“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:
- 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.
- 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.
- 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.
- 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.
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