Creative Wayfinding For Ambitious Optimists.

What if You’re Already on the Right Road?

May, 20, 2022

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

I was out for a walk the other morning exploring Kollwitzkiez, a neighbourhood here in Berlin for the first time.

I had been told it was an interesting area filled with old art nouveau architecture, cute boutiques, coffee shops, and restaurants. And while I’d been able to navigate to the general vicinity of the neighbourhood over the course of my meandering walk, I didn’t know where in the neighbourhood specifically any of the aforementioned attractions were.

As I turned off the busy boulevard that bordered that neighbourhood and onto a smaller residential street that lead toward its center, I kept my eyes peeled for any indication of which direction to turn next.

Block by block I continued, slowing at each intersection and peering down the street in both directions, seeking out the slightest sign of a potential point of interest.

Block by block, I was disappointed.

Each new cross street looked identical to the one I was already on: Mundane, residential, boring streets with little to differentiate between them.

I continued on in this manner for a couple more minutes, growing more and more skeptical of the promised quaintness of the neighbourhood. In my impatience, I decided to turn up the next street regardless of what it looked like in order to get off a street that was clearly not leading to anything interesting.

I reached the intersection, stopped, and contemplated whether to take a right or a left.

Before I could decide, however, I took my first good look in a few block down the street I was currently on.

Almost immediately, I noticed a sign for a specialty coffee shop on the corner opposite me. And beyond that an artisanal bakery. The opposite side of the street was lined with cafes and restaurants.

I turned and looked back at the way I had just come and saw for the first time an independent book shop and some interesting boutiques that had gone unnoticed as I had walked past, already looking ahead to the upcoming intersection.

In the end, it turned out the road I had been so keen to turn off of from the moment I stepped onto it was the road leading exactly where I wanted to go.

The experience got me thinking about how often the exact same situation plays out in our creative lives.

Don’t Be So Quick to Change Routes

It doesn’t take long for our eyes to start wandering in search of alternative routes when we’re not seeing the results we seek from the path we’re currently on.

We have a hard time actually believing that–by luck or by design–we could have actually found our way onto the correct street, and as a result are constantly looking for the next exit, which we imagine must surely have a better chance of leading somewhere interesting than the boring, mundane, residential route we’re currently on.

If we’re not happy with our current results, our logic goes, then surely the best approach is not to do more of the same but to do something, anything, different.

And sometimes, this logic might be sound.

But perhaps just as often, the logic is exactly backwards.

Our mistake in these situations is rooted in two incorrect, intertwined assumptions, one about each end of the road we’re on.

The first assumption is that any road that ends up somewhere interesting will be interesting over the length of its span.

Start at the Eiffel Tower (or any major landmark), however, and walk away from it in any direction, and it’s not long before the streets devolve into generic and uninteresting commercial, residential and finally, industrial blocks.

In the same way, while there may be occasional peak moments along our creative journeys, the practices and routes that will most reliably get us to our goals are by and large made up of boring, monotonous consistency.

The second assumption–a mirror image of the first–is that a road that starts off as boring and mundane is likely to stay boring and mundane.

There’s an oft-quoted (and oft-ignored) piece of investment advice about past returns not being a useful predictor of future returns.

This advice is most commonly applied as a caution against investing in a fund or company that has historically outperformed the market.

In other words, the fact that things have been good up until now doesn’t mean that things will stay good into the future.

But the opposite is also true.

When it comes to the route we take to our creative goals, this means that just because the path we’re on hasn’t lead us to the results we’re seeking so far, doesn’t mean it never will.

Indeed, the fact that we’ve already walked a long stretch of a boring, mundane, residential street might actually be a sign that we’re getting close to something interesting.

Something we might otherwise miss if we were to turn off too soon.

One of the core lessons I’ve learned from many years (and thousands of kilometers) of walking is that if you walk long enough in one direction, you almost always end up somewhere interesting.

I’ve also learned that if you continue walking past that, things are bound to get boring again.

And so the cycle continues.

Understanding this dynamic is essential for building a sustainable creative career.

It helps us stay the course and avoid shiny, short-term distractions that pull us off our course, and contextualizes both the highs and lows, the excitement and the boredom of creative life.

Perhaps most of all it cautions us that if we’re going to make a career of this, we need to build joy, sustenance, and gratification into our daily creative practice.

Because in the end, any destination we aim for is fleeting, and will soon enough be fading in our rear view mirror as we pass through and then press ahead onto the next one.

The only lasting reward is the one we build into the journey and carry with us each step of the way.


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.