many obstacles we encounter on a daily basis.

                                        Unfortunately, however, we often maintain this downward-looking perspective with us when navigating the world of opportunities and ideas.

                                        This severely limits our potential.

                                        The ideas and opportunities at or below our eye level are those we are already equal to. Should we choose to pursue them, we’d be capable of achieving them with our existing skillset, resources, and network. In other words, they don’t require much–if anything–in the way of stretching ourselves.

                                        That’s not to say there’s anything inherently wrong with these easily accessible opportunities.

                                        In fact, we’d be foolish not to pick much of the low-hanging fruit that surrounds us.

                                        The problem is that the opportunities and ideas at or below our eye level are likely the same opportunities and ideas almost everyone around us is also staring at.

                                        Which makes differentiating ourselves and our work difficult.

                                        This near-ubiquitous focus on the easily visible, however, also presents us with an opportunity.

                                        Because if we’re willing to embrace some uncertainty and stretch ourselves just a little, we can choose to raise our gaze and reach into a whole world of opportunities and ideas that have been largely ignored or avoided by our competitors.

                                        The challenge, however, is that despite them sitting right in front of us, we often can’t see them.

                                        Two Reasons We Miss Opportunities

                                        While some of the opportunities above our line of sight are firmly out of our (current) reach, many, like Kelly’s credit card sitting out in the open on the shelf are close enough to touch.

                                        Despite the relative accessibility of these ideas and opportunities, however, we’re prevented from reaching for them for one of two reasons.

                                        1. Lack of Certainty

                                        In many cases, we can clearly see the opportunities sitting on the shelf above our head.

                                        We’re often kept from reaching for and pulling them down, however, by our lack of certainty about what else might be hiding on the shelf.

                                        Perhaps our lizard brain calls to mind images of snakes and spiders and other unseen threats hiding beyond our line of sight, ready to strike the moment we reach our hand up.

                                        Or perhaps we simply can’t imagine these opportunities being that easy to access. And so instead of seizing them immediately, we sit and ponder and second guess ourselves.

                                        2. Misplaced Certainty

                                        In many cases, however, as with Kelly’s missing card, we’re kept from reaching for opportunities on the shelves above our heads simply because we’ve convinced ourselves the shelves are empty.

                                        The reason for our certainty is what I think of as Top Shelf Blindspots.

                                        These blindspots exist in the thin slivers of space that are blocked from our view when looking toward a surface slightly above our head.

                                        These blindspots are accompanied by a healthy dose of irony.

                                        When looking up at a shelf well above our heads we’re fully aware that we can’t see most of its contents.

                                        But the closer to eye level the shelf is, the more of its contents we can see. And when the 99% of the shelf space we can see appears to be empty, our brains fill in the remaining 1% of a gap in our perception and we become certain that the shelf is entirely empty.

                                        caption for image

                                        It doesn’t take much of a height difference to conceal opportunities of incredible value, either.

                                        A shelf just half an inch above eye level provides enough of a Top Shelf Blindspot to hide a credit card… or perhaps a gold ingot, or stacks of $100 bills, or countless other objects of value.

                                        In fact, while we spend most of our time chasing the big, obvious opportunities and ideas, I’d argue that many if not most of the truly impactful ones are much more modest in their size and packaging.

                                        If we’re going to spot and take advantage of the opportunities existing in our Top Shelf Blindspots, then, we often need someone with a little more height who can clearly see the contents on the shelf for what they are to give us a nudge to reach out and take hold of the opportunities in front of us.

                                        A few days after the incident with the credit card, this is what my friend (and CW reader) Alina helped me do.

                                        Others Can See What We Can’t

                                        We were walking to a coffee shop for a co-working session, catching each other up on our weeks.

                                        I had made some solid progress and was feeling pretty good about my updates, especially at having turned down an opportunity that, while excellent, felt like a distraction from what I felt I needed to be focusing on.

                                        I expected Alina to be proud of my judgment and boundary setting.

                                        After a pregnant pause, she responded instead with, “I just want to shake you right now.”

                                        Over the next 10 minutes, she proceeded to school me on all of the many opportunities lying out in the open, above my eye level but within easy reach, which I was currently missing… And had potentially just turned down.

                                        I was dumbfounded.

                                        Over the next few days, I spent a lot of time thinking about the opportunities Alina had outlined.

                                        But I probably spent more time thinking about what had kept me from seeing the opportunities in the first place.

                                        What was it exactly that had been blocking my view?

                                        Understanding The Shelf

                                        If we imagine opportunities above our eye level to be resting on one or more progressively higher shelves which block our view of the opportunities resting on them, it helps to know what the shelves are made of.

                                        The ideas and opportunities Alina had opened my eyes to involved taking my existing skills, knowledge, and products and applying them to a new audience.

                                        The audience in question, however, was one with which I had almost no network, no knowledge of their specific problems or workflows, and almost no working experience.

                                        These three traits: A lack of connections, lack of specific (or even general) knowledge, and lack of experience almost always form the basic frame of the shelves. But without being filled in, these frames don’t do much in the way of blocking our view.

                                        Unfortunately for us, we ourselves are more than willing to fill in those frames with a thick layer of our own assumptions.

                                        In my case, I had been well aware that this alternative audience for my work existed. I’d even done some limited work with some members of this group in the past, albeit in a slightly different capacity.

                                        I assumed that my past clients were the outliers, however.

                                        I assumed that to work with the vast majority of this audience I would need specialized skills and knowledge beyond what I already possessed.

                                        I assumed I would need connections to insiders that would be difficult or impossible to get.

                                        But the assumptions didn’t stop there.

                                        I assumed I wouldn’t enjoy working with them, and that the expectations would be more than I could meet, and that the effort of accessing this audience wouldn’t be worth the return.

                                        Perhaps most of all, I assumed I would surely be found out as an impostor.

                                        When you think about it, what is Impostor Syndrome, but a series of assumptions we make about the expectations of others and how we measure up?

                                        Stacked together, these assumptions had built up a thick, opaque shelf, completely obscuring my view of the opportunities lying out in the open on the other side of them.

                                        Until at least, someone with a little more height, and a little more perspective came along and gave me the boost I needed to help me see clearly the opportunities waiting for me to reach out and take them.

                                        So What to Do with This?

                                        The first and most important step is to acknowledge that Top Shelf Blindspots exist.

                                        This means being aware that in most cases, the most meaningful, impactful (and potentially lucrative) opportunities are lying out in the open, often just above our eye level, waiting to be picked up.

                                        To see them, we need to access some height and its accompanying perspective.

                                        To do this, we have two options.

                                        The first is to wait to grow ourselves.

                                        While our physical height may be limited by our genetics, there’s no limit to our metaphorical potential for growth and the perspective that comes with it.

                                        But this growth can take years.

                                        What’s more, growth and the accompanying perspective related to one topic, niche or industry often doesn’t transfer over to other aspects of our lives.

                                        And growth of any kind isn’t guaranteed.

                                        This means that if we’re serious about filling in our Top Shelf Blindspots and take advantage of the opportunities hiding in them, we can’t rely on ourselves.

                                        Instead, we need to make a habit of seeking out people in spaces related to and adjacent to ours who are taller than us. People like Alina who can give us a boost and point out all the opportunities they see lying out in the open but which are currently blocked from our view.

                                        While we have no way of knowing exactly where our Top Shelf Blindspots exist, we can be sure that we are surrounded by them.

                                        Knowing this, we can choose to grope around, hoping our fingers randomly land on some opportunity or another.

                                        Or, we can choose to surround ourselves with people who have the height and perspective to guide us to those opportunities we can’t see, but which are lying out in the open, just waiting for us to grab them.


                                        Explore how to navigate a creative life that matters

                                        This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                                        A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                                        Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                                        It’s something I’m proud to create and I’d be honoured to share it with you.


                                          Your Creative Workload Is Dangerously Precarious (Here’s How to Fix It)

                                          Earlier this week I was walking from the living room to the kitchen to put away a few groceries I’d just picked up.

                                          Between the fingers of my right hand were wedged two glass bottles, one kombucha, the other, juice. My left hand had a hold on my jacket and a rather large, round block of cheese, with a bag of apples tucked in the crook of my arm.

                                          Halfway to the kitchen, one of the bottles begin to slip between my fingers, followed closely by the other.

                                          As the bottles wobbled and slid, I instinctively dropped my jacket and the block of cheese from my one hand and just managed to regain control of both of the bottles, as well as the apples before they crashed to the floor.

                                          Disaster (read: sticky, spiky mess) averted.

                                          The incident got me thinking, however, about how often we get ourselves into trouble in our creative lives by first loading ourselves up with more than we can carry, and then, trying to maintain control of it all when one piece begins to slip.

                                          More Options Aren’t Always Better

                                          I think most of us are aware that we’re carrying more than we can sustain control over.

                                          The challenge is we’re confronted with a daily barrage of new tools, tactics, and ideas promising to deliver the results we’re chasing. Seduced by the promise of a quick and easy win, we pick them up without thinking about how they’ll affect the balance of the load we’re already carrying.

                                          And so on top of our client work or day job, we decide to start a podcast… and then a newsletter… followed by a YouTube channel… all while trying to stay active on TikTok, Instagram, and Twitter as well.

                                          Instead of stacking these new additions carefully to form a broad and sturdy foundation, however, we simply stack them on top of each other, forming an ever more precarious tower.

                                          Part of the reason we continue to add to our load is that it feels as though there’s nothing we can afford to drop.

                                          Our default response when any strategy fails to deliver the results we were promised is not to reduce our load and bring more focus to fewer activities, but to add more on.

                                          We think that by diversifying our options we’re increasing our chances of success when in reality, we’re increasing our chances of catastrophe.

                                          Part of the potential for catastrophe is rooted in the unsustainable workload we’ve loaded onto ourselves.

                                          More subtly, but perhaps more significantly, however, is the way that each new addition to the load we’re carrying further removes our focus away from the activities that really move the needle.

                                          If we want to avoid catastrophe, and build a healthy, sustainable creative workload, our task, then, is twofold:

                                          1. Reduce the amount we’re carrying overall.
                                          2. Reconfigure the types of tasks and projects we take on into a more resilient, balanced workload that prioritizes the activities that actually matter.

                                          The first step is to take stock of what we’re already carrying and identify those tasks that matter.

                                          3 Types of Activities that Make Up Your Workload

                                          Part of the challenge of reconfiguring our workload is that with our arms stacked high, we’re unable to see where exactly we’re going and which of our many activities are helping us get there.

                                          It feels as though if we were to drop any of our current activities–even if only for a while–we’d risk losing all our progress and having to start from scratch.

                                          But while we might think nothing we’re currently carrying is capable of surviving being dropped, this is rarely the case.

                                          In fact, if we take an objective look at everything we’re balancing, we find that our different activities fall into 3 distinct categories, only one of which is truly fragile.

                                          1. Droppable Activities

                                          Like my jacket and the block of cheese, there are always at least a few activities we’re carrying can be dropped without any consequence whatsoever.

                                          Sure they might gather a little dust during their time on the floor. But besides that, they can be picked up again when we’ve regained our balance and, after a quick brush off, be none the worse for wear.

                                          When our workload is feeling precarious and we’re feeling our grip start to slip, these activities and projects should be dropped immediately in order to maintain control of other more fragile items.

                                          For me, this category includes things like my Scrappy Podcasting Newsletter, Quick Podcast Tips series on Twitter, general social media engagement, partner & collaborator outreach, podcast guesting, and more.

                                          2. Bruiseable Activities

                                          Bruiseable activities are more like the bag of apples, which if dropped, risk some bruising, but will remain otherwise edible.

                                          Dropping a Bruiseable task is likely to result in a setback. For that reason, we’d rather not drop them, and if we do need to, they shouldn’t be neglected for long. With that said, the damage of a fall is unlikely to be catastrophic and can typically be recovered from.

                                          My Bruiseable activities include the Creative Wayfinding Newsletter, the Elements of Podcast Growth workshop series, my general health (which most commonly suffers to some extent around launches), and relationships with friends and family.

                                          3. Breakable Activities

                                          Finally, we have the Breakable activities, which, like the glass bottles will not only shatter when dropped (perhaps with no way to put back together) but may cause a significant mess for us or others to clean up.

                                          Activities may be considered Breakable because of their complexity, a reliance on timing, and much more.

                                          Perhaps more commonly, however, they may be fragile because a failure in one of these activities would undermine the trust you’ve built with your audience, clients, partners, or other stakeholders.

                                          The activities I classify as Breakable for myself are Podcast Marketing Academy, my Client Work, and my relationship with Kelly.

                                          The full picture of my activities looks like this:

                                          As in the graphic, we should be aiming for a pyramid-shaped distribution of activities, with a small number of Breakable activities on top, supported by a larger number of Bruiseable and Droppable activities beneath it.

                                          The idea is that should we begin to lose our grip, we have enough bandwidth to guarantee control over at least the Breakable activities, if not some of the Bruiseable activities as well.

                                          What we want to avoid at all costs is the inverse of this triangle.

                                          Carrying a high number of Breakable activities puts us in a precarious position, where the slightest slip immediately jeopardizes our entire load.

                                          The Benefits of a Balanced Creative Workload

                                          Taking a more intentional approach to the allocation of the activities that make up our workload helps us in a few important ways.

                                          First, knowing which categories our various projects fall into in advance helps us make quicker decisions about where to direct our time and attention when something begins to slip.

                                          Second, understanding that many of our activities can survive a fall lowers the pressure when things are still firmly within our control, knowing we don’t need to keep them all perfectly balanced. This further helps us maintain our control over everything we’re carrying.

                                          Finally, we’re able to be more intentional about the activities we’re balancing.

                                          This might mean reducing our allocation of Breakable activities down to a small number that we’ll be able to maintain control of even when the going gets rocky. It also allows us to assess new activities before picking them up in the first place.

                                          The more Breakable activities we’re carrying, the more likely we are to cause a mess, after all.

                                          Over time, a more balanced creative workload allows us to spend less energy simply holding on to everything we’re carrying and more energy actually doing creative work that matters.

                                          To us, and hopefully, to others.


                                          Explore how to navigate a creative life that matters

                                          This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                                          A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                                          Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                                          It’s something I’m proud to create and I’d be honoured to share it with you.


                                            How Your Identity As A Creator Will Elevate or Undermine You

                                            Last week I shared this post outlining the advantages that come with embracing the mentality of an underdog.

                                            I got a number of great messages in response from people who resonated strongly with the sentiment. That didn’t surprise me, as I think most of us here identify as underdogs, struggling for attention amid much larger, better-funded, better-staffed companies, publications, and creators.

                                            What did surprise me, however, was one email I got from a long-time reader and PMA alumni, Kelle Sparta, in which she–point by point by point–flatly refuted my encouragement of embracing the underdog mentality.

                                            What surprised me even more, however, was that I found myself agreeing wholeheartedly with every point she made.

                                            While there are certainly benefits to embracing the mentality of the underdog–it takes a certain level of defiance and even audacity to create change with our creative work after all–Kelle’s email shed light on some of the problems associated with holding onto the underdog mentality too tightly and for too long.

                                            So today, I want to share Kelle’s letter along with some further reflections on the identities we choose to adopt and put to work for us.

                                            Kelle’s Letter

                                            As someone who works with people on their identity, I am fluent in identity issues.

                                            Here’s the problem with identifying as an underdog.

                                            You are beginning from the assumption of you being “less than”.

                                            You see the entire world as your enemy that you have to overcome.

                                            You are assumed to be the loser and you have to overcome this assumption.

                                            While people may root for you, they will bet on the other guy – giving him all the resources.

                                            You are living in a state of lack all the time, fighting for scraps.

                                            This sets up an assumption that you must fight for everything so that when things do come easily, you reject or distrust them. When help is offered, you turn it down.

                                            There is an inherent assumption that you have to beat someone much bigger and stronger than you to be taken seriously.

                                            The odds are always against you. (If they weren’t, you wouldn’t be the underdog.)

                                            You’re constantly fighting for your place in the world. And this leaves you no space to be vulnerable and held, no place to be cared for.

                                            Because this is your identity, you will always magnetize to you people to serve in the role of your Goliath.

                                            This identity is a dominant/dominated roleplay with you always trying to be on top. This isn’t an evolved identity because to overcome and become the oppressor still leaves a winner and loser.

                                            This is a Young Warrior identity.

                                            Instead, consider the Spiritual Warrior identity where the only thing/person the overcome is yourself.

                                            Where you start from believing in your right to take up space in your own life.

                                            Where you are in competition with no one.

                                            Where the only person you need to be better than is your former self – and even that isn’t required.

                                            Where you are calm and in tune with yourself and the world around you.

                                            Where you have no natural predators.

                                            Where you are not choosing a winner and loser, but everyone gets to win.

                                            Where there is always enough and you can manifest more whenever you need it.

                                            Where you can share your true self and know that while you may be making yourself vulnerable, there are safe places in which to do that and that no one can hurt you without your permission.

                                            There are energies associated with the identity you pick.

                                            Choose wisely.

                                            Mind Your Identity

                                            I was immediately struck by the distinction between what Kelle described as the Young Warrior identity of the underdog and the Spiritual Warrior she describes in the second half.

                                            The underdog can be a valuable identity to own early on in our creative careers. We can use it to help us prove our worth and skill (to ourselves as much as others) and to build up confidence.

                                            But it’s always meant to be a way station en route to a more mature, evolved identity.

                                            The underdog is scrappy, daring, and resourceful, all traits that are needed–perhaps in abundance–early on.

                                            But while these traits may remain useful throughout our lives, as we mature as people and creators, we should aspire to rely more on our perspective, wisdom, and belief in the abundance of opportunities.

                                            Personally, I feel myself currently existing somewhere between these two identities.

                                            I’ve relied on (and benefited from) the underdog mentality to start and grow a successful creative business. But six years in, I’m beginning to realize the limits of just how far this mentality can take me.

                                            For one, fighting for everything is exhausting and unsustainable.

                                            As I’ve approached these limits, however, I’ve also begun to experience the benefits of (reluctantly at times) adopting the more ease- and abundance-focused mindset of Kelle’s Spiritual Warrior.

                                            One of the great lessons for me of the past year is that the biggest gains we stand to make as creators come through self-understanding and mastery.

                                            By looking inward instead of outward.

                                            Doing so gives helps us understand the environments, projects, and commitments in which we thrive and those in which we don’t. This allows us to put ourselves in positions where success will come more naturally.

                                            Similarly, self-awareness allows us to recognize that when we’re not getting the results we’re wanting, chances are, we ourselves are complicit in the problem.

                                            This understanding then gives us the power to shift our posture, and thus our results.

                                            Shift Your Stance to Shift Your Results

                                            As I’ve become more self-assured in myself, my work, and the unique place it occupies in the world, opportunities have started to show up with surprising consistency, and of a scale beyond what I would have imagined a couple years ago.

                                            Whereas I used to feel like I had to claw and fight for every scrap of progress, in relaxing my approach, things are flowing more easily with less effort.

                                            On the one hand, there’s no doubt that my work is simply better now, both when it comes to this newsletter as well as my work in podcasting. With that in mind, perhaps it’s not surprising that more opportunities are showing up now.

                                            But my stance around my work has also shifted significantly.

                                            Whereas I used to be defensive and protective of my work, forever looking over my shoulder that someone was going to come along and steal my ideas or do a better job of executing on the same concept, I no longer worry about that.

                                            I’ve realized that as long as I keep my gaze directed forward, and continue to put one foot in front of the other, there’s no possible threat of competition.

                                            I’m walking my own path, and everyone else is walking theirs.

                                            No one else can create in the way I do because they haven’t walked the same path to get here.

                                            The only way to guarantee failure is to try and walk the same path as someone else.

                                            An underdog mentality might be empowering (and even necessary) during a certain phase of our life cycle as creators.

                                            But it pales in comparison to the more mature, evolved identity of standing tall, confident that we’re doing the work that no one else could possibly create. The work that will go uncreated if we choose not to pursue it.

                                            Embodying this identity isn’t easy, however.

                                            As an underdog, it’s hard to let go of the feeling that we always need to be working just to keep our heads above water, let alone get ahead.

                                            The idea of competition is so ingrained into our culture that it’s hard to entertain, let alone embrace the idea that competition is optional, and that all we need to do is choose to approach our work that way.

                                            Like so much of creative work, this process takes time.

                                            In the meantime, I still believe there are distinct advantages to adopting and embracing the underdog mentality, especially when we’re first starting out.

                                            But I also now believe that holding on to the identity for too long will keep us stuck.

                                            So embrace the mentality of the underdog fully and fiercely for as long as it serves you.

                                            But know that a time will come when that mentality that has served you well for so long will become a burden.

                                            And when it does, don’t be afraid to shed it as you step into the new, more mature, more complete, more fully-formed version of yourself.


                                            Explore how to navigate a creative life that matters

                                            This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                                            A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                                            Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                                            It’s something I’m proud to create and I’d be honoured to share it with you.


                                              Stop Squeezing Your Ideas to Death (Do this Instead)

                                              Too often, I think, we misunderstand what we’re holding when it comes to our ideas.

                                              We treat them as difficult nuts to be cracked, subjecting them to pressure, heat, and force as we attempt to get through the hard outer casing to access the interior.

                                              Rather than unlocking creative sustenance, however, more often than not, this approach ends up squeezing our ideas to death.

                                              It’s understandable why we do this.

                                              When it feels like everyone we look up to is succeeding now, we feel pressure to keep up.

                                              And so we then take that pressure and direct it onto our ideas, attempting to accelerate their growth.

                                              But herein lies the problem.

                                              The value of a nut is not in the small amount of short-term sustenance it can supply as food, but in its long-term potential as a seed.

                                              And seeds must be handled very differently from nuts if we want to unlock that potential.

                                              So too must our ideas.

                                              Like anything in their infancy, ideas–even our very best, most promising ones–implode under pressure.

                                              We don’t expect a single sapling to bear enough fruit to feed us.

                                              In fact, most trees will take years of nurturing before they bear any fruit at all.

                                              And while the timelines may be different, the expectations should be the same around our ideas.

                                              Ideas, like seeds, must be given time and space to germinate, sprout, and anchor themselves firmly in fertile soil.

                                              Most of all, they must be nurtured.

                                              I think we forget that.

                                              That nurturing might take months.

                                              It might take years.

                                              For some, particularly big ideas, it might take decades.

                                              But with some patience and some support, in due time, our ideas will grow the strength and stability to support incredible growth and production.

                                              Until then, however, our job is not to squeeze everything we can from them before they’re ready to bear the pressure.

                                              But to focus on nurturing, providing a safe space for the idea to take root and develop.


                                              Explore how to navigate a creative life that matters

                                              This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

                                              A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

                                              Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

                                              It’s something I’m proud to create and I’d be honoured to share it with you.


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                                                Hi, I'm Jeremy, I'm glad you're here.

                                                No matter what you create, I'm guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.

                                                So do I. And so does everyone doing creative work.

                                                This is the Creative Wilderness.

                                                Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.

                                                If you're building something that matters, but aren't quite sure how to take the next step forward, I'd be honoured to have you join us.