Creative Wayfinding For Ambitious Optimists.

To Find Clarity, Start Walking Before You Know Your Destination

June, 6, 2021

It would be something of an understatement to say I’m a fan of walking.

Aside from taking at least one long walk every day, I take many of my calls while walking, read books about walking, generate all my best ideas while walking, and–as you may have noticed–like to write about walking as well.

No, I’m not a fan. I’m obsessed.

Kelly, on the other hand, isn’t quite as keen. Despite this, every so often I manage to convince her to go for a long walk together, such as the one we took last weekend.

The destination was a section of the coast just outside of town. I’d walked the rocky stretch and explored the abandoned decades-old bunkers carved into the hillside a handful of times before, but wanted to share the area with her as well. As we crossed the bridge over the river that marked the edge of town, we turned off the main road and headed up a small dirt trail that snaked its way through the tall grass in the direction of the sea.

“How did you find this path the first time you walked here?” Kelly asked.

I thought for a moment, but found that I didn’t actually have a good answer.

When I don’t know the terrain, I tend to simply start walking, following what’s often little more than a vague curiosity. At times that curiosity might be centered on a prominent landmark or geological feature. At other times, however, I choose my direction simply by chasing a patch of sunlight, a particularly alluring looking street, or an enthralling scent on the breeze. My typical mode of travel might be best described as “whimsical.” If anyone was ever going to accidentally stumble into Narnia, it surely would be me.

The first time I walked this route, my goal had been the sea. From our apartment, I could see white-capped waves crashing against the ragged shoreline further up the coast, and so, on my initial exploration had set out to find my way there.

I took the main road, crossed the bridge over the river that marked the edge of town, and then stopped, spotting a small, dirt trail snaking its way through the tall grass in the direction of the sea. I didn’t know where this path led, but I had nothing but time, and the road I was on was certainly not going to lead me to the coast. So I took the trail.

Fifteen minutes later, after a few wrong turns through an abandoned property development project and a bit of light bushwhacking, I had reached the shoreline.

This approach, of starting with little more than a vague destination, sometimes only a hunch, and then following my curiosity has served me well. It leads to unexpected discoveries, helps you understand the local geography, improves your sense of direction, and to top it off, is good for your health. This mode of travel doesn’t just apply to walking, however.

Create For The Sake Of It

This act of starting before we know where we’re going and picking up the thread on the fly mirrors the creative process exactly.

We start out with a bit of curiosity and a vague destination in mind, and, if we choose to follow that curiosity, have little choice but to do so blindly. While our end destination might not be specific when we set out, at some point, we hope, by walking long enough, we’ll pick up the thread and find it.

Which is precisely what’s happened to me in the past few weeks with this newsletter.

When I started this newsletter a little over a year ago, I had no idea where it was leading. I saw an opportunity to contribute in a format that excited me, and a curiosity and willingness to see where the path would lead.

Rather than writing to help a specific audience achieve a specific goal, I wrote what I wanted to write. More than that, each week, I wrote what I needed to hear.

This approach has kept the newsletter fun, fresh, and even a vital part of my life, and it’s been immensely gratifying to hear that it’s resonated so deeply with so many readers. At the same time, I’ve known that without being clear on who the newsletter is for and what the through-line is that ties it all together it would be hard to grow consistently. It’s hard to market something when you don’t really know what it is after all.

The word “wayfinding” first popped into my head in January and immediately resonated with me as the embodiment of what I was doing with this newsletter. That initial breakthrough then kicked off a long, slow process of gaining clarity, with more and more pieces of the puzzle coming into view over the past five months.

While I’m far from absolute clarity (can we ever actually achieve it?) on the future of this newsletter, I feel as though I can see juuuust far enough through the fog ahead to kick off this new chapter with at least some certainty about where the road leads.

To be clear, nothing about the content has changed, other than it’s going to be more focused, intentional, and sure of itself. I’d like to think it’s going to have a bit more swagger.

Whether you consider yourself a creator, marketer, entrepreneur, or mix of all the above (like me), I’m guessing you spend a good chunk of your days feeling lost (also like me). Maybe you feel a vague lack of direction. Maybe you feel completely unmoored, floating out at sea.

You may have wandered off the beaten path by accident or you may have left it intentionally in search of a better way forward. Regardless, my goal with this newsletter going forward is to help you navigate that sense of not knowing where you’re going or how to get there that comes with doing creative work. Because I’m right there with you, and we’re all in this together.

While I’m excited about this newly clarified direction, it’s clear that this is just the jumping off point. I sense a manifesto in the works along with a number of new offerings and one day, hopefully, a book.

After a year of walking blindly with only a vague sense of direction, I’ve picked up the thread. The through line, I’ve realized, that runs through this newsletter and everything that will follow is this: Practical wisdom for navigating the creative wilds.

Here’s to searching, seeking, hoping and dreaming–to me the essence of wayfinding.

Thanks for walking with me this far, it means the world.

I’m looking forward to seeing where this next leg of the journey takes us as we map it together.


Explore how to navigate a creative life that matters

This article originally appeared in my weekly Listen Up 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 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.