Creative Wayfinding For Ambitious Optimists.

The Magic of Zero-Expectation Creative Work

April, 22, 2023

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

This week, my partner, Kelly, and I celebrated our 5-year anniversary.

Like every relationship, ours has had its share of ebbs and flows, ups and downs. By and large, however, the challenges and conflicts we’ve faced have been few and far between and our daily experience of the relationship is one of joy, possibility, and ease.

To be honest, the level of ease continues to surprise and mystify us.

In fact, we spend a good amount of time trying to decipher the reason behind it.

So far, we’ve come up with a pretty solid list.

For starters, we genuinely like each other, and are fascinated by each other’s work (she works at a startup and is also in the process of launching her own startup).

It also surely helps that we don’t have kids.

But in further reflecting over our anniversary dinner, this week, we had a new revelation, which is this:

Neither of us seems to have any expectation of what this relationship should be.

We’re in the relationship because we recognize the value of being in it now, in the moment, in the day-to-day experience of it, not because of where we hope it will lead or what we hope it will become.

Instead of working toward some pre-defined archetypal (most likely mythical) idea of relationship—and life—we appear to be content to simply be… and see what emerges from that being.

What emerges, it seems, is a greater sense of possibility than would—or perhaps even could—exist with a set of expectations governing and constraining the relationship.

This zero-expectation mindset is a useful one to cultivate in our creative work and businesses as well.

As in any relationship, the experience and results we get from our relationship with our work are beyond our control.

At best, we can influence those outcomes based on what we personally bring to the relationship. But after we’ve shown up consistently with our best work, all we can do is let go and hope our energy, effort, and intention are reciprocated.

Introducing expectation to the mix sets us up for regular (and often severe) disappointment.

In more than 10 years of creative work, I can’t think of a single project or endeavour that has ever met my (usually secretly held) expectations, let alone exceeded them.

Early in my career, those shortfalls were crushing.

As I’ve relaxed or let go of my expectations around my desired results (and more often the timelines of achieving those results), however, the outcomes of any endeavour hold less significance.

Good or bad, thrilling or disappointing, every outcome is simply a way station on the way to some further destination that is currently hidden from view, somewhere beyond the horizon.

Which brings us to the second pitfall of expectation:

Expectation is a destination that is inherently limited by your existing map of the world.

That map doesn’t include the vast territory that will open up as you gain new knowledge, acquire new skills, and meet new people.

Nor does it take into account how the world—and you—will change over that span.

Said differently, expectation is the death of possibility.

And in a world ripe with always emerging possibilities, it’s a poor stance to take if we want to be in a position to take advantage of them.

Instead, in our relationship with our work, as in our relationship with others, the most productive stance we can take is to show up generously, consistently, with firm boundaries but without expectation, and be open to what life brings us.

We don’t have to like what life brings us, often enough we won’t.

But keep showing up in this way long enough and life has a way of reciprocating.


Explore how to navigate a creative life that matters

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

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

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

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


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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.