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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    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.

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    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.

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    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.

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    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.


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        Never Work a Day in Your Life

        Photo by Anthony Fomin on Unsplash

        “Do what you love and you’ll never work a day in your life.”

        For many creators, this was the dream we aspired to when we started thinking seriously (but not too seriously) about what we really wanted to do with our lives.

        Maybe you wanted to make movies, record music, play professional sports, write novels, maybe it was a job that didn’t even exist yet.

        Our individual dreams were varied, grouped together only by the refrain we grew accustomed to hearing, that we couldn’t do them as a career.

        For many of us, we didn’t allow ourselves to express our dream out loud, we only half believed it was possible, and as much as it annoyed us that our parents kept nagging us about having a backup plan in place, we kinda thought maybe we should have a backup plan in place.

        But we kept the dreams alive, kept working, and slowly what started as a dream and a hobby started turning into a craft.

        Honing Our Craft

        We realized that we could hone our inputs to influence our output, that with focused practice we could develop our skills further than we had thought possible, that it wasn’t all about innate talent.

        Most importantly, we realized that there were other people doing this work for a living and that maybe, just maybe we could model what they were already doing and maybe we could start doing our craft for a living as well.

        When we got our first client, we almost exploded with excitement.

        This was proof that this could work. This was validation that we had been right to keep our dream alive when everyone else told us it was impossible.

        That client didn’t pay that well, and our work still had a long way to go, but it was a start.

        Taking the Leap

        That first client led to more clients and pretty soon it was looking like maybe it was time to take the leap and turn our craft into our full-time gig.

        After too much deliberation, we built up the required resolve and made the transition to working for ourselves as professional creators.

        The thrill was immense, at least at the start.

        We were in control of our destinies, in control of our time, for many of us we could work from anywhere we wanted. A whole world of possibilities was suddenly open to us.

        If only we had the time and emotional bandwidth to take advantage of these new opportunities…

        Being the Boss Isn’t All It Was Cracked up to Be

        It didn’t take long for the initial thrill to fade into something more resembling an ever-increasing pressure, as we realized that we were in control of our destinies and that there would be no one to blame but ourselves if all these years of dreaming, working, and strategizing came crashing down around us.

        What’s more, this whole “never work a day in your life” thing sure seemed to be filled with a lot of work.

        Sure we still loved our craft and were proud of the work we created, but it didn’t feel like we spent a whole lot of time doing it anymore.

        Instead, our days seemed to be filled more and more with emails, bookkeeping, and researching our competition with increasing despair that we’ll never create work that good.

        Stagnation, and a Crossroads

        A couple of years in, we’re still getting by, getting some better clients, raising our rates, doing better work. But we’re beginning to question whether we can sustain this for another 30 years.

        Our days are still filled with less creating than we’d like, we’ve leveled up our skills but still don’t measure up to our competition, and the stress of doing good work while managing our business is really starting to wear us down.

        Assessing our options we figure that maybe we could hire people to contract work to, building out our team to lessen our own load. As we think more about it, however, it starts to sound like that might lead to us simply becoming a manager, leading to even less time doing our craft, and creating.

        We then figure that maybe if we raised our rates enough, and got big enough clients, we could afford to work for one or two clients at a time and not have to deal with the constant scrambling to keep the pipeline full, manage a dozen small clients while also finding time to create work they’re happy with.

        But how do we even find those clients? We don’t have the education, the pedigree, the raw talent or the learned skills to feel confident charging enough to make this plan work. And besides, even if we did have that confidence, we don’t have anyone in our network that would even consider paying that kind of money for the work we do.

        Dreaming of a Stable Life

        Finally, our mind turns to daydreaming about finding a day job and moving on from this endlessly exhausting life of constant attention on keeping all the balls we’re juggling in the air.

        The more we think about it the better it sounds.

        No pressure, limited responsibility, a steady paycheque, the ability to leave our work at the office when we come home in the evening.

        As enticing as this sounds at first, we know that this isn’t the answer. We know that we need to create, that there is work inside us that matters and needs to find its way out.

        But things can’t carry on like this, the endless client revisions, emails, phone calls, the emotional rollercoaster of creating work for other people.

        Where Next?

        As we run circles in our mind for weeks and then months, we realize that our whole life’s dream had been to do this work for ourselves.

        It had seemed near-impossible at the time, but we had achieved it, and fairly quickly at that.

        So what next?

        We had been so excited to realize our dream that we didn’t take the time to set our sights for the next star to shoot for.

        Instead, we got caught up in a reactive cycle of just striving to do more of what we were doing, without any intention behind it, no thought of why we were actually doing the work we were doing in the way we were doing it.

        As we look inward and reflect on what it is we really want from our lives, we realize that there is another dream buried inside us that we had yet to acknowledge.

        Repeat The Process

        We realize that our skills and experience have the potential to do more than provide a living for us and create work for our clients. We have the potential to create an impact with our work.

        The pieces of a new vision start coming together in our mind and our excitement builds as we begin to feel the pull on our internal compass aligning itself to a new North star.

        It doesn’t look easy, in fact it looks almost impossible.

        But we achieved the impossible once, who’s to say we can’t do it again?


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

        https://medium.com/@jeremyenns/dont-measure-worth-wrong-things-d29f13066cf2https://medium.com/@jeremyenns/dont-measure-worth-wrong-things-d29f13066cf2

        Cloud Cover

        Photo by pixpoetry on Unsplash

        I always love flights that take off on an overcast day.

        The wheels leave the runway and you’re thrilled by the sight of the mundane world below receding further and further away.

        As you reach the cloud cover you get jostled around as you climb through it, a shadow of doubt crosses your mind as to whether or not it’s supposed to be this bumpy, if the plane can actually handle this turbulence.

        And then, finally, there’s that magical moment of bursting through the clouds, emerging on the other side into a spectacularly bright, clear world of dazzling sunlight and clear skies.

        The stress of travel seems to melt away, and you can’t help but feel in awe of the experience.

        If you’re leaving a place that has more cloud than sun for large chunks of the year — Vancouver, London, or most recently for me, Tallinn — this might be the first time you’ve seen the sun in days, or even weeks, further amplifying the majesty of the moment.

        On a recent flight from Tallinn to London, I was struck by the similarities that this experience has with the work of being a creator.

        The Strata of any Creative Project

        We start on the ground with a clear view of where we’re going, sure there may be a few clouds in the sky, a few problems we don’t know quite how to solve yet, but the problem seems manageable and fairly straight-forward.

        As we begin to explore the work, we realize that there is more unknown than we had initially thought, more to learn, research, develop. That initially clear sky has clouded over, but we’re still generally sure of which direction to head in, with clear reference points and boundaries around us.

        We climb further into the project, getting it off the ground and soon find ourselves in the middle of the cloud cover.

        It’s at this point we often become disoriented and lost. The big picture view has been lost and all we can see is what’s right in front of us.

        Turbulence tosses us around, there are setbacks and sidesteps, sometimes we might rapidly lose altitude for a period of time and we wonder whether it might be best just to turn back.

        It’s worth remembering at this stage that there are clear skies up there if we have the will and the bravery to keep showing up, pushing ourselves to climb further and the faith that if we persist, we will eventually burst through the cloud layer and into that bright, dazzling world of sunlight above.

        Keep on the throttle and point your nose up.

        What About This?

        Photo by Annie Spratt on Unsplash

        It’s easy to get wrapped up in the seriousness of our work and forget the lightness we felt when we first started down the path that led us to where we are now.

        Sure, it’s important work and we should take it seriously, but it shouldn’t feel serious, or heavy, or somber.

        For many of us pursuing creative, entrepreneurial lives, we wrap our self-worth up so inextricably with the work we do that we become cautious about taking risks, worried that any failed experiments in our work reflect equally upon us as people.

        And then, of course, there’s the posturing.

        The need we all seem to feel to pretend that we know exactly what we’re doing at every moment, that every success was the result of a masterstroke of strategic planning, and any failures — if we share them — were the result of impossible to predict events that ruined our otherwise exquisite planning.

        It feels amateurish to come across as light-hearted and playful about our work–no matter how meaningful it is–when there are so many people who are so keen to display how seriously they take their work.

        We feel like we must not be real entrepreneurs, real leaders, real artists if we don’t approach the work we do with the same deadpan seriousness as the others we see around us.

        And so we adopt the air of one who has been given a weighty responsibility by the universe itself. A duty which, should we fail to fulfil, will surely result in the destruction of everyone and everything we know.

        We start by putting on this heavy mask only when others are around. But soon enough it becomes a part of us, and it starts to impact our work.

        We soon find ourselves experimenting less, playing it safe, afraid that any crack in the perfect, serious, exterior we’ve cultivated will leave us exposed to the world as the fraud we worry we might be.

        This is not the way to create work that matters.

        Work that matters is probably work that hasn’t been done before, or hasn’t been done the way you’re doing it.

        Work that matters requires you to show up every day with the understanding that what you’re doing today, this week, month or year might not work, but that trying it anyway is essential to finding out what might.

        Instead of pretending we know what we’re doing, doubling down on what we already know works, and playing it safe, we need to show up again and again and ask, “What about this?”

        Sure, there’s a place for strategy and thoughtful planning, but there’s also a place for play, for experimentation, for whimsy even.

        Don’t let your best ideas lie on the cutting room floor because they’re not serious solutions to the problem at hand.

        One day, someone’s going to pick up up those pieces and disrupt everything with a way of doing things that’s never been done before.

        It might as well be you.


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

        https://medium.com/swlh/embrace-eagerness-3c450af03afahttps://medium.com/swlh/embrace-eagerness-3c450af03afa

        Are You A Believer?

        Photo by Ran Berkovich on Unsplash

        There’s a difference between believing that our work and our ideas have the potential to change the world and believing that people will actually be excited to enroll in what we’re doing and help move our vision of the world forward.

        If we want to change the culture for the better, both are essential. But they’re not equally easy to come by.

        Most of us doing work that drives us have the former. We really truly believe that we’re on to an idea that could benefit those who interact with it.

        You could argue that we may even place outsized importance on the work we personally are doing and exaggerate, at least in our minds, the potential impact of our work, but that’s a topic for another time.

        For us, the problem isn’t a lack of belief in the potential of our work, but rather a lack of belief that people will be eager and willing to sign on for the journey.

        Our lack of belief is probably based on perfectly reasonable past experiences.

        We’ve created work we believed in before, released it to the world, invited others to take part…

        …and got crickets.

        And so while we believe in the potential of the work once we can get it into people’s hands, we don’t believe in our ability to get anyone else as excited about it as we are.

        That feels too salesy. It feels arrogant, too pushy, too intrusive.

        What do we know? Maybe our work, products or services won’t actually work for anyone else.

        If we’re going to change the world through the work we do, at some point we need to get over this doubt, or at least shoulder it aside and ignore it long enough to do the important job of sharing our work with the people it was designed to help.

        We need to believe that there are people out there who are actively looking for a solution to their problem, the one we have the answer to.

        We need to believe there are people out there who won’t feel like we’re intruding when we show up in their inbox or their newsfeed or on their doorstep.

        We need to believe that there are some people who spend all week looking forward to our newsletter, our podcast, our live video, and they will be disappointed if we don’t show up.

        If you believe in your idea and your work, you owe it to everyone who could benefit from it, everyone who is waiting for your solution to their problem, to actively seek them out and share your work with them.

        Create your work, hone your message, then find the people who will circle the calendar on the day you show up to share it.

        This is how you build a movement.


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

        https://medium.com/@jeremyenns/you-cant-yell-loud-enough-but-you-don-t-need-to-7435abacafa8https://medium.com/@jeremyenns/you-cant-yell-loud-enough-but-you-don-t-need-to-7435abacafa8

        What Tide Pools Taught Me About Life

        Photo by James Donaldson on Unsplash

        One of the great vacations my family took when I was a kid was a road trip down the Oregon coast and into Northern California.

        I was 12 years old when we hitched up our tent trailer to our minivan, pulled out of our driveway in Edmonton, Alberta, and headed for the US border, making our way through Montana before snaking our way up the Columbia River Gorge toward the coast.

        That trip was the beginning of what has become a life long love affair with Oregon, and particularly the coast, a place I find to be filled with magic, energy, and inspiration.

        I’ve returned a handful of times since that first trip, and each time end up discovering new places and walking away feeling renewed.

        While I don’t remember many specifics from that trip, there’s one memory — and some advice from a park ranger — that I recall every time I return. In fact, the advice has become a practice I apply increasingly in the rest of my life as well.

        Science(ish)!

        If you’ve never gone tide pooling, you’re missing out.

        (It’s possible you’re not missing out and that I’m just a nature nerd, but for now, let’s just compromise and say that I am a nature nerd and you also are missing out, cool?)

        Tide pools form when the tide comes in, covering a rocky, uneven, pothole-filled coast, and then goes out, leaving dozens or even hundreds of pools filled with seawater.

        Aside from seawater, however, these pools are inhabited by countless flora and fauna adapted specifically to live in this intertidal zone.

        Anemones, urchins, sea stars, crabs are some of the most common and obvious inhabitants, although apparently it’s not entirely uncommon to find octopi, eels and other more exotic surprises.

        This vacation down the Oregon coast was the first time I’d ever gone tide pooling. Mainly I was excited for the sea stars, which seemed thoroughly exotic to 12-year-old me.

        Sea Stars Galore

        Our first excursion was timed to coincide with a daily demonstration by the local park rangers who promised to explain all the tricks of the tide pooling trade (and much to my dismay inform us that we weren’t allowed to pick up the sea stars).

        As we started picking our way among the pools dotting the slick, rugged shoreline, I immediately spotted the main attraction, and feasted my eyes on the dozens of sea stars.

        Green, orange, even purple! There were the familiar five-legged variety, but there were also some less common and heretofore unknown to me, eight-legged stars.

        The Art of Tide Pooling

        Pretty soon, however, sea stars began to feel a little less exotic, and other than them, the tide pools started to seem kinda boring… I mean, sea stars themselves aren’t the most exciting creatures on Earth, all stuck to the wall, unmoving and all.

        Indeed, tide pools seemed to be little more than real-life, water-filled dioramas, with little to no movement in many of them, and only the gentle movement of the waves lapping in and out of other lower-lying pools.

        Perhaps seeing that I was moving from pool to pool, looking for about 3 seconds in each before moving on to the next one, clearly in search of something “interesting”, one of the rangers walked over.

        “Do you want to know a trick?” she asked.

        I didn’t really want to know a trick, but not feeling like I had much choice in the matter and that it might be rude to decline, I nodded.

        “Ok, so when you look into the pools they’re kinda boring right? What you need to do is pick a pool and just stare at it for 30 seconds or a minute. It doesn’t look like much is going on in the pools at first, but once you stop and really pay attention, you’ll start noticing all kinds of little critters that you didn’t see before!”

        Skeptical, but without much choice in the matter seeing as she was hovering over me, waiting for me to put her tip into action, I stared down at the pool in front of me and waited.

        Sure enough, as I stared for 15 seconds, then 30, then 45 I began to notice that activity abounded, albeit at a smaller scale than I had originally been looking for.

        There were tiny fish hiding in the swaying arms of anemonies, water beetles striding across the water’s surface, hermit crabs scuttling along the bottom, and more.

        It was a sight that once seen, could not be unseen, and the moment of seeing past the initial stasis as my eyes adjust to the micro activity has become something I look forward to and find wonder in every time I visit the coast and go tide pooling.

        Adjusting Your Scale Of Vision

        For some reason, the park ranger’s lesson has stuck with me for close to 20 years, and more recently, I’ve been thinking more about how that lesson translates into the rest of my life.

        How often do we let our first impressions of a person, place, or experience deter us from digging deeper and exploring further?

        With near-infinite and immediate access to seemingly everything, it often feels easier to put more weight on our initial reactions, and once any thrill has worn off, go looking for our next hit of excitement.

        This behaviour perhaps most obviously apparent in the world of online dating, and has certainly been well documented.

        But how many other areas of our lives are we passing up a chance at being truly awed because we were in too much of a rush to take a couple of minutes to let our eyes adjust, look a little more closely, and discover a fascinating world we didn’t know to look for?

        Everything is interesting if you approach it with curiosity and know what to look for. But it usually takes more than a cursory glance to have our curiosities piqued.

        Life is richer when we approach the things we encounter with this mindset, slow down, take the time to understand who and what we’re dealing with, and dig past our first impressions.

        By doing this consistently, we lead more interesting lives, bring out the best in ourselves and others, and experience states of wonder and awe more often.

        The Long View

        It’s Saturday night, around 11pm, and you’re fully down the rabbit hole, researching your competition, hopping from website to website, social channel to social channel, the pit in your stomach sinking lower and lower.

        Sure, you know comparison is the thief of joy or whatever that saying you heard once is, but you NEED TO KNOW.

        You justify it by reasoning that surely by keeping tabs on what the competition is up to it will only help you run your own business better.

        You sure as hell don’t know what the hell you’re doing, and by the looks of things, they certainly do. Maybe you could learn a thing or two.

        They have the types of high-end feature clients you dream of, their blog posts are shared regularly, they post engaging content on every conceivable social channel, of course they put out a highly ranked podcast as well, and what’s that? They’re getting into YouTube now too??

        Your first reaction, of course, is to immediately map out a plan for how you can do everything the competition is doing, BUT BETTER.

        “Maybe you’ll even get on TikTok,” you muse to yourself, “I need to one-up them somewhere.”

        You sign up for TikTok out of curiosity only to find they’re already there.

        “Damn It.”

        You add TikTok to your now multi-page list of required content and social channels on which you’ll out-produce everyone else in your industry and shut your computer.

        You resolve that Monday morning is the day you’re finally going to step up and get into the arena with the heavyweights whose shadows you’ve been living in up to this point.

        You don’t know how you’re going to do it, being a small shop without the team or resources of some of your larger competitors, but that shouldn’t matter should it? With the power of the internet at your disposal, you can accomplish anything right?

        Sure you’ll need to hustle. Stay up late. Maybe work weekends.

        But it’ll all be worth it when you grow to the point where you’re the one with the big clients, the fancy website, mountains of content.

        Right?

        Ummmmm No.

        I don’t know about you, but the “strategy” outlined above doesn’t really sound like a way I want to spend my life.

        I care about growing my business, continually improving, doing better, more interesting work for more interesting clients, but I don’t believe that flashier, more omnipresent marketing is the only way to do that.

        Yes, that method can 100% work for some businesses with some types of goals, and it’s what we help people do with our podcast and content amplification work at Counterweight Creative.

        But that’s not the type of business I want to be myself.

        For people like us, it’s essential to be clear on the type of business and lifestyle we want for ourselves, the types of clients we want to work with and how we want to be seen in the world.

        Often, that means distancing ourselves from the pressure to be everywhere all the time, because for most of us, that strategy is not in service of building the businesses and lives we really want.

        Now, believe me, I’m as susceptible as anyone to getting sucked into the comparison game. Of seeing what others are doing and wanting to add that piece into what I’m doing.

        Shiny objects abound and it’s easy to go chasing each and every one of them in search of a short term boost in attention.

        More and more, however, I’m finding myself gravitating to putting in time and effort into developing the areas that will pay off in the long haul. Actions that I take consistently now that may not be useful in the short term, but will pay off massively 3, 5, or 10 years from now.

        Unfortunately, in a world where most of us have a to-do list whose end only gets further and further out of sight with each passing day, practices aimed at investing in the long-term are often the first to get cut in favour of putting out short-term fires.

        Long Term Strategies

        Things like designing a client experience that goes beyond getting the work done and feels like magic and causes people to rave about you.

        Investing in helping your team develop as individuals as much outside of work as in the work they do for you.

        Developing a robust point of view and philosophy about the work you do and understanding how you can use your work to move the culture forward.

        Investing in developing real skills like communication, empathy, vulnerability, resilience and bravery on top of your field’s traditional hard, technical skills.

        I’m convinced that for people like us, people with big ideas, a desire to change the culture, and a belief that we can do it, these are the things we need to be focusing on developing and growing into.

        Forget Your Existing Metrics

        The results of these efforts aren’t as easily measurable as putting time into developing an Instagram strategy and seeing our follower count grow. But for most of us, Instagram is not an essential piece in moving our visions forward.

        Besides, your long term investments are going to far outlast Instagram.

        When we focus on the long term and invest in the areas we’re sure can only help us achieve our bigger purposes, the comparisons begin to fade, the pressure to do more eases and short-term tactics begin to feel like a distraction.

        We’re able to stay in our lane with confidence that whatever changes may come in our industries, societies, and the world, we’re equipping ourselves to be leaders in the future.

        Pretty soon we start to feel like while we might be trailing our competition in the short-term sprint for attention, we’re quietly pulling away in the long-term marathon for impact.


        Finishing Is Overrated

        Photo by Kelly Sikkema on Unsplash

        I was feeling sentimental, and a little nostalgic the other night as I walked home from the office.

        I didn’t have time to start another podcast before getting home, but I wanted to listen to something.

        In my nostalgic state, I found myself scrolling through old songs I had recorded years prior.

        My Origin Story

        My current role running a podcast agency was preceded by going to school to become an audio engineer and record producer.

        My dream had always been to split my time between producing music for others, while also writing and recording music myself, a dream that never panned out but ended up leading to greater things.

        The playlist of old recordings spanned a decade of sporadic work and meandering styles, from singer-songwriter to metal, to electronic to alternative rock to hardcore punk.

        I wrote and recorded single songs, releasing a couple of them under different monikers, which maybe 15 people downloaded in total.

        I envisioned these songs being the beginnings of larger projects, culminating in EPs or albums, but the closest I ever got was a few dozen songs existing in various states of completion on my hard drives.

        Finish The Work?

        In the world of creative work and entrepreneurship, there’s a huge emphasis placed on finishing or shipping the work.

        As creatives, we can find ourselves endlessly tweaking our work, convinced that it could always be better, afraid of overlooking some glaring flaw for which we’ll be criticized and written off as just another amateur trying to pass ourselves off as a pro.

        In such cases, I think the advice to just ship the work is valid and useful. But I don’t think it always is, and I think the sentiment can sometimes be downright unhelpful.

        Permission To Explore

        As I listened through the eccentric playlist, I started thinking about my larger trail of creative work that’s led me to where I am now.

        Besides the decade’s worth of aforementioned music, there are the sketches and drawings from junior high, angsty high-school poetry, my photography blog, tens of thousands of photos, more than a few of which were actually paid work, my old travel blog, the short-lived travel vlog I started during my first year of full-time travel, my podcast blog, recent explorations into calligraphy and hand lettering, this blog (apparently I’ve started a lot of blogs…), podcasts created for myself and clients, and more.

        As a kid, I even invented a new billiards-style game in my basement, printed off the rules and made my parents and friends play. I vaguely remember that the blue, black and purple balls were somehow important, and as such, I dubbed the game Bruises.

        Thinking through my past creative endeavors, I realized that I had pursued many of them with a significant amount of dedication and seriousness. Some of them, such as photography and music I’m sure still have a place in my future.

        And yet, even in those pursuits in which I really made a run at, I can’t say that I ever really finished any work to the extent that I would have liked.

        Perhaps that’s why I never succeeded as a musician or photographer, but I also never quite felt the pressing need to finish in those fields.

        One of the things I’ve come to most appreciate about myself is that I’ve started down many different, (mostly) unrelated paths, typically with a good deal of conviction and discipline, and then been fine dropping the pursuit and hopping over somewhere else once I lost interest or realized that the path didn’t lead quite where I thought it did.

        Choose Your Dips Wisely

        Most new pursuits are easy and exciting when you first start out. You’re able to put in work and see measurable improvement, maybe on a daily basis.

        Ultimately, however, you reach what Seth Godin calls The Dip, the point at which something stops being easy and exciting, where you realize that to achieve mastery and further success you must work through what I think of as The Hard Stuff.

        In thinking about my own creative history, I’ve recognized a pattern of starting things and sticking with them up to The Dip, before either petering out or dropping the pursuit immediately.

        While I’m convinced that to become exceptional at anything you have to work through The Dip, none of us has the bandwidth to work through every Dip we come across. We need to be selective about the Dips we lean into, because each one might take months, years, or even decades to reach the other side of.

        To discover the area in which we can do our best work, achieve the greatest fulfillment, and create the greatest impact, it’s essential that we start a lot of things, but finish only a few.

        Only by reaching the various Dips can we look into their gaping chasms and ask ourselves whether this is where we want to invest our precious time and creative energy.

        Most things we start won’t be.

        In those cases, accept them for what they are. Content yourself with remaining a novice, with keeping it a hobby, or with dumping it altogether.

        Forget finishing, ignore the sunk cost and move onto the thing that excites you.

        Eventually, we each find a dip that’s worth bringing our full selves to, putting in the work, and finishing.

        But until then, just get busy starting.


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

        https://medium.com/@jeremyenns/what-about-this-3ecce03fd88chttps://medium.com/@jeremyenns/what-about-this-3ecce03fd88c

        Somewhere Else

        Photo by Jesse Bowser on Unsplash

        Somewhere Else is an intriguing place.

        Where You Are is filled with too much noise, too much uncertainty, too many problems.

        The right people aren’t here to build out your community, network, and organization.

        It’s boring, there’s nothing fun to do, nothing unique.

        It’s easy to imagine that Somewhere Else has everything you’re looking for.

        The right people and networks, unique events and activities, everything that’s missing from Where You Are has somehow been cultivated there.

        You might transplant yourself to Somewhere Else and at least at the beginning, it’s everything you imagined it would be.

        Sure maybe you haven’t tapped into those networks, met those people, gone to more than a couple of those unique events, but they’re here, and in time you’ll become an insider, reaping the benefits of your new and improved location.

        A couple of years pass, however, maybe only a couple months, and Somewhere Else is starting to look a lot like Where You Are.

        You realize that it’s not just you. Everyone here in Somewhere Else is talking about Somewhere Further.

        While most of them just talk about Somewhere Further, you’ve done this before, you pack up your things and take the leap, sure that Somewhere Further is going to fulfill the hype that Somewhere Else promised, but failed to deliver on.

        The cycle repeats, taking you from Somewhere Further to Further Still, to Far Far Away.

        Optimism and excitement turns to the mundane, disappointment sets in, and your feet begin to itch.

        Soon enough, you start hearing people in Far Far Away talking about Where You Are as the most exciting place to be right now.

        It’s got everything, they say. An amazing network in your industry, tons of events, a vibrant art community, and don’t forget the craft beer scene.

        You’re skeptical, but it’s been a while since you left. Maybe Where You Are has transformed from the boring, static place it was when you were there to a thriving, energetic hub of innovation and excitement.

        Far Far Away was getting boring anyway, so once again you pack up once again and head back to Where You Are.

        It doesn’t take long to realize that not much has changed in Where You Are.

        You hang out with the same people you used to, work a similar job to the one you had, pass your time in the same ways you did when you first lived here.

        Sure the craft beer scene is good, but none of the new places have anything on the old spots you already knew about and visited regularly.

        How could people in Far Far Away have been so wrong about this place?

        Slowly, painfully, you begin to take stock of the evidence presented by your experience.

        Maybe Somewhere Else was never as intriguing as it appeared.

        And maybe Where You Are is what you make it.

        Most People Don’t Think

        Photo by Tachina Lee on Unsplash

        There are a lot of smart people in the world, no doubt about it.

        But most of them don’t spend much time thinking.

        I mean, sure, their brains process information as they walk around all day. Sometimes they actually come up with some pretty nifty solutions to interesting problems while they’re at it.

        Most of that thinking is reactive, however.

        There’s nothing wrong with reactive thinking. I’m glad my brain works reactively to make quick decisions, keep me safe, carry on conversations like a normal human without minutes of silence between responses while I mull over what to say next.

        When I say most people don’t think, I’m talking about deliberate, focused, strategic thinking on a specific topic or challenge.

        As people trying to solve interesting problems in a way that changes people for the better, this then is our opportunity.

        The way I see it, there are 5 reasons why most people (and maybe even you) don’t utilize their brains to their fullest potential.

        1. Thinking Time Is A Luxury

        We’re all busy. We’ve all got more on our to-do lists than will fit into the day already, not to mention all the new items that will have been added by day’s end.

        With so much to do, even if we’d like to block off some time every month, week, or even day for deliberate, strategic thinking, invariably, some fire or other flares up that requires our immediate attention.

        It’s no surprise that the first thing to be dropped from our schedule in those cases is that block of what looks suspiciously like “free time,” time that we may not expect to result in a defined outcome, time without an immediately measurable ROI, time with no urgency or outside expectation to it.

        For the better part of two years, I’ve struggled to book off the last Friday of every month as a strategy day where I do little but think about the big picture of my business.

        It was a day that I looked forward to every month, and without fail, I was sure that the time I spent in focused thought would surely result in my next breakthrough.

        In reality, I’ve probably only really completed 5 of these days.

        In every other instance, something came up that I felt couldn’t be ignored and out the window went the luxury strategic thinking day.

        I’ve since moved away from the infrequent large blocks of thinking time to shorter chunks scheduled daily.

        I’ll often set aside as little as 15 minutes to brainstorm on a problem, something I’ve come to refer to as a Brainstorming Sprint. Once I start, however, it’s not uncommon to get sucked in, and pretty soon everything else on my todo list starts to look a little less important.

        But in order to get sucked into our brainstorming, we first need to know what problem we’re trying to solve.

        2. You Need A Defined Problem

        If we’re able to block of the time for focussed thought, we run into a second challenge.

        Often, we don’t actually know what the problem is that we’re trying to solve, or what we should be thinking about.

        Most of our projects are of a scale that won’t be solved by simply sitting down and thinking on them for an hour, or even a day.

        The sheer size leaves us first procrastinating on putting any thought toward them because we can’t imagine where to start, and then spending any time we do dedicate to the problem looking at the project as a whole and vainly striving to elegantly solve it all in one fell swoop.

        What we need to do instead is find traction first.

        Recently, I sat down to spend an hour thinking about the Podcast Marketing Course I’m working on.

        I had roughly mapped out the modules about a month before, but hadn’t put any more time towards it since and now wasn’t quite sure where everything was at.

        As I sat down I went through my notes, zooming in and out on each of the six modules in the course, going through the bullet points under each subsection and subsection’s subsection until I was thoroughly lost, overwhelmed, and completely sure the project was worthless and would most certainly fail if I ever completed and released it.

        After half an hour of flailing about, not knowing which chunk of the elephant to bite off first, I forced myself to reset, look at one specific module of the course and methodically work through the outline for that section thoroughly and in order of presentation.

        With focus and constraints on what I was thinking about, I was almost immediately able to lock in and think through what the necessary points that needed to be conveyed were, rough out student worksheets, and do some research on necessary examples to illustrate those points.

        An hour later, the outline of the module was not only complete, but more detailed and thoughtful than I had originally anticipated it would be.

        Sometimes, you might need to spend an hour, or day even, simply breaking down the larger, amorphous problem into a series of smaller, understandable problems that can each be solved in one sitting.

        I’ve found that often, projects I’ve worked on have stalled and been procrastinated on for months only really felt hard because there were a few key decisions that needed to be made before the work could start.

        In the end, months of procrastination and lack of clarity have often been solved by decisions that were made with 5 minutes of focused thought.

        We’re ridiculous creatures us humans.

        3. Thinking Is Hard

        A lot of the problems we’re trying to solve are long-term projects, many of which with no clear, defined path to solving.

        Sometimes we have a roadmap at our disposal from someone who’s done something similar before, but not always.

        We might sit down, start at a blank page in front of us, get bored, check-in on Twitter and next-thing-you-know-our-scheduled-time-is–up-and-thank-God-it-is-cuz-that-was-uncomfortable-and-unproductive-and-I’m-never-doing-that-again.

        As we already discussed, you first need a clear problem that you’re working on defined to maximize your thinking time, but even once you have that, the scope of the problem can be overwhelming.

        I find that it’s often the blank page that is the greatest barrier at this phase. We feel like we should write something but don’t have any thoughts to actually write.

        So we keep staring at the page and end up thinking about thinking instead of thinking about the problem at hand.

        I like to start by writing down any questions I know will need to be answered, even if I don’t know the answers. I’ll also write down topics that I need to research and learn more about and then do some research and find articles, books, etc on the topics.

        I may not read them then, but I’ll bookmark them and past the URLs in my brainstorming document.

        We all think and work through problems in different ways, so experiment and find what works best for you. It might be pen and paper, digital note apps, voice memos that you then transcribe, mood boards, or anything else.

        I like bullet points and expandable lists so I do most of my brainstorming in Workflowy, but I know some people who are much more visual and use tools like Milanote to create more robust mood boards.

        Use what works best for you and just start writing, sketching or creating something. Get past the barrier of the blank page and the floodgates will often open.

        4. Productive Thinking Takes Discipline + Habit

        I’ve come to think of my thinking sessions much like a meditation practice, but instead of clearing my mind I aim to intentionally follow my curiosity down whatever trails it wants to follow.

        Much like meditation, I feel I’m able to get more benefit from the practice by building a routine around it and approaching it with discipline.

        Even when things are busy, I still set aside 15–30 minutes to work on some problem or other.

        When I’m not feeling particularly creative or in the mood and would rather work on something else, I force myself to settle in and spend that time thinking.

        Sure, sometimes it doesn’t amount to much, but some of my most productive sessions have come after telling myself I’d just spend 15 minutes thinking on a problem just to fulfill my obligation to myself, and 2 hours later have filled pages with notes and am clearer on the big picture solution.

        I’ve come to suspect that “not being in the mood” or “feeling uninspired” is just Resistance in disguise, and as such now redouble my resolve to push through those feelings when they arise.

        5. We Have An Idyllic View Of Thinking

        When I first started my ill-fated Last Friday of the Month Strategy Day policy, I had a whole ritual around the day.

        I would start the day with a walk to clear my head, calibrate myself for what I was working on, and then head to one of my favourite coffee shops to post up for the day.

        I’d fill out a monthly assessment and planning questionnaire that I had created to start things off in a structured way, and then get into more free-form thinking and brainstorming.

        After lunch I’d go for another walk and end up somewhere else cozy to work for a couple more hours. In the evening I’d treat myself to a nice dinner and maybe do something fun that I’d been putting off indulging in.

        The days were fantastic, and you can probably see why I looked forward to them. But they weren’t sustainable.

        While I loved the ritual and it worked to put me in the right headspace, I had become convinced that only when all the conditions were right could I do any thinking and strategizing that would amount in a breakthrough of any kind.

        Many of us have an idealized view of the philosopher, poet, writer, isolated somewhere in a cabin in the woods, free of distraction, free to tap into their best work and biggest ideas uninterrupted.

        The problem is that for most of us, these circumstances will never come about, and even if they did, I think many of us would be disappointed with the results.

        Better instead to take your conception of a strategy or deep thinking session down off of its pedestal and turn it into something more rugged and durable.

        Build a practice where you can tap into your most creative ideas and solve interesting problems in the most uninspiring locations.

        Sure, Walden Pond is a more romantic locale than an office cubicle or a poorly lit basement suite apartment, but if that’s what you’ve been given, learn to tune out your surroundings and let your mind run free regardless of where you are physically.

        Tap Into Your Genius

        Since beginning my structured Brainstorming Sprints, I’ve found myself procrastinating less, making more headway on the ideas I have, and coming up with more ideas overall.

        I’m convinced that this says less about me than it does about the benefit that we can all get from making space for focussed thought.

        We all have ideas that could result in meaningful work if only given a little chance to breathe, to ruminate, to explore their surroundings. Too often, however, they get crowded out by client work, social obligations, or our own Resistance telling us not to look any closer because it’s a stupid idea that will never work and you don’t even know how to approach it anyway…

        Push back on Resistance, define your problem, and let your genius breath.

        One day, we may all thank you for it.

        You Can’t Yell Loud Enough (But You Don’t Need To)

        There’s a lot of noise out there.

        A lot of it is spam, a lot of it is amateur, a lot of it is vapid.

        But a lot of it is good. Really good.

        You already know that of course. You might spend your days trying to shout above that noise in an attempt to be heard.

        You know your work has an audience out there that can be impacted by it, who can be changed by it, who may be actively looking for just what you’ve got.

        But they’ve done their best to tune out you and the rest of the noise out of sheer exhaustion.

        You strain your vocal cords, shout just a little louder, hoping to break through, catch just a sliver of their attention.

        You’re sure that once they hear your frantically delivered pitch they’ll be yours for life.

        But you can only shout so loud for so long before your voice gives out.

        What if getting heard wasn’t about shouting though?

        What if getting heard was actually about dropping your voice and speaking directly, intimately to people who were willing to lean in to hear what you had to say?

        What if instead of trying to share your message to a football stadium of people waiting for you to finish so the game can start up again, you shared it around a campfire, to a small, rapt audience who huddled closer, eyes fixed on you, ears tuned in to your every word, your every gesture.

        This is what building an audience today is about.

        This is how to create and share work that changes people.

        It isn’t quick. It isn’t easy.

        It requires you to commit to the long game. To show up again and again to a small group of people when what you really want is to show up for everyone.

        It requires you to build up trust, person by person. To speak so intimately to them that they feel like they’re the only one you’re speaking to at all.

        It requires you to understand that movements are built by creating a culture and an experience that people rave about, share, invite others into who could benefit.

        Be incredibly generous with your work, your knowledge, your time. Give everything away to your audience for now.

        Understand that the attention, the returns and the impact will come, there is a time to reap and a time to sow. Besides, you’ll have new work, better work, more meaningful work to share when the time comes to charge for it.

        But that time is not here yet.

        Prove your work can change even just one person, hone your message and build up just a little more momentum every day.

        You’re going to need to push the thing yourself at the start, but do the work and eventually, it will pull you forward on its own.

        Find out how to get in front of the right people where you don’t need to yell to catch and hold their attention, but where you can intrigue them enough to lean in a little closer to hear what else you have to say.

        This is the way for people like us to change the world.


        Creative Wayfinding For Ambitious Optimists.

        This Shouldn’t Be Easy

        Photo by Jeremy Perkins on Unsplash

        We’ve all heard the near-mythic stories about founders who worked 100 hours a week for years while they were starting up their businesses, making incredible sacrifices in every other area of their life before striking gold and rocketing up the Forbes net worth list.

        Most of us don’t aspire to be billionaires, or maybe even millionaires. We want to create work we believe in, work that matters and get paid fairly for it.

        For many of us, part of the draw is that a life in which we work our own gig appears to be full of more ease, more flexibility, more control over our routines and circumstances.

        While we may not aspire to build startups or businesses with massive teams, we understand that setting up our own little business for ourselves will still take work, commitment and sacrifices.

        So we take the familiar founder stories and scale them back to suite a smaller-scale operation.

        Setting Expectations

        We’re not really sure how someone could humanly work 100 hours a week, but 50 or 60 seems manageable, at least while we’re starting up.

        We feel like by putting in the long hours, by prioritizing our work over the rest of our lives, we’re following in the footsteps of a long line of entrepreneurs before us.

        This is exciting for a year, and our business grows, validating the time, effort and focus we put in. So we continue on as before, feeling that this must be the only way to build a business, that maybe after another year things will start getting easier.

        We commit to building up systems to allow us to work smarter, instead of harder. We might even bring on a contractor or employee or two to help free up our time more.

        This helps, at least a bit, shrinking our to-do list from four pages more than we can do today down to two and a half.

        There’s fewer minutiae, less client work on the list, more big picture decisions, but we start to feel the pressure of those decisions now that they will affect more than just us.

        Again, we wonder, “When is this going to get easier? Will this get easier?”

        Reassessing Your Dream Job

        It’s easy to fantasize about a life in which we work for ourselves and are in complete control of everything in our orbit.

        Clients show up precisely when we need them, they give us complete creative control over the work, and we get paid more than adequately for it.

        From the outside, it appears that we’re the only ones for which this entrepreneurial life is hard. Everyone we can see around us is experiencing massive growth, landing dream clients, creating incredible work, and posting a steady stream of photos on Instagram of them traveling the world, working from exotic locales.

        The reality of our day to day is so much harder than the life we left behind when we started down this road.

        We realize that the hard life we traded in, one filled with work we didn’t believe in, being told what to do by others who created a plan we had no say in, passing our weeks waiting for the weekend was replaced by a new, and much harder kind of hard.

        In this new hard, we are responsible for everything in our work, we often don’t know what to do and have no one to tell us what plan to follow, and the boundaries between our personal lives, our evenings, our weekends have all but disappeared.

        Not to mention we have to maintain the time, energy and inspiration to create work we’re proud of while juggling the business side of things.

        For some of us, we realize that this isn’t the easy life we thought it would be, and that easy is more important to us than doing the hard work of creating work that matters. And that’s fine.

        But for those of us who are committed to creating our best work, work that changes people, that has an impact, maybe we need to realize that this life shouldn’t be easy.

        We should realize that being a creator is a privilege, that if it were easy, everyone would do it, and that what we might lack in ease, we make up for with pride in the fact that our work is making a difference in the world.

        Sure, we can create systems and structure our lives to create more ease in our lives, but this work will never be easy.

        Creating work that matters requires us to continually wrestle with the unknown, to show up with vulnerability and generosity again and again and again, asking, “What about this?”, to continually be learning, connecting dots, thinking outside the box.

        And then once we land on something that shows promise, we have to summon all our courage, all our resources, and face The Hard Stuff and expose our work, and ourselves, to the world, risking rejection and failure.

        Whether or not it succeeds, we must then to do it all again, because it’s what we are called to do.

        Making work that matters is not an easy life. It might be the furthest thing from an easy life.

        But if you feel the calling to channel that spark inside you to create something meaningful, know that it’s worth it.

        For you, and for all of us.


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

        https://medium.com/@jeremyenns/never-work-day-life-752912302ca0https://medium.com/@jeremyenns/never-work-day-life-752912302ca0

        Never Work a Day in Your Life

        Photo by Anthony Fomin on Unsplash

        “Do what you love and you’ll never work a day in your life.”

        For many creators, this was the dream we aspired to when we started thinking seriously (but not too seriously) about what we really wanted to do with our lives.

        Maybe you wanted to make movies, record music, play professional sports, write novels, maybe it was a job that didn’t even exist yet.

        Our individual dreams were varied, grouped together only by the refrain we grew accustomed to hearing, that we couldn’t do them as a career.

        For many of us, we didn’t allow ourselves to express our dream out loud, we only half believed it was possible, and as much as it annoyed us that our parents kept nagging us about having a backup plan in place, we kinda thought maybe we should have a backup plan in place.

        But we kept the dreams alive, kept working, and slowly what started as a dream and a hobby started turning into a craft.

        Honing Our Craft

        We realized that we could hone our inputs to influence our output, that with focused practice we could develop our skills further than we had thought possible, that it wasn’t all about innate talent.

        Most importantly, we realized that there were other people doing this work for a living and that maybe, just maybe we could model what they were already doing and maybe we could start doing our craft for a living as well.

        When we got our first client, we almost exploded with excitement.

        This was proof that this could work. This was validation that we had been right to keep our dream alive when everyone else told us it was impossible.

        That client didn’t pay that well, and our work still had a long way to go, but it was a start.

        Taking the Leap

        That first client led to more clients and pretty soon it was looking like maybe it was time to take the leap and turn our craft into our full-time gig.

        After too much deliberation, we built up the required resolve and made the transition to working for ourselves as professional creators.

        The thrill was immense, at least at the start.

        We were in control of our destinies, in control of our time, for many of us we could work from anywhere we wanted. A whole world of possibilities was suddenly open to us.

        If only we had the time and emotional bandwidth to take advantage of these new opportunities…

        Being the Boss Isn’t All It Was Cracked up to Be

        It didn’t take long for the initial thrill to fade into something more resembling an ever-increasing pressure, as we realized that we were in control of our destinies and that there would be no one to blame but ourselves if all these years of dreaming, working, and strategizing came crashing down around us.

        What’s more, this whole “never work a day in your life” thing sure seemed to be filled with a lot of work.

        Sure we still loved our craft and were proud of the work we created, but it didn’t feel like we spent a whole lot of time doing it anymore.

        Instead, our days seemed to be filled more and more with emails, bookkeeping, and researching our competition with increasing despair that we’ll never create work that good.

        Stagnation, and a Crossroads

        A couple of years in, we’re still getting by, getting some better clients, raising our rates, doing better work. But we’re beginning to question whether we can sustain this for another 30 years.

        Our days are still filled with less creating than we’d like, we’ve leveled up our skills but still don’t measure up to our competition, and the stress of doing good work while managing our business is really starting to wear us down.

        Assessing our options we figure that maybe we could hire people to contract work to, building out our team to lessen our own load. As we think more about it, however, it starts to sound like that might lead to us simply becoming a manager, leading to even less time doing our craft, and creating.

        We then figure that maybe if we raised our rates enough, and got big enough clients, we could afford to work for one or two clients at a time and not have to deal with the constant scrambling to keep the pipeline full, manage a dozen small clients while also finding time to create work they’re happy with.

        But how do we even find those clients? We don’t have the education, the pedigree, the raw talent or the learned skills to feel confident charging enough to make this plan work. And besides, even if we did have that confidence, we don’t have anyone in our network that would even consider paying that kind of money for the work we do.

        Dreaming of a Stable Life

        Finally, our mind turns to daydreaming about finding a day job and moving on from this endlessly exhausting life of constant attention on keeping all the balls we’re juggling in the air.

        The more we think about it the better it sounds.

        No pressure, limited responsibility, a steady paycheque, the ability to leave our work at the office when we come home in the evening.

        As enticing as this sounds at first, we know that this isn’t the answer. We know that we need to create, that there is work inside us that matters and needs to find its way out.

        But things can’t carry on like this, the endless client revisions, emails, phone calls, the emotional rollercoaster of creating work for other people.

        Where Next?

        As we run circles in our mind for weeks and then months, we realize that our whole life’s dream had been to do this work for ourselves.

        It had seemed near-impossible at the time, but we had achieved it, and fairly quickly at that.

        So what next?

        We had been so excited to realize our dream that we didn’t take the time to set our sights for the next star to shoot for.

        Instead, we got caught up in a reactive cycle of just striving to do more of what we were doing, without any intention behind it, no thought of why we were actually doing the work we were doing in the way we were doing it.

        As we look inward and reflect on what it is we really want from our lives, we realize that there is another dream buried inside us that we had yet to acknowledge.

        Repeat The Process

        We realize that our skills and experience have the potential to do more than provide a living for us and create work for our clients. We have the potential to create an impact with our work.

        The pieces of a new vision start coming together in our mind and our excitement builds as we begin to feel the pull on our internal compass aligning itself to a new North star.

        It doesn’t look easy, in fact it looks almost impossible.

        But we achieved the impossible once, who’s to say we can’t do it again?


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

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        Cloud Cover

        Photo by pixpoetry on Unsplash

        I always love flights that take off on an overcast day.

        The wheels leave the runway and you’re thrilled by the sight of the mundane world below receding further and further away.

        As you reach the cloud cover you get jostled around as you climb through it, a shadow of doubt crosses your mind as to whether or not it’s supposed to be this bumpy, if the plane can actually handle this turbulence.

        And then, finally, there’s that magical moment of bursting through the clouds, emerging on the other side into a spectacularly bright, clear world of dazzling sunlight and clear skies.

        The stress of travel seems to melt away, and you can’t help but feel in awe of the experience.

        If you’re leaving a place that has more cloud than sun for large chunks of the year — Vancouver, London, or most recently for me, Tallinn — this might be the first time you’ve seen the sun in days, or even weeks, further amplifying the majesty of the moment.

        On a recent flight from Tallinn to London, I was struck by the similarities that this experience has with the work of being a creator.

        The Strata of any Creative Project

        We start on the ground with a clear view of where we’re going, sure there may be a few clouds in the sky, a few problems we don’t know quite how to solve yet, but the problem seems manageable and fairly straight-forward.

        As we begin to explore the work, we realize that there is more unknown than we had initially thought, more to learn, research, develop. That initially clear sky has clouded over, but we’re still generally sure of which direction to head in, with clear reference points and boundaries around us.

        We climb further into the project, getting it off the ground and soon find ourselves in the middle of the cloud cover.

        It’s at this point we often become disoriented and lost. The big picture view has been lost and all we can see is what’s right in front of us.

        Turbulence tosses us around, there are setbacks and sidesteps, sometimes we might rapidly lose altitude for a period of time and we wonder whether it might be best just to turn back.

        It’s worth remembering at this stage that there are clear skies up there if we have the will and the bravery to keep showing up, pushing ourselves to climb further and the faith that if we persist, we will eventually burst through the cloud layer and into that bright, dazzling world of sunlight above.

        Keep on the throttle and point your nose up.

        What About This?

        Photo by Annie Spratt on Unsplash

        It’s easy to get wrapped up in the seriousness of our work and forget the lightness we felt when we first started down the path that led us to where we are now.

        Sure, it’s important work and we should take it seriously, but it shouldn’t feel serious, or heavy, or somber.

        For many of us pursuing creative, entrepreneurial lives, we wrap our self-worth up so inextricably with the work we do that we become cautious about taking risks, worried that any failed experiments in our work reflect equally upon us as people.

        And then, of course, there’s the posturing.

        The need we all seem to feel to pretend that we know exactly what we’re doing at every moment, that every success was the result of a masterstroke of strategic planning, and any failures — if we share them — were the result of impossible to predict events that ruined our otherwise exquisite planning.

        It feels amateurish to come across as light-hearted and playful about our work–no matter how meaningful it is–when there are so many people who are so keen to display how seriously they take their work.

        We feel like we must not be real entrepreneurs, real leaders, real artists if we don’t approach the work we do with the same deadpan seriousness as the others we see around us.

        And so we adopt the air of one who has been given a weighty responsibility by the universe itself. A duty which, should we fail to fulfil, will surely result in the destruction of everyone and everything we know.

        We start by putting on this heavy mask only when others are around. But soon enough it becomes a part of us, and it starts to impact our work.

        We soon find ourselves experimenting less, playing it safe, afraid that any crack in the perfect, serious, exterior we’ve cultivated will leave us exposed to the world as the fraud we worry we might be.

        This is not the way to create work that matters.

        Work that matters is probably work that hasn’t been done before, or hasn’t been done the way you’re doing it.

        Work that matters requires you to show up every day with the understanding that what you’re doing today, this week, month or year might not work, but that trying it anyway is essential to finding out what might.

        Instead of pretending we know what we’re doing, doubling down on what we already know works, and playing it safe, we need to show up again and again and ask, “What about this?”

        Sure, there’s a place for strategy and thoughtful planning, but there’s also a place for play, for experimentation, for whimsy even.

        Don’t let your best ideas lie on the cutting room floor because they’re not serious solutions to the problem at hand.

        One day, someone’s going to pick up up those pieces and disrupt everything with a way of doing things that’s never been done before.

        It might as well be you.


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        Are You A Believer?

        Photo by Ran Berkovich on Unsplash

        There’s a difference between believing that our work and our ideas have the potential to change the world and believing that people will actually be excited to enroll in what we’re doing and help move our vision of the world forward.

        If we want to change the culture for the better, both are essential. But they’re not equally easy to come by.

        Most of us doing work that drives us have the former. We really truly believe that we’re on to an idea that could benefit those who interact with it.

        You could argue that we may even place outsized importance on the work we personally are doing and exaggerate, at least in our minds, the potential impact of our work, but that’s a topic for another time.

        For us, the problem isn’t a lack of belief in the potential of our work, but rather a lack of belief that people will be eager and willing to sign on for the journey.

        Our lack of belief is probably based on perfectly reasonable past experiences.

        We’ve created work we believed in before, released it to the world, invited others to take part…

        …and got crickets.

        And so while we believe in the potential of the work once we can get it into people’s hands, we don’t believe in our ability to get anyone else as excited about it as we are.

        That feels too salesy. It feels arrogant, too pushy, too intrusive.

        What do we know? Maybe our work, products or services won’t actually work for anyone else.

        If we’re going to change the world through the work we do, at some point we need to get over this doubt, or at least shoulder it aside and ignore it long enough to do the important job of sharing our work with the people it was designed to help.

        We need to believe that there are people out there who are actively looking for a solution to their problem, the one we have the answer to.

        We need to believe there are people out there who won’t feel like we’re intruding when we show up in their inbox or their newsfeed or on their doorstep.

        We need to believe that there are some people who spend all week looking forward to our newsletter, our podcast, our live video, and they will be disappointed if we don’t show up.

        If you believe in your idea and your work, you owe it to everyone who could benefit from it, everyone who is waiting for your solution to their problem, to actively seek them out and share your work with them.

        Create your work, hone your message, then find the people who will circle the calendar on the day you show up to share it.

        This is how you build a movement.


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        What Tide Pools Taught Me About Life

        Photo by James Donaldson on Unsplash

        One of the great vacations my family took when I was a kid was a road trip down the Oregon coast and into Northern California.

        I was 12 years old when we hitched up our tent trailer to our minivan, pulled out of our driveway in Edmonton, Alberta, and headed for the US border, making our way through Montana before snaking our way up the Columbia River Gorge toward the coast.

        That trip was the beginning of what has become a life long love affair with Oregon, and particularly the coast, a place I find to be filled with magic, energy, and inspiration.

        I’ve returned a handful of times since that first trip, and each time end up discovering new places and walking away feeling renewed.

        While I don’t remember many specifics from that trip, there’s one memory — and some advice from a park ranger — that I recall every time I return. In fact, the advice has become a practice I apply increasingly in the rest of my life as well.

        Science(ish)!

        If you’ve never gone tide pooling, you’re missing out.

        (It’s possible you’re not missing out and that I’m just a nature nerd, but for now, let’s just compromise and say that I am a nature nerd and you also are missing out, cool?)

        Tide pools form when the tide comes in, covering a rocky, uneven, pothole-filled coast, and then goes out, leaving dozens or even hundreds of pools filled with seawater.

        Aside from seawater, however, these pools are inhabited by countless flora and fauna adapted specifically to live in this intertidal zone.

        Anemones, urchins, sea stars, crabs are some of the most common and obvious inhabitants, although apparently it’s not entirely uncommon to find octopi, eels and other more exotic surprises.

        This vacation down the Oregon coast was the first time I’d ever gone tide pooling. Mainly I was excited for the sea stars, which seemed thoroughly exotic to 12-year-old me.

        Sea Stars Galore

        Our first excursion was timed to coincide with a daily demonstration by the local park rangers who promised to explain all the tricks of the tide pooling trade (and much to my dismay inform us that we weren’t allowed to pick up the sea stars).

        As we started picking our way among the pools dotting the slick, rugged shoreline, I immediately spotted the main attraction, and feasted my eyes on the dozens of sea stars.

        Green, orange, even purple! There were the familiar five-legged variety, but there were also some less common and heretofore unknown to me, eight-legged stars.

        The Art of Tide Pooling

        Pretty soon, however, sea stars began to feel a little less exotic, and other than them, the tide pools started to seem kinda boring… I mean, sea stars themselves aren’t the most exciting creatures on Earth, all stuck to the wall, unmoving and all.

        Indeed, tide pools seemed to be little more than real-life, water-filled dioramas, with little to no movement in many of them, and only the gentle movement of the waves lapping in and out of other lower-lying pools.

        Perhaps seeing that I was moving from pool to pool, looking for about 3 seconds in each before moving on to the next one, clearly in search of something “interesting”, one of the rangers walked over.

        “Do you want to know a trick?” she asked.

        I didn’t really want to know a trick, but not feeling like I had much choice in the matter and that it might be rude to decline, I nodded.

        “Ok, so when you look into the pools they’re kinda boring right? What you need to do is pick a pool and just stare at it for 30 seconds or a minute. It doesn’t look like much is going on in the pools at first, but once you stop and really pay attention, you’ll start noticing all kinds of little critters that you didn’t see before!”

        Skeptical, but without much choice in the matter seeing as she was hovering over me, waiting for me to put her tip into action, I stared down at the pool in front of me and waited.

        Sure enough, as I stared for 15 seconds, then 30, then 45 I began to notice that activity abounded, albeit at a smaller scale than I had originally been looking for.

        There were tiny fish hiding in the swaying arms of anemonies, water beetles striding across the water’s surface, hermit crabs scuttling along the bottom, and more.

        It was a sight that once seen, could not be unseen, and the moment of seeing past the initial stasis as my eyes adjust to the micro activity has become something I look forward to and find wonder in every time I visit the coast and go tide pooling.

        Adjusting Your Scale Of Vision

        For some reason, the park ranger’s lesson has stuck with me for close to 20 years, and more recently, I’ve been thinking more about how that lesson translates into the rest of my life.

        How often do we let our first impressions of a person, place, or experience deter us from digging deeper and exploring further?

        With near-infinite and immediate access to seemingly everything, it often feels easier to put more weight on our initial reactions, and once any thrill has worn off, go looking for our next hit of excitement.

        This behaviour perhaps most obviously apparent in the world of online dating, and has certainly been well documented.

        But how many other areas of our lives are we passing up a chance at being truly awed because we were in too much of a rush to take a couple of minutes to let our eyes adjust, look a little more closely, and discover a fascinating world we didn’t know to look for?

        Everything is interesting if you approach it with curiosity and know what to look for. But it usually takes more than a cursory glance to have our curiosities piqued.

        Life is richer when we approach the things we encounter with this mindset, slow down, take the time to understand who and what we’re dealing with, and dig past our first impressions.

        By doing this consistently, we lead more interesting lives, bring out the best in ourselves and others, and experience states of wonder and awe more often.

        The Long View

        It’s Saturday night, around 11pm, and you’re fully down the rabbit hole, researching your competition, hopping from website to website, social channel to social channel, the pit in your stomach sinking lower and lower.

        Sure, you know comparison is the thief of joy or whatever that saying you heard once is, but you NEED TO KNOW.

        You justify it by reasoning that surely by keeping tabs on what the competition is up to it will only help you run your own business better.

        You sure as hell don’t know what the hell you’re doing, and by the looks of things, they certainly do. Maybe you could learn a thing or two.

        They have the types of high-end feature clients you dream of, their blog posts are shared regularly, they post engaging content on every conceivable social channel, of course they put out a highly ranked podcast as well, and what’s that? They’re getting into YouTube now too??

        Your first reaction, of course, is to immediately map out a plan for how you can do everything the competition is doing, BUT BETTER.

        “Maybe you’ll even get on TikTok,” you muse to yourself, “I need to one-up them somewhere.”

        You sign up for TikTok out of curiosity only to find they’re already there.

        “Damn It.”

        You add TikTok to your now multi-page list of required content and social channels on which you’ll out-produce everyone else in your industry and shut your computer.

        You resolve that Monday morning is the day you’re finally going to step up and get into the arena with the heavyweights whose shadows you’ve been living in up to this point.

        You don’t know how you’re going to do it, being a small shop without the team or resources of some of your larger competitors, but that shouldn’t matter should it? With the power of the internet at your disposal, you can accomplish anything right?

        Sure you’ll need to hustle. Stay up late. Maybe work weekends.

        But it’ll all be worth it when you grow to the point where you’re the one with the big clients, the fancy website, mountains of content.

        Right?

        Ummmmm No.

        I don’t know about you, but the “strategy” outlined above doesn’t really sound like a way I want to spend my life.

        I care about growing my business, continually improving, doing better, more interesting work for more interesting clients, but I don’t believe that flashier, more omnipresent marketing is the only way to do that.

        Yes, that method can 100% work for some businesses with some types of goals, and it’s what we help people do with our podcast and content amplification work at Counterweight Creative.

        But that’s not the type of business I want to be myself.

        For people like us, it’s essential to be clear on the type of business and lifestyle we want for ourselves, the types of clients we want to work with and how we want to be seen in the world.

        Often, that means distancing ourselves from the pressure to be everywhere all the time, because for most of us, that strategy is not in service of building the businesses and lives we really want.

        Now, believe me, I’m as susceptible as anyone to getting sucked into the comparison game. Of seeing what others are doing and wanting to add that piece into what I’m doing.

        Shiny objects abound and it’s easy to go chasing each and every one of them in search of a short term boost in attention.

        More and more, however, I’m finding myself gravitating to putting in time and effort into developing the areas that will pay off in the long haul. Actions that I take consistently now that may not be useful in the short term, but will pay off massively 3, 5, or 10 years from now.

        Unfortunately, in a world where most of us have a to-do list whose end only gets further and further out of sight with each passing day, practices aimed at investing in the long-term are often the first to get cut in favour of putting out short-term fires.

        Long Term Strategies

        Things like designing a client experience that goes beyond getting the work done and feels like magic and causes people to rave about you.

        Investing in helping your team develop as individuals as much outside of work as in the work they do for you.

        Developing a robust point of view and philosophy about the work you do and understanding how you can use your work to move the culture forward.

        Investing in developing real skills like communication, empathy, vulnerability, resilience and bravery on top of your field’s traditional hard, technical skills.

        I’m convinced that for people like us, people with big ideas, a desire to change the culture, and a belief that we can do it, these are the things we need to be focusing on developing and growing into.

        Forget Your Existing Metrics

        The results of these efforts aren’t as easily measurable as putting time into developing an Instagram strategy and seeing our follower count grow. But for most of us, Instagram is not an essential piece in moving our visions forward.

        Besides, your long term investments are going to far outlast Instagram.

        When we focus on the long term and invest in the areas we’re sure can only help us achieve our bigger purposes, the comparisons begin to fade, the pressure to do more eases and short-term tactics begin to feel like a distraction.

        We’re able to stay in our lane with confidence that whatever changes may come in our industries, societies, and the world, we’re equipping ourselves to be leaders in the future.

        Pretty soon we start to feel like while we might be trailing our competition in the short-term sprint for attention, we’re quietly pulling away in the long-term marathon for impact.


        Finishing Is Overrated

        Photo by Kelly Sikkema on Unsplash

        I was feeling sentimental, and a little nostalgic the other night as I walked home from the office.

        I didn’t have time to start another podcast before getting home, but I wanted to listen to something.

        In my nostalgic state, I found myself scrolling through old songs I had recorded years prior.

        My Origin Story

        My current role running a podcast agency was preceded by going to school to become an audio engineer and record producer.

        My dream had always been to split my time between producing music for others, while also writing and recording music myself, a dream that never panned out but ended up leading to greater things.

        The playlist of old recordings spanned a decade of sporadic work and meandering styles, from singer-songwriter to metal, to electronic to alternative rock to hardcore punk.

        I wrote and recorded single songs, releasing a couple of them under different monikers, which maybe 15 people downloaded in total.

        I envisioned these songs being the beginnings of larger projects, culminating in EPs or albums, but the closest I ever got was a few dozen songs existing in various states of completion on my hard drives.

        Finish The Work?

        In the world of creative work and entrepreneurship, there’s a huge emphasis placed on finishing or shipping the work.

        As creatives, we can find ourselves endlessly tweaking our work, convinced that it could always be better, afraid of overlooking some glaring flaw for which we’ll be criticized and written off as just another amateur trying to pass ourselves off as a pro.

        In such cases, I think the advice to just ship the work is valid and useful. But I don’t think it always is, and I think the sentiment can sometimes be downright unhelpful.

        Permission To Explore

        As I listened through the eccentric playlist, I started thinking about my larger trail of creative work that’s led me to where I am now.

        Besides the decade’s worth of aforementioned music, there are the sketches and drawings from junior high, angsty high-school poetry, my photography blog, tens of thousands of photos, more than a few of which were actually paid work, my old travel blog, the short-lived travel vlog I started during my first year of full-time travel, my podcast blog, recent explorations into calligraphy and hand lettering, this blog (apparently I’ve started a lot of blogs…), podcasts created for myself and clients, and more.

        As a kid, I even invented a new billiards-style game in my basement, printed off the rules and made my parents and friends play. I vaguely remember that the blue, black and purple balls were somehow important, and as such, I dubbed the game Bruises.

        Thinking through my past creative endeavors, I realized that I had pursued many of them with a significant amount of dedication and seriousness. Some of them, such as photography and music I’m sure still have a place in my future.

        And yet, even in those pursuits in which I really made a run at, I can’t say that I ever really finished any work to the extent that I would have liked.

        Perhaps that’s why I never succeeded as a musician or photographer, but I also never quite felt the pressing need to finish in those fields.

        One of the things I’ve come to most appreciate about myself is that I’ve started down many different, (mostly) unrelated paths, typically with a good deal of conviction and discipline, and then been fine dropping the pursuit and hopping over somewhere else once I lost interest or realized that the path didn’t lead quite where I thought it did.

        Choose Your Dips Wisely

        Most new pursuits are easy and exciting when you first start out. You’re able to put in work and see measurable improvement, maybe on a daily basis.

        Ultimately, however, you reach what Seth Godin calls The Dip, the point at which something stops being easy and exciting, where you realize that to achieve mastery and further success you must work through what I think of as The Hard Stuff.

        In thinking about my own creative history, I’ve recognized a pattern of starting things and sticking with them up to The Dip, before either petering out or dropping the pursuit immediately.

        While I’m convinced that to become exceptional at anything you have to work through The Dip, none of us has the bandwidth to work through every Dip we come across. We need to be selective about the Dips we lean into, because each one might take months, years, or even decades to reach the other side of.

        To discover the area in which we can do our best work, achieve the greatest fulfillment, and create the greatest impact, it’s essential that we start a lot of things, but finish only a few.

        Only by reaching the various Dips can we look into their gaping chasms and ask ourselves whether this is where we want to invest our precious time and creative energy.

        Most things we start won’t be.

        In those cases, accept them for what they are. Content yourself with remaining a novice, with keeping it a hobby, or with dumping it altogether.

        Forget finishing, ignore the sunk cost and move onto the thing that excites you.

        Eventually, we each find a dip that’s worth bringing our full selves to, putting in the work, and finishing.

        But until then, just get busy starting.


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        Somewhere Else

        Photo by Jesse Bowser on Unsplash

        Somewhere Else is an intriguing place.

        Where You Are is filled with too much noise, too much uncertainty, too many problems.

        The right people aren’t here to build out your community, network, and organization.

        It’s boring, there’s nothing fun to do, nothing unique.

        It’s easy to imagine that Somewhere Else has everything you’re looking for.

        The right people and networks, unique events and activities, everything that’s missing from Where You Are has somehow been cultivated there.

        You might transplant yourself to Somewhere Else and at least at the beginning, it’s everything you imagined it would be.

        Sure maybe you haven’t tapped into those networks, met those people, gone to more than a couple of those unique events, but they’re here, and in time you’ll become an insider, reaping the benefits of your new and improved location.

        A couple of years pass, however, maybe only a couple months, and Somewhere Else is starting to look a lot like Where You Are.

        You realize that it’s not just you. Everyone here in Somewhere Else is talking about Somewhere Further.

        While most of them just talk about Somewhere Further, you’ve done this before, you pack up your things and take the leap, sure that Somewhere Further is going to fulfill the hype that Somewhere Else promised, but failed to deliver on.

        The cycle repeats, taking you from Somewhere Further to Further Still, to Far Far Away.

        Optimism and excitement turns to the mundane, disappointment sets in, and your feet begin to itch.

        Soon enough, you start hearing people in Far Far Away talking about Where You Are as the most exciting place to be right now.

        It’s got everything, they say. An amazing network in your industry, tons of events, a vibrant art community, and don’t forget the craft beer scene.

        You’re skeptical, but it’s been a while since you left. Maybe Where You Are has transformed from the boring, static place it was when you were there to a thriving, energetic hub of innovation and excitement.

        Far Far Away was getting boring anyway, so once again you pack up once again and head back to Where You Are.

        It doesn’t take long to realize that not much has changed in Where You Are.

        You hang out with the same people you used to, work a similar job to the one you had, pass your time in the same ways you did when you first lived here.

        Sure the craft beer scene is good, but none of the new places have anything on the old spots you already knew about and visited regularly.

        How could people in Far Far Away have been so wrong about this place?

        Slowly, painfully, you begin to take stock of the evidence presented by your experience.

        Maybe Somewhere Else was never as intriguing as it appeared.

        And maybe Where You Are is what you make it.

        Most People Don’t Think

        Photo by Tachina Lee on Unsplash

        There are a lot of smart people in the world, no doubt about it.

        But most of them don’t spend much time thinking.

        I mean, sure, their brains process information as they walk around all day. Sometimes they actually come up with some pretty nifty solutions to interesting problems while they’re at it.

        Most of that thinking is reactive, however.

        There’s nothing wrong with reactive thinking. I’m glad my brain works reactively to make quick decisions, keep me safe, carry on conversations like a normal human without minutes of silence between responses while I mull over what to say next.

        When I say most people don’t think, I’m talking about deliberate, focused, strategic thinking on a specific topic or challenge.

        As people trying to solve interesting problems in a way that changes people for the better, this then is our opportunity.

        The way I see it, there are 5 reasons why most people (and maybe even you) don’t utilize their brains to their fullest potential.

        1. Thinking Time Is A Luxury

        We’re all busy. We’ve all got more on our to-do lists than will fit into the day already, not to mention all the new items that will have been added by day’s end.

        With so much to do, even if we’d like to block off some time every month, week, or even day for deliberate, strategic thinking, invariably, some fire or other flares up that requires our immediate attention.

        It’s no surprise that the first thing to be dropped from our schedule in those cases is that block of what looks suspiciously like “free time,” time that we may not expect to result in a defined outcome, time without an immediately measurable ROI, time with no urgency or outside expectation to it.

        For the better part of two years, I’ve struggled to book off the last Friday of every month as a strategy day where I do little but think about the big picture of my business.

        It was a day that I looked forward to every month, and without fail, I was sure that the time I spent in focused thought would surely result in my next breakthrough.

        In reality, I’ve probably only really completed 5 of these days.

        In every other instance, something came up that I felt couldn’t be ignored and out the window went the luxury strategic thinking day.

        I’ve since moved away from the infrequent large blocks of thinking time to shorter chunks scheduled daily.

        I’ll often set aside as little as 15 minutes to brainstorm on a problem, something I’ve come to refer to as a Brainstorming Sprint. Once I start, however, it’s not uncommon to get sucked in, and pretty soon everything else on my todo list starts to look a little less important.

        But in order to get sucked into our brainstorming, we first need to know what problem we’re trying to solve.

        2. You Need A Defined Problem

        If we’re able to block of the time for focussed thought, we run into a second challenge.

        Often, we don’t actually know what the problem is that we’re trying to solve, or what we should be thinking about.

        Most of our projects are of a scale that won’t be solved by simply sitting down and thinking on them for an hour, or even a day.

        The sheer size leaves us first procrastinating on putting any thought toward them because we can’t imagine where to start, and then spending any time we do dedicate to the problem looking at the project as a whole and vainly striving to elegantly solve it all in one fell swoop.

        What we need to do instead is find traction first.

        Recently, I sat down to spend an hour thinking about the Podcast Marketing Course I’m working on.

        I had roughly mapped out the modules about a month before, but hadn’t put any more time towards it since and now wasn’t quite sure where everything was at.

        As I sat down I went through my notes, zooming in and out on each of the six modules in the course, going through the bullet points under each subsection and subsection’s subsection until I was thoroughly lost, overwhelmed, and completely sure the project was worthless and would most certainly fail if I ever completed and released it.

        After half an hour of flailing about, not knowing which chunk of the elephant to bite off first, I forced myself to reset, look at one specific module of the course and methodically work through the outline for that section thoroughly and in order of presentation.

        With focus and constraints on what I was thinking about, I was almost immediately able to lock in and think through what the necessary points that needed to be conveyed were, rough out student worksheets, and do some research on necessary examples to illustrate those points.

        An hour later, the outline of the module was not only complete, but more detailed and thoughtful than I had originally anticipated it would be.

        Sometimes, you might need to spend an hour, or day even, simply breaking down the larger, amorphous problem into a series of smaller, understandable problems that can each be solved in one sitting.

        I’ve found that often, projects I’ve worked on have stalled and been procrastinated on for months only really felt hard because there were a few key decisions that needed to be made before the work could start.

        In the end, months of procrastination and lack of clarity have often been solved by decisions that were made with 5 minutes of focused thought.

        We’re ridiculous creatures us humans.

        3. Thinking Is Hard

        A lot of the problems we’re trying to solve are long-term projects, many of which with no clear, defined path to solving.

        Sometimes we have a roadmap at our disposal from someone who’s done something similar before, but not always.

        We might sit down, start at a blank page in front of us, get bored, check-in on Twitter and next-thing-you-know-our-scheduled-time-is–up-and-thank-God-it-is-cuz-that-was-uncomfortable-and-unproductive-and-I’m-never-doing-that-again.

        As we already discussed, you first need a clear problem that you’re working on defined to maximize your thinking time, but even once you have that, the scope of the problem can be overwhelming.

        I find that it’s often the blank page that is the greatest barrier at this phase. We feel like we should write something but don’t have any thoughts to actually write.

        So we keep staring at the page and end up thinking about thinking instead of thinking about the problem at hand.

        I like to start by writing down any questions I know will need to be answered, even if I don’t know the answers. I’ll also write down topics that I need to research and learn more about and then do some research and find articles, books, etc on the topics.

        I may not read them then, but I’ll bookmark them and past the URLs in my brainstorming document.

        We all think and work through problems in different ways, so experiment and find what works best for you. It might be pen and paper, digital note apps, voice memos that you then transcribe, mood boards, or anything else.

        I like bullet points and expandable lists so I do most of my brainstorming in Workflowy, but I know some people who are much more visual and use tools like Milanote to create more robust mood boards.

        Use what works best for you and just start writing, sketching or creating something. Get past the barrier of the blank page and the floodgates will often open.

        4. Productive Thinking Takes Discipline + Habit

        I’ve come to think of my thinking sessions much like a meditation practice, but instead of clearing my mind I aim to intentionally follow my curiosity down whatever trails it wants to follow.

        Much like meditation, I feel I’m able to get more benefit from the practice by building a routine around it and approaching it with discipline.

        Even when things are busy, I still set aside 15–30 minutes to work on some problem or other.

        When I’m not feeling particularly creative or in the mood and would rather work on something else, I force myself to settle in and spend that time thinking.

        Sure, sometimes it doesn’t amount to much, but some of my most productive sessions have come after telling myself I’d just spend 15 minutes thinking on a problem just to fulfill my obligation to myself, and 2 hours later have filled pages with notes and am clearer on the big picture solution.

        I’ve come to suspect that “not being in the mood” or “feeling uninspired” is just Resistance in disguise, and as such now redouble my resolve to push through those feelings when they arise.

        5. We Have An Idyllic View Of Thinking

        When I first started my ill-fated Last Friday of the Month Strategy Day policy, I had a whole ritual around the day.

        I would start the day with a walk to clear my head, calibrate myself for what I was working on, and then head to one of my favourite coffee shops to post up for the day.

        I’d fill out a monthly assessment and planning questionnaire that I had created to start things off in a structured way, and then get into more free-form thinking and brainstorming.

        After lunch I’d go for another walk and end up somewhere else cozy to work for a couple more hours. In the evening I’d treat myself to a nice dinner and maybe do something fun that I’d been putting off indulging in.

        The days were fantastic, and you can probably see why I looked forward to them. But they weren’t sustainable.

        While I loved the ritual and it worked to put me in the right headspace, I had become convinced that only when all the conditions were right could I do any thinking and strategizing that would amount in a breakthrough of any kind.

        Many of us have an idealized view of the philosopher, poet, writer, isolated somewhere in a cabin in the woods, free of distraction, free to tap into their best work and biggest ideas uninterrupted.

        The problem is that for most of us, these circumstances will never come about, and even if they did, I think many of us would be disappointed with the results.

        Better instead to take your conception of a strategy or deep thinking session down off of its pedestal and turn it into something more rugged and durable.

        Build a practice where you can tap into your most creative ideas and solve interesting problems in the most uninspiring locations.

        Sure, Walden Pond is a more romantic locale than an office cubicle or a poorly lit basement suite apartment, but if that’s what you’ve been given, learn to tune out your surroundings and let your mind run free regardless of where you are physically.

        Tap Into Your Genius

        Since beginning my structured Brainstorming Sprints, I’ve found myself procrastinating less, making more headway on the ideas I have, and coming up with more ideas overall.

        I’m convinced that this says less about me than it does about the benefit that we can all get from making space for focussed thought.

        We all have ideas that could result in meaningful work if only given a little chance to breathe, to ruminate, to explore their surroundings. Too often, however, they get crowded out by client work, social obligations, or our own Resistance telling us not to look any closer because it’s a stupid idea that will never work and you don’t even know how to approach it anyway…

        Push back on Resistance, define your problem, and let your genius breath.

        One day, we may all thank you for it.

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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.

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