Creative Wayfinding For Ambitious Optimists.

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

June, 11, 2022

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

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.


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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.