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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Developing the Feel: A Prerequisite for Creative Success
When I lived in Vancouver, rock climbing was my biggest hobby.
My friends and I would climb outdoors pretty much every weekend, indoors at one of the local gyms two or three times a week, and plan trips to climb in the US a few times a year.
While it’s now been seven(😭) years since I’ve climbed regularly, there’s one climb that I still think about regularly.
It was at our local bouldering gym, The Hive.
If you’re not familiar with it, bouldering is a form of climbing based around short routes, no more than 15’ high or so that don’t require ropes or a harness. In an indoor gym, the floor is covered with a thick layer of foam, protecting climbers from the inevitable falls.
Bouldering routes are typically highly technical and are often referred to as “problems” to be solved. The best problems are as challenging mentally as they are physically.
There was one such problem that my friend Kevin and I had been working on literally for weeks.
We’d come to the gym to work on it two or three times every week but could never get more than halfway up.
Despite the hours we’d spent working on it, we were stumped.
Developing the Feel
There was one move in particular that we were stuck on.
It required a lunge up and out to a large, round sloping hold you could (supposedly) palm, but not wrap your fingers around to properly grasp.
Between us, Kevin and I had lunged out for this hold hundreds of times.
And hundreds of times our hands had slid from the surface, our momentum then pulling us off the wall and tumbling down to the foamy floor below.
Until one afternoon, something changed.
I made that same lunge I had made countless times before, barely believing at this point that the move was even possible.
But for whatever reason, this time, my hand stuck–albeit precariously–and I was able to maintain my balance, get my feet into position to push me upward, and four moves later I was at the top of the wall.
Stunned and elated by this breakthrough after dozens of unsuccessful attempts, I jumped down and immediately started up the wall again.
Once again, I lunged at the sloping hold that had given us so many problems, and once again my hand stuck, and I scampered up the rest of the wall.
I called Kevin over and scaled it once again.
After talking through my approach to the move, and a few attempts of his own, Kevin too made it up.
By the end of the climbing session, each of us had climbed it successfully a half-dozen times in a row.
Somehow, once we had developed the feel for successfully making what had previously felt like an impossible move, we could repeat that result with ease.
It turns out, the idea of Developing the Feel applies well beyond the world of climbing.
Developing The Feel In Your Work
It’s easy to look at people who string together success after success and feel like they have some intangible secret sauce that we just don’t have.
We assume it must just be their unique genius, raw talent, decades of dedication to their craft, or maybe even pure luck.
And sure, all of those things matter.
But the more likely reason for their success is that they worked hard in obscurity for a long time before achieving an initial breakthrough.
Once they achieved that first success, however, they developed the feel and it became easier to do it again.
Over time, creating content, products, and services that resonated with their audience became muscle memory, habit, something they could do in their sleep.
With the fundamentals rote, they then had the mental bandwidth to experiment further, and the returns began to compound.
Relax, This Was Always Going To Be the Hard Part
To me, this progression is an encouraging thought.
It means that even if we have a massive vision for the impact our work will create, we don’t need to worry about the specifics of how to achieve that end goal.
At least not right now.
Instead, all we need to focus on is achieving that first breakthrough success.
Because once we’ve done it once, it’s easier to do a second, third, and fourth time, to the point that it becomes our assumed outcome, and our momentum builds.
We can also take solace in the knowledge that that first breakthrough is always going to be the hardest to achieve.
This is the stage that requires the most grit, perseverance, and continual experimentation.
It’s also the stage with the most doubt, failure, and frustration.
Which is why this is the stage where most people give up, before ever achieving that first success. Before developing the feel for what will work for them and their audience.
Developing The Feel Requires Persistence
It might take a dozen attempts, it might take a hundred. Maybe more.
It might require having someone talk us through the moves to help achieve that initial success.
But if we can continue to show up consistently with fresh approaches to the problems we’re facing, eventually, we’ll develop the feel.
And once we do, much of what once felt impossible becomes not only repeatable, but automatic.
We’ll begin recreating your successes with less time, effort, and frustration. And what had previously taken us years to achieve for the first time will now be our minimum level of expectation for each new project.
Maybe it’s landing a new client, creating a piece of content that goes viral in our niche, or pulling off a 6-figure product launch.
Whatever your current challenge, achieve it once and the muscle memory will begin to develop.
Yes, there will still be failure, frustration, and even occasional despair perhaps, but once you’ve developed the feel the balance will begin to tip ever more toward success, ease, and fulfillment.
If things are hard right now, keep showing up and creating, with the knowledge that you’re just one breakthrough away from changing everything.
One day, you’re going to swing out for that hold and your hand is going to stick where it had slipped off dozens of times before.
But until that happens, keep climbing.
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Bushwhacking: The Unavoidable Phase of Any Journey Worth Taking
There’s no trail that leads up to the summit of Mt Breakenridge.
In fact, there’s not even a trail that leads to its base.
What does exist in the way of access is a decommissioned logging road requiring a vehicle with sufficiently high clearance, and a set of passengers willing to get out, chop up and clear fallen trees, and build bridges across the various washouts carved into the road, using fallen trees.
We didn’t know this going in, when my friends Tanner, Matt, and I decided to undertake what lives on as one of the most grueling, infuriating, dangerous—and correspondingly spectacular—excursions of our lives.
All we knew was that from our research poring over maps—satellite, topographical, and otherwise—of the area, the summit, and the valley leading up to it were irresistible.
And so, one July weekend in 2013, after several weeks of planning, we geared up, made the requisite 5 am pre-hike stop at Tim Hortons to pick up coffee and breakfast, and wound our—increasingly slow—way toward the summit.
A couple of hours—and several makeshift bridge builds— in, we reached the end of the line in terms of how far Matt’s truck could take us.
Which meant the real adventure was about to begin.
No sooner had we laced up our boots, hefted our packs, and hit the trail than it was time to remove them in order to ford a thigh-deep river.
If we had been looking for a portent of how the rest of the hike would proceed, this was it.
Over the next 2 hours, we proceeded to bushwhack our way through an almost impassible track of dense, 10-foot-high new-growth forest that had reclaimed what was once a spur of the logging road we drove in on.
On the far side of the new growth, we spent another couple hours scrambling over a series of precariously balanced scree slopes, overgrown with waist-high grass which made finding solid footing a challenge.
Then came the exposed slab faces, slick with seeping water, angling sharply upward toward the summit… and downward toward sheer cliff drops we did our best not to think about.
After each section, we rejoiced, relieved that we had now finished navigating what we were sure was the hard part… only to be greeted with some new challenge.
Finally, late into the evening, however, we reached a high alpine meadow, one of the most glorious in all my years hiking before or since.
And collapsed, in exhaustion, and in awe.
Before dawn the following morning, we donned our crampons and ice axes and made our way up the glacier, through the cloud layer, and to the summit.
Then, we headed back down, bushwhacking in reverse our way back to the truck, the highway, and finally, what was surely the best burger & milkshake anyone has ever tasted.
I think back on this trip regularly for many reasons.
For one, it was one of the most objectively miserable, difficult, and physically uncomfortable experiences of my life.
But it was also one of the most awe-inspiring and spectacular.
Sometimes, I think back to the blue hour descending on our basecamp—an alpine Eden at the base of a glacier—after watching the sun disappear behind the mountains across the valley.
More often, however, I think of the 10 hours of bushwhacking.
My shins bruising against the constant thwacking of springy new-growth branches. The dozen or so nearly-sprained ankles while navigating precarious scree slopes. And the constant, inescapable cloud of mosquitos clogging the air around my face.
I think about the bushwhacking we endured on the way up Mt Breakenridge for two reasons.
The first is as a reminder that no matter what I’m struggling with in the moment, at least it’s not as bad as that.
The second is as a reminder that some type of bushwhacking is unavoidable en route to any destination worth reaching.
There’s a lot we can do to strategize our way around various obstacles we face in our lives and work. But there are always going to be those stretches that we have no choice but to muscle through. And it’s these stretches where we often get stuck, searching for a less uncomfortable, less demanding way forward… that simply doesn’t exist.
And while head-down bushwhacking is not the solution to every obstacle we encounter, there are times when it is, in fact, the only one.
If we believe our destination is worth reaching, sooner or later, we need to face the discomfort inherent in forging ahead where there is no path.
And making 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.
Adapt or Die: The Decision You Face When What You Were Doing Stops Working
When I opened up the weather forecast earlier this week, this is what was waiting for me.
Of course, I knew Texas in July and August was hot. But this?
To a cold-blooded Canadian like me, this reads as more of a cruel joke than a weather forecast.
And yet, it appears that for the next few weeks I’ll be in Texas, this is the unavoidable reality.
On past trips to visit my partner Kelly’s family in Texas, I’ve simply avoided going outside altogether, hiding inside with the blinds drawn and the AC cranked.
The result of this approach is perhaps best told by my step counter app, which tends to contain conspicuous extended streaks of three-digit step totals during my time in the state.
And yet, while this approach helped me succeed at staying comfortable, it wasn’t without its downsides.
My daily walks are where and when I come up with the bulk of my ideas and work through the problems and challenges I’m facing in my business.
Without those daily walks, my creative mind begins to reflect the parched landscape outside.
In addition to a dearth of new ideas, these periods often coincide with my least productive work periods of work, even on tasks and projects that aren’t inherently “creative”.
Aware of the impact this has on my work and life, this time, I’ve decided to take a new approach.
While I’ve pushed my walks to the fringes of the day when the heat is least oppressive, I’ve otherwise accepted the sticky, sweaty discomfort that accompanies them regardless and ventured outside.
The change started with a realization: That I could wallow in the circumstances I found myself in. Or I could accept them and do what I could to work with and around them.
In the case of the current Texas heat wave, I’m fortunate.
I’ll be in Texas for just a few weeks and will then be off elsewhere, hopefully to cooler temperatures.
But as is becoming painfully clear, the heat—everywhere—is only rising and spreading. Which means sooner or later, all of us will need to find a way to live with it.
The same is true for the environments in which we do our creative work.
Whether it’s AI threatening to make us obsolete, Google or Instagram’s latest algorithm update, or old reliable tactics that no longer seem to work, the climate is constantly shifting around us.
And as it does, we face a choice.
We can bury our heads in the sand, holding onto hope that things will go back to the way they were.
Or we can adapt to the new conditions and make the most of them.
In many cases, this will probably mean letting go of the norms, expectations, and habits we’ve established around how we do things.
In many cases, the new normal will almost certainly be objectively worse than the old normal.
And yet, what choice do we have?
The summers of our youths won’t return simply because we preferred them.
Neither will the conditions that allowed our creative work and businesses to take root and grow.
And while we may have little control over the climate in which we find ourselves, we’re not at the mercy of it.
Not entirely at least.
We have at least one choice available to us:
Wallow and wither?
Or adapt & persevere?
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
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.
Whose Path Are You Following?
Imagine this:
Its 500,000 years ago.
And it’s raining, hard, on an undulating limestone landscape that stretches out ahead of you before terminating at the foot of a dramatic mountain range at the edge of the horizon.
Season by season the rains come and go.
And as they do, something imperceptible—but transformative—is happening.
As the rain falls, each drop, in search of somewhere to go, traces a path down the sloping hills before pooling in the nearest low point.
As it travels, it takes with it a souvenir of its journey: A grain or two of sediment from the limestone over (and through) which it’s traveled.
Drop by drop, this process continues—each square meter being pelted millions of times per hour in a heavy downpour.
Slowly, and then quickly, the drops begin to converge around the faint etchings carved out by previous drops.
And drop by drop, those etches widen into grooves, attracting more ever more water.
Years pass.
When the rain is not falling, some grooves make the perfect thoroughfare for small rodents and other creatures.
They too begin to leave their mark.
Decades pass.
The micro highways through the landscape are widened as they become suitable for larger constituents of the environment.
First fox, then coyote, then deer.
Centuries pass, then millennia.
And one day, unbeknownst to you, you find yourself walking down that same path.
A path that exists, not because it’s the most efficient path to where you’re looking to go. But because a single raindrop etched a near-insignificant groove in the landscape 500,000 years ago that other raindrops (perhaps by chance) happened to follow.
There are numerous paths each of us is walking (and thus widening) at any given moment.
From our larger life paths to the paths we’re following to build our businesses, grow our audiences, or get through our days.
Every so often, however, it’s worth pausing and asking ourselves:
Are we on these paths because they’re the most direct or efficient routes to our end destination?
Or have we simply been funneled toward them by forces beyond our perception?
In many, perhaps most cases, our answer will be the latter.
Which leaves us with a second question:
If a single raindrop can alter a landscape forever by charting a new course for itself, what might you be able do?
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.
When In Doubt, Follow the Winding Road
Last weekend, my partner Kelly and I took a weekend road trip through Italy and were plotting a course to Turin from Lucca, a charming old walled city near Florence.
Consulting the map, we opted for what appeared to be the coastal route, which snaked along the coast to Genoa before heading North to Turin.
We imagined the route passing through numerous quaint seaside Italian towns, one of which we might stop in for coffee, another for lunch, another still for an afternoon stroll and croissant.
The idyllic road trip itinerary in other words.
Filled with excitement, we locked the route into Google Maps and hit the road.
It didn’t take long to realize, however, that our excitement had been misplaced. Because barely 30 minutes into the drive, our route directed us onto a massive 8-lane tollway.
The highway was impressive in its own right and promised a smooth and efficient trip back to Turin.
But that efficiency was not without its cost.
In our case, that cost was the seaside towns and coastline we had imagined ourselves spending the day winding through.
My heart sinking, I asked Kelly to see if there was any other route we could take.
It turns out, there was just one, perhaps the polar opposite of the route we were currently on.
The Trade-Offs of Efficiency
The alternative route consisted of a tiny, one-lane road filled with seemingly infinite switchbacks that would add three hours to our trip.
And yet, one look at the squiggly line the road cut into the map told me this was the road we were looking for.
If there’s one thing I’ve learned in years of traveling by foot, by bike, and by car it’s that the winding road is always the one you want.
No, it’s never as efficient as the alternatives, and yes, it takes you much more time, effort, and even stress to get to your destination.
You need to leave earlier, stay on the road longer, and there are always more than a few hair-raising moments passing opposing vehicles while winding up narrow roads with no guard rail between the pavement and a precipitous drop.
Despite the obvious downsides, I’ve yet to take a winding road that wasn’t worth it.
Because what these roads lack in efficiency, they make up for (and more) in discovery, awe, and invigoration.
This is as true when charting a weekend road trip as it is in charting our creative lives and careers.
The Winding Road to Original Work
In our work, we tend to perpetually strive for the most efficient route to our end destination.
And we don’t have to look far to find them.
We can merge onto the highway and join the stream of traffic following the latest trends, committing fully to whatever content, formats, and platforms are hot in the moment.
Done skillfully, we can make a good career of this.
But the toll is steep.
It requires us to give up much of our originality, creating generic, often commoditized work for which there is proven demand, forgoing our creative instincts, curiosity, and fulfillment in exchange for efficiency and predictability.
Not that there’s much creative inspiration to be found on the highway in the first place.
What’s more, in seeking out the most efficient route through our lives we forget that the only true end destination to which we are hurtling is death.
Surely we’d rather take a more scenic—if at times challenging—route there?
The Destination Is Not the Point
That winding road will be full of switchbacks, wrong turns, and dead ends.
We’ll deal with more than a few hair-raising near-misses, landslides blocking a previously navigable road, and time when we’re so far off the map our GPS loses signal and we’re left to find our way forward through instinct, hunch, and experimentation.
And yet it’s undeniable that this route is infinitely enthralling, invigorating, and life-affirming.
It’s also the type of road with the best chance of leading us somewhere interesting.
When traveling this road we don’t always know what the end destination will be.
But then again, on winding roads, the destination is rarely the point.
And in fact, ending up somewhere entirely other than where you imagine when you left might just be the greatest gift the road could give you.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Small Steps
Step
Plant
Rejoin
Realign
Center.
Lean
Stretch
Counter
Balance
Breathe.
Scope
Push
Leap
Land
Pause.
Shimmy
Shift
Sprint
Scramble
Settle.
Survey
Chart
Test
Retreat
Repeat.
Hither
To
Fro
There
And back again
If you make (and let) them
Small steps will take you far.
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 Magic of Zero-Expectation Creative Work
This week, my partner, Kelly, and I celebrated our 5-year anniversary.
Like every relationship, ours has had its share of ebbs and flows, ups and downs. By and large, however, the challenges and conflicts we’ve faced have been few and far between and our daily experience of the relationship is one of joy, possibility, and ease.
To be honest, the level of ease continues to surprise and mystify us.
In fact, we spend a good amount of time trying to decipher the reason behind it.
So far, we’ve come up with a pretty solid list.
For starters, we genuinely like each other, and are fascinated by each other’s work (she works at a startup and is also in the process of launching her own startup).
It also surely helps that we don’t have kids.
But in further reflecting over our anniversary dinner, this week, we had a new revelation, which is this:
Neither of us seems to have any expectation of what this relationship should be.
We’re in the relationship because we recognize the value of being in it now, in the moment, in the day-to-day experience of it, not because of where we hope it will lead or what we hope it will become.
Instead of working toward some pre-defined archetypal (most likely mythical) idea of relationship—and life—we appear to be content to simply be… and see what emerges from that being.
What emerges, it seems, is a greater sense of possibility than would—or perhaps even could—exist with a set of expectations governing and constraining the relationship.
This zero-expectation mindset is a useful one to cultivate in our creative work and businesses as well.
As in any relationship, the experience and results we get from our relationship with our work are beyond our control.
At best, we can influence those outcomes based on what we personally bring to the relationship. But after we’ve shown up consistently with our best work, all we can do is let go and hope our energy, effort, and intention are reciprocated.
Introducing expectation to the mix sets us up for regular (and often severe) disappointment.
In more than 10 years of creative work, I can’t think of a single project or endeavour that has ever met my (usually secretly held) expectations, let alone exceeded them.
Early in my career, those shortfalls were crushing.
As I’ve relaxed or let go of my expectations around my desired results (and more often the timelines of achieving those results), however, the outcomes of any endeavour hold less significance.
Good or bad, thrilling or disappointing, every outcome is simply a way station on the way to some further destination that is currently hidden from view, somewhere beyond the horizon.
Which brings us to the second pitfall of expectation:
Expectation is a destination that is inherently limited by your existing map of the world.
That map doesn’t include the vast territory that will open up as you gain new knowledge, acquire new skills, and meet new people.
Nor does it take into account how the world—and you—will change over that span.
Said differently, expectation is the death of possibility.
And in a world ripe with always emerging possibilities, it’s a poor stance to take if we want to be in a position to take advantage of them.
Instead, in our relationship with our work, as in our relationship with others, the most productive stance we can take is to show up generously, consistently, with firm boundaries but without expectation, and be open to what life brings us.
We don’t have to like what life brings us, often enough we won’t.
But keep showing up in this way long enough and life has a way of reciprocating.
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.
Work with What You Have
While I have a wide variety of taste in music, my hands down favourite artist is Gregory Alan Isakov.
The first time I ever heard one of his songs was, was—believe it or not—in the background of a McDonald’s holiday commercial on TV (as a lifelong vegetarian and farmer, he donated the licensing fee to a sustainable farming non-profit).
Immediately, I was hooked.
Unable to get the Shazam app on my phone up in time, I did my best to memorize the lyrics I’d heard, ran to my computer, furiously typed them into Google, hit enter, and held my breath.
“Big Black Car by Gregory Alan Isakov” came back as the top result.
A quick listen confirmed that this was the song that had captivated me and from that moment on, (what I can only imagine will be) a lifelong bond was formed.
Since then, I’ve probably listened to Gregory’s music more than anyone other artist. I’ve seen him perform live 5 times, in 4 countries (most recently in Paris, though the most memorable show was in Edinburgh). I know all the lyrics to every one of his songs and can play at least a dozen on guitar.
Most of all, however, I’ve spent considerable time and angst wishing I could write songs like him.
See, something about his music resonates with me in a way that feels like I could have written it, as though he’s put the perfect words to my experience of life in a way I never could.
What’s more, our vocal ranges overlap nearly identically, meaning the melodies I might write, align as closely as the lyrics.
Despite the overlap, however, the fact remains that when it comes to songwriting, the magic I find in Gregory’s music is something I simply can’t replicate.
During the time of my life when I still imagined my greatest creative contributions would be as a songwriter and musician, this was a bitter pill to swallow. As my creative identity has shifted from musician to writer and teacher, however, I’ve come to peace with it.
At this point, I can appreciate the magic Greg’s music holds over me and simply behold and appreciate it.
Of course, with the shift in identity, new comparisons have emerged.
As a writer, I now envy James Clear’s single-minded drive, the clarity, precision & background research of his writing, and his systematic approach to building a brand around his work.
I envy Ann Handley’s seemingly effortless injection of wit and humour into business writing.
I envy Robert Macfarlane’s masterful vocabulary, especially when it comes to his lucid descriptions of the natural world.
And I envy David Hiatt’s incredibly personal, story-driven, bordering-on-poetic sales copy.
The list of comparisons doesn’t end there.
And of course, when I think of all the fantastic writers whose work I’ve yet to read, I think it’s safe to say the list of comparisons is potentially limitless.
And yet, despite all the myriad ways in which I might feel my own writing doesn’t measure up, I still regularly get emails like this one.
These emails remind me:
I can’t write songs like Gregory Alan Isakov.
I can’t write non-fiction like James Clear, Ann Handley, or Robert Macfarlane.
I can’t write sales copy like David Hieatt.
But I can do something.
I can work with what I have.
And do the best I can with it.
Because if I don’t do it, no one else will.
We often struggle to perceive our own creative magic.
But that doesn’t mean it doesn’t exist.
Don’t hide it.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
You Can Get There from Here
Though the way is far
The route appears impassable
And no map exists for where you seek to travel
Remember this.
No peak
No dream
No version of yourself
Is unattainable from where you stand today.
Though it may not be easy
Most certainly full of dangers, failed attempts, and unnamed terrors
The path exists
As does the destination.
And regardless of where you are now
Of how far
How small
How scared
You can get there from here.
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.
6 Lessons From Crosswords On Solving Sticky Creative Puzzles
As I write this, I’m working on a 10-day streak of solving the New York Times daily crossword.
Crosswords for me are both the perfect way to unwind and relax while also engaging my brain in an activity that feels challenging and productive.
Solving them requires a blend of logic, abstract thinking, cultural knowledge, and willingness to experiment, traits that, when you think about it, have a lot of overlap with those required to do successful creative work.
And while crosswords are certainly a useful way to flex our creative muscles in a different way than normal, where they really shine is in what they can teach us about solving sticky problems.
Solving sticky problems is a pretty good working definition of what creative work is at its core. In fact, our lives as creators consist of little more than attempting to solve sticky problems, either for ourselves, or our audiences.
- How do we get attention in a noisy world?
- How can we make a sustainable living doing creative work that matters?
- How do we rally and empower our audiences to challenge the status quo in our communities, industries, and the world?
All of these (and many, many more) are the problems we spend our days working to solve.
Which means the better we get at problem-solving as a skill, the greater our success and our impact in all our creative endeavours.
And while problem-solving, like most skills, is something we can only really improve with practice, there’s a lot we can learn from crossword solving that we can then apply to that practice.
1. The Clues Are Right in Front of You (You Just Need to Know How to Look at Them)
A typical crossword puzzle consists of three basic components.
- The 15×15 grid
- The clues
- You, the solver
The premise of the puzzle is that these three self-contained elements should be enough to fill in the puzzle.
Our creative careers can be thought of similarly. We, of course, are the solvers and the grid is the niche or industry we’re operating within.
The clues, however, are a little less obvious.
Then again, so are many crossword clues.
In any challenging puzzle, there will be a small handful of fairly obvious clues which allow us to fill in a few squares and get started. But after that, many–if not most–of the clues are intentionally vague or misleading.
Some clues we might puzzle over for an hour or more, before finally realizing that we’ve been approaching the clue from the wrong angle altogether. When we make the required mental shift, however, the answer seems obvious and we wonder how we didn’t see it all along.
Much like crosswords, the clues to our creative work are usually staring us in the face.
The challenge for us, then, is twofold.
- Learning to spot the clues in the first place
- Making the required mental shift to interpret them in a way that is helpful
Reinterpreting The Clues Around You
We tend to spend most of our time looking externally for clues as to what our correct next step is.
We read books and blog posts and listen to podcasts, looking for the clue–or better yet the answer–to appear in flashing neon letters, “THIS IS THE WAY FORWARD!”
The irony is that the clues are there in the books and blogs and podcasts, but they’re rarely obvious.
They’re more likely to exist in the subtext than in what’s been explicitly stated. In fact, in many cases, the original creator may not even be aware they’re communicating these clues.
To spot them then, we need to dig a little bit deeper than the surface level. To inquire into the thought process behind what’s being presented.
Then we need to inquire into ourselves.
Compared to our external quests for answers, we tend to spend little time seeking out the clues within ourselves. But in my experience, within ourselves is where we’re more likely to find the most useful clues.
The better we get to know ourselves and understand how our skills, tendencies, worldviews, beliefs, Keys to Victory, and more all intersect, the clearer the next step becomes, and the better our results.
But it’s not just the clues that we hold inside ourselves.
It turns out that many of the answers we’re seeking are also hidden away in our own internal nooks and crannies.
2. You Already Know the Answers
In almost every challenging crossword, I reach a point where I’m completely and utterly stumped.
Sometimes there are only a handful of squares remaining, sometimes a whole quarter of the puzzle is blank. At this point, I’ll write the puzzle off as impossible, concede defeat and walk away, looking forward to coming back to a fresh new puzzle the next day.
Inevitably, however, a few hours later, out of some sort of masochistic compulsion, I’ll return to puzzle over it some more.
And yet, somehow, after stepping away it rarely takes much puzzling.
Almost without fail, immediately upon sitting down and running through the clues, something clicks into place. Maybe I grasp the word I’ve been trying to remember or realize there’s a different interpretation of a clue.
What fascinates me about this is that even while I was stumped, beating my head against the wall the first time through, thinking the puzzle was impossible, the answers were already buried somewhere inside of me, and I was just unable to access them for one reason or another.
Like a Chinese finger trap, it often feels like the harder I fight to come to a solution to a clue, the less likely I am to find it.
In the same way, it often takes a break, some space, and a change of scenery to solve particularly frustrating creative problems.
For smaller daily problems, simply getting up and going for a walk is often enough to knock the answers loose. For larger, more vexing problems, it might take a week-long vacation, or even setting the project aside for an indeterminate period of time so we can recuperate and come back fresh.
I most regularly experience breakthroughs over the Christmas holidays when I take time off and do a lot of journaling and reflecting, often finding the answers to the problems I’ve been wrestling with for months reflected back in my writing.
The time off and change of scenery that accompanies attending conferences has proven to be another reliable method of gaining clarity for me.
When we’re stuck, it turns out, the best thing we can do is often not to keep staring at the problem, running through the same clues again and again with a tired mind, but giving ourselves some time and space to relax, back away from the problem for a time, and let our subconscious go to work uncovering the answers we already have within us.
Often, this is all it takes for the answers we’ve been seeking to rise to the surface.
Of course, while we might have many of the answers to a given puzzle within us, there are always going to be those we have to come to by other means.
3. Solve by Triangulating
If you’ve ever done the crosswords yourself, one of the things that might have frustrated you is the obscure pop-culture references from decades, or even centuries past.
When I first started doing crosswords regularly as an early 20-something, these were the clues that always stumped me.
At the time, I imagined that crosswords were simply intended for an older audience, and that I’d have to wait another 30-40 years until I reached my prime crossword-solving years.
Now, however, I’m beginning to suspect otherwise.
In almost any crossword, there’s at least one word that, even once solved, I have no idea what it means. In late-week puzzles, there are typically a handful of these.
Initially, I thought these blindspots were simply a result of my youth, or narrow knowledge. I’m convinced now, however, that this is an intentional decision by crossword creators.
See, while era-specific answers are certainly one type of potential blindspot for solvers, most puzzles have a similar selection of niche, domain-specific answers that would be equally unknowable to the average layperson. This leads me to believe that crossword creators purposefully attempt to design puzzles that almost no one person will have all the answers to.
That doesn’t mean they’re unsolvable, however.
In fact, this is one of the things that actually makes crosswords fun.
One of the interesting results of the format of a crossword is that in theory, you could solve the puzzle by knowing only half the answers. Fill in either all the across or all of the down clues and the puzzle is complete.
What this means is that you can triangulate (or perhaps biangulate?) your way to the answers of many clues about which you are, in fact, clueless.
This is precisely the process required to solve many of the creative problems we encounter.
It often feels like the only way to arrive at the answer is to study and research our way to finding the actual answer itself. But in fact, the shorter (perhaps even immediate) route to solving many problems is to simply fill in the blanks based on the adjacent knowledge we already have.
Marketing is the most obvious field in which to practice this type of triangulation.
While each of us is at least fairly knowledgeable in our primary field of work or core topic we create around, few of us have thoroughly studied the ins and outs of marketing theory.
In fact, I’d argue that marketing is such a multifaceted field that no one person can possibly have deep knowledge in each of the sub-categories that make it up such as psychology, copywriting, design, positioning, and so on, not to mention all the technology-specific applications of marketing.
And yet, if we’re going to get our work out in front of the people we seek to serve, we’re going to have to market it.
Which means we’re going to have to do our best to fill in the gaps and make educated guesses based on our existing knowledge.
There’s no way we can study long enough to know the answer to every possible problem we encounter.
But we don’t need them.
More often than not, our foundational knowledge and experience are enough to get us to a place where we can make an educated guess about those blank squares in front of us, and take the next step forward with confidence, slow and incremental as that progress may be.
4. One Square At a Time
During my first run through the clues of a challenging puzzle, I might be able to fill in less than 10% of the puzzle’s squares. The second pass, in many cases, may only result in one or two more answers.
Of course, challenging puzzles are not meant to be solved in just a couple passes, but when the initial cycles through the clues yield so little progress, it doesn’t leave you feeling great about your prospects of completion.
What fascinates me, however, is that while each pass through the clues may only fill in a few additional squares, those few squares are often juuuuuust enough to get us the next few squares.
Occasionally, we might fill in a long, 10-letter word that opens up the board. But most often our progress is made by filling in a square here, a square there, bit by bit until the puzzle is complete.
In the same way, few of the creative problems we struggle with have grand solutions we can simply plug in and be done with.
Instead, our problems will be solved by wearing away at them, bit by bit.
Much like moving through a dense patch of fog, each little bit of progress, irrelevant though it may seem, often illuminates juuuuuuust enough of the way ahead to make the next tiny bit of progress.
As we continue to circle back on the problems we’re grappling with, we find that over time, the little bits of knowledge, perspective, or clarity we’ve picked up elsewhere allow us to more clearly identify the structure of the problem at hand, until at some point, the answer becomes obvious.
Two of the things I marvel at the most when it comes to this approach to solving crosswords are:
- Just how big a difference one letter can often make
- How arriving at the answer to a clue in one corner of the puzzle often has its root in solving a clue in the far opposite corner, slowly but surely snaking your way across the puzzle.
The lesson is that we never know where the answers will come from.
Everything connects up in one way or another, and sometimes, even the smallest bit of progress in one area can lead to a breakthrough in another.
5. Sooner or Later, You Need to Leap
Even following all of the puzzle-strategies strategies listed above, we still often reach a point where we are well and truly stuck.
We’ve spent hours on the puzzle, taken breaks and come back, and triangulated our way to a semi-completed stalemate. I typically reach this point at least once a week, usually on one of the difficult weekend puzzles.
At this point, it feels as though we’ve exhausted our options and have no choice but to concede defeat.
And yet, we have one strategy left at our disposal, that we often overlook.
To take a leap and start making some (educated) guesses.
The wonderful thing about being well and truly stuck is that we have nothing to lose by taking a leap and penciling our best guesses into the empty squares. If none of our guesses stick? Well, we were about to give up anyway. But if we guess right on even one clue, it may be enough to solve the rest of the puzzle.
Despite the asymmetrical positive rewards of guessing, we often overlook it as a valid strategy.
In creative work, this guessing often occupies the gap between researching how to do something and actually doing it.
You can read a dozen books and listen to many more podcasts on how to successfully launch a product. But no amount of research will be able to fill in all the blanks for you to launch your specific product to your specific audience.
Those answers don’t exist out there. At least not yet.
Which means if you want to find them, sooner or later, you’ll have to make some educated guesses, and leap.
Chances are, your first guess might not be entirely correct. This is where a lot of creators get frustrated and give up.
As with crosswords, however, when it comes to creative work, our first guess is never the be-all, end-all. We have the opportunity to erase any of our guesses and pencil in something new, trying new solutions and seeing what opportunities they open up.
6. How Long Are You Willing to Stare at the Problem?
There’s one last piece to this puzzle-solving puzzle, and it’s best articulated Albert Einstein, who, refuting his own reputation said, “It’s not that I’m so smart, it’s just that I stay with problems longer.”
In fact, in perhaps the ultimate display of sticking with a problem, Einstein spent more than 30 years working on and puzzling over the problem of relativity.
This ability to stick with problems, it turns out, might be the most essential skill in solving sticky creative problems.
In crosswords, this ability to stick with the problem plays out in two ways, both of which map over to creative equivalents.
1. Sticking with the Individual Clue
When I’m first going through a puzzle, I’ll breeze through the clues, filling in the answers I know immediately and skipping the ones I have to exert any brainpower on whatsoever.
On a Monday puzzle, I might be able to solve the whole puzzle this way in a matter of minutes.
But in a late-week puzzle, there’s not much low-hanging fruit, meaning before long, a change in tactics is required.
At this point, I’ll continue to cycle through the clues sequentially, spending a bit more time puzzling over each. But at some point, there comes a time when the only way to solve a clue is to stop cycling and simply sit with the single clue, puzzling over its various possible interpretations and possible answers.
There’s something about this pausing and puzzling that is inherently uncomfortable.
Cycling through the clues provides a feeling of motion, momentum, and optimism.
Pausing and puzzling, however… It just makes you feel stuck.
The irony is that sitting with this feeling of being stuck is often the only way to get unstuck, both in regard to a tricky crossword clue and a tricky creative problem.
I can’t count the number of times I’ve breezed over a problem I’ve faced in my creative work because the answer wasn’t immediately obvious, telling myself I’d come back to it later and letting promising projects languish in the meantime.
Often, in fact, almost always, when I finally did come back to the problem, it took little more than 5 or 10 minutes of focused thought directed squarely at the specific problem to come up with an answer and kick-start the project.
Sometimes, cycling through the problems in front of us and filling in as many of the easy answers as quickly as possible is the best strategy.
But sooner or later, we reach a point with every project where the only way to move the project forward is to stop cycling, and focus our attention on the one problem that’s grinding everything to a halt .
Over time, conditioning ourselves to stick with problems trains us to take on more ambitious projects in the future.
This is because as we work our way through problems that had initially stumped us, we build up our confidence that we can work our way through future problems that might look difficult (or even impossible) when viewed at first approach.
This type of confidence is invaluable in creative work.
2. Sticking with the Puzzle
The second form of sticking with the problem applies to the puzzle as a whole.
With Sunday crosswords, in particular, I often find myself stuck around 30 or 45 minutes into working on the puzzle.
The average time for me to complete a Sunday puzzle however is probably between 2 and 2.5 hours.
This ratio between the time-to-frustration and the time-to-success (let’s call it roughly a 1:4 ratio) feels about right to me when applied to creative work as well.
Most successful creators I know were creating things online in one form or another for at least 5 years before things really started to click.
And yet, for most new creators, frustration often sets in between the 1-2 year mark.
This is the point at which we’ve tried a bunch of stuff, done a lot of research, educated ourselves (or so we think), and feel like things should be getting easier.
When it doesn’t, many creators give up.
What we can learn from both Einstein and crossword puzzles, however, is that perhaps our single biggest asset as creators is our ability to stick with the puzzle in front of us well past the point at which we become frustrated with it.
Keep in mind that at the macro level, the puzzle we’re working on is not tied to a particular project, niche, or medium.
Instead, the macro project we’re each trying to solve is building a meaningful, fulfilling life.
If doing creative work is an essential part of such a life for us, it’s worth remembering that there are many outlets for and expressions of our creativity.
You might be podcasting (and frustrated) now only to find out a year from now that the thing that clicks for you is a YouTube channel.
Or, you might be struggling to build a digital product business only to find in the future that what really lights you up the most is working 1:1 with people.
Sticking with the creative puzzle is about pushing through the frustration and continuing to cycle through all the clues presented to us, reframing them in our minds to find new possible answers which we’ve never before considered.
You Get to Choose the Puzzle to Solve
Viewing creative work as a puzzle is perhaps the most helpful lens available to us.
It implies frustration, the ability to think abstractly and solve non-obvious problems. It also implies that there is, in fact, a solution.
Unlike the crossword, however, that answer—and the clues that lead to it—aren’t the same for every player.
This is both a blessing and a curse
It means we might not immediately know when we’ve arrived at the end of the puzzle.
But it also means that perhaps we get to choose what solving the puzzle looks like. Which means if we choose, we can construct and solve a puzzle that plays to our natural strengths.
That’s not to say it will be quick or easy.
Any puzzle worth solving will certainly require us to walk away in frustration more than once.
But if we’re working on the right puzzle, we’ll find ourselves continually drawn back to spend more time staring at the problems in front of us until something shifts, unlocks, and the next step becomes apparent.
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.
Developing the Feel: A Prerequisite for Creative Success
When I lived in Vancouver, rock climbing was my biggest hobby.
My friends and I would climb outdoors pretty much every weekend, indoors at one of the local gyms two or three times a week, and plan trips to climb in the US a few times a year.
While it’s now been seven(😭) years since I’ve climbed regularly, there’s one climb that I still think about regularly.
It was at our local bouldering gym, The Hive.
If you’re not familiar with it, bouldering is a form of climbing based around short routes, no more than 15’ high or so that don’t require ropes or a harness. In an indoor gym, the floor is covered with a thick layer of foam, protecting climbers from the inevitable falls.
Bouldering routes are typically highly technical and are often referred to as “problems” to be solved. The best problems are as challenging mentally as they are physically.
There was one such problem that my friend Kevin and I had been working on literally for weeks.
We’d come to the gym to work on it two or three times every week but could never get more than halfway up.
Despite the hours we’d spent working on it, we were stumped.
Developing the Feel
There was one move in particular that we were stuck on.
It required a lunge up and out to a large, round sloping hold you could (supposedly) palm, but not wrap your fingers around to properly grasp.
Between us, Kevin and I had lunged out for this hold hundreds of times.
And hundreds of times our hands had slid from the surface, our momentum then pulling us off the wall and tumbling down to the foamy floor below.
Until one afternoon, something changed.
I made that same lunge I had made countless times before, barely believing at this point that the move was even possible.
But for whatever reason, this time, my hand stuck–albeit precariously–and I was able to maintain my balance, get my feet into position to push me upward, and four moves later I was at the top of the wall.
Stunned and elated by this breakthrough after dozens of unsuccessful attempts, I jumped down and immediately started up the wall again.
Once again, I lunged at the sloping hold that had given us so many problems, and once again my hand stuck, and I scampered up the rest of the wall.
I called Kevin over and scaled it once again.
After talking through my approach to the move, and a few attempts of his own, Kevin too made it up.
By the end of the climbing session, each of us had climbed it successfully a half-dozen times in a row.
Somehow, once we had developed the feel for successfully making what had previously felt like an impossible move, we could repeat that result with ease.
It turns out, the idea of Developing the Feel applies well beyond the world of climbing.
Developing The Feel In Your Work
It’s easy to look at people who string together success after success and feel like they have some intangible secret sauce that we just don’t have.
We assume it must just be their unique genius, raw talent, decades of dedication to their craft, or maybe even pure luck.
And sure, all of those things matter.
But the more likely reason for their success is that they worked hard in obscurity for a long time before achieving an initial breakthrough.
Once they achieved that first success, however, they developed the feel and it became easier to do it again.
Over time, creating content, products, and services that resonated with their audience became muscle memory, habit, something they could do in their sleep.
With the fundamentals rote, they then had the mental bandwidth to experiment further, and the returns began to compound.
Relax, This Was Always Going To Be the Hard Part
To me, this progression is an encouraging thought.
It means that even if we have a massive vision for the impact our work will create, we don’t need to worry about the specifics of how to achieve that end goal.
At least not right now.
Instead, all we need to focus on is achieving that first breakthrough success.
Because once we’ve done it once, it’s easier to do a second, third, and fourth time, to the point that it becomes our assumed outcome, and our momentum builds.
We can also take solace in the knowledge that that first breakthrough is always going to be the hardest to achieve.
This is the stage that requires the most grit, perseverance, and continual experimentation.
It’s also the stage with the most doubt, failure, and frustration.
Which is why this is the stage where most people give up, before ever achieving that first success. Before developing the feel for what will work for them and their audience.
Developing The Feel Requires Persistence
It might take a dozen attempts, it might take a hundred. Maybe more.
It might require having someone talk us through the moves to help achieve that initial success.
But if we can continue to show up consistently with fresh approaches to the problems we’re facing, eventually, we’ll develop the feel.
And once we do, much of what once felt impossible becomes not only repeatable, but automatic.
We’ll begin recreating your successes with less time, effort, and frustration. And what had previously taken us years to achieve for the first time will now be our minimum level of expectation for each new project.
Maybe it’s landing a new client, creating a piece of content that goes viral in our niche, or pulling off a 6-figure product launch.
Whatever your current challenge, achieve it once and the muscle memory will begin to develop.
Yes, there will still be failure, frustration, and even occasional despair perhaps, but once you’ve developed the feel the balance will begin to tip ever more toward success, ease, and fulfillment.
If things are hard right now, keep showing up and creating, with the knowledge that you’re just one breakthrough away from changing everything.
One day, you’re going to swing out for that hold and your hand is going to stick where it had slipped off dozens of times before.
But until that happens, keep climbing.
Bushwhacking: The Unavoidable Phase of Any Journey Worth Taking
There’s no trail that leads up to the summit of Mt Breakenridge.
In fact, there’s not even a trail that leads to its base.
What does exist in the way of access is a decommissioned logging road requiring a vehicle with sufficiently high clearance, and a set of passengers willing to get out, chop up and clear fallen trees, and build bridges across the various washouts carved into the road, using fallen trees.
We didn’t know this going in, when my friends Tanner, Matt, and I decided to undertake what lives on as one of the most grueling, infuriating, dangerous—and correspondingly spectacular—excursions of our lives.
All we knew was that from our research poring over maps—satellite, topographical, and otherwise—of the area, the summit, and the valley leading up to it were irresistible.
And so, one July weekend in 2013, after several weeks of planning, we geared up, made the requisite 5 am pre-hike stop at Tim Hortons to pick up coffee and breakfast, and wound our—increasingly slow—way toward the summit.
A couple of hours—and several makeshift bridge builds— in, we reached the end of the line in terms of how far Matt’s truck could take us.
Which meant the real adventure was about to begin.
No sooner had we laced up our boots, hefted our packs, and hit the trail than it was time to remove them in order to ford a thigh-deep river.
If we had been looking for a portent of how the rest of the hike would proceed, this was it.
Over the next 2 hours, we proceeded to bushwhack our way through an almost impassible track of dense, 10-foot-high new-growth forest that had reclaimed what was once a spur of the logging road we drove in on.
On the far side of the new growth, we spent another couple hours scrambling over a series of precariously balanced scree slopes, overgrown with waist-high grass which made finding solid footing a challenge.
Then came the exposed slab faces, slick with seeping water, angling sharply upward toward the summit… and downward toward sheer cliff drops we did our best not to think about.
After each section, we rejoiced, relieved that we had now finished navigating what we were sure was the hard part… only to be greeted with some new challenge.
Finally, late into the evening, however, we reached a high alpine meadow, one of the most glorious in all my years hiking before or since.
And collapsed, in exhaustion, and in awe.
Before dawn the following morning, we donned our crampons and ice axes and made our way up the glacier, through the cloud layer, and to the summit.
Then, we headed back down, bushwhacking in reverse our way back to the truck, the highway, and finally, what was surely the best burger & milkshake anyone has ever tasted.
I think back on this trip regularly for many reasons.
For one, it was one of the most objectively miserable, difficult, and physically uncomfortable experiences of my life.
But it was also one of the most awe-inspiring and spectacular.
Sometimes, I think back to the blue hour descending on our basecamp—an alpine Eden at the base of a glacier—after watching the sun disappear behind the mountains across the valley.
More often, however, I think of the 10 hours of bushwhacking.
My shins bruising against the constant thwacking of springy new-growth branches. The dozen or so nearly-sprained ankles while navigating precarious scree slopes. And the constant, inescapable cloud of mosquitos clogging the air around my face.
I think about the bushwhacking we endured on the way up Mt Breakenridge for two reasons.
The first is as a reminder that no matter what I’m struggling with in the moment, at least it’s not as bad as that.
The second is as a reminder that some type of bushwhacking is unavoidable en route to any destination worth reaching.
There’s a lot we can do to strategize our way around various obstacles we face in our lives and work. But there are always going to be those stretches that we have no choice but to muscle through. And it’s these stretches where we often get stuck, searching for a less uncomfortable, less demanding way forward… that simply doesn’t exist.
And while head-down bushwhacking is not the solution to every obstacle we encounter, there are times when it is, in fact, the only one.
If we believe our destination is worth reaching, sooner or later, we need to face the discomfort inherent in forging ahead where there is no path.
And making 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.
Adapt or Die: The Decision You Face When What You Were Doing Stops Working
When I opened up the weather forecast earlier this week, this is what was waiting for me.
Of course, I knew Texas in July and August was hot. But this?
To a cold-blooded Canadian like me, this reads as more of a cruel joke than a weather forecast.
And yet, it appears that for the next few weeks I’ll be in Texas, this is the unavoidable reality.
On past trips to visit my partner Kelly’s family in Texas, I’ve simply avoided going outside altogether, hiding inside with the blinds drawn and the AC cranked.
The result of this approach is perhaps best told by my step counter app, which tends to contain conspicuous extended streaks of three-digit step totals during my time in the state.
And yet, while this approach helped me succeed at staying comfortable, it wasn’t without its downsides.
My daily walks are where and when I come up with the bulk of my ideas and work through the problems and challenges I’m facing in my business.
Without those daily walks, my creative mind begins to reflect the parched landscape outside.
In addition to a dearth of new ideas, these periods often coincide with my least productive work periods of work, even on tasks and projects that aren’t inherently “creative”.
Aware of the impact this has on my work and life, this time, I’ve decided to take a new approach.
While I’ve pushed my walks to the fringes of the day when the heat is least oppressive, I’ve otherwise accepted the sticky, sweaty discomfort that accompanies them regardless and ventured outside.
The change started with a realization: That I could wallow in the circumstances I found myself in. Or I could accept them and do what I could to work with and around them.
In the case of the current Texas heat wave, I’m fortunate.
I’ll be in Texas for just a few weeks and will then be off elsewhere, hopefully to cooler temperatures.
But as is becoming painfully clear, the heat—everywhere—is only rising and spreading. Which means sooner or later, all of us will need to find a way to live with it.
The same is true for the environments in which we do our creative work.
Whether it’s AI threatening to make us obsolete, Google or Instagram’s latest algorithm update, or old reliable tactics that no longer seem to work, the climate is constantly shifting around us.
And as it does, we face a choice.
We can bury our heads in the sand, holding onto hope that things will go back to the way they were.
Or we can adapt to the new conditions and make the most of them.
In many cases, this will probably mean letting go of the norms, expectations, and habits we’ve established around how we do things.
In many cases, the new normal will almost certainly be objectively worse than the old normal.
And yet, what choice do we have?
The summers of our youths won’t return simply because we preferred them.
Neither will the conditions that allowed our creative work and businesses to take root and grow.
And while we may have little control over the climate in which we find ourselves, we’re not at the mercy of it.
Not entirely at least.
We have at least one choice available to us:
Wallow and wither?
Or adapt & persevere?
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
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.
Whose Path Are You Following?
Imagine this:
Its 500,000 years ago.
And it’s raining, hard, on an undulating limestone landscape that stretches out ahead of you before terminating at the foot of a dramatic mountain range at the edge of the horizon.
Season by season the rains come and go.
And as they do, something imperceptible—but transformative—is happening.
As the rain falls, each drop, in search of somewhere to go, traces a path down the sloping hills before pooling in the nearest low point.
As it travels, it takes with it a souvenir of its journey: A grain or two of sediment from the limestone over (and through) which it’s traveled.
Drop by drop, this process continues—each square meter being pelted millions of times per hour in a heavy downpour.
Slowly, and then quickly, the drops begin to converge around the faint etchings carved out by previous drops.
And drop by drop, those etches widen into grooves, attracting more ever more water.
Years pass.
When the rain is not falling, some grooves make the perfect thoroughfare for small rodents and other creatures.
They too begin to leave their mark.
Decades pass.
The micro highways through the landscape are widened as they become suitable for larger constituents of the environment.
First fox, then coyote, then deer.
Centuries pass, then millennia.
And one day, unbeknownst to you, you find yourself walking down that same path.
A path that exists, not because it’s the most efficient path to where you’re looking to go. But because a single raindrop etched a near-insignificant groove in the landscape 500,000 years ago that other raindrops (perhaps by chance) happened to follow.
There are numerous paths each of us is walking (and thus widening) at any given moment.
From our larger life paths to the paths we’re following to build our businesses, grow our audiences, or get through our days.
Every so often, however, it’s worth pausing and asking ourselves:
Are we on these paths because they’re the most direct or efficient routes to our end destination?
Or have we simply been funneled toward them by forces beyond our perception?
In many, perhaps most cases, our answer will be the latter.
Which leaves us with a second question:
If a single raindrop can alter a landscape forever by charting a new course for itself, what might you be able do?
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.
When In Doubt, Follow the Winding Road
Last weekend, my partner Kelly and I took a weekend road trip through Italy and were plotting a course to Turin from Lucca, a charming old walled city near Florence.
Consulting the map, we opted for what appeared to be the coastal route, which snaked along the coast to Genoa before heading North to Turin.
We imagined the route passing through numerous quaint seaside Italian towns, one of which we might stop in for coffee, another for lunch, another still for an afternoon stroll and croissant.
The idyllic road trip itinerary in other words.
Filled with excitement, we locked the route into Google Maps and hit the road.
It didn’t take long to realize, however, that our excitement had been misplaced. Because barely 30 minutes into the drive, our route directed us onto a massive 8-lane tollway.
The highway was impressive in its own right and promised a smooth and efficient trip back to Turin.
But that efficiency was not without its cost.
In our case, that cost was the seaside towns and coastline we had imagined ourselves spending the day winding through.
My heart sinking, I asked Kelly to see if there was any other route we could take.
It turns out, there was just one, perhaps the polar opposite of the route we were currently on.
The Trade-Offs of Efficiency
The alternative route consisted of a tiny, one-lane road filled with seemingly infinite switchbacks that would add three hours to our trip.
And yet, one look at the squiggly line the road cut into the map told me this was the road we were looking for.
If there’s one thing I’ve learned in years of traveling by foot, by bike, and by car it’s that the winding road is always the one you want.
No, it’s never as efficient as the alternatives, and yes, it takes you much more time, effort, and even stress to get to your destination.
You need to leave earlier, stay on the road longer, and there are always more than a few hair-raising moments passing opposing vehicles while winding up narrow roads with no guard rail between the pavement and a precipitous drop.
Despite the obvious downsides, I’ve yet to take a winding road that wasn’t worth it.
Because what these roads lack in efficiency, they make up for (and more) in discovery, awe, and invigoration.
This is as true when charting a weekend road trip as it is in charting our creative lives and careers.
The Winding Road to Original Work
In our work, we tend to perpetually strive for the most efficient route to our end destination.
And we don’t have to look far to find them.
We can merge onto the highway and join the stream of traffic following the latest trends, committing fully to whatever content, formats, and platforms are hot in the moment.
Done skillfully, we can make a good career of this.
But the toll is steep.
It requires us to give up much of our originality, creating generic, often commoditized work for which there is proven demand, forgoing our creative instincts, curiosity, and fulfillment in exchange for efficiency and predictability.
Not that there’s much creative inspiration to be found on the highway in the first place.
What’s more, in seeking out the most efficient route through our lives we forget that the only true end destination to which we are hurtling is death.
Surely we’d rather take a more scenic—if at times challenging—route there?
The Destination Is Not the Point
That winding road will be full of switchbacks, wrong turns, and dead ends.
We’ll deal with more than a few hair-raising near-misses, landslides blocking a previously navigable road, and time when we’re so far off the map our GPS loses signal and we’re left to find our way forward through instinct, hunch, and experimentation.
And yet it’s undeniable that this route is infinitely enthralling, invigorating, and life-affirming.
It’s also the type of road with the best chance of leading us somewhere interesting.
When traveling this road we don’t always know what the end destination will be.
But then again, on winding roads, the destination is rarely the point.
And in fact, ending up somewhere entirely other than where you imagine when you left might just be the greatest gift the road could give you.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Small Steps
Step
Plant
Rejoin
Realign
Center.
Lean
Stretch
Counter
Balance
Breathe.
Scope
Push
Leap
Land
Pause.
Shimmy
Shift
Sprint
Scramble
Settle.
Survey
Chart
Test
Retreat
Repeat.
Hither
To
Fro
There
And back again
If you make (and let) them
Small steps will take you far.
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 Magic of Zero-Expectation Creative Work
This week, my partner, Kelly, and I celebrated our 5-year anniversary.
Like every relationship, ours has had its share of ebbs and flows, ups and downs. By and large, however, the challenges and conflicts we’ve faced have been few and far between and our daily experience of the relationship is one of joy, possibility, and ease.
To be honest, the level of ease continues to surprise and mystify us.
In fact, we spend a good amount of time trying to decipher the reason behind it.
So far, we’ve come up with a pretty solid list.
For starters, we genuinely like each other, and are fascinated by each other’s work (she works at a startup and is also in the process of launching her own startup).
It also surely helps that we don’t have kids.
But in further reflecting over our anniversary dinner, this week, we had a new revelation, which is this:
Neither of us seems to have any expectation of what this relationship should be.
We’re in the relationship because we recognize the value of being in it now, in the moment, in the day-to-day experience of it, not because of where we hope it will lead or what we hope it will become.
Instead of working toward some pre-defined archetypal (most likely mythical) idea of relationship—and life—we appear to be content to simply be… and see what emerges from that being.
What emerges, it seems, is a greater sense of possibility than would—or perhaps even could—exist with a set of expectations governing and constraining the relationship.
This zero-expectation mindset is a useful one to cultivate in our creative work and businesses as well.
As in any relationship, the experience and results we get from our relationship with our work are beyond our control.
At best, we can influence those outcomes based on what we personally bring to the relationship. But after we’ve shown up consistently with our best work, all we can do is let go and hope our energy, effort, and intention are reciprocated.
Introducing expectation to the mix sets us up for regular (and often severe) disappointment.
In more than 10 years of creative work, I can’t think of a single project or endeavour that has ever met my (usually secretly held) expectations, let alone exceeded them.
Early in my career, those shortfalls were crushing.
As I’ve relaxed or let go of my expectations around my desired results (and more often the timelines of achieving those results), however, the outcomes of any endeavour hold less significance.
Good or bad, thrilling or disappointing, every outcome is simply a way station on the way to some further destination that is currently hidden from view, somewhere beyond the horizon.
Which brings us to the second pitfall of expectation:
Expectation is a destination that is inherently limited by your existing map of the world.
That map doesn’t include the vast territory that will open up as you gain new knowledge, acquire new skills, and meet new people.
Nor does it take into account how the world—and you—will change over that span.
Said differently, expectation is the death of possibility.
And in a world ripe with always emerging possibilities, it’s a poor stance to take if we want to be in a position to take advantage of them.
Instead, in our relationship with our work, as in our relationship with others, the most productive stance we can take is to show up generously, consistently, with firm boundaries but without expectation, and be open to what life brings us.
We don’t have to like what life brings us, often enough we won’t.
But keep showing up in this way long enough and life has a way of reciprocating.
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.
Work with What You Have
While I have a wide variety of taste in music, my hands down favourite artist is Gregory Alan Isakov.
The first time I ever heard one of his songs was, was—believe it or not—in the background of a McDonald’s holiday commercial on TV (as a lifelong vegetarian and farmer, he donated the licensing fee to a sustainable farming non-profit).
Immediately, I was hooked.
Unable to get the Shazam app on my phone up in time, I did my best to memorize the lyrics I’d heard, ran to my computer, furiously typed them into Google, hit enter, and held my breath.
“Big Black Car by Gregory Alan Isakov” came back as the top result.
A quick listen confirmed that this was the song that had captivated me and from that moment on, (what I can only imagine will be) a lifelong bond was formed.
Since then, I’ve probably listened to Gregory’s music more than anyone other artist. I’ve seen him perform live 5 times, in 4 countries (most recently in Paris, though the most memorable show was in Edinburgh). I know all the lyrics to every one of his songs and can play at least a dozen on guitar.
Most of all, however, I’ve spent considerable time and angst wishing I could write songs like him.
See, something about his music resonates with me in a way that feels like I could have written it, as though he’s put the perfect words to my experience of life in a way I never could.
What’s more, our vocal ranges overlap nearly identically, meaning the melodies I might write, align as closely as the lyrics.
Despite the overlap, however, the fact remains that when it comes to songwriting, the magic I find in Gregory’s music is something I simply can’t replicate.
During the time of my life when I still imagined my greatest creative contributions would be as a songwriter and musician, this was a bitter pill to swallow. As my creative identity has shifted from musician to writer and teacher, however, I’ve come to peace with it.
At this point, I can appreciate the magic Greg’s music holds over me and simply behold and appreciate it.
Of course, with the shift in identity, new comparisons have emerged.
As a writer, I now envy James Clear’s single-minded drive, the clarity, precision & background research of his writing, and his systematic approach to building a brand around his work.
I envy Ann Handley’s seemingly effortless injection of wit and humour into business writing.
I envy Robert Macfarlane’s masterful vocabulary, especially when it comes to his lucid descriptions of the natural world.
And I envy David Hiatt’s incredibly personal, story-driven, bordering-on-poetic sales copy.
The list of comparisons doesn’t end there.
And of course, when I think of all the fantastic writers whose work I’ve yet to read, I think it’s safe to say the list of comparisons is potentially limitless.
And yet, despite all the myriad ways in which I might feel my own writing doesn’t measure up, I still regularly get emails like this one.
These emails remind me:
I can’t write songs like Gregory Alan Isakov.
I can’t write non-fiction like James Clear, Ann Handley, or Robert Macfarlane.
I can’t write sales copy like David Hieatt.
But I can do something.
I can work with what I have.
And do the best I can with it.
Because if I don’t do it, no one else will.
We often struggle to perceive our own creative magic.
But that doesn’t mean it doesn’t exist.
Don’t hide it.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
You Can Get There from Here
Though the way is far
The route appears impassable
And no map exists for where you seek to travel
Remember this.
No peak
No dream
No version of yourself
Is unattainable from where you stand today.
Though it may not be easy
Most certainly full of dangers, failed attempts, and unnamed terrors
The path exists
As does the destination.
And regardless of where you are now
Of how far
How small
How scared
You can get there from here.
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.