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.

Think back to the last busker you saw playing music who had drawn a significant crowd.

Chances are, two things were immediately apparent:

1. They were unmistakably and incredibly talented.
2. They were playing covers of songs you (and everyone else) recognized

Along with picking the right location to set up and perform, these are two of the prerequisites for success as a busker. And if you can nail those criteria and learn how to work a crowd, you can do pretty well. For a busker at least.

But while many buskers might genuinely love busking, most have higher artistic ambitions.

And so, every so often, they’ll throw in one of their own songs.

When they do, a funny thing tends to happen.

The spell that has drawn and captivated the crowd is broken, the attention is lost, and people start to disperse.

Because original art isn’t what drew them in in the first place.

What drew them in was the sound of a song they already had a positive association with being performed expertly, perhaps in a novel way.

And while familiarity & regurgitation are fantastic shortcuts to engagement, they don’t lead to anything deeper.

And so, when presented with a new song they haven’t already made up their mind about, the audience would often rather move on than stay, listen critically, and decide whether it’s worth sticking around for.

Engagement Hacks ≠ True Fan Hacks

This peril of playing covers exists whether we’re busking for change on the street or likes online.

It’s possible—likely even— that with sufficient skill, we can build a repertoire of content that is almost guaranteed to get a positive reception, and perhaps even draw a crowd.

But building an audience by regurgitating other artists’ original work doesn’t often translate to interest in our own original work.

And yet, it can be hard to resist.

Playing covers is a surefire shortcut to attention and engagement, two assets we as creators are all desperate for, especially when we’re just starting out.

If we can find a hack that gives them to us faster, why wouldn’t we take it?

The problem is that playing covers doesn’t build any equity in your own art.

Sure we might have mastered the ability to get attention, but we haven’t invested in the harder work of building an actual fanbase.

Someone else might occupy the same street corner next week, playing a similar repertoire and it’s likely no one would notice the difference, let alone go out of their way to track us down or even follow us on tour.

What’s more, while we might be able to consistently attract attention with our repertoire of covers, attracting attention for our own art isn’t so easy.

Covers Don’t Count Toward the Clock

When playing covers, we can meticulously construct a repertoire that most people already know, and already have a positive association with.

With our own art, however, we’re starting from scratch. Perhaps even less than scratch given that we all tend to be skeptical of new content unless it’s entirely unignorable (usually when we’ve been told about it by at least a half-dozen other people).

When it comes to building an audience around original work, there’s simply no shortcutting the slow, grinding process of winning over one fan at a time, like the sea slowly eroding a cliff face until one day, years after we started, the whole thing comes crashing down.

For most of that time, progress will be slow and virtually unobservable. It’s the 10 years of silence every artist and creator must endure to create great work.

Despite the positive feedback it attracts, time spent playing covers doesn’t count towards the clock.

What’s more, we may end up boxing ourselves out of the ability to share our own work.

If we’re able to get attention, we get accustomed to it. And once we get accustomed to the attention and engagement it gets hard to create and perform to an empty room.

And so we’re incentivized to keep giving people what they already know and like because it serves our ego in the short term… even as it sacrifices our potential in the long term, all while making it harder and harder to ever make the pivot to building an audience around our own work.

Build Equity in Your Original Work

We’ve all seen and heard stories of creators who can hack attention and engagement to build a massive social following, but are incapable of selling products or services.

If we aspire to be more than that, we need to avoid the allure of short-term attention-hacking in favour of long-term equity-building around the work that only we can do.

It will be slow.

It will be painful.

We’ll constantly feel the pull to pander to the cheap and easy engagement of falling back on familiar cover songs.

But cover bands don’t sell albums.

They don’t sell out stadiums.

And no one follows them around the continent on tour.

At best, cover bands are a pleasant diversion, distraction, or addition to the ambiance of a place we’re already occupying.

As creators, artists, marketers, and founders, we can be more than that.

And if we want to make a sustainable (not to mention fulfilling) living from our work, we need 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 wilderness between us and our unique creative potential?”

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

I’ve had my favorite jacket for 6 years.

It’s lightly insulated, perfect for cool summer mornings and evenings, spring and fall, and—when layered between a wool sweater and waterproof shell—even winter.

Given its versatility, I’ve worn it almost every day of those six years.

As you might imagine after that much use, the wear is starting to show.

Or rather, it started to show several years ago and has continued to spread since.

While there are (amazingly) no outright holes, there are numerous snags and pulls and the fabric has been roughed up considerably on the back and shoulders where my backpack often sits.

Most notably, the jacket’s once bright blue finish has faded, in several places, almost entirely obscured by stains left from the dust of several dozen countries.

My partner, Kelly, despises the jacket.

She’s begun asking if I would stop wearing it if she bought me a new one.

But to be honest, I’m not sure I would.

I only bought this one, after all, after losing my previous jacket, the exact same model which I’d worn into a similar state over the previous 5 years—though that one was black and hid the stains better—until I left it in an AirBnb closet in a small town in Spain.

Sentimentality and nostalgia certainly play a role in my attachment.

We’ve been through a lot together, my jacket and me, after all.

But it’s more than that.

Because for all the joy in the unmarred perfection of a tool—be it a jacket, computer, vehicle, or, well… pretty much anything else—thosepristine countenances can’t compete with the fearless utility of their battle-worn counterparts.

In some cases, a well-worn tool becomes even better with age.

Baseball mitts, proper leather hiking boots, and good cast iron pans, for example, must all be worn in and well-seasoned before their useful life truly begins.

Most often, however, it’s not a new tool’s inherent properties that keep us from using it to the fullest, but our own psychology around the item.

When the surface is pristine and untouched, we go out of our way to keep it that way.

We tip-toe around even the tiniest potential sources of dirt or damage, in many cases even avoiding the tool’s intended use in order to preserve its outward appearance. It feels as though the moment it picks up that first scuff stain, its value will be lost immediately.

And yet, as someone who owns my tools far longer and wears them far harder than perhaps someone should, I’ve more often found the opposite to be true.

That the true life of a tool begins at precisely the moment it picks up that first scratch. And that its value only increases from there.

After the first nick, all bets are off.

The illusion of perpetual perfection has been shattered and we can now get to using the thing as intended.

With my jacket, that means pushing through brambles and scrambling along rock faces without the worry of scuffing up the finish getting in the way of enjoying the thrill of the moment.

This idea applies beyond clothing and manufactured tools, however.

Almost every hike I’ve ever been on has begun with the naive attempt to keep my hands clean for as long as possible.

Sooner or later, however, there inevitably comes an obstacle that can only be overcome by scrambling over, under, or around it on all fours.

With hands now irreversibly muddied, the spell is broken and there’s nothing keeping me from using them wherever they might make things even marginally easier, which, it turns out, is nearly constantly.

In hindsight, the thought of intentionally limiting your effectiveness in a misguided attempt to keep your hands clean is laughable.

And yet, we often can’t help ourselves.

Most inhibiting of all might be the lengths we take to keep our egos pristine and intact.

But try as we might to preserve a perfect exterior, it’s not until we picked up our first cuts, scrapes, scars, and bruises that our creative lives begin in earnest.

Once our surface has been marred we realize that there’s no longer any use in avoiding and tip-toeing around the places with the potential to leave us worn, weathered, and damaged.

Indeed, these are the places we must travel if we’re to uncover and create anything of value.

In the process, we’re likely to take on significant wear.

Over the years, our exterior will be worn down to the point that we no longer resemble the people we were when we started.

This isn’t the end of the world.

In fact, embracing this reality, and the scrapes and stains that accompany it is the start of 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.

Photosynthesis might be the closest thing to alchemy that exists.

I mean, when you really stop to think about it, the fact that trees can turn sunlight into wood with the help of carbon dioxide is nothing short of utterly alien and wildly fantastic.

But perhaps even more confounding is that this alchemy is far from rare.

More than 82% of the world’s biomass is made up of plants, each photosynthesizing in one way or another.

Beyond plants, fungi, bacteria, viruses, and every variety of animal species each use their own form of synthesis to grow and propagate.

Including us.

Our bodies reliably turn everything from leafy greens and root vegetables, to hamburgers, Pringles, and Twinkies into the blood, flesh, bone, and brain that enable us to live the vast variety of lives we lead.

Utterly magical.

And entirely ubiquitous.

Synthesis, it seems, is the default operating system for life.

It should come as no surprise then, that it’s the same process that governs the idea generation which powers our creative work, turning the raw material we consume into something unrecognizable.

And yet, most of us seem to have a better understanding of the photosynthesis performed by trees than the synthesis we rely on for our work.

While we might have some idea of our desired outputs, we rarely have a clear sense of what the inputs are.

The reasons, I think, are twofold.

1. Similar to trees requiring carbon dioxide and sunlight to make wood, the inputs we require to create our desired outputs are rarely obvious or directly related.
2. Even to produce similar outputs, each of us requires our own set of unique inputs.

To unlock our personal creative potential, then, one of the primary  cruxes  we need to solve is identifying the raw materials that we can most efficiently synthesize into our creative outputs.

Then, we need to trust that those (often obscure) inputs will lead to our desired results.

Personally, the raw materials I synthesize most efficiently into my writing and creative work are things like walking, views of the horizon, vistas, and trees, new places, and practicing different methods of transportation and navigation.

They also include consuming content on the natural world, adventures, storytelling, and fiction.

Despite knowing that these are the raw materials that power my creative synthesis, I’m not immune from the pull of more conventional content.

I constantly feel like I should be reading more business books, listening to more marketing podcasts, studying the same creators, and following the same guides everyone else seems to be obsessing over.

I regularly give in to this temptation.

But when I observe my most creative periods and the things I was doing that led to them, it’s clear that my best, most inspired, original work comes when I disconnect from those more obvious inputs.

To be fair, I’ve already consumed thousands of hours of that content, and at this point, the improvements of consuming more of it are likely to be incremental at best.

There’s certainly something to be learned from studying the mechanics, frameworks, and strategies.

But those aren’t the things that give your work heart or resonance or connection with others.

They’re merely the vehicles of delivery.

And if you’ve got nothing to deliver, the vehicle isn’t much use.

If you want to create work that moves people, and moves the needle for your business, start with identifying the raw materials that synthesize into your best, most resonant, most original work.

Surround yourself with them.

Then, let the alchemy begin.

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.

At some point, you’ve probably walked into an unfamiliar shopping mall and made a beeline to the directory.

For a moment or two, you scan the map blankly, trying to make sense of it until finally, your eyes find the red “You Are Here” arrow, and the map instantly snaps into focus.

Without this piece of information, the map lacks context.

And without context, no matter how finely detailed, how high the resolution, any map is effectively useless.

When navigating the physical world, we understand the necessity of knowing where we are innately.

It’s no mistake that when we open Google Maps we’re immediately presented with the unmistakable blinking blue dot indicating our current location. It’s the one constant of every conceivable route to every conceivable destination, after all.

Before embarking on a journey, a clear understanding of our starting point allows us to orient ourselves, identify obstacles along the way, and plot a course around them.

It also allows us to plan, equip, and train ourselves accordingly.

A 5k fun run requires a different level of training than a 42.2 km marathon, which again requires different training, preparation, and equipment from a mountaineering expedition of identical length.

Once the journey has begun, a clear understanding of where we have come from enables us to better project our future progress based on our past pace.

And yet, for all the value of understanding where we are, when it comes to our creative journeys, we tend to spend little time thinking about it.

Instead, we spend our time obsessing over both our destinations and the potential routes we might take to get there.

Where we start from, however, dictates the route we’ll take to a given destination.

A lack of awareness about where we currently are on the map, then, is one of the key cruxes that must be overcome if we want to make meaningful, efficient progress toward our goals.

The problem, of course, is that unlike shopping malls, when it comes to finding our place on our creative journey both the map and our position on it are a whole lot murkier.

Pinpointing Your Location

Pinpointing our location begins with a thorough accounting of both ourselves and our surroundings.

What assets, skills, and resources do we possess? What are our interests (or even better, obsessions)? What opportunities are available? What are our strengths, weaknesses, and liabilities? What milestones have we already attained, and which are we aiming for next?

The better we know ourselves and our surroundings, the better we’re able to identify others who have reached a similar destination to ours from a similar starting point, and contextualize our location based on their journey.

To this end, I’ve recently begun collecting every bit of data I can find on more established creators with similar business models to help me better understand where I am in relation to their trajectory.

Of specific interest to me is my friend Jay Clouse, who has a very similar business, audience, and style to me.

As someone earning $40k/mo as a creator, closing in on 20k newsletter subscribers, and 30k Twitter followers, he’s also someone who has had much of the success I’d like to emulate.

After analyzing the historical newsletter, audience, and financial growth data that Jay shares in his Creator Science Lab (affiliate link), and comparing it to my own, I have a pretty good sense that I’m about 18 months behind him.

Knowing precisely where we are in relation to our destination helps inform the decisions we make as we continue to make progress.

But understanding our timeline is just as (if not more) valuable.

Plotting Your Progress

A few years ago, a study of the London Tube system conducted a study in an effort to boost rider satisfaction.

What they found was shocking.

Going in, the assumption had been that the best way to improve rider satisfaction was to improve the speed of the system through faster trains and increased frequency. This would have been a multi-billion dollar project resulting in only incremental gains in efficiency.

The result of their research, however, was that they could increase rider satisfaction with one simple fix, at a fraction of the cost of the larger renovation.

The fix?

Installing screens in the stations that displayed the upcoming trains’ ETAs.

It turns out, people cared less about the actual length of the journey than they did the uncertainty of it.

The same is true for our creative expeditions.

Most of us are willing to do the hard work required to build sustainable careers around our creative work. The root of our frustration, however, lies often in the uncertainty around how long it’s going to take to reach our destination.

This anxiety leads us to jump from shiny object to shiny object, abandoning projects and strategies that would have worked if we’d just given them more time, and severely stunting our progress.

Understanding where we are on the larger journey eases that uncertainty.

When we see clearly that each of our chosen guides spent years working hard for little result before finally something clicked, we feel infinitely better about our own situation.

We can see that the low results:effort ratio is simply a phase of the journey we all have to navigate through.

And most importantly, we can set our expectations around how long it will take to reach the end of this phase and what we’ll encounter on the other side.

Chart Your Course Wisely

Of course, we need to take this type of mapping with a grain of salt.

No one person has started from the exact same place as any of us. Nor are they moving toward the exact same destination or working with the exact same assets & liabilities.

The more roughly similar routes we can identify, then, the better we’re able to triangulate our position based on the landmarks found in their stories.

Once we‘ve roughly identified our location, though, we’re able to plot the most efficient course to our destination.

We’re also able to confidently ignore advice and route suggestions that don’t apply to us, which can save us years of time and effort.

It’s not much use, after all, following the creative path of someone who has previously sold a company and is now able to work full-time on their creative projects with no need for them to generate income in the short term.

At least not if we don’t have similar circumstances.

Nor is it worth attempting to follow the path of someone who has a set of innate skills, obsessions, or connections that we don’t possess ourselves.

Sure, we can attempt to emulate these paths.

At best, we spend months or years getting ourselves to someone else’s starting point, from which we can following their progress to our destination.

At worst, we spend the time attempting to meet up with their route, only to find it utterly impassible… or at least, impassible to us.

Better to understand clearly where we’re coming from, and base our route, landmarks, and timelines on those coming from the same neighborhood as us.

Our guides might be fewer, and we may have to look harder to find them.

But once we do, the map snaps into focus, the way becomes clear, and all that’s left for us to do is walk.

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.

Nearly every week for the past three years, I’ve written and published an issue of this newsletter.

While the time required to produce an issue has varied over the years, according to my time tracking, the average is about 8 hours per week.

Eight hours a week is no small amount of time.

Eight hours times 136 issues is an even larger amount of time (1,088 hours, or 27 forty-hour work weeks).

All spent without any direct ROI.

To this point, I’ve never sought out sponsors for the newsletter, and while I occasionally mention my paid products and services, the topics I write about here are not directly aligned with or related to my paid offers.

As pure content marketing for my business, in other words, it’s hard to justify the continued creation of the newsletter.

Any strategist worth their salt would advise I quit the newsletter (or at the very least streamline it) and put the time I’m currently spending on it to use creating content that is more clearly aligned with my actual paid offers.

And yet, despite this misalignment, it’s clear to me that in many less intangible—but no less real—ways, the time spent creating this newsletter has a positive impact on every other aspect of my business.

The reason is that the newsletter acts as something of a release valve.

And despite the seeming inefficiency of spending a full day each week on a task that doesn’t directly support the business, it plays a vital role in easing pressure elsewhere and allowing my larger creative system to function more efficiently on the whole.

Since becoming aware of this phenomenon in my own work, I’ve become convinced that more creators could benefit from their own creative release valves, inefficient though they might seem.

To understand the role Release Valves play in our creative systems, we first need some context for the role our content is currently playing in our businesses and creative platforms.

The Content–Art Spectrum

One of the core frameworks I teach in  Podcast Marketing Academy  is what I call the Content–Art Spectrum.

Anything we create exists somewhere on the spectrum, though we’re rarely aware of, or intentional about where.

At one end of the spectrum is Pure Content, work that is created only for an audience with no thought for our personal interests or creative fulfillment.

At the other end is Pure Art, work created only for ourselves, with zero regard for existing demand or audience interest.

Some creators are able to exist and thrive at the extreme ends of the spectrum, but for most of us, the sweet spot is somewhere in between.

Finding that sweet spot, however, is easier said than done.

There’s no denying the fact that it’s vastly easier to gain traction and build an audience by creating work that aligns with what an existing, clearly-defined audience is already looking for and consuming.

But there’s also no denying that while we might recognize the business value of Pure Content, for those of us who skew towards the Art end of the spectrum, creating an unending stream of it is an unsustainable, soul-sucking endeavour.

And this is precisely where having a Release Valve comes in handy.

How A Release Valve Unblocks Your Creative Work

My personal struggles with the Content–Art Spectrum go back almost 10 years.

In 2015, I wrote around 50 articles for my photography blog.

In 2017, I began my first stint publishing to my podcast blog, which lasted about 9 months and resulted in around 40 articles before I ran out of steam.

In 2020, I had my second podcast stint publishing another 50–100 articles over a several month-span.

Most of the articles I published during those years are work I’m still proud of.

And yet, despite the solid output in both quantity and quality, however, I never really gained traction with my writing, and always, ultimately, ended up stalling out.

In hindsight, the reason for both of those outcomes is clear.

I was stuck in limbo between Content and Art.

While my articles were often addressed at existing podcast creator questions and pain points, they tended to skew toward the philosophical. They were long, expansive, and—while heavy on thoughtful questions and insights—were light on actionable, clearly defined next steps.

As a result, they didn’t align with what my potential audience was actively looking for, nor did they align with the work I truly wanted to create.

It wasn’t until my third podcast writing stint, in the Fall of 2021—coincidentally, a year and a half into writing Creative Wayfinding—that I finally found my groove.

The difference was immediately apparent.

With Creative Wayfinding as an outlet to follow for my more expansive, philosophical explorations of creative work, I was free to take a more Content-oriented approach to my podcast writing.

The result was more useful, tactical, and consumable writing on the podcast side, which almost immediately found traction and began to grow.

This is the power of a release valve.

Benefits of a Release Valve

The primary benefit of a Release Valve might be in how it removes the pressure of your business-serving content to satisfy your personal artistic needs and vice versa.

But the benefits don’t end there.

Another obvious benefit is that because Release Valve projects are typically only tangentially related (if at all) to our businesses, there’s less pressure on them to perform.

This gives us more freedom to grapple with unpolished ideas and experiment, both with the components we use to create them—format, style, tone, medium, etc—and how we market and promote them.

And while the experiments we run on our Release Valve projects may not directly lead to the growth of our commercial projects, the lessons learned often apply directly.

Another benefit is that without the pressure on your work to ultimately lead your audience to an outcome—most likely a sale—Release Valve projects often feel more honest, authentic, personal, and generous.

The reason is that they are.

Pure Art, after all, is created primarily to satisfy your own curiosities and impulses.

When our Release Valves skew to the artistic, then, there’s a good chance that the people who engage with us are getting a pure and genuine insight into who we truly are as people.

The irony is that when people have an opportunity to get to know us in this deeply personal way, they’re much more likely to want to work with us.

At least for my creative business, the data backs this up.

During the last  Podcast Marketing Academy  launch, 75% of customers were subscribed to Creative Wayfinding, while only 58% subscribed to the more directly-aligned  Scrappy Podcasting Newsletter .

Of course, not everyone’s Release Valve projects will have such significant cross-over interest from their commercial projects.

But in my experience, there are always members of any audience who care more about the person behind the work than work itself.

Release Valves give them an opportunity to go deeper with a behind-the-scenes look at the inner workings of the creator’s brains.

Which in turn, ends up making it more likely that they’ll ultimately buy when the right offer presents itself.

Find Your Release Valve

While the benefits of Release Valve projects are clear, committing to them isn’t easy.

Most of us already have endless lists of tasks and projects that are directly related to audience growth or revenue generation.

In the face of those lists, adding a significant time expense that doesn’t lead to the tangible growth of our businesses feels absurd, if not outright irresponsible.

And yet, what’s the use of pursuing more directly relevant projects and tasks if we’re undermining them by trying to shoehorn both sound business strategy and creative fulfillment into them?

The truth is that for most of us, the work required to build a business around our creative work requires significant compromise on our default artistic impulses.

But that doesn’t mean we need to ignore our art completely.

It just means we need to find a way to channel it productively.

When we have a Release Valve for our purest creative impulses, we’re better able to commit to the less fulfilling (but necessary) work on the commercial front without feeling as though we’ve sold out or lost touch with an important and vital part of ourselves.

This doesn’t mean that your Release Valves won’t be valuable to an audience or that your Content won’t make heavy use of your artistry. It’s just that they’re not optimized for them.

If you’re one of the rare few who can sustain yourself both creatively and financially by living on either end of the Content–Art Spectrum, I envy you.

For the rest of us, the next best option is to create a system in which our energy and ideas are channeled to the outlets where they provide the greatest fulfillment and sustainability on both the artistic and commercial fronts.

The first step is realizing that no one channel needs to satisfy each need.

Then, identify the points in your own system where the pressure is building up, install a Release Valve upstream, and let your creative energy flow.

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.

“Fuck that,” my friend, Jordon, exclaimed, breaking the pregnant silence that had descended on the table.

We were out for celebratory drinks a few days after our friend Hamilton had arrived in Winnipeg at the tail end of a long, grueling adventure… albeit one that hadn’t quite gone to plan.

For the past four weeks, Hamilton had been paddle-boarding his way from just outside his home in Saskatoon, Saskatchewan to Winnipeg.

It was a route only a handful of people had ever traveled, with few points of contact with civilization.

As such, there was little documentation, including any accurate idea of how long the route actually was or how long it would take to paddle.

A proper adventure in other words.

At the time of Jordon’s exclamation, Hamilton had just finished talking through his daily routine of the previous weeks living on the rivers and lakes, which went something like this:

• 4:30 am – Wake up at first light. Cook porridge, pack up tent. If lucky, it’s not raining and everything stays dry.
• 5:00 am – Load gear onto paddleboard. Get onto the water
• 8:30 am – Pull off the river if possible for a break and a snack. Can’t take too long, however, in order to make as much progress before the July sun is fully overhead.
• Noon – Pull off for lunch. Try to find some shade as it’s getting hot out on the water with no cover. Rest for an hour or so before getting back on the water.
• 4:30 pm – Start looking for a good spot on the bank to set up camp for the night.
• 5:30 pm – Set up camp, cook dinner, retreat into the tent to escape the incessant swarm of mosquitos, black flies, and horseflies.
• 7:00 pm – Go to bed exhausted, muscles aching.
• 4:30 am – Wake up at first light and do it all again. And again. And again. For weeks on end.

It was in the pause that followed Hamilton’s breakdown that Jordon broke the silence with a wry grin and a shake of his head.

“Fuck that.”

Jordon’s reaction was the rational one.

And yet, with each of the daily trials Hamilton listed, a broad smile couldn’t help but creep a little further across my face and I suppressed the urge to blurt out “sign me up!”

The difference in reaction might not be surprising.

Hamilton and I had previously spent 3 months together cycling 3,500km across Europe, camping out nearly every night from September to December, several of which dipped below freezing.

A few years later, along with another friend, we’d spent ten days walking 300km of the Camino Portugues, including several days in a row which approached marathon-length distances… all while carrying 40 lb backpacks.

These experiences were painful, difficult, and often monotonous.

They were also utterly delicious.

Of course, not everyone finds weeks or months-long human-powered expeditions delicious.

Most, like Jordon, find them absurd and pointless.

But Delicious Challenges come in many varieties, not least of all the form of creative projects.

And in my experience, it’s these projects that we find irresistible despite their apparent absurdity that are the projects most worthy of our pursuit.

How to Spot a Delicious Challenge

We each have our own preferred flavours of Delicious Challenges.

Personally, I salivate equally at the thought of figuring out complex marketing automations, the years-long process of building a brand from the ground up, and sitting down to write a  16,000+ word article on podcast sponsorships .

My partner, Kelly, a software developer, finds challenges related to setting up complex user flows and developing intricate systems particularly delicious.

But while the particulars may differ for each of us, Delicious Challenges all have a few things in common:

1. Delicious Challenges are objectively hard – In fact, to most people, they likely look impossibly hard. And while we are fully aware of the difficulty going in, it only enhances the appeal of the project to us.
2. Delicious Challenges are not conventionally fun or enjoyable – While others might recognize the value or necessity in undertaking a task or project you find delicious, they would rather avoid it unless they had no other choice.
3. Delicious Challenges are magnetic – Despite the difficulty, you find yourself magnetically pulled toward them, perhaps even drooling or giddy with excitement at the thought of immersing yourself in the problem, no matter how painful and frustrating it may be. This often leads to incomprehension or incredulity from others.
4. Delicious Challenges are uncertain – Going in, there’s no guarantee that you’ll be able to successfully complete the challenge. They are full of unknown and there is a strong chance of failure. Again, this only enhances the appeal to you, however.

Condensed around a particular project, these traits represent a powerful opportunity.

The Opportunities of Delicious Challenges

The outsized opportunity presented by Delicious Challenges is based on simple supply and demand.

The work in any field that is the easiest to do is quickly done to death, driving down its value. The work that is hardest to do, however, and the problems that are most difficult to solve, often remain unaddressed.

And it’s these problems where most of the upside lies.

Consider AI, a Delicious Challenge engineers and scientists have been pursuing for decades which is now beginning to transform the world in front of our eyes… and making some people and companies extremely wealthy in the process.

As creators, we might not be pursuing challenges with the power to re-order humanity’s relationship with technology, but the principle remains the same.

The more objectively difficult a project is, the higher the value of solving it likely is.

In the process of identifying and pursuing Delicious Challenges, then, we give ourselves an unfair advantage over the vast majority of our competitors.

Using Delicious Challenges to Your Advantage

In almost every field, there are people pursuing a goal based only on the inherent opportunity it represents.

In all likelihood, we’ve all been those people at one point or another, and there’s nothing wrong with it.

The problem, however, is that when our only motivation for a project is the promised outcome, it’s hard to compete with anyone who finds the process of working toward that outcome legitimately enjoyable.

While we might put our heads down and slog through the muck required to reach our destination, those who find find the challenge delicious prance their way through it, lapping it up and reveling in each new difficulty or problem that we, in turn, despair in.

So often this type of genuine enthusiasm more than makes up for a gap in knowledge, skill, budget, or any other advantage a pure opportunist might have.

Because when the going gets tough, the crowd thins out as the opportunities elsewhere suddenly start to look a lot more appealing.

Our opportunity then is to avoid the opportunities that we don’t find particularly delicious in favour of the ones we do.

Where each new challenge is not yet another obstacle to overcome but a delightfully complex puzzle to gleefully solve.

The Pleasure is in the Pain

It’s worth noting that Delicious Challenges aren’t all sunshine and rainbows.

In fact, they’re likely to be riddled with pain, frustration, misery, and perhaps occasional bouts of hopelessness.

And yet, with truly Delicious Challenges, these feelings are not only overpowered by the project’s pull on us, but actively enhance it.

Because ultimately, part of the allure of Delicious Challenges is in their use as a measuring stick of our knowledge, abilities, cunning, and fortitude.

For some, that might involve writing a book. For others, starting a startup. Others still might their measure in solving near-impossible jigsaw puzzles, or cryptic crosswords, by walking across countries or rowing across an ocean.

Logical people might look at all of these as foolish endeavours. As wastes of time with low odds of success.

And yet, despite what logic might dictate, when a Delicious Challenge presents itself to you, it’s almost impossible to resist.

So don’t.

Because the Delicious Challenges that are the most illogical and incomprehensible to others are your greatest opportunity to do something few others are capable of.

And reap the rewards in the process.

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

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

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

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

The idea of cruxes extends to creative projects as well.

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

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

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

Many Types of Creative Cruxes

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

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

The cruxes at the heart of creative projects vary similarly.

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

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

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

In other words, famous musicians and famous songs.

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

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

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

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

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

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

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

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

Identifying A Project’s Crux

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

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

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

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

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

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

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

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

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

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

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

Not All Cruxes Are Created Equal

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

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

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

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

The same idea applies to creative cruxes.

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

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

The same is true for any crux.

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

Observe, Assess, Identify

Every successful project has a crux.

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

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

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

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

Others on distribution, funding, or access.

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

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

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

But you don’t need to.

You’ve got all the keys you need.

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

Explore how to navigate a creative life that matters

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

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

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

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