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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Whose Path Are You Following?

June, 24, 2023

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.

The Enormous Hidden Danger of Obvious Tiny Problems

July, 16, 2222

Last weekend I bought myself a long-overdue new pair of shoes.

My previous pair of New Balances were well over a year old, and, based on my daily step-count, had accumulated more than 3,500km of use, the rough equivalent of walking from San Fransisco to Chicago.

The mesh covering the toes had torn in several places, the insoles had each become a mangled mess, and any hint of tread on the soles had long been worn away to pure smoothness.

Needless to say, the shoes had seen better days.

This was perhaps best evidenced by the fact that at least once per outing, a rock would find its way in through some hole or another.

When it did, I would invariably follow the same process most of us do when faced with a rock in our shoe.

Upon first noticing the rock, we tell ourselves it’s manageable and keep walking.

As we walk, we scrunch and squirm our feet, attempting to shift the stone to a more tolerable position. With so little room to maneuver, however, if we do manage to move the stone it’s only to an equally (or perhaps even more) irritating location.

On we walk despite the discomfort, annoyed at the thought of halting our progress in order to deal with such a tiny annoyance. We’re making great time, after all…

“Maybe if I keep walking long enough, I’ll wear the stone into nothing,” we muse to ourselves hopefully.

Sooner or later, however, we reach a point where we’re forced to confront the fact that we can continue no further without addressing the issue, and that the only solution is to stop walking, remove the shoe, dump the stone, and then lace back up.

If we’re lucky, we’ll have paused to remove the stone before the skin has been worn raw or broken.

If we’ve waited too long, however… Well, we’re in for a difficult, painful journey ahead.

Left unattended, even the smallest grain of sand will cause a blister that hobbles and eventually renders us no longer able to move forward at all.

Of course, removing and re-tieing a shoe is far from an arduous procedure.

And yet for some reason, the thought of stopping to perform it always presents an outsized feeling of annoyance.

So we put it off and continue walking, often to our own detriment.

This behaviour isn’t confined to rocks in our shoes.

We face various sources of friction in our creative work as well.

And while the fixes are often as simple as pausing to remove a stone from our shoe, we delay, telling ourselves it’s nothing and that we can push through.

And yet, as with a stone against skin, even the tiniest sources of friction will eventually hobble us if left unaddressed.

Maybe friction exists between you and a team member or collaborator and has the potential to fester into larger problems.

Maybe friction exists in a part of your creative process that has the potential to sap the joy from the parts you once loved.

Maybe friction exists between you and an entirely misaligned business or creative platform you’ve built, which is successful… but grates against you with every movement.

It’s always frustrating and inconvenient in the moment to pause, take off our shoes and remove the irritant.

The loss of momentum and delay feel hard to justify.

Even more so when we’re walking through an environment that almost guarantees that we’ll pick up a new stone as soon as we return to our feet.

But these stones we pick up can’t be worn down. The friction they cause can’t be outlasted.

So if we don’t slow down and address the friction as it appears, we won’t make it to our destination at all, no matter the pace we’ve kept up to that point.

Are Your Creative Heroes Leading You to Failure?

July, 9, 2222

It’s hard to walk around the town centres of many major cities these days without noticing a conspicuous array of empty stone pedestals.

These pedestals, of course, were at one point occupied by statues of historically significant figures who, in the past few years, have had their legacies re-examined through a modern lens.

Statues, we’re realizing, celebrate, honour, and uphold more than just the person depicted.

In many cases, a statue might be better thought of as a personification of a set of values. Its presence is not only a reminder of those values, but a reinforcement, and in many cases an aspirational ideal.

This is true for every stone-carved general, sword drawn, horse reared, eternally charging into battle to defend his homeland.

It’s true for every bronze-molded sports icon revelling in the moment of victory over seemingly insurmountable odds.

And it’s true for the statues we’ve erected internally for our personal creative idols.

Much like physical statues reflect and reinforce the values and aspirations of a given society, the heroes we place on our internal pedestals reflect and reinforce our personal values and aspirations.

Our choice of heroes, then, is one of the most impactful choices we as creators make, as they have a heavy influence on both the outcomes we seek and the routes we choose to get there.

And yet, so often we unwittingly follow our heroes down paths that have no hope of delivering us to the destination we seek.

Choosing Heroes for the Wrong Reasons

Like most statues, we tend to erect internal statues based on our heroes’ accomplishments alone.

Maybe they’ve built the type of business or creative platform we aspire to build. Maybe they’ve won awards, accolades, and honours we dream of winning. Or maybe we simply aspire to lead the same day-to-day life they do.

Accomplishments are both easy to observe and easy to aspire to.

But they don’t tell the whole story.

We don’t need to look further than any of the real-world statues that have been torn down in recent years to see that many people who’ve made significant accomplishments have done so while also wreaking pain and destruction on those around them.

While it’s (hopefully) unlikely that our creative heroes’ journeys involved slavery, colonization or mass degradation of other people, there are plenty of other problematic narratives we may be subconsciously internalizing from them.

In some cases, the lessons we internalize from these narratives may be outright sleazy or unethical.

But more common (and perhaps the more dangerous) are the banal variety of implied directives that are simply unpractical, unrealistic, or misaligned with our personal circumstances, skills, and dispositions.

When internalized, these takeaways send us happily off in the wrong direction, thinking we’re making progress toward our goals, when they are in fact keeping us in stuck in place.

Problematic Origin Stories

My partner, Kelly, and I were talking about this idea recently and she immediately referenced two of her own former heroes who she’d soured on after learning more about their backstories.

The two women in question are full-time humour writers and for a long time, served as proof to Kelly that humour writing was a viable career path.

Each of them are supremely talented (and funny) writers, and have built huge followings through their popular blogs, written several books, and are living what appears to be the picture-perfect writer’s life.

As Kelly started researching their backstories and deconstructing her heroes’ journeys, however, another common thread emerged.

It turns out that they both had wealthy husbands that had allowed them to work full-time on their writing for multiple years without any pressure for their writing to support them.

What’s more, in getting to know one of these heroes at a conference, Kelly discovered that even as a published author of multiple books, her hero was still not making enough from her writing for it to actually be considered a viable career option.

The realization was crushing.

These statues which had formerly represented hope and possibility were now monuments to what now felt like an all but impossible goal.

The Tortured Artist

Another common example of a problematic hero’s journey is that of the tortured artist.

Yes, there’s something poetically compelling about a person who produces transcendent work but can’t bear to live with themselves or the world they inhabit. This inherent tension and drama is often exactly the thing that draws us to these people and their stories.

But if we’re honest, do any of us actually want to live those lives?

Personally, I’d rather make great work and live a happy, rich, fulfilling life while doing so.

While these examples are each problematic in their own ways, there’s another origin story that is more pervasive, and perhaps more destructive.

This is the origin story where our hero got to where they are by being picked or discovered.

Pick Me! Pick Me!

Maybe it’s the movie star who was randomly spotted on the street by a director and cast into the role that changed their life.

Or the writer who was able to land a publishing deal because they knew the right people.

Or perhaps the creator who was picked, not by a person, but by an algorithm, that for some unknown reason caused them to go viral and delivered their big break.

There are countless stories of successful creators who broke through based on being discovered by being in just the right place at just the right time and essentially being delivered a heaping serving of luck.

And to some extent, we all benefit from luck at some point in our creative careers.

Indeed, I’m convinced that a massive part of creative success is simply producing good work long enough for luck to catch up with us.

But erecting statues to heroes who got where they are based on a singularly lucky (and perhaps unrepeatable) event is a dangerous practice. They reinforce the idea we already desperately want to believe that some day, we might get picked as well.

And when we hold out for getting picked, we tend to cut corners with our creative practice.

Why learn to market ourselves effectively when one day someone, once we’ve been discovered, someone else will do it for us?

Why focus on learning the ins and outs of audio and video production, web design, and copywriting? We’re just the talent after all, and soon enough that talent will get noticed and amplified by someone with all the resources we currently lack.

Except…

The odds simply aren’t in our favour.

In all likelihood, neither you nor I are going to get picked.

And with that in mind, we’re better off erecting statues to more realistic heroes. The type of heroes whose paths to success are actually possible for us to follow.

Empowering Origin Stories

My biggest personal creative hero is Seth Godin.

I admire the deeply personal impact his work has had on countless creators, entrepreneurs, and marketers and aspire one day to leave a similar legacy of positive change on the people who’ve interacted with my work.

But while I admire Seth’s achievements, what I admire most is the path he’s taken to get there.

See, Seth is notorious for his publishing habit.

In addition to 30+ books, over the course of his career, he’s published more than 7000 blog posts. The vast majority of those have come in a daily publishing streak that has stretched for almost two decades

His persistence isn’t limited to his blog, however.

While working as a book packager, Seth sold his first book only to follow it up with 900 straight rejection letters from publishers.

While we all might hope for better luck for ourselves, there’s something comforting to me in Seth’s origin story.

It conveys the idea that if all else fails, we as creators can win through sheer attrition. By outlasting and wearing down all the forces aligned against us until it becomes impossible for us not to succeed.

To me, it’s these stories of mundane persistence that are most worthy of our statues.

Audit (& Tear Down) Your Statues

Whether you’re aware of it or not, you’ve likely got your own array of internal statues you’ve erected to your various heroes.

Some of these may have been intentionally constructed while others may slowly and subtly taken form over time.

Regardless of how they got there, these statues influence how you show up in the world as a creator and a human. They influence the goals you set, the paths you choose to reach them, and how you choose to view your progress along the journey.

Every so often, it’s worth re-examining them, questioning the values they embody and the messages they send, and considering whether or not those messages are aligned with where you’re currently looking to go and how you’re looking to get there.

Many of your statues won’t be.

In these cases, don’t think twice about tearing them down.

Then, atop the empty pedestals, consider erecting new statues to replace them.

Perhaps your statues will honour those who persisted through countless rejections until they could no longer be ignored.

Perhaps it will be those who discovered their gifts and and created meaningful work late in life.

Or perhaps it will be those who created in their spare time, who never achieved fame or fortune but who found enormous personal fulfillment or community impact through their work.

Whoever you choose to choose to build up in your mind, remember that our heroes, and the statues we erect to honour them matter.

Choose them wisely.

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.

Speak First

July, 2, 2222

We all wish the muse would speak to us more often.

That it would whisper the perfect words in our ear, guide our hand across the canvas, set us on automatic mode as it takes over and does the work.

Once we’ve tasted that flow state once, where it feels as though something other than us is in control, we long to experience it every time we sit down to work.

This is often the source of our very best work after all, when we feel connected to something greater than ourselves. Something expansive, universal.

And so we’re tempted to wait for it. To hold off on doing the work until the muse speaks to us.

What we fail to realize is that creating meaningful work is not about being the muse’s translator. It’s about participating in a protracted conversation with the muse.

And in a conversation, both parties need to carry the load.

Sometimes, when the muse is silent, we need to do the talking, to show up and do the work without external guidance or input.

Sometimes that work is good.

Sometimes it’s utter garbage. When it is, we simply need to keep up our end of the conversation, keep blathering on until the muse finally interjects, smacks us over the head, and says, “Will you shut up and listen already? It’s my turn to speak.”

Who knows how long you’ll have to carry the conversation on your own before the muse responds.

But as with any conversation, the one we carry on with the muse is most productive, most natural when there are two willing and eager participants.

It’s always hardest to break the silence.

But if it needs to be broken, better to be the one to do 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.

The Creative Magic of Not Having All the Answers

June, 18, 2222

As you might imagine from the occasional poems I write and publish for the newsletter, I certainly have some interest in poetry.

But that interest is more closely tied to writing poems than reading them.

See, while I recognize the value of good poetry (is there another medium with more meaning-per-word?), I suffer from the same problem that keeps most people from reading, let alone enjoying it.

In short, it makes me feel dumb.

It probably stems from high school English class assignments to interpret a poem and write an essay on its themes and meanings, but I’ve internalized this belief that I’m supposed to understand absolutely what a poem is saying after reading it.

On the rare occasions I do read poetry, that understanding is conspicuously absent.

It’s surprising, then, that one of my favourite podcast discoveries from the past year is a show called Poetry Unbound.

Here’s the show’s description:

Your poetry ritual: An immersive reading of a single poem, guided by Pádraig Ó Tuama. Unhurried, contemplative and energizing. New episodes on Monday and Friday, about 15 minutes each. Two seasons per year, with occasional special offerings. Anchor your life with poetry.

I discovered the show through an interview the host, Pádraig Ó Tuama gave on one of my other favourite shows, On Being.

And despite some initial skepticism, my interest was piqued, and I decided to give it a shot.

I don’t remember which episode I listened to first. But what I do remember is that my whole conception of what it meant to read and consume poetry was immediately shattered and then reconstructed into something entirely different.

And with it, the way I viewed all sorts of creative puzzles and problems in my life and business.

You’re Not Supposed to Know

Pádraig opened that first episode as he always does, with a full, read-through of the poem.

As usual, I had no idea what it was trying to say.

But what stood out to me as Pádraig–an accomplished poet himself–finished reading and began talking through the poem, was that he clearly had no idea exactly what the poem was about either.

And yet that not knowing didn’t hamper his enjoyment of the poem.

If anything, it increased it.

His analysis of the poem was filled with suppositions, hunches, and personal reflections on what the piece was bringing up for him.

It was clear that for Pádraig, the value of poetry is not in the knowing exactly what the poet meant when they wrote the poem, but in the wondering about what it could mean, even–or perhaps especially–if that meaning is only true for you.

As I’ve been thinking about this approach to poetry over the past few months, it’s struck me that it’s the same approach the most successful creators and entrepreneurs bring to their work.

And yet, most of us have been ill-equipped to embrace this essential mindset.

First, You Have to Unlearn

Our culture places a high value on knowing.

Our education system spends over a decade ingraining in us the idea that there is not only a single definitive answer to any problem for us, but in fact a single definitive answer for everyone.

Armed with this worldview, we head off into the post-school world looking for singular answers and certainty.

As creators, this leads us to seek out the “one key strategy” or “secret growth hack” that will guarantee success. We feel as though there is some definitive right way to build a successful creative platform, product, business, or career, and that someone out there has the answer, we just need to find it.

But this desire for the right answer often limits both the quantity and quality of the work we publish.

We often feel as though our work must be airtight, impermeable to critique, and absolutely defensible in order to share it publicly.

We imagine the army of trolls waiting to tear us down for publishing anything less than codified fact, and so steer well clear of publishing ideas based on our flimsy feeling hunches, suppositions, and wonderings.

And yet, it’s those very wonderings that are at the heart of any original idea, business, content, product, or art.

Anything that can be definitively known must, by definition, be unoriginal.

And anything new, that hasn’t yet existed can’t possibly be known. It can only be imagined. Wondered at.

In our thirst for knowing, we’ve forgotten the value in this wondering.

The Value of Wonder(ing)

The value of wondering spans across every aspect of our work, from individual pieces of content, to the strategies we use to market and sell our work, to the arc of our careers.

Wondering About Content

At the micro, content-level, wondering is at the heart of both original and resonant work, both of which are required traits to grow a creative platform.

And at the heart of both originality and resonance is an element of surprise.

As Robert Frost succinctly put it, “No surprise for the writer, no surprise for the reader.”

Indeed, all of my very favourite essays and creative content I’ve produced are the ones that ended up in a place I couldn’t have predicted or imagined when I sat down and wrote the first line.

It turns out, those are typically the ones that resonate most with others as well.

If we want to create this type of surprising, original, resonant work, however, we need to leave room for that surprise. That room can only come from exploring topics and ideas about which we don’t have all the answers.

In fact, the unraveling and discovery of a subject should be the driving motivator behind everything we create.

One of the most perspective-shifting quotes I’ve ever heard came from a non-fiction author being interviewed about his latest book.

When asked about what inspired him to write this book in particular he replied, “I realized I didn’t know as much as I wanted to about the topic so I decided to write a book on it.”

This dynamic plays out abundantly across the arts.

Few songs flow fully formed from a songwriter’s mouth, nor paintings from the brushes of painters nor poems from the pen of poets.

Most often, original creative work starts as a small nagging thread of an idea that is then pulled and unraveled inch by inch.

All of this is driven by the process of wondering.

Great content follows the same process.

If we want to set our work apart, our best bet is not to share what we already know to be true.

Instead, it’s to start with a question about what we don’t know, and then follow its twists and turns and surprises to its logical conclusion.

One that no one else has likely yet arrived at.

Wondering About Strategy

Wondering is as much at the core of any successful marketing or audience growth strategy as it is of creating the content that strategy is designed to spread.

This is because no matter how successful a given tactic or strategy has been for someone else, it’s unlikely to give us the same results straight off the shelf.

Experimentation is at the heart of all successful marketing, and wondering is at the heart of all experimentation.

We might wonder:

What would happen if we committed to Tweeting every day for a year?
What if we started sending out a weekly newsletter?
What if we focused on leveraging other people’s audiences to grow our own?
What if the strategy we’re following right now isn’t actually the best fit for our personal disposition?

When we’re feeling stuck, instead of seeking out another off-the-shelf solution, the most productive action we can take might just be to start wondering. To start asking questions of ourselves and our current approach, and then following them where they lead.

In my experience, this wondering often opens up new ways to approach strategies to which we’d previously felt resistance, as well as entirely new strategies, that shouldn’t work… but for us, somehow do.

To find them, however, we need to get curious.

Wondering About Career

Finally, there’s the wondering that drives our careers.

This is the wondering that drives all great storytelling. The wondering that comes from knowing the beginning but not the ending.

It’s the tension that keeps us engaged, wanting to find out what will happen next.

We often think we want clarity and certainty in our work, but clarity and certainty have the same effect on our careers and lives as knowing how a magic trick was performed.

Once we know the answers, the magic is lost.

How many people do you know whose days, weeks, and careers follow the same rote pattern?

Day in, day out, season by season the work remains more or less the same, knowing each day what the next will bring. Predictable, repetitive, known.

And most often, boring and unfulfilling.

Is that what we really want for our careers?

How much creativity and inspiration can exist in such a sterile environment?

Because a state of absolute knowing and certainty can only exist as long as no new ideas or opportunities are permitted to enter.

Wondering at the level of our lives and careers allows us to imagine a version of our life beyond the one we currently occupy.

More importantly, wondering allows us to imagine a version of ourselves beyond who we currently are and what we’re currently capable of.

And only once this destination is established can we plot a course to get there.

Nothing Is as It Seems (If We Approach It That Way)

There are few more widely read and quoted poems than Robert Frost’s, The Road Not Taken.

I was first introduced to it in one of the aforementioned high school English classes and was delighted to find for once a delightfully simple and straightforward poem that required little in the way of interpretive genius.

I was surprised then, years later, to find that even this simple, seemingly obvious poem has multiple suggested interpretations, chief among that the poem’s commonly understood directive to “follow your own path” is actually ironic in nature.

On the one hand, it’s frustrating to realize that even this most accessible of poems with a clear and encouraging directive is not as clear-cut as it seems.

On the other hand, however, I can’t help but feel some delight.

The delight of finding a treasure chest buried just beneath the sod in your back yard.

Of realizing that the mundane world you thought you knew so well contains some hidden magic.

What if that were true for every aspect of our work?

What if every idea, strategy, project, medium, offer, and career path had hidden depths, and alternative interpretations beyond how they were initially presented to us?

Waiting to be discovered.

Waiting to be questioned.

Waiting to be wondered at.

I’d like to think that’s true.

And perhaps all we need to do to make it true is to approach our work, and our lives, with the assumption that it is.

Knowing is finite. Wondering is infinite.

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 Work Requires Some Swagger (Here’s How to Find Yours)

June, 11, 2222

I looked up from my laptop just in time to see her hop deftly down from the roof of the apartment across the courtyard and land, perfectly, effortlessly balanced on the thin ledge that gave way to a five-story drop.

There had been no fear. No second-guessing as she approached the roof’s edge. No hint of a wobble as she confidently stuck her landing on the thin ledge that couldn’t have been more than two inches wide.

It was an awe-inspiring performance.

I sat and watched and admired and envied the confident swagger she possessed as she moved further along the ledge until she was directly across from my living room window.

She paused, looked up, locked eyes with me. Then, she leaned forward over the edge.

My heart leaped. She plummeted.

Five, ten, fifteen feet.

Then, just as she approached the ground, with the same lazy, confident swagger with which she had approached the roof’s edge, she unfurled her wings, caught an updraft, and arced up past my window, the sun glinting off her jet black plumage in what could only be interpreted as a wink in my direction.

Oh to be a crow.

Find Your Creative Swagger

For something as mundane as a crow taking flight from the roof of an apartment building, the image has been surprisingly difficult to shake.

What captivated me in the moment, however, and what continues to stick with me is the energy with which the crow approached the edge of the building.

No hesitation. No caution. No second-guessing.

Simply intention and fluid execution.

We could all stand to bring more of this energy to our creative work.

Because what is creative work if not an infinite series of ledges we inch our way towards… and then leap.

Sure the goal is to stick the landing on the far side of the gap, but in my experience, sticking the landing is a lot easier when we’re secure in the knowledge that we can catch ourselves if we miss.

Part of this creative swagger is born of skill acquisition and mastery.

Like a backcountry explorer who understands how to find food, construct shelter, and navigate an unknown wilderness, we can equip ourselves with the creative equivalents to be able to handle the challenges we are likely to face as we navigate our own creative wilderness.

These skills might be idea generation and communication, community building, sales, product development, audience development, copywriting, and more.

Equipped with these skills, we can confidently enter new markets and launch new projects with the knowledge that given enough time, we’ll be able to find a way to assess our surroundings and create something that resonates (and sells).

But perhaps the larger contributor to creative swagger comes from our past experiences of falling… and then extending our wings to catch ourselves before we hit the ground.

When we understand this, it becomes clear that taking a tumble after making a leap and missing our landing is not something to be avoided but one to be embraced, and even sought out as early and often as possible.

Because each time we’re forced to extend our wings and catch ourselves, we build up a little more confidence in ourselves and our skills.

In fact, the higher the perch from which we’ve fallen and caught ourselves, the more our confidence grows.

As it does, we approach each new ledge with a little more swagger, knowing that whatever happens, we have within us the ability to catch ourselves, recover, and then ride the next thermal upward, with a little more confidence, a little more wisdom, a little more swagger than last time.

And then, we approach the next ledge, lean forward, and leap once more.

Perhaps with what could only be interpreted by anyone watching as a wink.

Explore how to navigate a creative life that matters

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

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

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

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

The Creative Expectations Manifesto

June, 4, 2222

Creative work is not a sprint
But it’s also not a marathon
Because there is no finish line (except, of course, death)
Creative progress is best measured in decades
The first of which, you’ll spend largely in obscurity and indifference
And no matter how many decades you have after that, there will never be enough time
You’ll never get through your to-do, to-read, or to-create lists
You’ll never have large swaths of time to dedicate to your creative work
Your craft will always live in the small pockets you carve out for it
But these are more than enough to create work that matters
Though it will require a never-ending series of hard, painful choices about what to pursue and what to abandon
If you’re lucky, you’ll be able to pursue a tiny fraction of your creative ideas
And most of them will flop
But the ones that hit make up for it and more
Going through the flops (maybe dozens of them) is the only way to get to the hits
No matter how many hits you have, you’ll never feel like you’ve “made it”
It will never get easier
In fact, it will get harder
Because the scale and complexity of the problems you take on will scale alongside your own progression
No matter how much you grow & progress, you’ll never figure it all out
But the mystery is exactly what makes this work special
If you’re not happy in your work now, you’re not going to be happy with more money, a larger audience, or greater opportunities
Speaking of success, you likely won’t become famous
You won’t become a household name
You won’t impact millions of people
You won’t be remembered
Rejection and indifference by the masses are the norm
But the narrower you focus, the greater your chances of both resonance & success
And a narrow, highly resonant audience is enough to make a thriving career of this
Your goal is to find 1,000 (maybe fewer) people for whom your work is their favourite thing
And you can achieve that
But you’re probably not yet ready
Because your work isn’t as good as you think
And yet it also has more potential than you imagine
To find it, you’re going to have to veer away from other people’s frameworks, strategies, and paths to creative success
The only path to your creative potential is the one you carve
To find it, you need to get better at listening
Because you don’t know your audience as well as you think
More importantly, you don’t know yourself
Unlocking your best work will require you to dig deeper into your motivations, curiosities, and questions
To acknowledge that you don’t have an inherent purpose
And that you might never find your “passion”
But you don’t need purpose or passion or clarity to do meaningful, successful work
Humble curiosity is enough
And the courage to follow it, especially when no one else has beat a path in that direction
At the forks in the road, much of the time you’ll guess wrong
Things won’t work out the way you want or expect them to
But often enough, they’ll work out better, in the most surprising and unexpected ways
You can’t engineer or plot your course to these outcomes
The only way to get there is to keep moving forward
The odds of achieving creative success are long
Most people aren’t willing or able to stick with it long enough to beat them
But knowing what you’re up against is the best way to improve your chances
You’re already on the right path
If you keep walking, you’ll end up where you’re meant to be.

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.

Things Will Never Get Easier (But That’s Not a Bad Thing)

May, 28, 2222

A few months ago, my friend Thom said something that stopped me in my tracks.

We were talking about the frustrations and challenges associated with our current creative projects and businesses when he shared a recent revelation from a therapy session.

“I had this realization that no matter what I do or achieve, things are never going to get easier.”

For context, Thom is currently self-financing a bootstrapped software company, a creative project littered with challenges and frustration.

At the time of our conversation, he had no paying users and was pouring thousands of dollars into the project’s development per month. Given the scale of the current problems on his plate, it’s easy to see why he might believe that things would get easier in the future.

Perhaps it would be easier when he breaks even on cashflow…

When he’s generating $10k in monthly recurring revenue…

When he can hire more staff…

When he’s built up a base of raving product evangelists around his product…

On the surface, all of these expectations seem entirely reasonable.

The problem is that they fail to account for a crucial part of our mental programming as humans, and especially as creators, which, when unacknowledged, keeps us in a state of scarcity, lack, and frustration regardless of our progress and accomplishments.

The When-Then Trap

The root of the problem is what Khe Hy refers to as the “When-Then Trap”.

In other words, “When [I accomplish _________], then [It will be easy / I’ll be able to… / I’ll be happy / _________).”

We all have these When-Then statements subconsciously running through our heads by the dozen.

And while both halves of the statement will vary depending on our goals, personalities, projects we’re working on, and more, the outcomes, or “then” half of the statement is always rooted at some level in our personal happiness.

Like Thom, my “…thens” are most often expressed in relation to the idea of things being easier than they are now.

Based on my own observations, this is true for most creators.

Chasing the Easy Life

It’s no wonder ease is such a pervasive ideal among creators.

Gaining traction with any type of creative business is hard.

And contrary to what we imagine when we’re first starting out, that difficulty doesn’t diminish with our first paying customer, when we quit our day job go full-time on the business, or when we hit any of our arbitrary follower, subscriber, or financial milestones.

And yet, despite the fact that the ease we seek continues to evade us regardless of our accomplishments, for some reason, we carry on believing it’s juuuuuuust around the next corner.

Thom’s realization, then, that things were never going to get easier is entirely logical, based on all of our collective experience.

It’s also dangerously radical.

Because if things are never going to get easier, what’s the point of continuing to pour so much of ourselves (perhaps even an unsustainable amount) into our work?

The answer is not that our work is hopeless and we should simply throw in the towel immediately.

But if (or more like when) we find ourselves stuck in this particular, ease-related when-then trap, we should recognize it as a sign that we need to drastically recalibrate our conception of–and relationship with–our work.

The first step is to recalibrate our core expectations about what creative success really looks like.

“The Source of All Unhappiness is Misaligned Expectations”

I first heard this quote six years ago.

It rang true as soon as I heard it then and has only gained relevance and validation in the years since.

Because let’s be honest, a creative career is rife with opportunities for misaligned expectations.

These expectations are shaped largely by the daily barrage of messaging–whether well-intentioned, subversive, or implicit–about the scale we can achieve through our creative work and the timeframe we can achieve it in.

But it’s not just the implicit and explicit messaging. The proof of what’s possible as a creator is clearly visible all around us.

View, subscriber, and follower counts are all publicly visible on many platforms, and we don’t have to look far to find case studies filling in the gaps on less-accessible data such as revenue, email subscriber counts, and more.

Between my inbox and podcast feed this week, for example, I’ve seen at least a half dozen interviews, breakdowns, and case studies of 7-figure newsletters.

The message this type of content presents is clear: This is the standard for success as a creator.

But is it reasonable to anchor our expectations to outcomes like this when less than 4% of the estimated 50 million creators even earn a living off their creative work, let alone build 7-figure businesses?

Of course not.

And yet we can’t help but internalize them.

Not only do we internalize these lofty expectations about the scale we can achieve with our work, however, but we also internalize misaligned expectations around the process and time it will take to achieve them.

In doing so, we imagine we’re just one project, one offer, one funnel away (IYKYK) from all our creative dreams coming true. And when each new project fails to deliver the expected results within a matter of months (if not immediately) our eyes begin wandering, looking for the next one thing that will.

As you’ve no doubt experienced yourself, reality generally doesn’t match up with these expectations.

The real irony, however, is misaligned expectations like these actually make it harder for us to achieve any level of sustainable lasting success as creators.

So why do we maintain these (often wildly) misaligned expectations in the face of all evidence that suggests otherwise?

Why Our Misaligned Expectations Persist

There are two primary culprits at play.

1. We Haven’t Done the Math

I was listening to an interview with the subversive productivity expert Oliver Burkeman recently where he recounted a story about coming face to face with his own misaligned expectations around time.

Burkeman shared how he had spent much of his life in search of the perfect productivity system.

This system, he imagined, would allow him to consistently get to the bottom of his daily, weekly, and yearly to-do lists with time to spare.

But that was just the start.

The perfect productivity system would free up the time to spend thinking deeply about his big picture life’s work. It would allow him to take on those tasks, projects, and pursuits that were consistently pushed off into the realm of “someday”. It would give him ample time to spend more time with his family, his friends, and other important people in his life.

After years of searching for, building, refining, and writing about the perfectly productive life, however, Burkeman had a stark realization that was eerily similar to Thom’s:

There simply isn’t–and never will be–enough time to do everything he wanted to.

Said differently, the list of things he wanted to fit into his single, limited, lifetime was mathematically incompatible with the length of said lifetime.

I don’t know about you, but this is a delusion I too have laboured under for much of my life.

I came face to face with the reality last year when I looked through my list of potential creative projects I was eager to start on and counted up 77 of them.

Many of these projects would require months or years of investment to see through, meaning that even without adding to it, my project list is already impossible to complete.

(Of course, I have, in fact, added to the list which is now up to 133.)

Time is perhaps the least flexible constraint on our potential, but there are many other scenarios, including talent, physical limitations, geographic location, and more where the math may simply not work in the favour of our goals and expectations.

In the face of these situations, we have little choice but to acknowledge them and make difficult and even painful decisions about how to adapt ourselves and our expectations to fit with reality.

While acknowledging these constraints and making the required decisions, trade offs and compromises to accommodate them can be painful, it can also be freeing.

With a clear-eyed view of the reality we’re living and creating in, we can be more confident about the choices we make about how to allocate our limited time, finances, talents, and other resources.

I don’t know about you, but for me, understanding how precious and limited time, in particular, is, motivates me to make the absolute most of it with both my life and work.

While recalibrating our expectations related to the limited resources available to us is no easy task, at least we have a fixed frame of reference (objective math) around which to adjust them.

This is not the case when it comes to the other primary reason our expectations persistently fail to sync up with reality, however.

And it’s this reason that for Thom, and for most of us, things are unlikely to ever get easier.

2. Our Expectations Scale with Our Achievements

How many of the goals you set for yourself two (or five or ten) years ago have you already passed?

Chances are, you’ve racked up dozens of achievements big and small in your creative career thusfar. Some of those achievements you might have even previously attached to some version of the When-Then Trap.

And yet, now, on the other side of those achievements, is your life as good, easy, or happy as you thought it would be before you crossed that bridge?

If you’re a normal, well-adjusted person, no, it’s not.

There are two reasons for this.

The Hedonic Treadmill

The Hedonic Treadmill is based on the concept of Hedonic Adaptation, which describes how we as humans tend to revert back to a mean level of happiness regardless of the positive or negative outcomes.

You might have heard of the famous study comparing lottery winners and victims of catastrophic accidents which found that a year after the events that changed their lives, both groups reported surprisingly similar levels of day-to-day happiness.

This is Hedonic Adaptation.

On the one hand, this is a fantastic consolation.

It allows us to have some solace in the fact that no matter the negative circumstances that might befall us, we’re likely to revert to our current level of happiness.

On the other hand, it’s entirely demoralizing, knowing that no matter what we do, or how much we achieve, any initial bumps in happiness and satisfaction are likely to revert back to more or less our current state.

And so we find ourselves on the Hedonic Treadmill, continually chasing the next thing on the horizon, hoping that will be the thing that will finally deliver the permanent, lasting happiness and ease we seek, even as we achieve greater and greater levels of “success”.

But while the Hedonic Treadmill might be baked into our core operating system as humans, as creators, in particular, we’re more than willing participants, which leads us to the second reason ease remains so elusive for so many of us.

Creators, are Adventurous, Competitive People (Who Enjoy a Good Challenge)

Much like a game of tic-tac-toe loses its appeal almost immediately after figuring out the basic mechanics of the game, we as creators tend to lose interest the moment the challenge fades from our current projects.

No sooner have we mastered one skill or medium than we’re immediately looking to add on something new.

Over time, our skills, systems, knowledge, teams, and budgets compound, opening up ever-more exciting, complex, and ambitious opportunities to us, many of which we couldn’t have even conceived of just a few years before.

Being naturally curious, adventurous, and competitive people, we as creators gravitate to these opportunities and all the associated problems and challenges like moths to a flame.

Paired with the absolute limitations of reality such as time, this is the reason why for many of us, things will never get easier.

Two years from now, we’ll have mastered the problems we’re currently pulling our hair out over and replaced them with new, more difficult problems. Five years from now, we’ll have mastered (and replaced) those problems.

And so the truth becomes clear.

Things will remain difficult because we will continually choose for them to be difficult.

Which presents us with a choice.

Matching Our Mode of Operating with Reality

By acknowledging the reality we’re creating within and into, we’re able to recalibrate our expectations and make decisions about how we spend our creative energies from a more empowered place.

If we accept the fact that things will never get easier and adjust our expectations accordingly, the absurdity of the schedules many of us (🙋‍♂️) subject ourselves to quickly becomes apparent.

Because what’s the point of spending your evenings and weekends sprinting toward some imagined finish line if we know that once we’ve crossed it, we’re immediately going to roll right into another sprint, with an even further finish line?

For me, the logical conclusion of this set of expectations is clear.

If ease doesn’t exist as a singular, lasting destination, it’s essential that it be built into the journey.

The same is true for happiness, fulfillment, or anything else we might be chasing or “When-Then-ing”.

Maybe that means being more selective with the projects we take on, the people we work and engage with, or the hours we work.

Maybe it’s focusing on the platforms, mediums, and strategies that we actually enjoy using even when all the hype is currently focused elsewhere.

And maybe it’s realizing that there is really only one true Then-When statement, one which we have complete control over.

When I choose to be, then I’ll be happy, fulfilled, and at ease.

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 if You’re Already on the Right Road?

May, 20, 2222

I was out for a walk the other morning exploring Kollwitzkiez, a neighbourhood here in Berlin for the first time.

I had been told it was an interesting area filled with old art nouveau architecture, cute boutiques, coffee shops, and restaurants. And while I’d been able to navigate to the general vicinity of the neighbourhood over the course of my meandering walk, I didn’t know where in the neighbourhood specifically any of the aforementioned attractions were.

As I turned off the busy boulevard that bordered that neighbourhood and onto a smaller residential street that lead toward its center, I kept my eyes peeled for any indication of which direction to turn next.

Block by block I continued, slowing at each intersection and peering down the street in both directions, seeking out the slightest sign of a potential point of interest.

Block by block, I was disappointed.

Each new cross street looked identical to the one I was already on: Mundane, residential, boring streets with little to differentiate between them.

I continued on in this manner for a couple more minutes, growing more and more skeptical of the promised quaintness of the neighbourhood. In my impatience, I decided to turn up the next street regardless of what it looked like in order to get off a street that was clearly not leading to anything interesting.

I reached the intersection, stopped, and contemplated whether to take a right or a left.

Before I could decide, however, I took my first good look in a few block down the street I was currently on.

Almost immediately, I noticed a sign for a specialty coffee shop on the corner opposite me. And beyond that an artisanal bakery. The opposite side of the street was lined with cafes and restaurants.

I turned and looked back at the way I had just come and saw for the first time an independent book shop and some interesting boutiques that had gone unnoticed as I had walked past, already looking ahead to the upcoming intersection.

In the end, it turned out the road I had been so keen to turn off of from the moment I stepped onto it was the road leading exactly where I wanted to go.

The experience got me thinking about how often the exact same situation plays out in our creative lives.

Don’t Be So Quick to Change Routes

It doesn’t take long for our eyes to start wandering in search of alternative routes when we’re not seeing the results we seek from the path we’re currently on.

We have a hard time actually believing that–by luck or by design–we could have actually found our way onto the correct street, and as a result are constantly looking for the next exit, which we imagine must surely have a better chance of leading somewhere interesting than the boring, mundane, residential route we’re currently on.

If we’re not happy with our current results, our logic goes, then surely the best approach is not to do more of the same but to do something, anything, different.

And sometimes, this logic might be sound.

But perhaps just as often, the logic is exactly backwards.

Our mistake in these situations is rooted in two incorrect, intertwined assumptions, one about each end of the road we’re on.

The first assumption is that any road that ends up somewhere interesting will be interesting over the length of its span.

Start at the Eiffel Tower (or any major landmark), however, and walk away from it in any direction, and it’s not long before the streets devolve into generic and uninteresting commercial, residential and finally, industrial blocks.

In the same way, while there may be occasional peak moments along our creative journeys, the practices and routes that will most reliably get us to our goals are by and large made up of boring, monotonous consistency.

The second assumption–a mirror image of the first–is that a road that starts off as boring and mundane is likely to stay boring and mundane.

There’s an oft-quoted (and oft-ignored) piece of investment advice about past returns not being a useful predictor of future returns.

This advice is most commonly applied as a caution against investing in a fund or company that has historically outperformed the market.

In other words, the fact that things have been good up until now doesn’t mean that things will stay good into the future.

But the opposite is also true.

When it comes to the route we take to our creative goals, this means that just because the path we’re on hasn’t lead us to the results we’re seeking so far, doesn’t mean it never will.

Indeed, the fact that we’ve already walked a long stretch of a boring, mundane, residential street might actually be a sign that we’re getting close to something interesting.

Something we might otherwise miss if we were to turn off too soon.

One of the core lessons I’ve learned from many years (and thousands of kilometers) of walking is that if you walk long enough in one direction, you almost always end up somewhere interesting.

I’ve also learned that if you continue walking past that, things are bound to get boring again.

And so the cycle continues.

Understanding this dynamic is essential for building a sustainable creative career.

It helps us stay the course and avoid shiny, short-term distractions that pull us off our course, and contextualizes both the highs and lows, the excitement and the boredom of creative life.

Perhaps most of all it cautions us that if we’re going to make a career of this, we need to build joy, sustenance, and gratification into our daily creative practice.

Because in the end, any destination we aim for is fleeting, and will soon enough be fading in our rear view mirror as we pass through and then press ahead onto the next one.

The only lasting reward is the one we build into the journey and carry with us each step of the way.

Explore how to navigate a creative life that matters

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

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

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

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

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

April, 30, 2222

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

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

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

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

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

Of course, this observation is far from groundbreaking.

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

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

But herein lies the problem.

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

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

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

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

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

Interstitial Opportunities

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

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

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

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

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

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

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

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

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

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

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

You likely experience this regularly.

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

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

Creative work certainly requires inspiration.

And building a creative business requires guidance and education.

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

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

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

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

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

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

Notice it.

Push back on it.

Recognize the interstitial as an opportunity.

And instead of filling it, simply sit.

Allow yourself to be bored.

Allow your mind to wander.

Make space for ideas to fill.

Or not.

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

But nature abhors a vacuum.

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

Explore how to navigate a creative life that matters

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

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

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

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

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