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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    What Every Creative Project Needs to Reach Maturity

    In an ideal scenario, the sun is out and shining in full force on the long weekend you decide to head out to a cabin on a lake.

    This goes double when you have 9 people along for the weekend trip and the cabin is only meant to accommodate 6.

    And it goes triple when two of those nine are younger than 9 years old.

    Alas, this past weekend was not ideal.

    Sure, there were those few hours of sun when we pulled up to my Dad’s cabin on Friday evening before the rain started…

    And the couple of breaks in the downpour on Saturday and Sunday before everyone decided to pack up and head home a day earlier than planned.

    But other than that, it was a decidedly indoor weekend.

    If it was just the adults, the setting would have been downright cozy. The perfect setting for eating, drinking, reading, relaxing, board games, and conversation.

    But within an hour or two of the rain starting, it became painfully obvious that the confines of the cabin were too small to contain the energy and expectations of my 8-year-old nephew, fresh out of school for the summer.

    And while the weekend was full of disruptions, distractions, a constant stream of requests, and several minor meltdowns, among all the noise, there was something that stood out to me:

    The things we create—whether children or creative work—tend to behave in similar ways.

    They’re needy.

    For their first years, utterly dependent on us.

    And they require ample room to run around and explore aimlessly before finding and settling into themselves.

    But perhaps most of all, our creations are uniquely capable of driving us to the absolute brink of our sanity.

    And do so on a near-daily basis for much of the first decade of their lives.

    Sure, the stakes and responsibilities are vastly different.

    But I don’t think it’s unreasonable to think that the requirements for shepherding our creative projects to their potential are similar to those of raising a child to theirs.

    Love.

    Time.

    Attention.

    Space.

    Trust.

    And a level of patience that seems entirely unreasonable to anyone on the outside.

    Yes, they’ll misbehave.

    They’ll ignore our wishes.

    Fall short.

    Disappoint, frustrate, and annoy us more times than we can count.

    But if we stick by them and provide them the opportunity, they’ll surprise us and enrich our lives in ways we could never have imagined.


    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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        Getting Past Your First Creative Failure

        I broke my Wordle streak this morning.

        It’s not the first time. After discovering Wordle in January and quickly becoming obsessed, I built up a fairly impressive streak before encountering my first defeat 148 days later.

        That first loss was crushing.

        I was disappointed in my strategy and furious with the Wordle team for using what I perceived to be a cheap word.

        Of course, it wasn’t a cheap word.

        It was a common, well-known word that happened to have a large number of relatives only one letter apart. After identifying four of the five letters with my first 5 guesses, my final guess essentially amounted to a shot in the dark to pick the correct final letter out of three possible options.

        I missed.

        And I lost.

        In the bitterness that defined the day of the loss, I briefly thought about quitting Wordle. Of not giving them the satisfaction of me returning after such humiliation.

        But the following morning rolled around, habit kicked in, and I found myself back in the saddle, embarking on the beginnings of a new streak.

        That one lasted 4 days.

        Again, fury. At myself, at Wordle, at the indignity of losing twice in one week to a game I thought I had long ago mastered.

        But once again, I returned.

        Did I really think I had another choice?

        More streaks followed. And more streaks ended.

        None as long as my first streak but none as short as my second.

        Most streaks were ended thanks to situations akin to my very first loss. Today, for example I guessed “PATCH” instead of “CATCH” (though “HATCH” and “WATCH” were also potential options for my final guess).

        Some streaks were ended by hubris.

        One because I was traveling and simply forgot.

        The only commonality between each of my perfect streaks is that sooner or later, they ended.

        As the losses have mounted, now four or five strong, my posture toward the game has shifted.

        Sure, I’m still disappointed when I lose. But I no longer dwell on it throughout the day, think about quitting the game out of spite, or even experience any sense of frustration.

        The more I lose, the more it becomes clear that, as with any game, losing is not only a potential outcome but an inevitable one.

        To believe otherwise is either ignorant or arrogant.

        Losing is a Part of the Creative Game

        When we haven’t yet experienced a significant creative loss—a launch that flops, a poorly conceived project, a client that leaves us for a competitor—we tend to adopt one of two unhelpful postures.

        The first is hubris, burying our heads in the sand and convincing ourselves our hot streak will never end.

        The second is fear, living and creating beneath the constant spectre of the inevitable failure we’re certain is right around the corner.

        In both cases, our posture impacts the quality—and more importantly, the courageousness—of our work.

        Whether consciously or not, we avoid putting ourselves in situations that might invite that first and most terrible defeat.

        Which is unfortunate.

        Because the avoidance of work that is daring enough to have the potential to fail in a significant way is far more detrimental to our success than any failure itself.

        When we think about failure, we tend to focus on (and exaggerate) the obvious potential downsides: wasted time and effort, financial ruin, and (perceived) public judgment.

        And it’s true, all of these outcomes are real possibilities.

        But perhaps we should be more afraid of the prospect of spending years of our lives producing de-fanged work that has absolutely zero chance of breaking through to, connecting with, or moving people.

        Seek Out the Losses

        Let’s not sugarcoat it, failing at a project you’ve put months or years of your life into is nothing short of heartbreaking.

        It will make you question your ability—and worth—as a creator and even a person.

        At least the first time.

        But if you’re able to pick yourself up after that first loss, get back on the horse, and find your way to your second loss… well, let’s be honest, that one’s going to be heartbreaking as well, but a little bit less so.

        As the losses pile up, as they inevitably will, however, they begin to take on a different hue.

        Sure the opportunity cost and financial downsides of failure are very real (the public judgment usually isn’t), but the meaning you ascribe them shifts.

        You realize that the losses are not a reflection of you as a person or creator. They’re simply a natural and inevitable part of the game you’ve chosen to play.

        That often enough, the best possible scenario is simply a shot in the dark, where missing the target is in fact the most likely outcome.

        That you’ve managed to come back from each of them before, and can—and will—do so again.

        Persist in creating work daring enough to invite the possibility of both significant success and significant failure and you’ll find that the bite of failure is just as capable of losing its fangs as your work is in the face of it.

        Which means that perhaps, the sooner we can rack up those initial losses, the sooner we can get around to making more daring, more courageous, more meaningful work.


        Explore how to navigate a creative life that matters

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

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

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

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


          The Right Work

          For all its importance, the right thing to be working on is hard to spot
          The right work is rarely obvious
          Rarely urgent
          Rarely appearing to move the needle

          The right work is that for which the outcome is irrelevant
          For which the benefit is simply creating it
          For yourself For others
          For what’s gained through the experience.

          The right work is that which moves you closer to your personal potential
          That helps you discover more of yourself
          Embrace more of yourself
          Become more of yourself.

          The measure of the right work is not gauged by views or listens or likes
          Nor in resonance or reach or impact
          No, the right work is measured in far smaller numbers
          Binary in fact
          The answer to a simple question:

          Did the act of making it move you
          Closer to who you are
          To who you could be
          To what you’re capable of?

          There’s a time for content
          For practical work designed to do a specific job
          That work must be done
          But make no mistake

          The right work is the work you do for yourself
          And if you want to achieve all you’re capable of, that work can’t be put off or ignored.


          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.


            All the Downside, None of the Upside

            It’s been warm and humid here lately.

            And without air conditioning in the apartment, we’ve come to map our daily routine to the arc of the sun.

            We start our days with windows open and the fans on.

            Around 10 am, we shut the windows and draw the thick curtains in our East-facing living room.

            At 3:30 pm or so, my office, facing west shifts into range of the sun and I close both the window and wooden shutters to keep the room from quickly warming 10 degrees and becoming unbearable to work in.

            This daily dance works, for the most part.

            Apart from the hottest of days, the apartment remains entirely comfortable even without the aid of an AC unit.

            At least until bedtime.

            Despite opening all the windows and positioning the fans for maximal air flow through the apartment, it simply doesn’t cool off enough outside by 10 or 11 pm for the bedroom to reach a comfortable sleeping temperature (for me, ~18C).

            If we left the windows open over night, the room would cool down fairly quickly, I suspect.

            There are a couple of problems standing in the way of doing so, however.

            For one, our bedroom windows open onto a fairly busy street, with a good amount of noise from both traffic and the bar across the street, Café Imperio.

            Second, the bedroom windows are fitted with wooden shutters, which, while they do an exquisite job of blocking out the light from the street lamps immediately outside our second floor window… also do an admirable job of blocking any air flow, even if the windows are cracked.

            The challenge was a formidable one: How to allow the air flow in while minimizing the light and street noise?

            After a string of fitful, sweaty nights with the windows and shutters closed, I decided I needed to take it on.

            And so, before getting into bed, I did my best to close the shutters far enough to block out the majority of light, while at the same time leaving the windows behind them open far enough to allow in a steady stream of cool air throughout the night.

            And the noise? Well, that I’d just have to do my best to tune out.

            The result of my effort was the worst night of sleep yet.

            The reason became apparent when I groggily opened the shutters in the morning.

            It turns out that in pushing the shutters closed far enough to even somewhat darken the room, the windows behind them had been closed to the point where there was no longer a gap through to the cool night air.

            They were, however, open far enough to allow the street noise in. Plenty of it.

            The result was a room that was significantly brighter and noisier, without any noticeable decrease in temperature.

            Said differently, I’d managed to amplify both of the nuisances I was trying to mitigate while leaving my desired positive outcome unchanged.

            It made me think of how we often do this to ourselves with our creative work and businesses.

            We all have aspects of our work that we’d rather avoid.

            Social media, email newsletters, prospecting, pitching and follow ups all come to mind immediately.

            We know these tasks have potential positive benefits associated with them. But achieving them requires us to put up with some level of discomfort.

            And so we do our best to mitigate the discomforts of the task at hand while still nominally completing it.

            Maybe it’s a social strategy that’s entirely based on repurposed and reposted content, without any genuine interaction or originality.

            Or maybe it’s a weekly newsletter that gets hastily written at 5 pm on Friday using the dregs of our creative energy.

            Whatever the situation, the result is the same.

            While we may manage to partially mitigate the discomfort and nuisance we were seeking to avoid, in the process, we completely suppress any chance of the positive outcome we were hoping to achieve.

            As in my situation, leaving the window cracked has a way of leaving us with all of the downside and none of the up.

            In some cases, the negative effects may extend beyond just our personal experience with the task.

            We’re better off not writing a newsletter at all (and avoid the flood of unsubscribes), for example, than write an uninspired, uninteresting one, written and sent only because we know we’re supposed to email our list every week.

            What we need to realize is that every upside comes inextricably entangled with one or more accompanying downsides.

            Which means we have a choice to make.

            Do we accept that in many cases, to get the thing we desire, we’ll have to put up with some things we don’t?

            Or do we decide that maybe, the thing we wanted isn’t worth everything that comes along with it?

            Either option is perfectly fine. But we should make the choice intentionally.

            Open the window and accept the cool night breeze along with the street noise and light.

            Or close it, and block it all out.

            Just don’t leave it cracked.


            Explore how to navigate a creative life that matters

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

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

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

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


              The Secret to Interesting Work (Is Staring You in the Face)

              It’s not often that the foreword of a book sticks with you more than the book itself.

              But there’s this line in the foreword of Malcolm Gladwell’s What the Dog Saw that I’ve thought about nearly every week for the past ten years.

              The book is a collection of Gladwell’s favourite essays that were originally published in The New Yorker. The essays cover topics like ketchup vs mustard, women’s hair dye in the 1960s, and various other immediately compelling topics…

              Ok, ok, so maybe the topics don’t seem all that interesting at first blush, but the way Gladwell explores them most certainly is.

              Which brings us back to the foreword, in which he addresses one of the most common questions he receives from readers.

              “Where do you come up with these quirky ideas for stories? And how do you then make these boring, mundane objects, events, and people interesting?”

              His response?

              “If you believe that everything is interesting, you’ll find that it is.”

              Everything around us has a hidden story, he goes on to share, and if we’re willing to dig into it and peek beneath the surface, we’ll often find a fascinating world of twists and turns and intrigue.

              This is an important idea for us as creators, but one we don’t often give the attention it deserves.

              We like to think that the foundation of successful creative work is our skill at our craft, or perhaps the strategies and tactics we use to get our work in front of an audience.

              And to be sure, craft and marketing are essential parts of the work.

              But the role of both our craft and our marketing are to communicate ideas. And in order to communicate ideas, we first need to find them.

              And not just any ideas.

              Work that cuts through the noise is based on novel, original, unique and refreshing ideas.

              The kind that open our eyes to something we didn’t know existed.

              Or help us see something familiar in an entirely new light.

              So much of our success as creators, then, is determined by our ability to consistently find the interesting in the mundane.

              But as Gladwell’s quote hints at, while interesting ideas and stories are all around us, often staring us in the face, they require some belief, curiosity, and digging in order to get to the heart of them.

              Without a healthy appetite of curiosity and an eye for the interesting, then, we’ll always struggle to produce anything new or fresh.

              If our inputs are generic and uninteresting, why should we expect our output to be anything else?

              Luckily, the world is packed full of interesting inputs if we know how to look at it, and even luckier, training ourselves to look for interest is a skill you can learn.

              Best of all, approaching the world with the belief that it’s full of interesting stories engages a positive feedback loop.

              With each new discovery, the world itself becomes a bit more interesting, stoking our curiosity to wonder at what other stories and ideas we might be walking past every day without noticing.

              A couple years ago, for example, I was prompted (who knows why) to look up the different types of columns used in classical Greek and Roman construction (seriously, what led me to look this up?).

              Now, on a regular basis I notice the Ionic, Doric, Corinthian, and Tuscan columns that ornament many neoclassical buildings around the world.

              Or there was the time I finally looked up the answer to a long-running question in my mind about whether the Michelin restaurant rating system stemmed from the Michelin tire company.

              It does.

              And there’s a whole story there.

              I’m unlikely to ever use any of this knowledge in any practical sense.

              But having it makes the world–and life–feel richer, more interesting, more inspiring.

              All of which lead to more and better creative work.

              It’s hard to create interesting work while living in a boring world after all.

              The good news is none of us live in a boring world, even if it might seem that way from the outside.

              If it does, the solution is fairly straightforward.

              Pick something mundane you encounter regularly in your daily life and learn the story behind it.

              If the original topic isn’t all that interesting, keep following the related Wikipedia links until you land on something truly fascinating.

              I guarantee it won’t take long.

              The more you can attune your brain to find interesting stories and ideas, the more information it has to create interesting work.

              It won’t happen overnight, but in time it will become second nature.

              Make your world interesting and your work will follow suit.

              And hey, an interesting life is just more fun to live.


              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.


                (Re)Finding Your Creative Rhythm

                We all have an optimal rhythm.

                A pace and a cadence at which we do our best work, are our best selves, and live our best lives.

                When we operate in time with our natural rhythm the work becomes effortless as we relax into flow.

                We put our usual perfectionism, overanalyzing, and judgment aside and let and let instinct, impulse, and intuition take the wheel.

                Life and all its happenings and circumstances, however, has a way of disrupting that rhythm.

                Which means that the ability to regain our rhythm is an essential skill.

                Sometimes that means picking up after only a couple beats out of time. Sometimes it means picking up in the middle of an entirely different song.

                The trick is not to fret over the beats we’ve missed, but to feel and find and pick up the beat where it is now.

                When we find and live in the rhythm, everything else takes care of itself.


                Explore how to navigate a creative life that matters

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

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

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

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


                  The Creative Poker Game

                  Pursuing creative work is a bit like buying into a game of poker.

                  We can refrain from betting on every single hand we’re dealt and still have our chips slowly eaten away at as hand after hand we pay the minimum ante to simply stay in the game.

                  We can spend the whole game playing it safe, waiting for the perfect timing for our perfect hand only to have the opportunity fail to materialize.

                  Or, maybe it does materialize…

                  When it does, our eyes light up, we go all in, play the hand perfectly… and yet against all odds another player might happen to have something even better.

                  We leave the game dejected, with the knowledge that even our best wasn’t good enough to win.

                  Great creators, like great poker players, understand that sometimes you have to bluff your way through when it feels like you don’t have much to work with.

                  And sure, sometimes you get caught and are forced to admit that you were in over your head and it’s time to go back to the drawing board.

                  But sometimes you get away with it, and are emboldened to move forward with more confidence.

                  Great players know how to read the table, to sense opportunity, and move to take what they can get. To see confidence and distinguish strength from bravado. To swim in the currents of emotion and timing and chance and opportunity.

                  They know that the game is about so much more than simply the cards you’re dealt.

                  They know that it’s hard to win without ever taking a risk or pushing your luck.

                  And that even when your luck eventually runs out (and it will), it’s not the end of the world.

                  You can always buy in again after all.

                  And unlike poker, the cost of buying back in to your next creative endeavour is measured not in money but in curiosity, hope, and an idea worth exploring.


                  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.


                    On Finding Yourself (And Why it Matters as a Creator)

                    I’ll be honest, I kind of hate the phrase “finding yourself”.

                    At its best, it’s a boring cliche. At its worst, it’s synonymous with privileged westerners jet-setting across the world to places where their self-serving spiritual tourism does more harm than good.

                    And yet, I also feel it’s a phrase and an idea that we can’t quite seem to do away with.

                    Perhaps it’s the fact that we’re thrust into our lives and our selves without an instruction manual.

                    Perhaps it’s the fact that we’ve all had the experience of feeling some part of ourselves that we didn’t know existed suddenly click into place, in the process, realizing that we are more than we had imagined.

                    Perhaps it’s that we’ve simply read Eat, Pray, Love (or in my case, Into the Wild) too many times.

                    Despite the cliche, at some level, the idea of finding ourselves rings true.

                    And if we want to achieve our potential, creatively or otherwise, finding and piecing together the scattered pieces of ourselves might just be a necessary part of the process of getting there.

                    But what exactly are we looking for when we set off in search of ourselves?

                    The idea of finding ourselves implies that we don’t quite know who or what we are. And if we don’t already know ourselves, how do we know what we’re looking for or when we’ve found it?

                    Mirror Images

                    The idea of finding ourselves implies an internal journey of discovery, development, and progression.

                    But that internal journey is often facilitated by an accompanying external journey.

                    This idea is a core part of the classic Hero’s Journey framework which has both informed (and been perpetuated by) much of modern storytelling as well as showing up in stories and myths across cultures for thousands of years.

                    As such, it’s no wonder that to some extent, we seem to have some innate awareness of this correlation between the external world and our individual internal worlds.

                    But if we want to take a more active, intentional approach in filling in the missing gaps in ourselves and moving closer to our potential as both creators and humans, it helps to view this external/internal relationship more literally and concretely.

                    Because if we know where to look, the external world is strewn with tangible landmarks that can help us triangulate, map, and navigate our abstract inner terrain.

                    Into the Cave

                    I’ve spent the majority of the past 8 years traveling in the geographic sense, visiting (and in many cases living in) more than 40 countries across 5 continents.

                    But I’ve also been traveling in an abstract sense–through books, podcasts, movies, music, essays, ideas, and more–for much longer.

                    Regardless the mode of travel, I regularly find myself stumbling onto places, art, ideas, and more that resonate in a way that feels as though they’re a part of me, separated at birth only to be rediscovered and reclaimed, and reintegrated now, decades later.

                    I like to imagine these pieces of myself in the world as something akin to quantum particles, separated but operating in perfect unison.

                    The first time I remember experiencing this particular sensation of resonance was on a multi-day hike on the west coast of Vancouver Island.

                    My friend Evan and I had set up camp at the end of the first of four days we’d be hiking.

                    While Evan napped on the beach in the late afternoon sun, I decided to explore our surroundings.

                    From our camp, the trail headed up and inland for a few Kilometers, bypassing the high, coastal cliffs before descending and meeting up once again with the coast later the following day. Because the tide was currently out, however, I was able to hopscotch my way along the rocky shore, out around the edge of our cove, and skirt up the coast along the base of the cliffs.

                    As I rounded the corner, walking a rocky tightrope between the sea and the rocks, the cliffside on my right unexpectedly opened up into a yawning sea cave.

                    The cave was big enough to feel expansive while small enough to feel intimate, maybe twenty feet tall, thirty feet wide, and forty feet deep.

                    I crossed the threshold and entered.

                    It was like stepping into a cathedral. The crashing of the incoming waves quieted, while somehow also becoming one with the rock walls, reverberating back and enveloping me from all sides.

                    I was awed.

                    This stumbled upon sea cave felt like home in a way I’d never felt before, and for an hour, I simply sat on the stone floor, stared out at the sea, and reveled in the alignment of person and place.

                    Landmarks Are Everywhere

                    While this experience was the first I remember, and to date, still one of the strongest, I’ve now had this resonant experience of finding a part of myself out in the world dozens of times.

                    Physical locations are a common source of resonance.

                    These locations may be grand and powerful, like the sea cave on Vancouver Island or the sea cliffs of the UK and Ireland. Rocky coastlines and the deep, relentless pounding of the surf always tend feel like home to me.

                    But they can also be small, mundane even.

                    A coffee shop that strikes just the right vibe, or a city park, or a certain random street corner.

                    They can also be places I’ve never been. A living room on Pinterest, or a kitchen in a movie or TV show. It often doesn’t take more than a short glimpse to recognize a bit of myself buried in a place.

                    But physical places aren’t the only places I’ve found myself.

                    Just as often, I’ll discover some part of myself in a song, video, book, poem, creative project, or even another person who may have more fully-realized and developed some trait that is nascent in me.

                    I’m sure the feeling of reunion with some lost piece of ourselves feels different for all of us.

                    For me it’s often a visceral kind of resonance in my chest or stomach, goosebumps, or welling up of emotion. Other times, it’s a sense of peace, quiet, and alignment.

                    Whatever the specific sensation feels like, once we recognize what that particular sense of resonance feels like for us and are able to attune ourselves to its frequency, these pieces of ourselves aren’t all that hard to find.

                    What’s harder is knowing what to do with these abstract data points.

                    Because what are you supposed to do with a feeling that some part of you exists in a sea cave, after all?

                    Note Pieces, Follow Patterns

                    Since I started thinking more intentionally about finding myself in the external world a couple of years ago, I’ve been collecting and cataloging them.

                    I dump notes, photos, and ideas of resonant pieces into a Notion doc and have a playlist of all the music that feels as though I could have been the one to write it. I’ve even experimented with creating mood boards comprised of various visual elements.

                    At times this collection is active and intentional, where I’ll scour Pinterest or Unsplash for imagery that resonates strongly.

                    More often, the process is passive, where I’ll stumble across something that brings on an unexpected visceral physical reaction.

                    The more I’ve collected and organized these data points, however, the more patterns have emerged.

                    Visually, I’m drawn to symmetry, reflection, and balance. I like geometry, landscapes, and natural colour palettes.

                    Thematically, I’m captivated by stories about time (especially time travel), portals into other worlds, and adventure to far-off places.

                    Characteristically, I love underdogs, rebels, and outsiders who find creative ways to persist and prevail against impossible odds.

                    As the patterns have become clear, so too has the feeling that the patterns have both existed, and heavily influenced my life choices long before I was aware of them.

                    Made plain, however, they’ve become a compass to create work, make decisions, and live a life that is more highly aligned with my unique interests, strengths, and perspectives.

                    This place of alignment is the place where all of our best creative work comes from. The things we’re most drawn to, it seems, are the things that–when channeled effectively–most draw others to us.

                    Which is why finding ourselves and recognizing the patterns is such a powerful tool.

                    Before we can recognize these patterns, however, we need to find the pieces that comprise them.

                    This requires us to venture out beyond our familiar borders, physically, creatively, intellectually, and more without judgment or expectation as to what we’ll find or where we’ll find it.

                    But find it we will.

                    These hidden pieces are already a part of us. But we often need an external mirror to catch the light just right and reflect back in such a way that we catch a glimpse of a side of ourselves we’ve never noticed before.

                    While they might not make sense immediately in the moment, each new mirror we encounter, each new landmark, each new anchor, offers us an opportunity–and an invitation–to understand ourselves more deeply.

                    I think TS Eliot said it best.

                    We shall not cease from exploration
                    And the end of all our exploring
                    Will be to arrive where we started
                    And know the place for the first time.


                    Explore how to navigate a creative life that matters

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

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

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

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


                      The Upside of Non-Competitive Games

                      Over the past month, I’ve been playing tennis about three times a week.

                      These matches have largely been divided between two friends, Evan and Hamilton, with very different styles and experience levels.

                      In comparing how I play versus each of these different opponents, I’ve noticed an interesting trend that highlights a helpful lesson about the situations and environments we subject our creative work to.

                      A Tale of Two Opponents

                      Evan and I have both been playing tennis for years, albeit mainly against each other during the month or so I visit him in Winnipeg every summer.

                      Historically, he’s tended to win the majority of our games we play, although we’re very well matched and every point feels like a toss up.

                      Hamilton, on the other hand is essentially brand new to the sport.

                      This past month was the first time he’s played regularly, and while his improvement has been remarkable, his game is still highly inconsistent. When he’s on, he can make some great shots and carry extended rallies. When he’s off, however, he hits far too many shots either long or into the net to win sets consistently.

                      The stats tell the story.

                      Of the 50 or so head to head sets we’ve played over the past month, Hamilton probably won 3.

                      As a competitive person, I’d typically prefer to play tight, competitive games where I can test myself against a skilled opponent. And yet over the past month, I found myself enjoying my lopsided matches against Hamilton far more than the close ones with Evan.

                      But it wasn’t the feeling of winning that made me enjoy these matches more.

                      It was the feeling of improvement.

                      Which surprised me. Because I’d always imagined that the best way to improve your skill in any field was to play against others at or above your level.

                      Now, however, I’m not so sure.

                      The Problem with Competitive Games

                      While the matches I play with Evan are tight, competitively, they’re also tight stylistically.

                      Evan is as competitive as I am, and W\when we face off, it’s clear that we both care more about winning than improving.

                      As a result, we revert to safe shots we both know are well within our capabilities, preferring to simply keep the ball in play and wait for the other person to make a mistake, rather than attempting more aggressive (and difficult) shots that would test both ourselves to make and our opponents to return.

                      This approach leads to some extended, competitive rallies… but they’re not all that fun or interesting.

                      What’s more, because we’re not attempting many shots beyond our current skill level, it’s hard to say that we’re improving, despite the amount of time we spend playing.

                      Against Hamilton, however, things are different.

                      Because of the obvious skill differential, I have an overwhelming amount of confidence in my ability to come back if I fall a few points behind.

                      As a result, I feel the freedom to experiment with my game in a way I don’t against Evan.

                      Facing Hamilton, I’m aggressive, seeking the edges of the court and adding more speed to my swings than I necessarily have control over.

                      Most of those shots don’t actually work out.

                      Over the course of our games, however, the success percentage of those aggressive shots has steadily improved. With the increased level of comfort and competence, I’ve started working them into the games against Evan.

                      And I’ve started winning.

                      How Competition Stunts Our Growth

                      When it comes to our work, perhaps the most competitive environment of all is that of counting on our work to earn us an income.

                      And while this is the goal many of us are actively working toward, placing ourselves in this environment too early can ultimately stunt our growth and limit our potential.

                      When our work needs to deliver results, we tend to abandon the loose, experimental, explorative style we played with when the stakes were low.

                      Instead, we focus on a tighter, more measured style focused on limiting mistakes.

                      The problem is that mistakes are the most reliable path to growth.

                      Placing ourselves in environments without room for mistakes then, is a surefire way to remain stuck on the creative treadmill of constant exertion without significant improvement.

                      Ironically, it feels to us as though we’re playing the game the way it’s supposed to be played.

                      We’re running across every inch of the court and even getting ourselves into some extended rallies. But the rallies are characterized by safe shots to the center of the court, mimicking what we see the other players serving up. We rarely, if ever test ourselves by pushing shots to the fringes, testing the boundaries of our opponents, the court, and ourselves.

                      Play Games You Can Come Back From

                      There’s no doubt that if we want to reach our creative potential, sooner or later we’ve got to test our work in the most competitive environments.

                      But in order to get our work to the level where it has a chance to thrive in those environments, we need to spend much more time playing games we know we can come back from, with ample opportunity to make mistakes.

                      Then we need to take advantage of those opportunities and make the mistakes.

                      Most often, this is about testing the smallest viable version of an idea before landing on one that resonates, and only then going all in on it.

                      In practice, this might mean turning a particularly resonant Tweet into a blog post… into a workshop… before ultimately turning it into a course.

                      Keep in mind that there is almost certainly a time to focus on limiting mistakes.

                      Many a Wimbledon title is decided by which of the two world-class players makes just one fewer mistake than the other.

                      The thing is the way you win a Wimbledon title is far from the way you get to a Wimbledon final.

                      The path to Wimbledon, like the path to our potential is filled with countless low stakes games where we can test our ideas, refine our form, and build up our stamina, all with the knowledge that we can make our way back from any mistake we’re likely to make.

                      For every minute a champion spends soaking in the roar of the crowd under the primetime lights, they spend hundreds more on the practice court, without the fans, the glory, and the pressure.

                      Don’t forget to give yourself the same luxury.


                      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.


                        A Two-Step Approach to Engineering Your Next Lucky Break

                        Among my many creative side projects, photography, (specifically landscape & travel) has been one of the longest-running.

                        Like most photographers, I’ve always had something of a photographic bucket list in the back of my mind.

                        Over the years, I’ve managed to check some of the images off the list, while others have remained persistently elusive.

                        Last week, however, I was finally able to capture one of those elusive bucket list photos I’d been chasing for years: A lightning strike.

                        Part of the reason this photo had taken so long to check off the list is that capturing lightning in a photo is highly dependent on luck.

                        • There’s the luck of being in the right place at the right time when the storm rolls in.
                        • The luck of being able to find an interesting viewpoint or perspective.
                        • The luck of having your equipment available and ready for use.
                        • The luck of lightning striking at all, let alone in a pleasing or interesting position within the frame.
                        • And the luck of having the shutter open when it does.

                        This reliance on luck doesn’t just apply to capturing lighting in a photo, however. It also applies to that feeling of capturing lighting in a bottle with any business or creative project.

                        The good news is that there’s a lot we can do to load the dice in our favour and improve our luck.

                        The process of improving our luck and increasing our odds of capturing lightning in a bottle can be boiled down to to two distinct phases.

                        Phase 1: Preparation

                        If we want to improve our odds of harnessing and capturing lightning with our creative projects rather than getting struck down by it, the first phase is to prepare ourselves.

                        This preparation consists of two parts.

                        Equipping Ourselves

                        When I say I hadn’t captured a photo of a lightning strike until last week, it wasn’t for lack of trying.

                        Over the nearly 10 years I’ve been practicing photography, I’ve trained my camera on brewing thunderstorms many times. On a number of occasions, I’d managed to capture small, feeble forks of lightning. But never anything truly impressive.

                        In addition to the time spent out in the field, I’d read articles, watched YouTube videos, and spent hours experimenting both with camera settings and editing techniques.

                        And while that past effort may have felt wasted in the moment, all of it was essential to setting the stage for future success.

                        The importance of this period of equipping ourselves can’t be overstated.

                        While lightning might be captured in a single moment, that moment is almost always preceded by an often years-long period of equipping ourselves with the skills and resources that allow us to grab hold of the opportunity when it presents itself.

                        In addition to skills and resources, we develop, however, proper preparation also bestows us with another, harder to measure trait that is essential for grabbing hold of our lightning bolts.

                        Honing Our Intuition

                        We often think of lightning as a rare and unpredictable event.

                        But this couldn’t be further from the truth.

                        There are many places in the world where thunderstorms are a regular–even daily–occurrence for at least portions of the year.

                        Add to this the fact that we’re typically able to see thunderstorms coming from a distance, and that most storms consist of dozens of individual strikes and it becomes clear that there’s actually an abundance of lightning available for the catching.

                        Once we’re equipped, then, the next step is getting ourselves into position to make the catch.

                        Before we can get ourselves into position, however, we need to be able to recognize when the conditions are brewing to create what I call The Potential for Interesting.

                        In some cases, we can rely on weather forecasts–industry reports, trends, and data–to predict the approximate times and locations of this potential.

                        This type of forecasting is valuable in getting (and keeping) us prepared.

                        But our chances of catching lightning in a bottle drastically improve when we’ve developed the intuition to recognize the quickly changing conditions that portend a gathering storm from the ground, and understand innately where and how to position ourselves to take advantage of it.

                        This intuition is built up over years of missed opportunities, wrong guesses, and failed attempts.

                        And it’s these attempts, even–if not *especially–*those that end in failure that are the key to developing this type of reliable intuition.

                        While you can study the theory and mechanics of any craft, industry, or pursuit, intuition can only be earned through experience–lots of it. Most of it leaving you with nothing to show for it.

                        And while this phase of creative development is frustrating, beneath the surface, the foundation is being laid, our instincts being honed, and our odds being improved for future success.

                        Phase 2: Practice

                        Regularly creating and publishing our work equips us with the skills and intuition that will form the foundation of our ongoing creative practice.

                        But the positive effects of our creative practice can be multiplied by adding a liberal dose of patience.

                        While our intuition might be enough to get us into a promising position, we’re almost certainly going to have to wait (sometimes for an extended period) for lightning to strike near enough for us to capture it.

                        There are two distinct types of patience needed to catch lightning in a bottle. To understand them, it helps to understand the mechanics of capturing lightning in a photo.

                        Outlasting Boredom

                        Far from a high-stakes, guns-at-noon shootout requiring a lightning-quick trigger finger, the challenge of photographing lightning is outlasting the inevitable boredom that sets in during the process.

                        And it’s this ability to outlast boredom that is the first essential form of patience for capturing any kind of lightning.

                        For last week’s photo, I saw the storm gathering and set up my camera equipment on my balcony around 9:30 pm.

                        Then I pulled up a chair… and waited.

                        And waited.

                        And waited.

                        After 30 minutes without capturing anything interesting, I thought about packing up and heading in.

                        An hour in, having captured a kind-of interesting (yet unremarkable) image of lightning cracking inside the clouds, I thought about it more seriously.

                        But the storm persisted, and so, I decided, would I.

                        The shot I ended up using was captured around 10:45, but all told, I sat outside with my camera for more than two hours as the storm rolled southward across the city.

                        Regardless of the project we’re working on, the patience to sit tight and persist when nothing interesting seems to be happening is a pre-requisite for achieving anything interesting.

                        It’s also one of the defining traits separating professionals from amateurs.

                        Amateurs are always looking for the drive-by, quick win.

                        They hear about a hot new trend–be it drop-shipping, TikTok, Clubhouse, NFTs, or whatever comes next–abandon whatever they were doing before, buy into the hype and try to hit it big. When they fail to see immediate results, however, they grow bored and start looking for the next hot new thing.

                        Professionals, on the other hand, enter a space with the Potential for Interesting and are content to sit tight and wait while the conditions continue to develop.

                        As a result of this patience, professionals tend to find themselves in perfect position when that potential becomes reality, often well after the dabblers and the amateurs have moved on.

                        But the willingness to sit outside, passing the time as the storm builds is only one type of patience required.

                        Putting Up with the Misses

                        I ended my two hour sit out on the balcony with one interesting photo.

                        This one “hit” was in addition to several hundred “misses”, uninteresting photos that I deleted immediately.

                        When it comes to catching lightning, this type of success rate is par for the course, both with photography, and any kind of creative work.

                        **See, the only way to capture lightning in a photograph is to press the shutter and hope that lightning happens to strike while the shutter is open.

                        As a photographer, this means that going in, your assumption is that almost 100% of the photos you take will be useless, mistimed, uninteresting images. But while these “misses” might be useless as images, they’re an indispensable part of the process of capturing that one “hit” image that stands out.

                        Because the more time the shutter is open, the greater the chance of capturing a strike.

                        The same concept applies to any creative medium.

                        We can position ourselves in the heart of a thunderstorm, but if our shutter isn’t open when the lightning strikes, we have no hope of catching it.

                        Keep the Shutter Open

                        We can think of the amount of time our shutter is open as the surface area our work covers.

                        If we only published a new podcast episode, blog post, or video sporadically every couple of months, we don’t give ourselves much surface area to capture lightning when it does strike.

                        If, on the other hand, we’re publishing something new on a regular weekly or even daily basis, the surface area of our work increases, and our odds improve.

                        The more ideas we put out into the world, the deeper we explore those ideas, and the longer we stick with them, the more opportunities we give other people to find and resonate with them. We can further increase that surface area by focusing on evergreen content that will remain relevant for months or years after we publish it.

                        This is the equivalent of increasing the shutter time on a camera.

                        It’s almost impossible to capture a lightning strike when the shutter is only open for 1/30th of a second.

                        Leave the shutter open for 30 seconds at a time, however, and set the camera to automatically take one 30-second shot after another for an hour, and the process of capturing a lightning strike is reduced to a simple waiting game.

                        While our odds may have improved, however, we still need to continue to open the shutter again and again and again, publishing new work with the full knowledge that most of it won’t get noticed, catch on, or produce any kind of meaningful result, regardless of its quality.

                        And it’s this patience that is where most creators fall short.

                        Many creators have the skill and intuition to catch lighting in a bottle with any one of their creative projects. Few, however, have the patience to get into position and then wait patiently for their lucky break to strike.

                        In one sense, the act of capturing lightning will always be entirely unpredictable and dependent on luck. No matter how highly skilled, intuitive or patient we are, we’ll never know exactly when, where, or how lightning will strike, after all.

                        In another sense, however, we can actively improve our luck to the point that we can have some confidence, perhaps even certainty that if we prepare our practice and remain patient, sooner or later we’ll end up with a crackling ball of energy in a bottle of our own.


                        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.


                          Where Do We Go From Here?

                          The problem with reaching the summit is that the only path leads back the way you came.

                          And so you’re left with a choice.

                          Remain on the summit and attempt to convince yourself that you’ve gone far enough.

                          Head back down the way you came.

                          Or decide which peak on the horizon to head for next.

                          There’s no path leading forward, as no one’s traveled that way before.

                          At least not from your current vantage point.

                          This is the challenge of achievement.

                          That the more you achieve, the fewer beaten paths lay ahead of you.

                          Until you achieve so much that the last trail ends.

                          And the only option left is to blaze a new trail yourself.

                          No matter what you’ve achieved and how far you’ve come, this is always the greatest test.

                          If you’re lucky, the conditions are such that you can see further ahead than anyone else and begin to map out your route.

                          If you’re not, you may have ascended into the realm of fog and cloud with no option but to blunder your way forward until visibility improves.

                          Either way, the only way forward is forward.


                          Explore how to navigate a creative life that matters

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

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

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

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


                            Creative Wayfinding For Ambitious Optimists.

                            Cooking with Simple Ingedients

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

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

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

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

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

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

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

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

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

                            Bread is not alone in its simple, durable remarkability.

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

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

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

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

                            Simplicity is a Feature Not a Bug

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

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

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

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

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

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

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

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

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

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

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

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

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

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

                            The Magic is in the Process

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

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

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

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

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

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

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

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

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

                            Applying Time & Patience to Your Creative Work

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

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

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

                            And they begin to obsess over it.

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

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

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

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

                            Think Ryan Holiday with Stoicism applied to modern life.

                            Brene Brown with vulnerability.

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

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

                            Which is all any of us needs.

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

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

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


                            Explore how to navigate a creative life that matters

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

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

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

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


                              Getting Past Your First Creative Failure

                              I broke my Wordle streak this morning.

                              It’s not the first time. After discovering Wordle in January and quickly becoming obsessed, I built up a fairly impressive streak before encountering my first defeat 148 days later.

                              That first loss was crushing.

                              I was disappointed in my strategy and furious with the Wordle team for using what I perceived to be a cheap word.

                              Of course, it wasn’t a cheap word.

                              It was a common, well-known word that happened to have a large number of relatives only one letter apart. After identifying four of the five letters with my first 5 guesses, my final guess essentially amounted to a shot in the dark to pick the correct final letter out of three possible options.

                              I missed.

                              And I lost.

                              In the bitterness that defined the day of the loss, I briefly thought about quitting Wordle. Of not giving them the satisfaction of me returning after such humiliation.

                              But the following morning rolled around, habit kicked in, and I found myself back in the saddle, embarking on the beginnings of a new streak.

                              That one lasted 4 days.

                              Again, fury. At myself, at Wordle, at the indignity of losing twice in one week to a game I thought I had long ago mastered.

                              But once again, I returned.

                              Did I really think I had another choice?

                              More streaks followed. And more streaks ended.

                              None as long as my first streak but none as short as my second.

                              Most streaks were ended thanks to situations akin to my very first loss. Today, for example I guessed “PATCH” instead of “CATCH” (though “HATCH” and “WATCH” were also potential options for my final guess).

                              Some streaks were ended by hubris.

                              One because I was traveling and simply forgot.

                              The only commonality between each of my perfect streaks is that sooner or later, they ended.

                              As the losses have mounted, now four or five strong, my posture toward the game has shifted.

                              Sure, I’m still disappointed when I lose. But I no longer dwell on it throughout the day, think about quitting the game out of spite, or even experience any sense of frustration.

                              The more I lose, the more it becomes clear that, as with any game, losing is not only a potential outcome but an inevitable one.

                              To believe otherwise is either ignorant or arrogant.

                              Losing is a Part of the Creative Game

                              When we haven’t yet experienced a significant creative loss—a launch that flops, a poorly conceived project, a client that leaves us for a competitor—we tend to adopt one of two unhelpful postures.

                              The first is hubris, burying our heads in the sand and convincing ourselves our hot streak will never end.

                              The second is fear, living and creating beneath the constant spectre of the inevitable failure we’re certain is right around the corner.

                              In both cases, our posture impacts the quality—and more importantly, the courageousness—of our work.

                              Whether consciously or not, we avoid putting ourselves in situations that might invite that first and most terrible defeat.

                              Which is unfortunate.

                              Because the avoidance of work that is daring enough to have the potential to fail in a significant way is far more detrimental to our success than any failure itself.

                              When we think about failure, we tend to focus on (and exaggerate) the obvious potential downsides: wasted time and effort, financial ruin, and (perceived) public judgment.

                              And it’s true, all of these outcomes are real possibilities.

                              But perhaps we should be more afraid of the prospect of spending years of our lives producing de-fanged work that has absolutely zero chance of breaking through to, connecting with, or moving people.

                              Seek Out the Losses

                              Let’s not sugarcoat it, failing at a project you’ve put months or years of your life into is nothing short of heartbreaking.

                              It will make you question your ability—and worth—as a creator and even a person.

                              At least the first time.

                              But if you’re able to pick yourself up after that first loss, get back on the horse, and find your way to your second loss… well, let’s be honest, that one’s going to be heartbreaking as well, but a little bit less so.

                              As the losses pile up, as they inevitably will, however, they begin to take on a different hue.

                              Sure the opportunity cost and financial downsides of failure are very real (the public judgment usually isn’t), but the meaning you ascribe them shifts.

                              You realize that the losses are not a reflection of you as a person or creator. They’re simply a natural and inevitable part of the game you’ve chosen to play.

                              That often enough, the best possible scenario is simply a shot in the dark, where missing the target is in fact the most likely outcome.

                              That you’ve managed to come back from each of them before, and can—and will—do so again.

                              Persist in creating work daring enough to invite the possibility of both significant success and significant failure and you’ll find that the bite of failure is just as capable of losing its fangs as your work is in the face of it.

                              Which means that perhaps, the sooner we can rack up those initial losses, the sooner we can get around to making more daring, more courageous, more meaningful work.


                              Explore how to navigate a creative life that matters

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

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

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

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


                                The Right Work

                                For all its importance, the right thing to be working on is hard to spot
                                The right work is rarely obvious
                                Rarely urgent
                                Rarely appearing to move the needle

                                The right work is that for which the outcome is irrelevant
                                For which the benefit is simply creating it
                                For yourself For others
                                For what’s gained through the experience.

                                The right work is that which moves you closer to your personal potential
                                That helps you discover more of yourself
                                Embrace more of yourself
                                Become more of yourself.

                                The measure of the right work is not gauged by views or listens or likes
                                Nor in resonance or reach or impact
                                No, the right work is measured in far smaller numbers
                                Binary in fact
                                The answer to a simple question:

                                Did the act of making it move you
                                Closer to who you are
                                To who you could be
                                To what you’re capable of?

                                There’s a time for content
                                For practical work designed to do a specific job
                                That work must be done
                                But make no mistake

                                The right work is the work you do for yourself
                                And if you want to achieve all you’re capable of, that work can’t be put off or ignored.


                                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.


                                  All the Downside, None of the Upside

                                  It’s been warm and humid here lately.

                                  And without air conditioning in the apartment, we’ve come to map our daily routine to the arc of the sun.

                                  We start our days with windows open and the fans on.

                                  Around 10 am, we shut the windows and draw the thick curtains in our East-facing living room.

                                  At 3:30 pm or so, my office, facing west shifts into range of the sun and I close both the window and wooden shutters to keep the room from quickly warming 10 degrees and becoming unbearable to work in.

                                  This daily dance works, for the most part.

                                  Apart from the hottest of days, the apartment remains entirely comfortable even without the aid of an AC unit.

                                  At least until bedtime.

                                  Despite opening all the windows and positioning the fans for maximal air flow through the apartment, it simply doesn’t cool off enough outside by 10 or 11 pm for the bedroom to reach a comfortable sleeping temperature (for me, ~18C).

                                  If we left the windows open over night, the room would cool down fairly quickly, I suspect.

                                  There are a couple of problems standing in the way of doing so, however.

                                  For one, our bedroom windows open onto a fairly busy street, with a good amount of noise from both traffic and the bar across the street, Café Imperio.

                                  Second, the bedroom windows are fitted with wooden shutters, which, while they do an exquisite job of blocking out the light from the street lamps immediately outside our second floor window… also do an admirable job of blocking any air flow, even if the windows are cracked.

                                  The challenge was a formidable one: How to allow the air flow in while minimizing the light and street noise?

                                  After a string of fitful, sweaty nights with the windows and shutters closed, I decided I needed to take it on.

                                  And so, before getting into bed, I did my best to close the shutters far enough to block out the majority of light, while at the same time leaving the windows behind them open far enough to allow in a steady stream of cool air throughout the night.

                                  And the noise? Well, that I’d just have to do my best to tune out.

                                  The result of my effort was the worst night of sleep yet.

                                  The reason became apparent when I groggily opened the shutters in the morning.

                                  It turns out that in pushing the shutters closed far enough to even somewhat darken the room, the windows behind them had been closed to the point where there was no longer a gap through to the cool night air.

                                  They were, however, open far enough to allow the street noise in. Plenty of it.

                                  The result was a room that was significantly brighter and noisier, without any noticeable decrease in temperature.

                                  Said differently, I’d managed to amplify both of the nuisances I was trying to mitigate while leaving my desired positive outcome unchanged.

                                  It made me think of how we often do this to ourselves with our creative work and businesses.

                                  We all have aspects of our work that we’d rather avoid.

                                  Social media, email newsletters, prospecting, pitching and follow ups all come to mind immediately.

                                  We know these tasks have potential positive benefits associated with them. But achieving them requires us to put up with some level of discomfort.

                                  And so we do our best to mitigate the discomforts of the task at hand while still nominally completing it.

                                  Maybe it’s a social strategy that’s entirely based on repurposed and reposted content, without any genuine interaction or originality.

                                  Or maybe it’s a weekly newsletter that gets hastily written at 5 pm on Friday using the dregs of our creative energy.

                                  Whatever the situation, the result is the same.

                                  While we may manage to partially mitigate the discomfort and nuisance we were seeking to avoid, in the process, we completely suppress any chance of the positive outcome we were hoping to achieve.

                                  As in my situation, leaving the window cracked has a way of leaving us with all of the downside and none of the up.

                                  In some cases, the negative effects may extend beyond just our personal experience with the task.

                                  We’re better off not writing a newsletter at all (and avoid the flood of unsubscribes), for example, than write an uninspired, uninteresting one, written and sent only because we know we’re supposed to email our list every week.

                                  What we need to realize is that every upside comes inextricably entangled with one or more accompanying downsides.

                                  Which means we have a choice to make.

                                  Do we accept that in many cases, to get the thing we desire, we’ll have to put up with some things we don’t?

                                  Or do we decide that maybe, the thing we wanted isn’t worth everything that comes along with it?

                                  Either option is perfectly fine. But we should make the choice intentionally.

                                  Open the window and accept the cool night breeze along with the street noise and light.

                                  Or close it, and block it all out.

                                  Just don’t leave it cracked.


                                  Explore how to navigate a creative life that matters

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

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

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

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


                                    The Secret to Interesting Work (Is Staring You in the Face)

                                    It’s not often that the foreword of a book sticks with you more than the book itself.

                                    But there’s this line in the foreword of Malcolm Gladwell’s What the Dog Saw that I’ve thought about nearly every week for the past ten years.

                                    The book is a collection of Gladwell’s favourite essays that were originally published in The New Yorker. The essays cover topics like ketchup vs mustard, women’s hair dye in the 1960s, and various other immediately compelling topics…

                                    Ok, ok, so maybe the topics don’t seem all that interesting at first blush, but the way Gladwell explores them most certainly is.

                                    Which brings us back to the foreword, in which he addresses one of the most common questions he receives from readers.

                                    “Where do you come up with these quirky ideas for stories? And how do you then make these boring, mundane objects, events, and people interesting?”

                                    His response?

                                    “If you believe that everything is interesting, you’ll find that it is.”

                                    Everything around us has a hidden story, he goes on to share, and if we’re willing to dig into it and peek beneath the surface, we’ll often find a fascinating world of twists and turns and intrigue.

                                    This is an important idea for us as creators, but one we don’t often give the attention it deserves.

                                    We like to think that the foundation of successful creative work is our skill at our craft, or perhaps the strategies and tactics we use to get our work in front of an audience.

                                    And to be sure, craft and marketing are essential parts of the work.

                                    But the role of both our craft and our marketing are to communicate ideas. And in order to communicate ideas, we first need to find them.

                                    And not just any ideas.

                                    Work that cuts through the noise is based on novel, original, unique and refreshing ideas.

                                    The kind that open our eyes to something we didn’t know existed.

                                    Or help us see something familiar in an entirely new light.

                                    So much of our success as creators, then, is determined by our ability to consistently find the interesting in the mundane.

                                    But as Gladwell’s quote hints at, while interesting ideas and stories are all around us, often staring us in the face, they require some belief, curiosity, and digging in order to get to the heart of them.

                                    Without a healthy appetite of curiosity and an eye for the interesting, then, we’ll always struggle to produce anything new or fresh.

                                    If our inputs are generic and uninteresting, why should we expect our output to be anything else?

                                    Luckily, the world is packed full of interesting inputs if we know how to look at it, and even luckier, training ourselves to look for interest is a skill you can learn.

                                    Best of all, approaching the world with the belief that it’s full of interesting stories engages a positive feedback loop.

                                    With each new discovery, the world itself becomes a bit more interesting, stoking our curiosity to wonder at what other stories and ideas we might be walking past every day without noticing.

                                    A couple years ago, for example, I was prompted (who knows why) to look up the different types of columns used in classical Greek and Roman construction (seriously, what led me to look this up?).

                                    Now, on a regular basis I notice the Ionic, Doric, Corinthian, and Tuscan columns that ornament many neoclassical buildings around the world.

                                    Or there was the time I finally looked up the answer to a long-running question in my mind about whether the Michelin restaurant rating system stemmed from the Michelin tire company.

                                    It does.

                                    And there’s a whole story there.

                                    I’m unlikely to ever use any of this knowledge in any practical sense.

                                    But having it makes the world–and life–feel richer, more interesting, more inspiring.

                                    All of which lead to more and better creative work.

                                    It’s hard to create interesting work while living in a boring world after all.

                                    The good news is none of us live in a boring world, even if it might seem that way from the outside.

                                    If it does, the solution is fairly straightforward.

                                    Pick something mundane you encounter regularly in your daily life and learn the story behind it.

                                    If the original topic isn’t all that interesting, keep following the related Wikipedia links until you land on something truly fascinating.

                                    I guarantee it won’t take long.

                                    The more you can attune your brain to find interesting stories and ideas, the more information it has to create interesting work.

                                    It won’t happen overnight, but in time it will become second nature.

                                    Make your world interesting and your work will follow suit.

                                    And hey, an interesting life is just more fun to live.


                                    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.


                                      (Re)Finding Your Creative Rhythm

                                      We all have an optimal rhythm.

                                      A pace and a cadence at which we do our best work, are our best selves, and live our best lives.

                                      When we operate in time with our natural rhythm the work becomes effortless as we relax into flow.

                                      We put our usual perfectionism, overanalyzing, and judgment aside and let and let instinct, impulse, and intuition take the wheel.

                                      Life and all its happenings and circumstances, however, has a way of disrupting that rhythm.

                                      Which means that the ability to regain our rhythm is an essential skill.

                                      Sometimes that means picking up after only a couple beats out of time. Sometimes it means picking up in the middle of an entirely different song.

                                      The trick is not to fret over the beats we’ve missed, but to feel and find and pick up the beat where it is now.

                                      When we find and live in the rhythm, everything else takes care of itself.


                                      Explore how to navigate a creative life that matters

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

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

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

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


                                        The Creative Poker Game

                                        Pursuing creative work is a bit like buying into a game of poker.

                                        We can refrain from betting on every single hand we’re dealt and still have our chips slowly eaten away at as hand after hand we pay the minimum ante to simply stay in the game.

                                        We can spend the whole game playing it safe, waiting for the perfect timing for our perfect hand only to have the opportunity fail to materialize.

                                        Or, maybe it does materialize…

                                        When it does, our eyes light up, we go all in, play the hand perfectly… and yet against all odds another player might happen to have something even better.

                                        We leave the game dejected, with the knowledge that even our best wasn’t good enough to win.

                                        Great creators, like great poker players, understand that sometimes you have to bluff your way through when it feels like you don’t have much to work with.

                                        And sure, sometimes you get caught and are forced to admit that you were in over your head and it’s time to go back to the drawing board.

                                        But sometimes you get away with it, and are emboldened to move forward with more confidence.

                                        Great players know how to read the table, to sense opportunity, and move to take what they can get. To see confidence and distinguish strength from bravado. To swim in the currents of emotion and timing and chance and opportunity.

                                        They know that the game is about so much more than simply the cards you’re dealt.

                                        They know that it’s hard to win without ever taking a risk or pushing your luck.

                                        And that even when your luck eventually runs out (and it will), it’s not the end of the world.

                                        You can always buy in again after all.

                                        And unlike poker, the cost of buying back in to your next creative endeavour is measured not in money but in curiosity, hope, and an idea worth exploring.


                                        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.


                                          On Finding Yourself (And Why it Matters as a Creator)

                                          I’ll be honest, I kind of hate the phrase “finding yourself”.

                                          At its best, it’s a boring cliche. At its worst, it’s synonymous with privileged westerners jet-setting across the world to places where their self-serving spiritual tourism does more harm than good.

                                          And yet, I also feel it’s a phrase and an idea that we can’t quite seem to do away with.

                                          Perhaps it’s the fact that we’re thrust into our lives and our selves without an instruction manual.

                                          Perhaps it’s the fact that we’ve all had the experience of feeling some part of ourselves that we didn’t know existed suddenly click into place, in the process, realizing that we are more than we had imagined.

                                          Perhaps it’s that we’ve simply read Eat, Pray, Love (or in my case, Into the Wild) too many times.

                                          Despite the cliche, at some level, the idea of finding ourselves rings true.

                                          And if we want to achieve our potential, creatively or otherwise, finding and piecing together the scattered pieces of ourselves might just be a necessary part of the process of getting there.

                                          But what exactly are we looking for when we set off in search of ourselves?

                                          The idea of finding ourselves implies that we don’t quite know who or what we are. And if we don’t already know ourselves, how do we know what we’re looking for or when we’ve found it?

                                          Mirror Images

                                          The idea of finding ourselves implies an internal journey of discovery, development, and progression.

                                          But that internal journey is often facilitated by an accompanying external journey.

                                          This idea is a core part of the classic Hero’s Journey framework which has both informed (and been perpetuated by) much of modern storytelling as well as showing up in stories and myths across cultures for thousands of years.

                                          As such, it’s no wonder that to some extent, we seem to have some innate awareness of this correlation between the external world and our individual internal worlds.

                                          But if we want to take a more active, intentional approach in filling in the missing gaps in ourselves and moving closer to our potential as both creators and humans, it helps to view this external/internal relationship more literally and concretely.

                                          Because if we know where to look, the external world is strewn with tangible landmarks that can help us triangulate, map, and navigate our abstract inner terrain.

                                          Into the Cave

                                          I’ve spent the majority of the past 8 years traveling in the geographic sense, visiting (and in many cases living in) more than 40 countries across 5 continents.

                                          But I’ve also been traveling in an abstract sense–through books, podcasts, movies, music, essays, ideas, and more–for much longer.

                                          Regardless the mode of travel, I regularly find myself stumbling onto places, art, ideas, and more that resonate in a way that feels as though they’re a part of me, separated at birth only to be rediscovered and reclaimed, and reintegrated now, decades later.

                                          I like to imagine these pieces of myself in the world as something akin to quantum particles, separated but operating in perfect unison.

                                          The first time I remember experiencing this particular sensation of resonance was on a multi-day hike on the west coast of Vancouver Island.

                                          My friend Evan and I had set up camp at the end of the first of four days we’d be hiking.

                                          While Evan napped on the beach in the late afternoon sun, I decided to explore our surroundings.

                                          From our camp, the trail headed up and inland for a few Kilometers, bypassing the high, coastal cliffs before descending and meeting up once again with the coast later the following day. Because the tide was currently out, however, I was able to hopscotch my way along the rocky shore, out around the edge of our cove, and skirt up the coast along the base of the cliffs.

                                          As I rounded the corner, walking a rocky tightrope between the sea and the rocks, the cliffside on my right unexpectedly opened up into a yawning sea cave.

                                          The cave was big enough to feel expansive while small enough to feel intimate, maybe twenty feet tall, thirty feet wide, and forty feet deep.

                                          I crossed the threshold and entered.

                                          It was like stepping into a cathedral. The crashing of the incoming waves quieted, while somehow also becoming one with the rock walls, reverberating back and enveloping me from all sides.

                                          I was awed.

                                          This stumbled upon sea cave felt like home in a way I’d never felt before, and for an hour, I simply sat on the stone floor, stared out at the sea, and reveled in the alignment of person and place.

                                          Landmarks Are Everywhere

                                          While this experience was the first I remember, and to date, still one of the strongest, I’ve now had this resonant experience of finding a part of myself out in the world dozens of times.

                                          Physical locations are a common source of resonance.

                                          These locations may be grand and powerful, like the sea cave on Vancouver Island or the sea cliffs of the UK and Ireland. Rocky coastlines and the deep, relentless pounding of the surf always tend feel like home to me.

                                          But they can also be small, mundane even.

                                          A coffee shop that strikes just the right vibe, or a city park, or a certain random street corner.

                                          They can also be places I’ve never been. A living room on Pinterest, or a kitchen in a movie or TV show. It often doesn’t take more than a short glimpse to recognize a bit of myself buried in a place.

                                          But physical places aren’t the only places I’ve found myself.

                                          Just as often, I’ll discover some part of myself in a song, video, book, poem, creative project, or even another person who may have more fully-realized and developed some trait that is nascent in me.

                                          I’m sure the feeling of reunion with some lost piece of ourselves feels different for all of us.

                                          For me it’s often a visceral kind of resonance in my chest or stomach, goosebumps, or welling up of emotion. Other times, it’s a sense of peace, quiet, and alignment.

                                          Whatever the specific sensation feels like, once we recognize what that particular sense of resonance feels like for us and are able to attune ourselves to its frequency, these pieces of ourselves aren’t all that hard to find.

                                          What’s harder is knowing what to do with these abstract data points.

                                          Because what are you supposed to do with a feeling that some part of you exists in a sea cave, after all?

                                          Note Pieces, Follow Patterns

                                          Since I started thinking more intentionally about finding myself in the external world a couple of years ago, I’ve been collecting and cataloging them.

                                          I dump notes, photos, and ideas of resonant pieces into a Notion doc and have a playlist of all the music that feels as though I could have been the one to write it. I’ve even experimented with creating mood boards comprised of various visual elements.

                                          At times this collection is active and intentional, where I’ll scour Pinterest or Unsplash for imagery that resonates strongly.

                                          More often, the process is passive, where I’ll stumble across something that brings on an unexpected visceral physical reaction.

                                          The more I’ve collected and organized these data points, however, the more patterns have emerged.

                                          Visually, I’m drawn to symmetry, reflection, and balance. I like geometry, landscapes, and natural colour palettes.

                                          Thematically, I’m captivated by stories about time (especially time travel), portals into other worlds, and adventure to far-off places.

                                          Characteristically, I love underdogs, rebels, and outsiders who find creative ways to persist and prevail against impossible odds.

                                          As the patterns have become clear, so too has the feeling that the patterns have both existed, and heavily influenced my life choices long before I was aware of them.

                                          Made plain, however, they’ve become a compass to create work, make decisions, and live a life that is more highly aligned with my unique interests, strengths, and perspectives.

                                          This place of alignment is the place where all of our best creative work comes from. The things we’re most drawn to, it seems, are the things that–when channeled effectively–most draw others to us.

                                          Which is why finding ourselves and recognizing the patterns is such a powerful tool.

                                          Before we can recognize these patterns, however, we need to find the pieces that comprise them.

                                          This requires us to venture out beyond our familiar borders, physically, creatively, intellectually, and more without judgment or expectation as to what we’ll find or where we’ll find it.

                                          But find it we will.

                                          These hidden pieces are already a part of us. But we often need an external mirror to catch the light just right and reflect back in such a way that we catch a glimpse of a side of ourselves we’ve never noticed before.

                                          While they might not make sense immediately in the moment, each new mirror we encounter, each new landmark, each new anchor, offers us an opportunity–and an invitation–to understand ourselves more deeply.

                                          I think TS Eliot said it best.

                                          We shall not cease from exploration
                                          And the end of all our exploring
                                          Will be to arrive where we started
                                          And know the place for the first time.


                                          Explore how to navigate a creative life that matters

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

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

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

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


                                            The Upside of Non-Competitive Games

                                            Over the past month, I’ve been playing tennis about three times a week.

                                            These matches have largely been divided between two friends, Evan and Hamilton, with very different styles and experience levels.

                                            In comparing how I play versus each of these different opponents, I’ve noticed an interesting trend that highlights a helpful lesson about the situations and environments we subject our creative work to.

                                            A Tale of Two Opponents

                                            Evan and I have both been playing tennis for years, albeit mainly against each other during the month or so I visit him in Winnipeg every summer.

                                            Historically, he’s tended to win the majority of our games we play, although we’re very well matched and every point feels like a toss up.

                                            Hamilton, on the other hand is essentially brand new to the sport.

                                            This past month was the first time he’s played regularly, and while his improvement has been remarkable, his game is still highly inconsistent. When he’s on, he can make some great shots and carry extended rallies. When he’s off, however, he hits far too many shots either long or into the net to win sets consistently.

                                            The stats tell the story.

                                            Of the 50 or so head to head sets we’ve played over the past month, Hamilton probably won 3.

                                            As a competitive person, I’d typically prefer to play tight, competitive games where I can test myself against a skilled opponent. And yet over the past month, I found myself enjoying my lopsided matches against Hamilton far more than the close ones with Evan.

                                            But it wasn’t the feeling of winning that made me enjoy these matches more.

                                            It was the feeling of improvement.

                                            Which surprised me. Because I’d always imagined that the best way to improve your skill in any field was to play against others at or above your level.

                                            Now, however, I’m not so sure.

                                            The Problem with Competitive Games

                                            While the matches I play with Evan are tight, competitively, they’re also tight stylistically.

                                            Evan is as competitive as I am, and W\when we face off, it’s clear that we both care more about winning than improving.

                                            As a result, we revert to safe shots we both know are well within our capabilities, preferring to simply keep the ball in play and wait for the other person to make a mistake, rather than attempting more aggressive (and difficult) shots that would test both ourselves to make and our opponents to return.

                                            This approach leads to some extended, competitive rallies… but they’re not all that fun or interesting.

                                            What’s more, because we’re not attempting many shots beyond our current skill level, it’s hard to say that we’re improving, despite the amount of time we spend playing.

                                            Against Hamilton, however, things are different.

                                            Because of the obvious skill differential, I have an overwhelming amount of confidence in my ability to come back if I fall a few points behind.

                                            As a result, I feel the freedom to experiment with my game in a way I don’t against Evan.

                                            Facing Hamilton, I’m aggressive, seeking the edges of the court and adding more speed to my swings than I necessarily have control over.

                                            Most of those shots don’t actually work out.

                                            Over the course of our games, however, the success percentage of those aggressive shots has steadily improved. With the increased level of comfort and competence, I’ve started working them into the games against Evan.

                                            And I’ve started winning.

                                            How Competition Stunts Our Growth

                                            When it comes to our work, perhaps the most competitive environment of all is that of counting on our work to earn us an income.

                                            And while this is the goal many of us are actively working toward, placing ourselves in this environment too early can ultimately stunt our growth and limit our potential.

                                            When our work needs to deliver results, we tend to abandon the loose, experimental, explorative style we played with when the stakes were low.

                                            Instead, we focus on a tighter, more measured style focused on limiting mistakes.

                                            The problem is that mistakes are the most reliable path to growth.

                                            Placing ourselves in environments without room for mistakes then, is a surefire way to remain stuck on the creative treadmill of constant exertion without significant improvement.

                                            Ironically, it feels to us as though we’re playing the game the way it’s supposed to be played.

                                            We’re running across every inch of the court and even getting ourselves into some extended rallies. But the rallies are characterized by safe shots to the center of the court, mimicking what we see the other players serving up. We rarely, if ever test ourselves by pushing shots to the fringes, testing the boundaries of our opponents, the court, and ourselves.

                                            Play Games You Can Come Back From

                                            There’s no doubt that if we want to reach our creative potential, sooner or later we’ve got to test our work in the most competitive environments.

                                            But in order to get our work to the level where it has a chance to thrive in those environments, we need to spend much more time playing games we know we can come back from, with ample opportunity to make mistakes.

                                            Then we need to take advantage of those opportunities and make the mistakes.

                                            Most often, this is about testing the smallest viable version of an idea before landing on one that resonates, and only then going all in on it.

                                            In practice, this might mean turning a particularly resonant Tweet into a blog post… into a workshop… before ultimately turning it into a course.

                                            Keep in mind that there is almost certainly a time to focus on limiting mistakes.

                                            Many a Wimbledon title is decided by which of the two world-class players makes just one fewer mistake than the other.

                                            The thing is the way you win a Wimbledon title is far from the way you get to a Wimbledon final.

                                            The path to Wimbledon, like the path to our potential is filled with countless low stakes games where we can test our ideas, refine our form, and build up our stamina, all with the knowledge that we can make our way back from any mistake we’re likely to make.

                                            For every minute a champion spends soaking in the roar of the crowd under the primetime lights, they spend hundreds more on the practice court, without the fans, the glory, and the pressure.

                                            Don’t forget to give yourself the same luxury.


                                            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.


                                              A Two-Step Approach to Engineering Your Next Lucky Break

                                              Among my many creative side projects, photography, (specifically landscape & travel) has been one of the longest-running.

                                              Like most photographers, I’ve always had something of a photographic bucket list in the back of my mind.

                                              Over the years, I’ve managed to check some of the images off the list, while others have remained persistently elusive.

                                              Last week, however, I was finally able to capture one of those elusive bucket list photos I’d been chasing for years: A lightning strike.

                                              Part of the reason this photo had taken so long to check off the list is that capturing lightning in a photo is highly dependent on luck.

                                              • There’s the luck of being in the right place at the right time when the storm rolls in.
                                              • The luck of being able to find an interesting viewpoint or perspective.
                                              • The luck of having your equipment available and ready for use.
                                              • The luck of lightning striking at all, let alone in a pleasing or interesting position within the frame.
                                              • And the luck of having the shutter open when it does.

                                              This reliance on luck doesn’t just apply to capturing lighting in a photo, however. It also applies to that feeling of capturing lighting in a bottle with any business or creative project.

                                              The good news is that there’s a lot we can do to load the dice in our favour and improve our luck.

                                              The process of improving our luck and increasing our odds of capturing lightning in a bottle can be boiled down to to two distinct phases.

                                              Phase 1: Preparation

                                              If we want to improve our odds of harnessing and capturing lightning with our creative projects rather than getting struck down by it, the first phase is to prepare ourselves.

                                              This preparation consists of two parts.

                                              Equipping Ourselves

                                              When I say I hadn’t captured a photo of a lightning strike until last week, it wasn’t for lack of trying.

                                              Over the nearly 10 years I’ve been practicing photography, I’ve trained my camera on brewing thunderstorms many times. On a number of occasions, I’d managed to capture small, feeble forks of lightning. But never anything truly impressive.

                                              In addition to the time spent out in the field, I’d read articles, watched YouTube videos, and spent hours experimenting both with camera settings and editing techniques.

                                              And while that past effort may have felt wasted in the moment, all of it was essential to setting the stage for future success.

                                              The importance of this period of equipping ourselves can’t be overstated.

                                              While lightning might be captured in a single moment, that moment is almost always preceded by an often years-long period of equipping ourselves with the skills and resources that allow us to grab hold of the opportunity when it presents itself.

                                              In addition to skills and resources, we develop, however, proper preparation also bestows us with another, harder to measure trait that is essential for grabbing hold of our lightning bolts.

                                              Honing Our Intuition

                                              We often think of lightning as a rare and unpredictable event.

                                              But this couldn’t be further from the truth.

                                              There are many places in the world where thunderstorms are a regular–even daily–occurrence for at least portions of the year.

                                              Add to this the fact that we’re typically able to see thunderstorms coming from a distance, and that most storms consist of dozens of individual strikes and it becomes clear that there’s actually an abundance of lightning available for the catching.

                                              Once we’re equipped, then, the next step is getting ourselves into position to make the catch.

                                              Before we can get ourselves into position, however, we need to be able to recognize when the conditions are brewing to create what I call The Potential for Interesting.

                                              In some cases, we can rely on weather forecasts–industry reports, trends, and data–to predict the approximate times and locations of this potential.

                                              This type of forecasting is valuable in getting (and keeping) us prepared.

                                              But our chances of catching lightning in a bottle drastically improve when we’ve developed the intuition to recognize the quickly changing conditions that portend a gathering storm from the ground, and understand innately where and how to position ourselves to take advantage of it.

                                              This intuition is built up over years of missed opportunities, wrong guesses, and failed attempts.

                                              And it’s these attempts, even–if not *especially–*those that end in failure that are the key to developing this type of reliable intuition.

                                              While you can study the theory and mechanics of any craft, industry, or pursuit, intuition can only be earned through experience–lots of it. Most of it leaving you with nothing to show for it.

                                              And while this phase of creative development is frustrating, beneath the surface, the foundation is being laid, our instincts being honed, and our odds being improved for future success.

                                              Phase 2: Practice

                                              Regularly creating and publishing our work equips us with the skills and intuition that will form the foundation of our ongoing creative practice.

                                              But the positive effects of our creative practice can be multiplied by adding a liberal dose of patience.

                                              While our intuition might be enough to get us into a promising position, we’re almost certainly going to have to wait (sometimes for an extended period) for lightning to strike near enough for us to capture it.

                                              There are two distinct types of patience needed to catch lightning in a bottle. To understand them, it helps to understand the mechanics of capturing lightning in a photo.

                                              Outlasting Boredom

                                              Far from a high-stakes, guns-at-noon shootout requiring a lightning-quick trigger finger, the challenge of photographing lightning is outlasting the inevitable boredom that sets in during the process.

                                              And it’s this ability to outlast boredom that is the first essential form of patience for capturing any kind of lightning.

                                              For last week’s photo, I saw the storm gathering and set up my camera equipment on my balcony around 9:30 pm.

                                              Then I pulled up a chair… and waited.

                                              And waited.

                                              And waited.

                                              After 30 minutes without capturing anything interesting, I thought about packing up and heading in.

                                              An hour in, having captured a kind-of interesting (yet unremarkable) image of lightning cracking inside the clouds, I thought about it more seriously.

                                              But the storm persisted, and so, I decided, would I.

                                              The shot I ended up using was captured around 10:45, but all told, I sat outside with my camera for more than two hours as the storm rolled southward across the city.

                                              Regardless of the project we’re working on, the patience to sit tight and persist when nothing interesting seems to be happening is a pre-requisite for achieving anything interesting.

                                              It’s also one of the defining traits separating professionals from amateurs.

                                              Amateurs are always looking for the drive-by, quick win.

                                              They hear about a hot new trend–be it drop-shipping, TikTok, Clubhouse, NFTs, or whatever comes next–abandon whatever they were doing before, buy into the hype and try to hit it big. When they fail to see immediate results, however, they grow bored and start looking for the next hot new thing.

                                              Professionals, on the other hand, enter a space with the Potential for Interesting and are content to sit tight and wait while the conditions continue to develop.

                                              As a result of this patience, professionals tend to find themselves in perfect position when that potential becomes reality, often well after the dabblers and the amateurs have moved on.

                                              But the willingness to sit outside, passing the time as the storm builds is only one type of patience required.

                                              Putting Up with the Misses

                                              I ended my two hour sit out on the balcony with one interesting photo.

                                              This one “hit” was in addition to several hundred “misses”, uninteresting photos that I deleted immediately.

                                              When it comes to catching lightning, this type of success rate is par for the course, both with photography, and any kind of creative work.

                                              **See, the only way to capture lightning in a photograph is to press the shutter and hope that lightning happens to strike while the shutter is open.

                                              As a photographer, this means that going in, your assumption is that almost 100% of the photos you take will be useless, mistimed, uninteresting images. But while these “misses” might be useless as images, they’re an indispensable part of the process of capturing that one “hit” image that stands out.

                                              Because the more time the shutter is open, the greater the chance of capturing a strike.

                                              The same concept applies to any creative medium.

                                              We can position ourselves in the heart of a thunderstorm, but if our shutter isn’t open when the lightning strikes, we have no hope of catching it.

                                              Keep the Shutter Open

                                              We can think of the amount of time our shutter is open as the surface area our work covers.

                                              If we only published a new podcast episode, blog post, or video sporadically every couple of months, we don’t give ourselves much surface area to capture lightning when it does strike.

                                              If, on the other hand, we’re publishing something new on a regular weekly or even daily basis, the surface area of our work increases, and our odds improve.

                                              The more ideas we put out into the world, the deeper we explore those ideas, and the longer we stick with them, the more opportunities we give other people to find and resonate with them. We can further increase that surface area by focusing on evergreen content that will remain relevant for months or years after we publish it.

                                              This is the equivalent of increasing the shutter time on a camera.

                                              It’s almost impossible to capture a lightning strike when the shutter is only open for 1/30th of a second.

                                              Leave the shutter open for 30 seconds at a time, however, and set the camera to automatically take one 30-second shot after another for an hour, and the process of capturing a lightning strike is reduced to a simple waiting game.

                                              While our odds may have improved, however, we still need to continue to open the shutter again and again and again, publishing new work with the full knowledge that most of it won’t get noticed, catch on, or produce any kind of meaningful result, regardless of its quality.

                                              And it’s this patience that is where most creators fall short.

                                              Many creators have the skill and intuition to catch lighting in a bottle with any one of their creative projects. Few, however, have the patience to get into position and then wait patiently for their lucky break to strike.

                                              In one sense, the act of capturing lightning will always be entirely unpredictable and dependent on luck. No matter how highly skilled, intuitive or patient we are, we’ll never know exactly when, where, or how lightning will strike, after all.

                                              In another sense, however, we can actively improve our luck to the point that we can have some confidence, perhaps even certainty that if we prepare our practice and remain patient, sooner or later we’ll end up with a crackling ball of energy in a bottle of our own.


                                              Explore how to navigate a creative life that matters

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

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

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

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


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                                                Hi, I'm Jeremy, I'm glad you're here.

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

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

                                                This is the Creative Wilderness.

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

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