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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    Adapt or Die: The Decision You Face When What You Were Doing Stops Working

    When I opened up the weather forecast earlier this week, this is what was waiting for me.

    CleanShot 2023-07-31 at 07.40.36@2x.png

    Of course, I knew Texas in July and August was hot. But this?

    To a cold-blooded Canadian like me, this reads as more of a cruel joke than a weather forecast.

    And yet, it appears that for the next few weeks I’ll be in Texas, this is the unavoidable reality.

    On past trips to visit my partner Kelly’s family in Texas, I’ve simply avoided going outside altogether, hiding inside with the blinds drawn and the AC cranked.

    The result of this approach is perhaps best told by my step counter app, which tends to contain conspicuous extended streaks of three-digit step totals during my time in the state.

    And yet, while this approach helped me succeed at staying comfortable, it wasn’t without its downsides.

    My daily walks are where and when I come up with the bulk of my ideas and work through the problems and challenges I’m facing in my business.

    Without those daily walks, my creative mind begins to reflect the parched landscape outside.

    In addition to a dearth of new ideas, these periods often coincide with my least productive work periods of work, even on tasks and projects that aren’t inherently “creative”.

    Aware of the impact this has on my work and life, this time, I’ve decided to take a new approach.

    While I’ve pushed my walks to the fringes of the day when the heat is least oppressive, I’ve otherwise accepted the sticky, sweaty discomfort that accompanies them regardless and ventured outside.

    The change started with a realization: That I could wallow in the circumstances I found myself in. Or I could accept them and do what I could to work with and around them.

    In the case of the current Texas heat wave, I’m fortunate.

    I’ll be in Texas for just a few weeks and will then be off elsewhere, hopefully to cooler temperatures.

    But as is becoming painfully clear, the heat—everywhere—is only rising and spreading. Which means sooner or later, all of us will need to find a way to live with it.

    The same is true for the environments in which we do our creative work.

    Whether it’s AI threatening to make us obsolete, Google or Instagram’s latest algorithm update, or old reliable tactics that no longer seem to work, the climate is constantly shifting around us.

    And as it does, we face a choice.

    We can bury our heads in the sand, holding onto hope that things will go back to the way they were.

    Or we can adapt to the new conditions and make the most of them.

    In many cases, this will probably mean letting go of the norms, expectations, and habits we’ve established around how we do things.

    In many cases, the new normal will almost certainly be objectively worse than the old normal.

    And yet, what choice do we have?

    The summers of our youths won’t return simply because we preferred them.

    Neither will the conditions that allowed our creative work and businesses to take root and grow.

    And while we may have little control over the climate in which we find ourselves, we’re not at the mercy of it.

    Not entirely at least.

    We have at least one choice available to us:

    Wallow and wither?

    Or adapt & persevere?


    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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        Creative Tire Chocks: How to Identify & Remove the Tiny Obstacles Keeping You Majorly Stuck

        If you ever find yourself parking a trailer, tire chocks are an invaluable piece of equipment.

        Tire chocks are essentially wedges, often concave and plastic (though 2×4 pieces of lumber are commonly used as well) that are placed behind or in front of the wheels of a vehicle to keep it from rolling.

        When placed intentionally, these simple tools perform their job remarkably well.

        Unfortunately, the same principles of leverage that allow tire chocks to keep everything from jumbo jets to 450 tonne mining trucks in place, also apply to our creative projects.

        Only, we don’t often realize the chock is in place.

        If you’ve ever found yourself inexplicably stalled on a project that you can’t seem to make progress on, chances are, there’s an unseen chock wedged in a key location.

        And until you find it and remove it, chances are, you’re not going anywhere.

        Overcoming a Year-Long Chock

        Until recently, I had been stuck on a tire chock with one of my projects for more than a year.

        The project is a quiz audit allowing podcast creators to answer a series of questions about their current approach to marketing and then receive a personalized grading and breakdown of each of the categories of marketing.

        I was excited about the idea, knew it would be incredibly valuable for my audience of podcast creators, and recognized that it was going to be a central part of the  Podcast Marketing Academy  marketing strategy going forward.

        Despite my excitement and the clear incentives, however, I found myself inexplicably stuck.

        For a year.

        Finally, a couple weeks ago, I forced myself to sit down and do a simple brain-dump a list of possible questions that might eventually make up the audit.

        Almost like magic, as soon as I had written down the first few questions and their possible responses, the rest of questions followed.

        From there, I signed up for the quiz software I’d been eyeing since I first had the idea for the audit, uploaded up the quiz and quickly set up the scoring system.

        Then, I designed the landing page, wrote out all the copy and analysis on the results page, and scripted out the follow-up email course.

        Within just a few days, the project I’d been stalled on for more than a year was nearly complete.

        So what happened?

        The (Unfortunate) Power of Leverage

        At first glance, it seems silly that a simple low-stakes task like brain-dumping a list of potential questions might be the chock that holds up an entire project.

        And yet, in my experience, almost all creative project chocks are equally small and seemingly simple.

        Which is exactly why we overlook them.

        The truth is, if placed in juuuuuust the right location, even a tiny chock can hold back the weight of a much larger object.

        In fact, relatively small 100 lb chocks are routinely used to prevent the aforementioned 450 tonne (1,000,000 lb) mining trucks from rolling down hills.

        Is it so surprising, then, that seemingly insignificant tasks routinely stall our creative projects?

        The good news is that despite chocks being both plentiful and incredibly effective in their ability to prevent our progress, in the end, they’re fairly easy obstacles to overcome.

        At least if we know where to look for them and how to remove them.

        Three Types of Creative Chocks

        A chock keeping a project in place can be almost anything. But in my experience, they most commonly fall into one of three categories.

        1. An external circumstance that needs to fall into place
        2. An action or task to complete
        3. A decision to be made

        Let’s have a closer look at each type.

        An External Circumstance That Needs To Fall Into Place

        These chocks show up most regularly in projects involving other people.

        In these cases, the chock is often a task or decision that someone other than us needs to make for the project to move forward.

        Another type of chock in this category might be that the timing isn’t quite right for our project and we need to wait for the conditions to change for our project to be viable.

        This category of chocks are particularly frustrating because, while we may be able to influence the situation, we don’t have direct control to remove the chock ourselves.

        Fortunately, these types of external chocks are less common than the other two categories, over which we have full and direct control.

        An Action or Task to Complete

        Perhaps most commonly, the chock on a creative project is one, often simple task that holds the rest of the project up until it’s been completed.

        This was the case in my own quiz audit project.

        And as in my case, the reason we tend to avoid and procrastinate on these tasks is often not the work involved with the task itself, but an underlying lack of clarity.

        That lack of clarity might be centered on whether this is, in fact, the right task to work on, whether it will achieve the desired result, how to approach the task in the first place, or any number of other doubts, big and small, rational and irrational.

        The irony is that these tasks are often exceedingly small, taking no more than 15 or 30 minutes to knock out of the way, paving the way for the rest of the project to roll downhill and build momentum.

        And yet, our desire for certainty before starting them often keeps us inert for weeks, months, or even years.

        When encountering this type of chock, the most productive action we can take is to simply force ourselves to take the first step forward without perfect clarity.

        Because more often than not, once we take that step, we realize we already have all the clarity we need.

        A Decision to be Made

        The final category of creative chock is a decision that must be made in order for a project to move forward.

        This might be a decision about which software to use for a project, how to allocate tasks among your team, mapping out a schedule, or determining the priority of a given project in relation to other initiatives.

        These chocks are perhaps the most insidious, because we’re often not aware of them.

        These decisions can be large and important, but as with most chocks, are more often small and inconsequential, though often magnified in scope and significance in our minds.

        To remove these chocks, I personally like to convert them into a task, getting them out of the vague recesses of my brain and into my task manager where I can schedule them to be addressed.

        In most cases, when made plain and approached directly, a decision I’ve spent weeks mulling over can be made in a matter of minutes or even seconds.

        Removing Creative Chocks & Building Momentum

        For all the problems chocks make for us, they present an incredible opportunity.

        Because once we train ourselves to spot and remove them, we quickly realize that most of the challenges keeping us from progress are not giant, immovable boulders blocking our path, but tiny pebbles to be nudged aside.

        Once out of the way, we then build momentum, making it harder for future chocks to slow or stall us.

        The first step when we’re stuck, then, is to identify the type and location of the chock.

        Personally, I’ve created a field in my Notion project management system specifically to write down the current chock that’s holding each project up.

        Because, if a project isn’t moving forward, it’s almost certainly because of a chock.

        Clearly identifying the chock as specifically as possible reduces my frustration around projects I feel stuck on and gives me a clear map to getting them moving.

        Once the chock has been identified and removed, the next step is to focus on building momentum.

        Chocks are most easily placed when we’re standing still, such as at the start of a project or between distinct phases such as moving from building a product to marketing it.

        But they also have a way of lodging themselves in front of the wheels of projects that aren’t getting our full time or attention.

        To avoid this, it’s helpful to choose your timing to remove your current chock wisely, ensuring you have the bandwidth to continue rolling with the project once the impediment has been removed.

        If you don’t, there’s a good chance the next task in line will quickly solidify into a new chock, stalling any potential to build momentum.

        Of course, no matter how much momentum we build, various chocks will always find a way to stall and disrupt our work.

        They call to mind Archimedes’ famous quote about leverage, which in this case, might be slightly rephrased as:

        “Give me a wedge and a gap to place it, and I shall hold back the world.”

        Learn, to spot and remove them, however, and the world is yours for the taking.


        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 Last Gatekeeper

          There’s no piece of paper that can prove, beyond doubt, the worth of your work.
          Neither wax seal Nor gold star
          Nor signature of this person or that
          Can validate your knowledge, skill, or competence
          And give you permission to move forward.​ ​

          To create
          Build
          Disrupt
          Serve.

          Just you.

          Alone.
          Afraid.
          A fraud.
          In your own mind at least…

          Stopped dead at an amber light,
          Waiting (hoping, praying) for it to turn.
          For some sign or another from the universe
          To give you the go-ahead
          To signal “NOW IS THE TIME!”
          In flashing neon letters
          Impossible to miss. ​

          A pity.
          Many a life was wasted in waiting.
          A gift never given.
          An idea never expressed,
          That would benefit us all. ​

          What would it change to know
          That even once all the gates have been opened
          And the road stands unimpeded
          You must still face one last gatekeeper.
          The one that has always and will always have the power
          To grant or deny you passage.
          Who is unmoved
          By all the certificates, seals, stars, and signatures in the world. ​

          In the end, this is the only gatekeeper that must be won over
          Whether by reason, cunning, force, or persistence.
          The gate is already open
          Waiting for you to take the first step through.


          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.


            Thinking In Drafts: A Subtle Mental Shift to Unlock More & Better Creative Work

            A few years ago, I heard author Tim Grahl give a talk about his experience with writing his fantastic book on making a living as a creative,  Running Down A Dream .

            He shared that before publishing the book, he’d been working on some version of of it for nearly ten years.

            Many of the drafts during that time involved scrapping nearly everything he had previously written and starting from scratch.

            In some versions, the content wasn’t right.

            In some versions, the tone wasn’t right.

            In some versions, everything seemed like it should have been right… but it still felt wrong in some intangible way.

            Over the course of those ten years, Tim shared each of the many iterations of his book with a tight-knit group of guides, peers, and accountability partners who understood his goals, style, and potential, and asked for their unvarnished feedback.

            That feedback was often painful. Good feedback usually is.

            But draft by draft by draft, Tim was able to take that feedback and improve each version of the book until it was good enough to finally ship.

            Not perfect, perhaps, but good enough to put out into the world with pride.

            Tim’s story sounds extreme.

            But for many creative fields, a years-long process of painful revisions is entirely normal.

            We know every movie has multiple cuts, test screenings, revisions, and even reshoots before the final, public release.

            We know the initial manuscript of a book is only the very first in a long series of milestones on the road to getting it published.

            And yet we rarely apply the idea of working in drafts to our own creative practices.

            Which is a shame.

            Because the emotional and creative dynamics of working on a draft are dramatically different from working on something we know will be the definitive, finished product.

            Drafts Dial Down the Pressure

            Whether it’s a big project like a product launch or website, or a smaller piece of content like a newsletter issue, podcast episode, or YouTube video, we tend to approach everything we publish as though we only have one chance to get it right.

            There are a couple of problems with this approach, however, that undermine our long-term progress.

            The first and most obvious problem is classic perfectionism.

            We’re less likely to ever ship our work when we only have one shot to get it right. Because how could we possibly create the best version of any project now when we know that by next month (let alone next year) we’ll be more knowledgeable, talented, and capable?

            The second problem is that if we do manage to ship it, we tend to put too much emotional stock in the feedback we receive.

            A positive reception can lead us to believe our work is done. No further improvements required.

            A single piece of negative feedback on the other hand might convince us that the entire idea is stupid and not worth investing in further.

            Both responses sell our work short.

            Unlike finished versions, the goal of a draft is simple: Create something that is merely good enough to get the next round of feedback on.

            Good enough to put into the world and assess how the world interacts with it before heading back to the drawing board to work on the next draft.

            When we approach our work in drafts we tap into a bit of creative magic.

            It allows us some detachment from criticism as we know we’ll have an opportunity to make improvements in the future.

            This allows us to ship our work more boldly, understanding that of course there are flaws! Of course it’s not perfect! It’s only a draft after all, not the finished product.

            In fact, the finished product might never arrive.

            But thinking in drafts allows us to adopt a mindset of experimentation, iteration, and bravery as we put out version after version after version of our work out into the world for it to collide with, shape, and be shaped by in return.

            Even if we never achieve perfection, however, the continual pursuit of it has a way of opening doors and leading to unexpected creative success.

            Results Come From Iteration, Not Perfection

            I recently attended a workshop where Tiago Forte, the creator behind the wildly successful course (and now book)  Building A Second Brain  talked about his process for building the course into a multi-million dollar business.

            He started by sharing this graph which details the cohort launches from June 2014 to July 2022.

            caption for image

            Then he gave this context.

            “Notice the left, half of this graph, there are cohort launches in there but you can barely tell, right?

            I basically consider cohorts one through nine as betas.

            In retrospect, they were tests. They were so small and insignificant compared to what would happen later that all that really mattered for those first nine cohorts was that we learned, and that the revenue was just enough to make it to the next cohort.”

            That’s thinking in drafts.

            Like Tiago, I’ve applied thinking in drafts to big projects like Podcast Marketing Academy where  each launch and cohort builds a little bit on the last .

            But I’ve also applied it to smaller—even micro—projects.

            Take this newsletter, for example.

            With three years of writing to pull from, I’ve started revisiting my favourite ideas, updating them, and republishing them in the newsletter a second time.

            Often, the second draft of an idea is almost unrecognizable from the first.

            Take this issue, which I originally published in October 2020. I was happy enough with the issue at the time, but I didn’t feel like I’d fully got my head around the idea.

            In revisiting it, I’ve been able to update it with new ideas and examples I’ve picked up as my thinking has evolved.

            Being a topic that I’ve already thought about on a near-daily basis for more than two years already, I have no doubt that this draft will be further revised and updated in the future.

            Nothing Is Set In Stone

            While thinking in drafts is valuable as part of your creative practice, its most liberating use case may be in choosing to view your life and career through the lens of drafts.

            Sure you might not be where you’d like to be right now. But no matter where that is, it’s only one in a series of continually improving drafts.

            Your goal today, this month, or this year is not to achieve or become the perfect final version of yourself.

            Your goal today (and every day) is simply to put yourself out into the world and collect feedback, so that tomorrow’s version can be a tiny bit better.

            We can approach our work and our lives with a whole lot less seriousness when the next thing we do isn’t the be-all end-all, definitive version of what we’re trying to create or who we’re trying to be.

            If you’re not getting the results you’d like with the work you create, that’s not a referendum on you or the idea behind your work.

            Instead, it’s simply a sign that there’s more work to be done. That you need to write a few more drafts to get your work and yourself to where they need to be.

            Identify your group of guides, peers, and accountability partners who understand what you’re trying to achieve. Ask them regularly to give you their unvarnished feedback.

            Then get back to work and make the next draft.


            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 Neglected (But Essential) Facet of Creative Productivity

              The decorations are up.

              Christmas music wafting out of every shop door.

              Mulled wine is being served on seemingly every street corner.

              There’s no ignoring that the holiday season is officially upon us.

              But perhaps the best indicator that the end of another year is here is the one bombarding us on our social media, newsletter, and podcast feeds.

              No, I’m not talking about the recent wave of Black Friday sales notices.

              I’m talking about the stream of content challenging us to “not wait until January 1st to start on our 2023 goals” that crops up around December 1 every year.

              Urging us to push through the end of the year.

              To continue the relentless grind we’ve subjected ourselves to all year in order to continue (or build) our momentum.

              I know the advice is well-intentioned.

              But it still irks me.

              Not just because I think we deserve (and require) a break from the relentless grind it takes to start and grow a creative business.

              But because this type of thinking takes such a narrow view of what it takes to achieve creative progress.

              The Neglected Facet of Creative Productivity

              Let’s not kid ourselves, frequent and decisive action is essential to making progress toward our goals.

              As a result, most productivity advice revolves around how to take more action and get more done.

              More action = more progress the thinking seems to go.

              And at least in part, that’s certainly true.

              But there’s an essential prerequisite for productive action that standard productivity hacks and hustle culture consistently neglect, which is this:

              For action to amount to anything, it needs to be focused and directed in the right direction.

              That requires clarity.

              And clarity rarely finds us when we’re in the thick of implementation & action.

              Rather, it almost always finds us immediately after a period of intense action, when we’re able to slow down, step back, and gain enough distance from the fray to gain some perspective.

              Without taking regular steps back to reorient ourselves, we risk barreling forward, head down… making fantastic progress in the entirely wrong direction.

              Far from slowing our momentum, then, regular rests, reprieves, and reorientations are not only essential to recharging our energy stores, they’re a core component of long-term creative productivity.

              Which means that rather than pushing through December at breakneck speed, the very best thing we can do for our creative work and businesses is to slow down.

              Slow Down to Speed Up

              There are few better opportunities to slow down, step back, and gain perspective on where we’re at, than the end of each year.

              It’s one of the vanishingly rare times we as a society allow ourselves to collectively slow down and reflect.

              If you’re like me, at this time of year you might regularly be finding yourself preoccupied with big-picture dreaming, brainstorming, and idea exploration… at the expense of your daily task list.

              The “push through to the new year” advice encourages us to ignore these frivolous distractions and focus on squeezing just a little bit more productivity out of the year.

              But while the value of big-picture dreaming, visioning, and planning may be hard to quantify, without it, our work tends to lilt toward the mundane, generic, and bland.

              Despite its necessity, however, we rarely make space for it, often deferring to the more tangible outcomes of action.

              It’s worth noting that those in the “push through” camp are often staunch and vocal advocates of completing a structured annual review, a practice I too find an incredible amount of value in. But that review is often boxed into a single day, afternoon, or couple-hour-long time block.

              The problem with this approach is that I’d wager there are challenges, puzzles, and problems in your life and work that will take more than a couple of hours to solve.

              In fact, there’s a good chance the (perhaps only) reason they’ve persisted this long has been a lack of time and space to slow down, sit back, and ponder.

              Nature abhors a vacuum, after all, and big ideas and breakthroughs have an uncanny way of showing up when we create the space for them.

              So while I’m guessing you, like me, still have a long list of unfinished goals and projects on your annual to-do list, it’s possible that the single most productive thing you could do with the remainder of the year is to set them aside.

              Slow down.

              Pause.

              Plant your feet.

              Orient yourself.

              So that when you’re ready, you can push off toward the next goal with energy, focus, and intention.


              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.


                Directing Your Energy Wisely

                Every weekday for the past six months, I’ve eaten a bowl of soup for lunch.​

                I like soup, but despite what the considerable streak might suggest, I’m not obsessed.

                In reality, it’s a case of simple utility. ​

                High-quality, premade soup is available at every store near me in a variety of flavours. It’s quick and easy to heat up, healthy, hearty, and delicious.

                Over the months, the consistency of fare has introduced a sort of unintended ritual to the middle of my day.

                At noon my alarm goes off, signaling the end of my morning deep work time block.

                At this point , I head to the kitchen, pull the soup container out of the fridge, pour it into a bowl, and put the bowl into the microwave. ​

                A minute and forty-five seconds. Take out and stir. Back in for another minute and thirty seconds.​

                During the first minute forty-five, I take the stairs up two floors of my coworking space to the bathroom.

                During the second minute thirty, I wash out the soup container for recycling. It takes me forty-five seconds to wash the container, leaving me forty-five seconds to start my lunchtime sudoku.

                As you can tell, I have the process down to a science.

                Or at least I thought I did, until this past Wednesday.

                A Surprising Discovery

                I might not have made the discovery of I hadn’t been wearing my favourite shirt.

                It’s a light grey, long-sleeved button-up, the perfect canvas for stray drops of the neon orange lentil curry I was heating up that day.

                As such, I was on guard, fully aware of my every move as I placed the brimming bowl back in the microwave after it’s stir, set the timer for a minute thirty, and took the container to the sink to rinse out.​

                Had I been wearing any other shirt, I would have turned the hot water faucet on full, allowing the pressurized spray to blast the remaining soup from the inside of the container, splashing the sides of the sink in the process. ​

                Once the container was clean, I would fill it up and use it to splash water across the sides and bottom of the sink until they were once again clean and white.​

                This had been a standard part of my lunch-time ritual to that point.

                It seemed obvious to me that the full power of the faucet was the fastest and most effective way to clean out the container.​

                As my hand hovered over the handle, however, I hesitated.

                I envisioned a neon wave splattering out out of the sink and across my shirt, ruining it in an instant.

                Instead, I turned the tap slowly, drawing a thin, focused stream of water.

                I carefully directed the stream around the sides of the container before—equally-carefully—pouring the contents directly into the drain, making sure to avoid even the slightest splash as I did so.​

                I tossed the container in the recycling, pleased with the potential disaster my careful planning had averted and looked over to the microwave timer. ​

                Sixty seconds. ​

                Huh.

                Not only had I managed to keep my shirt clean, but I’d also taken less time to clean the container, hadn’t needed to clean the sink, and used less water to boot.​

                Was it a mistake? An outlier?

                Being of scientific inclination, I tested the process again on Thursday, and then on Friday. ​

                The results were the same.

                Thirty seconds to wash the container under low pressure versus the forty-five under high.​

                How could this be? Surely less power, less energy, less input shouldn’t result in the same outcome in less time.

                Should it? ​

                Focus > Pressure​

                So often, our instinct is to devote all the energy we have available toward the problem we’re trying to solve or the work we’re trying to create.​

                Sometimes, this is called for, and may in fact be the best way to achieve our desired result. ​

                But not always.

                Especially if the energy we’re directing at the problem is unfocused, inconsistent, or erratic.

                In fact, as with the soup container, sometimes more energy just creates more of a mess to clean up once we finish the task at hand.

                In most cases, we’re better off beginning with less—but more focused—energy, and then ramping up as need be.

                In my experience, brute force and maximum pressure are rarely the most efficient problem solving methods.

                Just the right amount of energy, directed at just the right place, on the other hand, often is.

                Which means the next time you find yourself wishing for more time, money, or force to direct toward a problem, it might be worth pausing.

                Because there’s a good chance you already have all the resources you need. They’re just not being focused effectively.


                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.


                  Triage: A Necessary Skill for Progressing in Your Creative Career

                  Before powering down at the end of every day, I review my task list and bump everything I didn’t complete to a future date, often the next day.

                  On good days, it’s a small number of non-urgent or unimportant tasks.

                  On less-than-good days it’s a large number of both urgent and important tasks that got crowded out by even more urgent and important tasks.

                  Regardless of the day, however, for the past six months there’s been one particular task that’s appeared on my task list every single day… and without fail, been bumped, incomplete, to the next day.

                  The task?

                  “Catch up on email”

                  I know, it’s wildly optimistic to harbour any kind of belief that this task could ever truly be completed. In fact, the mountain of unreplied-to email has only grown since adding the daily reminder.

                  And yet, I persist in deluding myself.

                  I created the task after wrapping up the PMA5 launch in the spring.

                  Launches have a way of crowding out everything but the most essential daily action items—of which there are always more than can possibly get done—and after spending 10 weeks in launch and then cohort delivery mode, I had fallen severely behind on all manner of non-urgent correspondence.

                  I did what I could to chip away at my inbox following the launch, but it wasn’t enough.

                  Because before I could catch up, I once again found myself neck deep in planning, executing, and delivering the launch of my next cohort, adding another 2.5 months of email backlog.

                  Last Friday night, from 9-11 pm I sat down and made the most significant dent in my inbox to date, working through 75 of the 300 or so emails awaiting a response.

                  It felt good to make a dent in the mountain.

                  But more interestingly, in going through the emails that had been piling up, I made a realization that instantly reframed my email problems.

                  The Price of Projects Gaining Traction

                  In sifting through and responding to the emails, I noticed that the majority of them fall into one of two categories:

                  1. New subscribers to either Creative Wayfinding or Scrappy Podcasting who are responding to the prompt in my welcome emails to tell me a bit about themselves and their work.
                  2. Requests to collaborate, guest on podcasts, contribute to projects, etc.

                  Based on these categories it’s clear that far from being a problem, the number and type of emails occupying my inbox are a sign that things are working.

                  The first category is the direct result of people subscribing to my newsletters (my #1 goal in my business). The second, a result of becoming better known and seen as an interesting voice in my industry.

                  Despite the positive underlying causes of my inbox overwhelm, the situation bothers me.

                  For one, the lack of responsiveness doesn’t send the message I want myself or my brand to convey, especially to new subscribers reaching out for the first time.

                  More personally, I have a natural inclination toward, structure and order, which means the lack of control over a task as simple as answering email is deeply uncomfortable.

                  And yet, one of the things I’ve had to come to terms with over the past two years as more and more of my projects have started to gain traction is that this type of discomfort is an inevitable price of creative progress.

                  Obligation Overwhelm

                  At the beginning of a project, our obligations tend to be low.

                  caption for image

                  We likely don’t have an audience expecting anything from us on a consistent schedule. We don’t have paying customers and clients with deadlines and deliverables. And we don’t have partners and other stakeholders to whom we’ve made promises.

                  On the personal side, the project likely isn’t supporting us financially, so we have little obligation to ourselves to keep the project running.

                  Pure creative freedom in other words.

                  What’s more, we’re in experimentation mode, which means we might be playing with half a dozen (or more!) ideas, testing them out to see which has the greatest potential.

                  As some of those projects inevitably begin to gain traction, however, our obligations to each of them increase.

                  caption for image

                  As traction leads to growth, it doesn’t take long for our obligations to even one such project to begin to crowd out other pursuits.

                  Which means that if we want to navigate this stage of the creative journey intact, triage becomes an increasingly important skill for us to develop.

                  Because the more success our projects accrue, the more difficult the choices we’ll face about what gets our best time and attention, what gets the leftovers, and what gets ignored.

                  Creative Triage

                  When we first begin to bump up against the limits of our bandwidth, the choices about what to focus on and what to ignore are fairly easy to make.

                  Other low-traction projects are often the first to be pushed outside the limits of our current bandwidth to focus on the more promising endeavours.

                  But as the project continues to gain momentum (which of course is our goal), it’s only a matter of time before other aspects of our lives begin to be pushed outside of our ability to stay on top of them.

                  Relationships with family and friends, our health, hobbies, and yes, correspondence—both business and personal—all have a way of becoming secondary to the demands of a successful—yet not fully self-sufficient creative project.

                  caption for image

                  As with any type of triage, creative triage involves making many painful decisions.

                  In fact, the more painful a decision, the more potential upside the decision likely offers.

                  This means turning down promising projects and opportunities you desperately want to take on.

                  It means letting many of the fires in your business burn unabated—often indefinitely.

                  It means learning to accept the inevitable discomfort of never being able to get to everything you want to, or perhaps even feel you need to do.

                  All this, in the service of making progress on the small number of things that matter most—both for the project to be successful, as well as for yourself.

                  Such is the price of success.

                  We can try to fight the need to triage our various projects, tasks, and endeavours, attempting to maintain control over everything on our plate even as the demands of our creative platform exceed our bandwidth.

                  More often than not, this achieves little but undermining the quality and consistency of our work, not to mention our health, sanity, and satisfaction.

                  The alternative is to choose to embrace making difficult choices about where we focus our time and attention as an essential skill we must develop to reach the next level of success.

                  Because in the end, we’re most often held back not by the opportunities we fail to grab ahold of, but by those we fail to release.


                  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.


                    Triangulation: The Math Equation Behind Creative Clarity

                    Spend much time wandering the countryside of the UK and it’s only a matter of time before you begin to notice a curious set of landmarks.

                    These landmarks generally come in the form of squat, truncated obelisks or pillars about three feet tall that are most often perched atop prominent hills.

                    The landmarks have an aura of mystique around them, which they also seem to transfer onto the landscape.

                    Other than a cryptic set of inscriptions consisting of a few letters and numbers, they lack any kind of identifying signage.

                    They are concrete, decidedly utilitarian, obviously manufactured… And yet somehow manage to feel like a natural part of their surroundings.

                    Looking at them, it’s easy to think that they have always been there, and will always be there.

                    The truth, while interesting in its own right, is far more pedestrian.

                    The pillars—or trig points as they’re locally known—were initially constructed between 1935 and 1962 as part of the Retriangulation of Britain, an effort to provide more accurate maps of the country.

                    In case you need a refresher, triangulation is a mathematical concept stating that if you know the distance between two reference points, you can calculate the exact distance to any third point by measuring the angles to it at each of those initial references.

                    caption for image

                    In other words, if we know the distance between A & B and the angles of x & y, **we can determine the distances of both AC and BC.

                    It’s a simple but brilliant concept with a long history dating back nearly 2,000 years.

                    In addition to being used to create the first truly accurate maps of countries, triangulation has been used to determine the heights of mountains (such as Mt. Everest) and even to determine the size of the Earth.

                    It’s safe to say that triangulation is one of the most tried and true mapping techniques we have available.

                    And while the mapping of physical geography has now been overtaken by more accurate and responsive GPS networks, when it comes to mapping and navigating the landscapes of our creative work, the older analog method of triangulation persists as perhaps the best tool we have available.

                    Triangulating Your Location

                    Perhaps the two most fundamental and persistent challenges we face as creators are understanding where we’re going and understanding how to get there.

                    While we often think of our most pressing problems as tactical (ie. “How do I grow my email list?”). In my experience, however, when we have clarity on our destination and direction, the tactics take care of themselves.

                    Clarity then, is a necessary first step to real progress toward our destination.

                    While we innately understand this, however, our understanding tends to lead us into the trap of waiting for clarity before attempting to move forward at all.

                    This is far from an efficient or useful way to gain clarity, however.

                    Because while clarity may be a pre-requisite for meaningful forward progress, movement is a pre-requisite for clarity.

                    Unfortunately, this idea doesn’t align with the way most of us think about progress, that any effort that doesn’t lead us closer to our goals is wasted.

                    But this couldn’t be further from the truth.

                    In fact,that effort—and the accompanying movement—is a necessary part of establishing a series of reference points necessary to triangulate where we are in relation to where we want to be.

                    caption for image

                    If we’re feeling lost or stuck, then, the most productive action we can take might be to simply pick a direction and climb the nearest hill to establish a new reference point.

                    It’s entirely likely—probable even—that the direction we pick won’t be the shortest or most efficient route to our ultimate destination. But if it gets us moving and helps us find clarity, it may just end up being the fastest, **even if it takes us in the entirely opposite direction from where we want to end up.

                    When it comes to clarity, all reference points are helpful. And the more we have, the more their benefits compound.

                    While we can triangulate our way to a given destination based on as little as two reference points, the accuracy and range of our route-making increases the more reference points we have.

                    So too does the level of nuance in our understanding of the landscape through which we’re traveling as well as our awareness of opportunities adjacent to our route.

                    caption for image

                    What’s more, the reference points we establish have a way of being useful beyond simply calculating our immediate next step.

                    Sure, the hill ahead of us will provide a useful vantage point from which to plan our next move. But the trig point we set there may continue to be a useful reference in helping us triangulate the moves we’ll make 6 months or 6 years from now.

                    As a result, each hill we ascend increases the resolution of our internal map, both of the terrain we’ve already covered, as well as that which lays ahead.

                    It’s slow going, slogging up hill after hill, only to find we need to adjust our course, descend, and aim for a different hill on the horizon.

                    And yet this is precisely the type of wayfinding that sets us up for long-term success in any field.

                    One that, thanks to our extensive exploration and cartography we now know better than almost anyone else.


                    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.


                      Acorn Picking: How to Spot Ideas & Opportunities Hiding In Plain Sight

                      The final stretch of my morning walk to coffee passes through a wide oak-lined path.

                      Over the past month, the ground has regularly been littered with acorns, crunching underfoot as I walk by, the branches above filled with dozens more.

                      There’s something I love about the size, shape, and feel of acorns. The symbolism of small beginnings and slow growth is a nice reminder as well. And so almost every day I’ll either stoop to pick up, or reach to pluck down a handful of the smooth seeds to bring back home to decorate the base of my office plant.

                      As winter has drawn steadily nearer, however, fresh acorns are becoming harder to come by.

                      That doesn’t keep me from looking, however.

                      At this point, most of the acorns on the ground have either been trampled and crushed by the time I walk by or are lying next to the proliferation of dog shit in the tree planters beside the path.

                      And so I’ve turned my gaze to the increasingly bare trees.

                      One quiet morning, when there was no one else around, I decided to examine the trees more closely.

                      As I stopped in front of one of the trees to have a better look, I immediately saw great bunches of acorns still crowding the branches just above the reach of the average person.

                      Around the back of the tree, off the path and overhanging a low retaining wall, the bounty of acorns continued, these all well within arms reach.

                      Finally, I realized that there were, in fact, still plenty of acorns within reach, directly along my walking route. They were disguised behind leaves, however, and difficult to spot while walking by at full speed.

                      It made me think about how similar spotting and collecting acorns is to spotting and collecting good ideas.

                      Ideas Are More Abundant than We Realize

                      The most obvious and easily accessible ideas in any space are always the first to be picked over.

                      Some of those get claimed and put to use by other people. Others get tossed aside, trampled, and covered in whatever the idea equivalent of dog shit is.

                      It’s often at precisely this point when most of us make our entrance into a new space, survey the landscape, and draw the mistaken conclusion that the bubble has burst and there are no good ideas left to be had.

                      Of course, there are almost always still plenty of good ideas worth picking, but in order to find them, we need to get creative

                      Fortunately, the distribution of acorns on the oak tree provides a framework for finding the seeds of ideas anywhere.

                      4 Methods For Idea Discovery

                      When we understand where ideas tend to get picked over fastest—within easy reach along the most well-traveled path—it’s not hard to come up with solutions to find and harvest the less accessible ideas.

                      These solutions are divided into four categories.

                      1. Exertion

                      The first opportunity is to work harder than other people are willing to.

                      When it comes to picking acorns this might mean jumping in order to grasp the acorns that would otherwise be out of reach.

                      For ideas, this might be getting in more reps in our niche or with our subject matter or medium than other, more opportunistic people are willing to put in.

                      Get to know the ins and outs of any space by working in it and plenty of non-obvious opportunities have a way of presenting themselves.

                      2. Ingenuity

                      While exertion is certainly one way to access hard-to-reach ideas, ingenuity and creativity allow us to reach higher.

                      On an oak tree, this might mean getting a ladder, using a stick to knock down acorns suspended higher up in the tree, or shaking the trunk until they fall.

                      In our creative work, ingenuity might mean pattern-matching ideas that have worked in other industries or niches with ours, or focusing on growing a network in the space that continually presents feeds us new perspectives and ideas organically, rather than needing to go out and find them ourselves.

                      3. Inconvenience

                      As I discovered with the oak, there are often plenty of good ideas within easy reach if we’re willing to step off the most well-traveled path.

                      Every niche and industry has a dominant audience segment that the majority of people & brands cater to. But that doesn’t mean they’re the only segment. In fact, they’re often the hardest to gain traction with because of the amount of noise and competition.

                      Explore the fringes of your space and you’ll find all kinds of ideas and opportunities ripe for the picking.

                      4. Patience

                      Finally, there’s the method of simply slowing down enough to actually see our surroundings for what they are as we pass through them before writing them off as barren & devoid of opportunity.

                      We’d be surprised by what turns up when we settle into a space and participate in the existing community for a while.

                      On the oak, simply stopping to stand beneath it for 30 seconds was enough to spot acorns that had previously been invisible to me.

                      Perhaps the epitome of this approach is the patience of continuing to return to the tree, day after day, season after season, year after year, with the knowledge that even if the tree is barren today, it’s only a matter of time before new acorns begin to emerge.

                      The spaces in which we live and work are constantly shifting, morphing, and evolving.

                      Which means new opportunities are always developing, budding beneath the surface, and waiting to break through.

                      When they do, the people who will be in position to take advantage of them will be those who have been patiently tending to the space long before the new batch of ideas showed up.

                      Our challenge then, as creator entrepreneurs might not be finding ideas.

                      But finding the tree we’re willing to weather the seasons under, and then reaping the bounty it provides.


                      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.


                        Pushback Rallies: How to Do More with the Creative Opportunities You’re Given

                        Ever since Roger Federer announced his retirement a few weeks ago, I’ve been going back and watching through highlight reels from his career.

                        Many of Federer’s highlight reel moments are of him masterfully dictating the flow of the game and utterly dominating his opponents.

                        In these clips, Federer feels like some mix of artist, chess master, and evil genius.

                        Through precise and strategic shot-making, he guides his opponents around the court, setting up the pieces with subtle manipulation… before dropping the hammer with an elegant, seemingly effortless checkmate.

                        These clips clearly display a master of his craft at the height of his powers.

                        But there’s another, very different type of highlight reel rally that appears again and again in these compilations of Federer’s career. One where it’s Federer being chased around the court.

                        These rallies are defined less by skill and more by a certain type of grit.

                        I think of them as Push Back Rallys. And there’s a lot we can learn from them.

                        Specifically, there’s a certain decisive shot in the middle of these rallies that we all need to learn to make as creator-entrepreneurs as well.

                        Let’s set the scene.

                        Hitting Off the Back Foot

                        In a typical Push Back Rally, the opponent has taken control of the pace and it’s all Federer can do to simply return the ball in play.

                        He’s clearly on the defensive, struggling to keep up, constantly hitting off his back foot, unable to plant and step into his shots in order to generate more power or accuracy.

                        You can tell it’s only a matter of time before he cracks, handing his opponent the point.

                        And then the decisive moment.

                        His opponent attacks. Federer lunges to get into position, but he’s half a step too slow.

                        You can almost see the same calculation we as the viewers are making play out in his head.

                        “Is it even worth fighting to keep this rally going? I’m in a weak position… Maybe I’d be better conceding the point, conserving my energy, and resetting for the next one “

                        But just as you think he’s giving up, something in his posture shifts, almost imperceptibly.

                        He’s off-balance, unplanted, and out of position. The safe shot is to simply get the ball back over the net, extend the rally, and hope for a better opportunity on the next shot.

                        Instead, through force of will alone, he goes on the attack.

                        With this one shot, he manages to swing control of the rally in his favour, and a few shots later the point is his.

                        Examples of Push Back Rallys abound in tennis.

                        It’s a sport governed by momentum where single shots can—and often do—change the complexion of points as well as entire games, sets, and matches.

                        But the idea applies elsewhere as well, including our creative work.

                        Don’t Wait for the Perfect Setup

                        Unlike Federer, most of us default to waiting for the circumstances to be perfect—feet planted firmly in a position of power with ample time to pick our spot, step in, and swing with perfectly controlled form—before making our move.

                        These opportunities rarely if ever present themselves to us, however.

                        And so we spend most of our creative lives on our back foot, reacting to what comes our way, just trying to get the ball back over the net, without ever pressing the offensive without making our opponent react to our will.

                        There’s certainly a time to defend.

                        To do what we can to keep the ball in play, extending the game while conserving and building up our energy.

                        But as a larger strategy, simply extending the game is unlikely to win us many points.

                        Sooner or later, we have to shift to the offensive, to assert ourselves and seize control of the flow of play.

                        We won’t be given an obvious or advantageous opening to do so.

                        When the time comes, we’ll likely be on our back foot, out of position, without as much time as we’d like to step up and really swing through our shot.

                        In watching Federer, it strikes me just how many of his career-defining winning shots came during Pushback Rallies, where the odds were stacked against him and the logical choice seemed to be to wait for a better opportunity.

                        It makes me wonder.

                        How many of the losses or draws we settle for in our lives and work could actually be winning points if we were willing to dig a little deeper, get a little more uncomfortable, and go on the offensive, even when all the circumstances are telling us to do the opposite?

                        Because in the end, these are the opportunities we’re given.

                        What we do with them is up 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.


                          Cooking with Simple Ingedients

                          There are few things in life better than a loaf of freshly baked bread.

                          At least for me, there’s a good chance that if there’s fresh bread in the house, I’ll eat pretty much nothing else until it’s gone.

                          Part of fresh bread’s appeal comes down to its tangible attributes. The smell it fills the house with as it bakes, the way it feels in your mouth as you bite through the hard crust into the soft, still-warm center, and of course, the flavour, understated though it may be.

                          Another part of the appeal, however, is its hearty simplicity.

                          Fresh bread is humble, unpretentious, made of simple ingredients that have remained largely unchanged over centuries if not millennia.

                          In an increasingly experimental culinary world highlighted by flashy, exotic, Instagram-worthy ingredients and presentations, good simple bread persists—and in many cases remains uniquely capable of stealing the show out from under a more ostentatious main course.

                          Perhaps part of the magic of good bread is that it defies our expectations of what a few simple ingredients are capable of adding up to.

                          Or perhaps we’re presented with so much bland, mundane, mass-produced bread that when it’s done right, we can’t help but take notice.

                          Whatever it is, for all its simplicity, good bread is–often literally–remarkable.

                          Bread is not alone in its simple, durable remarkability.

                          Beer, wine, cheese, olive oil, a steaming bowl of soup, stew or goulash—all of which pair excellently with a fresh loaf of bread by the way—are just a few products of simple ingredients that have continued to persist, comfort, and delight through the centuries.

                          In a world that is changing ever more quickly, the fact that these foods, made often from just a few simple ingredients have not only endured in their appeal is incredible.

                          But what if these foods have persisted not in spite of their simple, pedestrian, unassuming ingredients but because of them?

                          And if so, what can we learn about cooking with simple ingredients when it comes to our creative practices?

                          Simplicity is a Feature Not a Bug

                          A basic loaf of sourdough bread is made from just three ingredients, flour, salt, and water.

                          For most of us, these ingredients are not only easily-accessible, but ubiquitous. If we don’t already have our cupboard stocked with them, we can get them quickly and cheaply.

                          The basic building blocks of creative work are even more ubiquitous.

                          At its core, all creative work comes down to just two basic ingredients:

                          1. A novel idea
                          2. A way to express it

                          We’re all equally capable of finding good ideas if we’re willing to learn how to look for, notice, and develop them.

                          And while there are certainly complex and expensive ways of expressing ideas, most of us have the ability, both physically & technically, to share our ideas in either written or recorded form.

                          Writing, in particular, has persisted as a durable form of communicating ideas for millennia.

                          Despite the limited number of prerequisites, we have a hard time believing that these simple ingredients are enough to succeed creatively.

                          And so we start adding in trendy, exotic, and flashy ingredients, thinking that what our recipe is missing is more spice, more garnish, or more “Wow” factor.

                          In the hands of a skilled chef, these finishing touches might elevate a dish from great to extraordinary.

                          In the hands of an amateur, they lead to a dish that may look impressive… but leaves a disappointing taste in your mouth.

                          Perhaps it’s the most skilled chef of all who is able to deliver an extraordinary, remarkable experience without the ornamentation. With nothing but a few simple ingredients, prepared masterfully.

                          And indeed, it’s precisely the method of preparation that has the ability to transform many a set of simple ingredients into something exponentially greater than the sum of their parts.

                          The Magic is in the Process

                          For all the joy a loaf of fresh bread is capable of bringing us, it’s surprising we don’t bake them more often.

                          The reason, I think, is that while the ingredients may be simple and readily available, the process required to transform those ingredients into something special requires more time, patience, and commitment than we’re typically willing to invest.

                          A single loaf of sourdough, for example, can take over a week to create, with regular attention and adjustments to the fermenting sourdough starter mix.

                          So instead, more often than not, we settle for an off-the-shelf, pre-packaged loaf that—while it might occupy the same space in our stomach—lacks the substance and the magic of the carefully and attentively prepared alternative.

                          It turns out, sourdough is not alone in its patient magic.

                          The same slow, caring, attentive process transforms all kinds of simple ingredients into something special.

                          Wine, whiskey, beer, barbecue, stew, cheese, and many other foods all improve with age. Many even require it.

                          Balsamic vinegar, for example, takes anywhere from 12-25 years to prepare from scratch.

                          The same concept holds true for us as creators, both in regard to our individual ideas and projects as well as our broader careers.

                          Applying Time & Patience to Your Creative Work

                          Every full-time creator I know has a slew of ideas for blog posts, podcast episodes, or videos they’ve been patiently allowing to ferment for multiple years without publishing.

                          On the surface, these ideas are almost always simple, mundane, quotidian.

                          And yet… for one reason or another, there’s something about the idea they can’t quite shake or articulate.

                          And they begin to obsess over it.

                          When the time finally comes to publish, the process of fermentation has done what it always does: Transformed the simple base ingredients into something entirely unrecognizable and, perhaps even, remarkable.

                          The same process of fermentation occurs at the career level as well.

                          It’s absurd to think that someone who’s been creating around a topic, genre, or medium for two years would have anywhere near the level of nuanced insight, mastery of the tools, or ability to articulate ideas as effectively as someone who’s been baking with those same ingredients for a decade (let alone three, or five).

                          The most successful creators are often those who dedicate an entire body of work to a simple topic others overlook as unworthy of more than a single blog post or podcast episode.

                          Think Ryan Holiday with Stoicism applied to modern life.

                          Brene Brown with vulnerability.

                          Krista Tippett with what it means to be a human today.

                          None of their work is defined by exotic spice or extravagant garnish, but instead, a few simple ingredients, given decades to ferment and transform into something magical.

                          Which is all any of us needs.

                          The ingredients are all around us. In fact, we likely already have them.

                          Which means the surest path to success might be to stop looking outward for the ingredients we feel we’re missing and instead look inward.

                          To the simple ingredients that have already been fermenting, perhaps for years, unseen, waiting patiently to be combined, nurtured, and distilled into something entirely magical.


                          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.

                            Creative Cruxes: The Key Required to Unlock Any Creative Project

                            The “crux” of a rock climbing route is the point requiring the single most difficult move—or combination of moves—presented by the climb.

                            A crux can occur anywhere on a route, from the very first move to the very last and everywhere in between.

                            Regardless of where it occurs, if you can’t solve the crux, you can’t complete the route, even if you can execute the rest of the route flawlessly.

                            This simple truth leads many climbers to spend months or even years working only on a specific route’s crux in order to solve it, sometimes camping out on the side of a cliff face, thousands of feet above the ground for days at a time in order to practice.

                            The idea of cruxes extends to creative projects as well.

                            Unlike the climbing world, however, where the crux of a given route is often clearly documented in guidebooks and discussed at length among fellow climbers, creative cruxes tend to fly under the radar.

                            The result is often wasting months on a project we never had a hope of pulling off, all because we couldn’t solve the crux when we arrived at it.

                            If we want to improve the odds of success for any of our projects, then, it helps if we can identify the crux early, and develop a plan to navigate them.

                            Many Types of Creative Cruxes

                            In climbing, some cruxes might only be solved through brute strength.

                            Others might demand flexibility, balance, or perhaps the ability to leap four feet up and to the left and grab onto a half-inch wide ledge with just your fingertips.

                            The cruxes at the heart of creative projects vary similarly.

                            Some projects hinge on access to a specific network of people, such as the hit podcast (and now Netflix series)  Song Exploder .

                            If you’re not familiar with it, the show features interviews with popular musicians in which they break apart their hit songs piece by piece, detailing the inspiration and then the musical construction that went into creating them.

                            While the premise is interesting in its own right, the massive success of the show hinges on the audiences’ existing awareness of both the artists and the songs.

                            In other words, famous musicians and famous songs.

                            Without access to that level of guests, the show would likely fall flat.

                            In other projects, the crux might be your ability to fulfill the stakes you’ve set for a project with a publicly stated goal.

                            This is the case for my friend (and CW reader!) Daren Smith, whose  10k Creator project  documents his journey to building a 10k audience and $10k/mo creator business.

                            Without regular momentum toward the goal, the project quickly loses its appeal to any potential audience.

                            Additional common creative cruxes revolve around budget, access to distribution channels, time, skill, trust, reputation, and an existing level of fame or recognition.

                            Sometimes these cruxes are easy to spot and plan for well in advance.

                            Often, however, they’re less obvious and more nuanced.

                            And it’s these types of cruxes that often result in us spending enormous amounts of time pursuing projects that we never stood a chance at solving in the first place.

                            Identifying A Project’s Crux

                            The best way to identify a project’s crux is to start with a simple question.

                            “What needs to happen for this project to work?”

                            “Work” in this case is about more than just checking off the tasks required to ship the project.

                            Instead, it’s about creating something that is worth both our—and others’—time.

                            This means both creating a meaningful finished product, but also getting the attention and engagement of its intended audience, and—in many cases—getting paid for it.

                            For each project, the question of what’s required for the project to work will likely turn up a number of outcomes and scenarios that all must be true.

                            In some cases, a project may have multiple cruxes that must be solved in order to achieve its intended outcome.

                            In others, the core challenge of executing the project successfully might all funnel back to one key crux, that, when solves, unlocks and opens up the project.

                            Regardless, identifying a project’s crux points gives us the map of what’s required to achieve success.

                            It also allows us to properly assess whether or not a project is worth pursuing at all.

                            In many cases, identifying a crux we can’t solve early in a project’s exploration allows us to avoid wasting significant time, money, and heartbreak on a project that hinged on a crux we never had any hope of solving.

                            Not All Cruxes Are Created Equal

                            The crux is usually the single most difficult part of a project.

                            But depending on our existing skills, personalities, and assets we may have an easier—or harder—time with some cruxes than others.

                            In climbing, for example, a 6’7” tall climber might be able to simply reach around a given route’s crux negating it entirely.

                            On another crux, however, that same height might work against them.

                            The same idea applies to creative cruxes.

                            The crux of a podcast interviewing YouTubers with 1M+ subscribers about the first video they ever posted online is your ability to access and convince YouTubers with 1M+ subscribers to come on the show.

                            This is a much easier crux to overcome if you personally are a YouTuber with 1M+ subscribers and are already on a first-name basis with all your potential guests.

                            The same is true for any crux.

                            The trick, then, is to pursue projects with cruxes that are particularly challenging to others, but that play to our existing strengths and capabilities.

                            Observe, Assess, Identify

                            Every successful project has a crux.

                            Which means every day, we’re surrounded by opportunities to study and identify them.

                            When you come across a product, offer, or piece of content that works, ask yourself why.

                            The answer you come up with will be slightly different for each project you come across, but over time patterns will emerge.

                            Some projects hinge on the personality, expertise, or perspective of the creator.

                            Others on distribution, funding, or access.

                            With each new crux you identify in other creators’ successful projects, you improve your ability to identify the crux points in your own.

                            And once you’ve identified the crux, you’ve identified the lock that you must find the key to fit in order to unlock the project.

                            You won’t have access to the keys required to unlock each and every lock you encounter.

                            But you don’t need to.

                            You’ve got all the keys you need.

                            Your goal is to find the right locks to fit them in.


                            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 Tire Chocks: How to Identify & Remove the Tiny Obstacles Keeping You Majorly Stuck

                              If you ever find yourself parking a trailer, tire chocks are an invaluable piece of equipment.

                              Tire chocks are essentially wedges, often concave and plastic (though 2×4 pieces of lumber are commonly used as well) that are placed behind or in front of the wheels of a vehicle to keep it from rolling.

                              When placed intentionally, these simple tools perform their job remarkably well.

                              Unfortunately, the same principles of leverage that allow tire chocks to keep everything from jumbo jets to 450 tonne mining trucks in place, also apply to our creative projects.

                              Only, we don’t often realize the chock is in place.

                              If you’ve ever found yourself inexplicably stalled on a project that you can’t seem to make progress on, chances are, there’s an unseen chock wedged in a key location.

                              And until you find it and remove it, chances are, you’re not going anywhere.

                              Overcoming a Year-Long Chock

                              Until recently, I had been stuck on a tire chock with one of my projects for more than a year.

                              The project is a quiz audit allowing podcast creators to answer a series of questions about their current approach to marketing and then receive a personalized grading and breakdown of each of the categories of marketing.

                              I was excited about the idea, knew it would be incredibly valuable for my audience of podcast creators, and recognized that it was going to be a central part of the  Podcast Marketing Academy  marketing strategy going forward.

                              Despite my excitement and the clear incentives, however, I found myself inexplicably stuck.

                              For a year.

                              Finally, a couple weeks ago, I forced myself to sit down and do a simple brain-dump a list of possible questions that might eventually make up the audit.

                              Almost like magic, as soon as I had written down the first few questions and their possible responses, the rest of questions followed.

                              From there, I signed up for the quiz software I’d been eyeing since I first had the idea for the audit, uploaded up the quiz and quickly set up the scoring system.

                              Then, I designed the landing page, wrote out all the copy and analysis on the results page, and scripted out the follow-up email course.

                              Within just a few days, the project I’d been stalled on for more than a year was nearly complete.

                              So what happened?

                              The (Unfortunate) Power of Leverage

                              At first glance, it seems silly that a simple low-stakes task like brain-dumping a list of potential questions might be the chock that holds up an entire project.

                              And yet, in my experience, almost all creative project chocks are equally small and seemingly simple.

                              Which is exactly why we overlook them.

                              The truth is, if placed in juuuuuust the right location, even a tiny chock can hold back the weight of a much larger object.

                              In fact, relatively small 100 lb chocks are routinely used to prevent the aforementioned 450 tonne (1,000,000 lb) mining trucks from rolling down hills.

                              Is it so surprising, then, that seemingly insignificant tasks routinely stall our creative projects?

                              The good news is that despite chocks being both plentiful and incredibly effective in their ability to prevent our progress, in the end, they’re fairly easy obstacles to overcome.

                              At least if we know where to look for them and how to remove them.

                              Three Types of Creative Chocks

                              A chock keeping a project in place can be almost anything. But in my experience, they most commonly fall into one of three categories.

                              1. An external circumstance that needs to fall into place
                              2. An action or task to complete
                              3. A decision to be made

                              Let’s have a closer look at each type.

                              An External Circumstance That Needs To Fall Into Place

                              These chocks show up most regularly in projects involving other people.

                              In these cases, the chock is often a task or decision that someone other than us needs to make for the project to move forward.

                              Another type of chock in this category might be that the timing isn’t quite right for our project and we need to wait for the conditions to change for our project to be viable.

                              This category of chocks are particularly frustrating because, while we may be able to influence the situation, we don’t have direct control to remove the chock ourselves.

                              Fortunately, these types of external chocks are less common than the other two categories, over which we have full and direct control.

                              An Action or Task to Complete

                              Perhaps most commonly, the chock on a creative project is one, often simple task that holds the rest of the project up until it’s been completed.

                              This was the case in my own quiz audit project.

                              And as in my case, the reason we tend to avoid and procrastinate on these tasks is often not the work involved with the task itself, but an underlying lack of clarity.

                              That lack of clarity might be centered on whether this is, in fact, the right task to work on, whether it will achieve the desired result, how to approach the task in the first place, or any number of other doubts, big and small, rational and irrational.

                              The irony is that these tasks are often exceedingly small, taking no more than 15 or 30 minutes to knock out of the way, paving the way for the rest of the project to roll downhill and build momentum.

                              And yet, our desire for certainty before starting them often keeps us inert for weeks, months, or even years.

                              When encountering this type of chock, the most productive action we can take is to simply force ourselves to take the first step forward without perfect clarity.

                              Because more often than not, once we take that step, we realize we already have all the clarity we need.

                              A Decision to be Made

                              The final category of creative chock is a decision that must be made in order for a project to move forward.

                              This might be a decision about which software to use for a project, how to allocate tasks among your team, mapping out a schedule, or determining the priority of a given project in relation to other initiatives.

                              These chocks are perhaps the most insidious, because we’re often not aware of them.

                              These decisions can be large and important, but as with most chocks, are more often small and inconsequential, though often magnified in scope and significance in our minds.

                              To remove these chocks, I personally like to convert them into a task, getting them out of the vague recesses of my brain and into my task manager where I can schedule them to be addressed.

                              In most cases, when made plain and approached directly, a decision I’ve spent weeks mulling over can be made in a matter of minutes or even seconds.

                              Removing Creative Chocks & Building Momentum

                              For all the problems chocks make for us, they present an incredible opportunity.

                              Because once we train ourselves to spot and remove them, we quickly realize that most of the challenges keeping us from progress are not giant, immovable boulders blocking our path, but tiny pebbles to be nudged aside.

                              Once out of the way, we then build momentum, making it harder for future chocks to slow or stall us.

                              The first step when we’re stuck, then, is to identify the type and location of the chock.

                              Personally, I’ve created a field in my Notion project management system specifically to write down the current chock that’s holding each project up.

                              Because, if a project isn’t moving forward, it’s almost certainly because of a chock.

                              Clearly identifying the chock as specifically as possible reduces my frustration around projects I feel stuck on and gives me a clear map to getting them moving.

                              Once the chock has been identified and removed, the next step is to focus on building momentum.

                              Chocks are most easily placed when we’re standing still, such as at the start of a project or between distinct phases such as moving from building a product to marketing it.

                              But they also have a way of lodging themselves in front of the wheels of projects that aren’t getting our full time or attention.

                              To avoid this, it’s helpful to choose your timing to remove your current chock wisely, ensuring you have the bandwidth to continue rolling with the project once the impediment has been removed.

                              If you don’t, there’s a good chance the next task in line will quickly solidify into a new chock, stalling any potential to build momentum.

                              Of course, no matter how much momentum we build, various chocks will always find a way to stall and disrupt our work.

                              They call to mind Archimedes’ famous quote about leverage, which in this case, might be slightly rephrased as:

                              “Give me a wedge and a gap to place it, and I shall hold back the world.”

                              Learn, to spot and remove them, however, and the world is yours for the taking.


                              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 Last Gatekeeper

                                There’s no piece of paper that can prove, beyond doubt, the worth of your work.
                                Neither wax seal Nor gold star
                                Nor signature of this person or that
                                Can validate your knowledge, skill, or competence
                                And give you permission to move forward.​ ​

                                To create
                                Build
                                Disrupt
                                Serve.

                                Just you.

                                Alone.
                                Afraid.
                                A fraud.
                                In your own mind at least…

                                Stopped dead at an amber light,
                                Waiting (hoping, praying) for it to turn.
                                For some sign or another from the universe
                                To give you the go-ahead
                                To signal “NOW IS THE TIME!”
                                In flashing neon letters
                                Impossible to miss. ​

                                A pity.
                                Many a life was wasted in waiting.
                                A gift never given.
                                An idea never expressed,
                                That would benefit us all. ​

                                What would it change to know
                                That even once all the gates have been opened
                                And the road stands unimpeded
                                You must still face one last gatekeeper.
                                The one that has always and will always have the power
                                To grant or deny you passage.
                                Who is unmoved
                                By all the certificates, seals, stars, and signatures in the world. ​

                                In the end, this is the only gatekeeper that must be won over
                                Whether by reason, cunning, force, or persistence.
                                The gate is already open
                                Waiting for you to take the first step through.


                                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.


                                  Thinking In Drafts: A Subtle Mental Shift to Unlock More & Better Creative Work

                                  A few years ago, I heard author Tim Grahl give a talk about his experience with writing his fantastic book on making a living as a creative,  Running Down A Dream .

                                  He shared that before publishing the book, he’d been working on some version of of it for nearly ten years.

                                  Many of the drafts during that time involved scrapping nearly everything he had previously written and starting from scratch.

                                  In some versions, the content wasn’t right.

                                  In some versions, the tone wasn’t right.

                                  In some versions, everything seemed like it should have been right… but it still felt wrong in some intangible way.

                                  Over the course of those ten years, Tim shared each of the many iterations of his book with a tight-knit group of guides, peers, and accountability partners who understood his goals, style, and potential, and asked for their unvarnished feedback.

                                  That feedback was often painful. Good feedback usually is.

                                  But draft by draft by draft, Tim was able to take that feedback and improve each version of the book until it was good enough to finally ship.

                                  Not perfect, perhaps, but good enough to put out into the world with pride.

                                  Tim’s story sounds extreme.

                                  But for many creative fields, a years-long process of painful revisions is entirely normal.

                                  We know every movie has multiple cuts, test screenings, revisions, and even reshoots before the final, public release.

                                  We know the initial manuscript of a book is only the very first in a long series of milestones on the road to getting it published.

                                  And yet we rarely apply the idea of working in drafts to our own creative practices.

                                  Which is a shame.

                                  Because the emotional and creative dynamics of working on a draft are dramatically different from working on something we know will be the definitive, finished product.

                                  Drafts Dial Down the Pressure

                                  Whether it’s a big project like a product launch or website, or a smaller piece of content like a newsletter issue, podcast episode, or YouTube video, we tend to approach everything we publish as though we only have one chance to get it right.

                                  There are a couple of problems with this approach, however, that undermine our long-term progress.

                                  The first and most obvious problem is classic perfectionism.

                                  We’re less likely to ever ship our work when we only have one shot to get it right. Because how could we possibly create the best version of any project now when we know that by next month (let alone next year) we’ll be more knowledgeable, talented, and capable?

                                  The second problem is that if we do manage to ship it, we tend to put too much emotional stock in the feedback we receive.

                                  A positive reception can lead us to believe our work is done. No further improvements required.

                                  A single piece of negative feedback on the other hand might convince us that the entire idea is stupid and not worth investing in further.

                                  Both responses sell our work short.

                                  Unlike finished versions, the goal of a draft is simple: Create something that is merely good enough to get the next round of feedback on.

                                  Good enough to put into the world and assess how the world interacts with it before heading back to the drawing board to work on the next draft.

                                  When we approach our work in drafts we tap into a bit of creative magic.

                                  It allows us some detachment from criticism as we know we’ll have an opportunity to make improvements in the future.

                                  This allows us to ship our work more boldly, understanding that of course there are flaws! Of course it’s not perfect! It’s only a draft after all, not the finished product.

                                  In fact, the finished product might never arrive.

                                  But thinking in drafts allows us to adopt a mindset of experimentation, iteration, and bravery as we put out version after version after version of our work out into the world for it to collide with, shape, and be shaped by in return.

                                  Even if we never achieve perfection, however, the continual pursuit of it has a way of opening doors and leading to unexpected creative success.

                                  Results Come From Iteration, Not Perfection

                                  I recently attended a workshop where Tiago Forte, the creator behind the wildly successful course (and now book)  Building A Second Brain  talked about his process for building the course into a multi-million dollar business.

                                  He started by sharing this graph which details the cohort launches from June 2014 to July 2022.

                                  caption for image

                                  Then he gave this context.

                                  “Notice the left, half of this graph, there are cohort launches in there but you can barely tell, right?

                                  I basically consider cohorts one through nine as betas.

                                  In retrospect, they were tests. They were so small and insignificant compared to what would happen later that all that really mattered for those first nine cohorts was that we learned, and that the revenue was just enough to make it to the next cohort.”

                                  That’s thinking in drafts.

                                  Like Tiago, I’ve applied thinking in drafts to big projects like Podcast Marketing Academy where  each launch and cohort builds a little bit on the last .

                                  But I’ve also applied it to smaller—even micro—projects.

                                  Take this newsletter, for example.

                                  With three years of writing to pull from, I’ve started revisiting my favourite ideas, updating them, and republishing them in the newsletter a second time.

                                  Often, the second draft of an idea is almost unrecognizable from the first.

                                  Take this issue, which I originally published in October 2020. I was happy enough with the issue at the time, but I didn’t feel like I’d fully got my head around the idea.

                                  In revisiting it, I’ve been able to update it with new ideas and examples I’ve picked up as my thinking has evolved.

                                  Being a topic that I’ve already thought about on a near-daily basis for more than two years already, I have no doubt that this draft will be further revised and updated in the future.

                                  Nothing Is Set In Stone

                                  While thinking in drafts is valuable as part of your creative practice, its most liberating use case may be in choosing to view your life and career through the lens of drafts.

                                  Sure you might not be where you’d like to be right now. But no matter where that is, it’s only one in a series of continually improving drafts.

                                  Your goal today, this month, or this year is not to achieve or become the perfect final version of yourself.

                                  Your goal today (and every day) is simply to put yourself out into the world and collect feedback, so that tomorrow’s version can be a tiny bit better.

                                  We can approach our work and our lives with a whole lot less seriousness when the next thing we do isn’t the be-all end-all, definitive version of what we’re trying to create or who we’re trying to be.

                                  If you’re not getting the results you’d like with the work you create, that’s not a referendum on you or the idea behind your work.

                                  Instead, it’s simply a sign that there’s more work to be done. That you need to write a few more drafts to get your work and yourself to where they need to be.

                                  Identify your group of guides, peers, and accountability partners who understand what you’re trying to achieve. Ask them regularly to give you their unvarnished feedback.

                                  Then get back to work and make the next draft.


                                  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 Neglected (But Essential) Facet of Creative Productivity

                                    The decorations are up.

                                    Christmas music wafting out of every shop door.

                                    Mulled wine is being served on seemingly every street corner.

                                    There’s no ignoring that the holiday season is officially upon us.

                                    But perhaps the best indicator that the end of another year is here is the one bombarding us on our social media, newsletter, and podcast feeds.

                                    No, I’m not talking about the recent wave of Black Friday sales notices.

                                    I’m talking about the stream of content challenging us to “not wait until January 1st to start on our 2023 goals” that crops up around December 1 every year.

                                    Urging us to push through the end of the year.

                                    To continue the relentless grind we’ve subjected ourselves to all year in order to continue (or build) our momentum.

                                    I know the advice is well-intentioned.

                                    But it still irks me.

                                    Not just because I think we deserve (and require) a break from the relentless grind it takes to start and grow a creative business.

                                    But because this type of thinking takes such a narrow view of what it takes to achieve creative progress.

                                    The Neglected Facet of Creative Productivity

                                    Let’s not kid ourselves, frequent and decisive action is essential to making progress toward our goals.

                                    As a result, most productivity advice revolves around how to take more action and get more done.

                                    More action = more progress the thinking seems to go.

                                    And at least in part, that’s certainly true.

                                    But there’s an essential prerequisite for productive action that standard productivity hacks and hustle culture consistently neglect, which is this:

                                    For action to amount to anything, it needs to be focused and directed in the right direction.

                                    That requires clarity.

                                    And clarity rarely finds us when we’re in the thick of implementation & action.

                                    Rather, it almost always finds us immediately after a period of intense action, when we’re able to slow down, step back, and gain enough distance from the fray to gain some perspective.

                                    Without taking regular steps back to reorient ourselves, we risk barreling forward, head down… making fantastic progress in the entirely wrong direction.

                                    Far from slowing our momentum, then, regular rests, reprieves, and reorientations are not only essential to recharging our energy stores, they’re a core component of long-term creative productivity.

                                    Which means that rather than pushing through December at breakneck speed, the very best thing we can do for our creative work and businesses is to slow down.

                                    Slow Down to Speed Up

                                    There are few better opportunities to slow down, step back, and gain perspective on where we’re at, than the end of each year.

                                    It’s one of the vanishingly rare times we as a society allow ourselves to collectively slow down and reflect.

                                    If you’re like me, at this time of year you might regularly be finding yourself preoccupied with big-picture dreaming, brainstorming, and idea exploration… at the expense of your daily task list.

                                    The “push through to the new year” advice encourages us to ignore these frivolous distractions and focus on squeezing just a little bit more productivity out of the year.

                                    But while the value of big-picture dreaming, visioning, and planning may be hard to quantify, without it, our work tends to lilt toward the mundane, generic, and bland.

                                    Despite its necessity, however, we rarely make space for it, often deferring to the more tangible outcomes of action.

                                    It’s worth noting that those in the “push through” camp are often staunch and vocal advocates of completing a structured annual review, a practice I too find an incredible amount of value in. But that review is often boxed into a single day, afternoon, or couple-hour-long time block.

                                    The problem with this approach is that I’d wager there are challenges, puzzles, and problems in your life and work that will take more than a couple of hours to solve.

                                    In fact, there’s a good chance the (perhaps only) reason they’ve persisted this long has been a lack of time and space to slow down, sit back, and ponder.

                                    Nature abhors a vacuum, after all, and big ideas and breakthroughs have an uncanny way of showing up when we create the space for them.

                                    So while I’m guessing you, like me, still have a long list of unfinished goals and projects on your annual to-do list, it’s possible that the single most productive thing you could do with the remainder of the year is to set them aside.

                                    Slow down.

                                    Pause.

                                    Plant your feet.

                                    Orient yourself.

                                    So that when you’re ready, you can push off toward the next goal with energy, focus, and intention.


                                    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.


                                      Directing Your Energy Wisely

                                      Every weekday for the past six months, I’ve eaten a bowl of soup for lunch.​

                                      I like soup, but despite what the considerable streak might suggest, I’m not obsessed.

                                      In reality, it’s a case of simple utility. ​

                                      High-quality, premade soup is available at every store near me in a variety of flavours. It’s quick and easy to heat up, healthy, hearty, and delicious.

                                      Over the months, the consistency of fare has introduced a sort of unintended ritual to the middle of my day.

                                      At noon my alarm goes off, signaling the end of my morning deep work time block.

                                      At this point , I head to the kitchen, pull the soup container out of the fridge, pour it into a bowl, and put the bowl into the microwave. ​

                                      A minute and forty-five seconds. Take out and stir. Back in for another minute and thirty seconds.​

                                      During the first minute forty-five, I take the stairs up two floors of my coworking space to the bathroom.

                                      During the second minute thirty, I wash out the soup container for recycling. It takes me forty-five seconds to wash the container, leaving me forty-five seconds to start my lunchtime sudoku.

                                      As you can tell, I have the process down to a science.

                                      Or at least I thought I did, until this past Wednesday.

                                      A Surprising Discovery

                                      I might not have made the discovery of I hadn’t been wearing my favourite shirt.

                                      It’s a light grey, long-sleeved button-up, the perfect canvas for stray drops of the neon orange lentil curry I was heating up that day.

                                      As such, I was on guard, fully aware of my every move as I placed the brimming bowl back in the microwave after it’s stir, set the timer for a minute thirty, and took the container to the sink to rinse out.​

                                      Had I been wearing any other shirt, I would have turned the hot water faucet on full, allowing the pressurized spray to blast the remaining soup from the inside of the container, splashing the sides of the sink in the process. ​

                                      Once the container was clean, I would fill it up and use it to splash water across the sides and bottom of the sink until they were once again clean and white.​

                                      This had been a standard part of my lunch-time ritual to that point.

                                      It seemed obvious to me that the full power of the faucet was the fastest and most effective way to clean out the container.​

                                      As my hand hovered over the handle, however, I hesitated.

                                      I envisioned a neon wave splattering out out of the sink and across my shirt, ruining it in an instant.

                                      Instead, I turned the tap slowly, drawing a thin, focused stream of water.

                                      I carefully directed the stream around the sides of the container before—equally-carefully—pouring the contents directly into the drain, making sure to avoid even the slightest splash as I did so.​

                                      I tossed the container in the recycling, pleased with the potential disaster my careful planning had averted and looked over to the microwave timer. ​

                                      Sixty seconds. ​

                                      Huh.

                                      Not only had I managed to keep my shirt clean, but I’d also taken less time to clean the container, hadn’t needed to clean the sink, and used less water to boot.​

                                      Was it a mistake? An outlier?

                                      Being of scientific inclination, I tested the process again on Thursday, and then on Friday. ​

                                      The results were the same.

                                      Thirty seconds to wash the container under low pressure versus the forty-five under high.​

                                      How could this be? Surely less power, less energy, less input shouldn’t result in the same outcome in less time.

                                      Should it? ​

                                      Focus > Pressure​

                                      So often, our instinct is to devote all the energy we have available toward the problem we’re trying to solve or the work we’re trying to create.​

                                      Sometimes, this is called for, and may in fact be the best way to achieve our desired result. ​

                                      But not always.

                                      Especially if the energy we’re directing at the problem is unfocused, inconsistent, or erratic.

                                      In fact, as with the soup container, sometimes more energy just creates more of a mess to clean up once we finish the task at hand.

                                      In most cases, we’re better off beginning with less—but more focused—energy, and then ramping up as need be.

                                      In my experience, brute force and maximum pressure are rarely the most efficient problem solving methods.

                                      Just the right amount of energy, directed at just the right place, on the other hand, often is.

                                      Which means the next time you find yourself wishing for more time, money, or force to direct toward a problem, it might be worth pausing.

                                      Because there’s a good chance you already have all the resources you need. They’re just not being focused effectively.


                                      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.


                                        Triage: A Necessary Skill for Progressing in Your Creative Career

                                        Before powering down at the end of every day, I review my task list and bump everything I didn’t complete to a future date, often the next day.

                                        On good days, it’s a small number of non-urgent or unimportant tasks.

                                        On less-than-good days it’s a large number of both urgent and important tasks that got crowded out by even more urgent and important tasks.

                                        Regardless of the day, however, for the past six months there’s been one particular task that’s appeared on my task list every single day… and without fail, been bumped, incomplete, to the next day.

                                        The task?

                                        “Catch up on email”

                                        I know, it’s wildly optimistic to harbour any kind of belief that this task could ever truly be completed. In fact, the mountain of unreplied-to email has only grown since adding the daily reminder.

                                        And yet, I persist in deluding myself.

                                        I created the task after wrapping up the PMA5 launch in the spring.

                                        Launches have a way of crowding out everything but the most essential daily action items—of which there are always more than can possibly get done—and after spending 10 weeks in launch and then cohort delivery mode, I had fallen severely behind on all manner of non-urgent correspondence.

                                        I did what I could to chip away at my inbox following the launch, but it wasn’t enough.

                                        Because before I could catch up, I once again found myself neck deep in planning, executing, and delivering the launch of my next cohort, adding another 2.5 months of email backlog.

                                        Last Friday night, from 9-11 pm I sat down and made the most significant dent in my inbox to date, working through 75 of the 300 or so emails awaiting a response.

                                        It felt good to make a dent in the mountain.

                                        But more interestingly, in going through the emails that had been piling up, I made a realization that instantly reframed my email problems.

                                        The Price of Projects Gaining Traction

                                        In sifting through and responding to the emails, I noticed that the majority of them fall into one of two categories:

                                        1. New subscribers to either Creative Wayfinding or Scrappy Podcasting who are responding to the prompt in my welcome emails to tell me a bit about themselves and their work.
                                        2. Requests to collaborate, guest on podcasts, contribute to projects, etc.

                                        Based on these categories it’s clear that far from being a problem, the number and type of emails occupying my inbox are a sign that things are working.

                                        The first category is the direct result of people subscribing to my newsletters (my #1 goal in my business). The second, a result of becoming better known and seen as an interesting voice in my industry.

                                        Despite the positive underlying causes of my inbox overwhelm, the situation bothers me.

                                        For one, the lack of responsiveness doesn’t send the message I want myself or my brand to convey, especially to new subscribers reaching out for the first time.

                                        More personally, I have a natural inclination toward, structure and order, which means the lack of control over a task as simple as answering email is deeply uncomfortable.

                                        And yet, one of the things I’ve had to come to terms with over the past two years as more and more of my projects have started to gain traction is that this type of discomfort is an inevitable price of creative progress.

                                        Obligation Overwhelm

                                        At the beginning of a project, our obligations tend to be low.

                                        caption for image

                                        We likely don’t have an audience expecting anything from us on a consistent schedule. We don’t have paying customers and clients with deadlines and deliverables. And we don’t have partners and other stakeholders to whom we’ve made promises.

                                        On the personal side, the project likely isn’t supporting us financially, so we have little obligation to ourselves to keep the project running.

                                        Pure creative freedom in other words.

                                        What’s more, we’re in experimentation mode, which means we might be playing with half a dozen (or more!) ideas, testing them out to see which has the greatest potential.

                                        As some of those projects inevitably begin to gain traction, however, our obligations to each of them increase.

                                        caption for image

                                        As traction leads to growth, it doesn’t take long for our obligations to even one such project to begin to crowd out other pursuits.

                                        Which means that if we want to navigate this stage of the creative journey intact, triage becomes an increasingly important skill for us to develop.

                                        Because the more success our projects accrue, the more difficult the choices we’ll face about what gets our best time and attention, what gets the leftovers, and what gets ignored.

                                        Creative Triage

                                        When we first begin to bump up against the limits of our bandwidth, the choices about what to focus on and what to ignore are fairly easy to make.

                                        Other low-traction projects are often the first to be pushed outside the limits of our current bandwidth to focus on the more promising endeavours.

                                        But as the project continues to gain momentum (which of course is our goal), it’s only a matter of time before other aspects of our lives begin to be pushed outside of our ability to stay on top of them.

                                        Relationships with family and friends, our health, hobbies, and yes, correspondence—both business and personal—all have a way of becoming secondary to the demands of a successful—yet not fully self-sufficient creative project.

                                        caption for image

                                        As with any type of triage, creative triage involves making many painful decisions.

                                        In fact, the more painful a decision, the more potential upside the decision likely offers.

                                        This means turning down promising projects and opportunities you desperately want to take on.

                                        It means letting many of the fires in your business burn unabated—often indefinitely.

                                        It means learning to accept the inevitable discomfort of never being able to get to everything you want to, or perhaps even feel you need to do.

                                        All this, in the service of making progress on the small number of things that matter most—both for the project to be successful, as well as for yourself.

                                        Such is the price of success.

                                        We can try to fight the need to triage our various projects, tasks, and endeavours, attempting to maintain control over everything on our plate even as the demands of our creative platform exceed our bandwidth.

                                        More often than not, this achieves little but undermining the quality and consistency of our work, not to mention our health, sanity, and satisfaction.

                                        The alternative is to choose to embrace making difficult choices about where we focus our time and attention as an essential skill we must develop to reach the next level of success.

                                        Because in the end, we’re most often held back not by the opportunities we fail to grab ahold of, but by those we fail to release.


                                        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.


                                          Triangulation: The Math Equation Behind Creative Clarity

                                          Spend much time wandering the countryside of the UK and it’s only a matter of time before you begin to notice a curious set of landmarks.

                                          These landmarks generally come in the form of squat, truncated obelisks or pillars about three feet tall that are most often perched atop prominent hills.

                                          The landmarks have an aura of mystique around them, which they also seem to transfer onto the landscape.

                                          Other than a cryptic set of inscriptions consisting of a few letters and numbers, they lack any kind of identifying signage.

                                          They are concrete, decidedly utilitarian, obviously manufactured… And yet somehow manage to feel like a natural part of their surroundings.

                                          Looking at them, it’s easy to think that they have always been there, and will always be there.

                                          The truth, while interesting in its own right, is far more pedestrian.

                                          The pillars—or trig points as they’re locally known—were initially constructed between 1935 and 1962 as part of the Retriangulation of Britain, an effort to provide more accurate maps of the country.

                                          In case you need a refresher, triangulation is a mathematical concept stating that if you know the distance between two reference points, you can calculate the exact distance to any third point by measuring the angles to it at each of those initial references.

                                          caption for image

                                          In other words, if we know the distance between A & B and the angles of x & y, **we can determine the distances of both AC and BC.

                                          It’s a simple but brilliant concept with a long history dating back nearly 2,000 years.

                                          In addition to being used to create the first truly accurate maps of countries, triangulation has been used to determine the heights of mountains (such as Mt. Everest) and even to determine the size of the Earth.

                                          It’s safe to say that triangulation is one of the most tried and true mapping techniques we have available.

                                          And while the mapping of physical geography has now been overtaken by more accurate and responsive GPS networks, when it comes to mapping and navigating the landscapes of our creative work, the older analog method of triangulation persists as perhaps the best tool we have available.

                                          Triangulating Your Location

                                          Perhaps the two most fundamental and persistent challenges we face as creators are understanding where we’re going and understanding how to get there.

                                          While we often think of our most pressing problems as tactical (ie. “How do I grow my email list?”). In my experience, however, when we have clarity on our destination and direction, the tactics take care of themselves.

                                          Clarity then, is a necessary first step to real progress toward our destination.

                                          While we innately understand this, however, our understanding tends to lead us into the trap of waiting for clarity before attempting to move forward at all.

                                          This is far from an efficient or useful way to gain clarity, however.

                                          Because while clarity may be a pre-requisite for meaningful forward progress, movement is a pre-requisite for clarity.

                                          Unfortunately, this idea doesn’t align with the way most of us think about progress, that any effort that doesn’t lead us closer to our goals is wasted.

                                          But this couldn’t be further from the truth.

                                          In fact,that effort—and the accompanying movement—is a necessary part of establishing a series of reference points necessary to triangulate where we are in relation to where we want to be.

                                          caption for image

                                          If we’re feeling lost or stuck, then, the most productive action we can take might be to simply pick a direction and climb the nearest hill to establish a new reference point.

                                          It’s entirely likely—probable even—that the direction we pick won’t be the shortest or most efficient route to our ultimate destination. But if it gets us moving and helps us find clarity, it may just end up being the fastest, **even if it takes us in the entirely opposite direction from where we want to end up.

                                          When it comes to clarity, all reference points are helpful. And the more we have, the more their benefits compound.

                                          While we can triangulate our way to a given destination based on as little as two reference points, the accuracy and range of our route-making increases the more reference points we have.

                                          So too does the level of nuance in our understanding of the landscape through which we’re traveling as well as our awareness of opportunities adjacent to our route.

                                          caption for image

                                          What’s more, the reference points we establish have a way of being useful beyond simply calculating our immediate next step.

                                          Sure, the hill ahead of us will provide a useful vantage point from which to plan our next move. But the trig point we set there may continue to be a useful reference in helping us triangulate the moves we’ll make 6 months or 6 years from now.

                                          As a result, each hill we ascend increases the resolution of our internal map, both of the terrain we’ve already covered, as well as that which lays ahead.

                                          It’s slow going, slogging up hill after hill, only to find we need to adjust our course, descend, and aim for a different hill on the horizon.

                                          And yet this is precisely the type of wayfinding that sets us up for long-term success in any field.

                                          One that, thanks to our extensive exploration and cartography we now know better than almost anyone else.


                                          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.


                                            Acorn Picking: How to Spot Ideas & Opportunities Hiding In Plain Sight

                                            The final stretch of my morning walk to coffee passes through a wide oak-lined path.

                                            Over the past month, the ground has regularly been littered with acorns, crunching underfoot as I walk by, the branches above filled with dozens more.

                                            There’s something I love about the size, shape, and feel of acorns. The symbolism of small beginnings and slow growth is a nice reminder as well. And so almost every day I’ll either stoop to pick up, or reach to pluck down a handful of the smooth seeds to bring back home to decorate the base of my office plant.

                                            As winter has drawn steadily nearer, however, fresh acorns are becoming harder to come by.

                                            That doesn’t keep me from looking, however.

                                            At this point, most of the acorns on the ground have either been trampled and crushed by the time I walk by or are lying next to the proliferation of dog shit in the tree planters beside the path.

                                            And so I’ve turned my gaze to the increasingly bare trees.

                                            One quiet morning, when there was no one else around, I decided to examine the trees more closely.

                                            As I stopped in front of one of the trees to have a better look, I immediately saw great bunches of acorns still crowding the branches just above the reach of the average person.

                                            Around the back of the tree, off the path and overhanging a low retaining wall, the bounty of acorns continued, these all well within arms reach.

                                            Finally, I realized that there were, in fact, still plenty of acorns within reach, directly along my walking route. They were disguised behind leaves, however, and difficult to spot while walking by at full speed.

                                            It made me think about how similar spotting and collecting acorns is to spotting and collecting good ideas.

                                            Ideas Are More Abundant than We Realize

                                            The most obvious and easily accessible ideas in any space are always the first to be picked over.

                                            Some of those get claimed and put to use by other people. Others get tossed aside, trampled, and covered in whatever the idea equivalent of dog shit is.

                                            It’s often at precisely this point when most of us make our entrance into a new space, survey the landscape, and draw the mistaken conclusion that the bubble has burst and there are no good ideas left to be had.

                                            Of course, there are almost always still plenty of good ideas worth picking, but in order to find them, we need to get creative

                                            Fortunately, the distribution of acorns on the oak tree provides a framework for finding the seeds of ideas anywhere.

                                            4 Methods For Idea Discovery

                                            When we understand where ideas tend to get picked over fastest—within easy reach along the most well-traveled path—it’s not hard to come up with solutions to find and harvest the less accessible ideas.

                                            These solutions are divided into four categories.

                                            1. Exertion

                                            The first opportunity is to work harder than other people are willing to.

                                            When it comes to picking acorns this might mean jumping in order to grasp the acorns that would otherwise be out of reach.

                                            For ideas, this might be getting in more reps in our niche or with our subject matter or medium than other, more opportunistic people are willing to put in.

                                            Get to know the ins and outs of any space by working in it and plenty of non-obvious opportunities have a way of presenting themselves.

                                            2. Ingenuity

                                            While exertion is certainly one way to access hard-to-reach ideas, ingenuity and creativity allow us to reach higher.

                                            On an oak tree, this might mean getting a ladder, using a stick to knock down acorns suspended higher up in the tree, or shaking the trunk until they fall.

                                            In our creative work, ingenuity might mean pattern-matching ideas that have worked in other industries or niches with ours, or focusing on growing a network in the space that continually presents feeds us new perspectives and ideas organically, rather than needing to go out and find them ourselves.

                                            3. Inconvenience

                                            As I discovered with the oak, there are often plenty of good ideas within easy reach if we’re willing to step off the most well-traveled path.

                                            Every niche and industry has a dominant audience segment that the majority of people & brands cater to. But that doesn’t mean they’re the only segment. In fact, they’re often the hardest to gain traction with because of the amount of noise and competition.

                                            Explore the fringes of your space and you’ll find all kinds of ideas and opportunities ripe for the picking.

                                            4. Patience

                                            Finally, there’s the method of simply slowing down enough to actually see our surroundings for what they are as we pass through them before writing them off as barren & devoid of opportunity.

                                            We’d be surprised by what turns up when we settle into a space and participate in the existing community for a while.

                                            On the oak, simply stopping to stand beneath it for 30 seconds was enough to spot acorns that had previously been invisible to me.

                                            Perhaps the epitome of this approach is the patience of continuing to return to the tree, day after day, season after season, year after year, with the knowledge that even if the tree is barren today, it’s only a matter of time before new acorns begin to emerge.

                                            The spaces in which we live and work are constantly shifting, morphing, and evolving.

                                            Which means new opportunities are always developing, budding beneath the surface, and waiting to break through.

                                            When they do, the people who will be in position to take advantage of them will be those who have been patiently tending to the space long before the new batch of ideas showed up.

                                            Our challenge then, as creator entrepreneurs might not be finding ideas.

                                            But finding the tree we’re willing to weather the seasons under, and then reaping the bounty it provides.


                                            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.


                                              Pushback Rallies: How to Do More with the Creative Opportunities You’re Given

                                              Ever since Roger Federer announced his retirement a few weeks ago, I’ve been going back and watching through highlight reels from his career.

                                              Many of Federer’s highlight reel moments are of him masterfully dictating the flow of the game and utterly dominating his opponents.

                                              In these clips, Federer feels like some mix of artist, chess master, and evil genius.

                                              Through precise and strategic shot-making, he guides his opponents around the court, setting up the pieces with subtle manipulation… before dropping the hammer with an elegant, seemingly effortless checkmate.

                                              These clips clearly display a master of his craft at the height of his powers.

                                              But there’s another, very different type of highlight reel rally that appears again and again in these compilations of Federer’s career. One where it’s Federer being chased around the court.

                                              These rallies are defined less by skill and more by a certain type of grit.

                                              I think of them as Push Back Rallys. And there’s a lot we can learn from them.

                                              Specifically, there’s a certain decisive shot in the middle of these rallies that we all need to learn to make as creator-entrepreneurs as well.

                                              Let’s set the scene.

                                              Hitting Off the Back Foot

                                              In a typical Push Back Rally, the opponent has taken control of the pace and it’s all Federer can do to simply return the ball in play.

                                              He’s clearly on the defensive, struggling to keep up, constantly hitting off his back foot, unable to plant and step into his shots in order to generate more power or accuracy.

                                              You can tell it’s only a matter of time before he cracks, handing his opponent the point.

                                              And then the decisive moment.

                                              His opponent attacks. Federer lunges to get into position, but he’s half a step too slow.

                                              You can almost see the same calculation we as the viewers are making play out in his head.

                                              “Is it even worth fighting to keep this rally going? I’m in a weak position… Maybe I’d be better conceding the point, conserving my energy, and resetting for the next one “

                                              But just as you think he’s giving up, something in his posture shifts, almost imperceptibly.

                                              He’s off-balance, unplanted, and out of position. The safe shot is to simply get the ball back over the net, extend the rally, and hope for a better opportunity on the next shot.

                                              Instead, through force of will alone, he goes on the attack.

                                              With this one shot, he manages to swing control of the rally in his favour, and a few shots later the point is his.

                                              Examples of Push Back Rallys abound in tennis.

                                              It’s a sport governed by momentum where single shots can—and often do—change the complexion of points as well as entire games, sets, and matches.

                                              But the idea applies elsewhere as well, including our creative work.

                                              Don’t Wait for the Perfect Setup

                                              Unlike Federer, most of us default to waiting for the circumstances to be perfect—feet planted firmly in a position of power with ample time to pick our spot, step in, and swing with perfectly controlled form—before making our move.

                                              These opportunities rarely if ever present themselves to us, however.

                                              And so we spend most of our creative lives on our back foot, reacting to what comes our way, just trying to get the ball back over the net, without ever pressing the offensive without making our opponent react to our will.

                                              There’s certainly a time to defend.

                                              To do what we can to keep the ball in play, extending the game while conserving and building up our energy.

                                              But as a larger strategy, simply extending the game is unlikely to win us many points.

                                              Sooner or later, we have to shift to the offensive, to assert ourselves and seize control of the flow of play.

                                              We won’t be given an obvious or advantageous opening to do so.

                                              When the time comes, we’ll likely be on our back foot, out of position, without as much time as we’d like to step up and really swing through our shot.

                                              In watching Federer, it strikes me just how many of his career-defining winning shots came during Pushback Rallies, where the odds were stacked against him and the logical choice seemed to be to wait for a better opportunity.

                                              It makes me wonder.

                                              How many of the losses or draws we settle for in our lives and work could actually be winning points if we were willing to dig a little deeper, get a little more uncomfortable, and go on the offensive, even when all the circumstances are telling us to do the opposite?

                                              Because in the end, these are the opportunities we’re given.

                                              What we do with them is up 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.


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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.