Creative Wayfinding For Ambitious Optimists.

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

May, 28, 2022

🧭 This blog post is adapted from my Creative Wayfinding Newsletter.

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.


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

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

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

    This is the Creative Wilderness.

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

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