Creative Wayfinding For Ambitious Optimists.

You Are Here: Why Knowing Your Destination Isn’t Enough to Make Progress

February, 4, 2023

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

At some point, you’ve probably walked into an unfamiliar shopping mall and made a beeline to the directory.

For a moment or two, you scan the map blankly, trying to make sense of it until finally, your eyes find the red “You Are Here” arrow, and the map instantly snaps into focus.

Without this piece of information, the map lacks context.

And without context, no matter how finely detailed, how high the resolution, any map is effectively useless.

When navigating the physical world, we understand the necessity of knowing where we are innately.

It’s no mistake that when we open Google Maps we’re immediately presented with the unmistakable blinking blue dot indicating our current location. It’s the one constant of every conceivable route to every conceivable destination, after all.

Before embarking on a journey, a clear understanding of our starting point allows us to orient ourselves, identify obstacles along the way, and plot a course around them.

It also allows us to plan, equip, and train ourselves accordingly.

A 5k fun run requires a different level of training than a 42.2 km marathon, which again requires different training, preparation, and equipment from a mountaineering expedition of identical length.

Once the journey has begun, a clear understanding of where we have come from enables us to better project our future progress based on our past pace.

And yet, for all the value of understanding where we are, when it comes to our creative journeys, we tend to spend little time thinking about it.

Instead, we spend our time obsessing over both our destinations and the potential routes we might take to get there.

Where we start from, however, dictates the route we’ll take to a given destination.

A lack of awareness about where we currently are on the map, then, is one of the key cruxes that must be overcome if we want to make meaningful, efficient progress toward our goals.

The problem, of course, is that unlike shopping malls, when it comes to finding our place on our creative journey both the map and our position on it are a whole lot murkier.

Pinpointing Your Location

Pinpointing our location begins with a thorough accounting of both ourselves and our surroundings.

What assets, skills, and resources do we possess? What are our interests (or even better, obsessions)? What opportunities are available? What are our strengths, weaknesses, and liabilities? What milestones have we already attained, and which are we aiming for next?

The better we know ourselves and our surroundings, the better we’re able to identify others who have reached a similar destination to ours from a similar starting point, and contextualize our location based on their journey.

To this end, I’ve recently begun collecting every bit of data I can find on more established creators with similar business models to help me better understand where I am in relation to their trajectory.

Of specific interest to me is my friend Jay Clouse, who has a very similar business, audience, and style to me.

As someone earning $40k/mo as a creator, closing in on 20k newsletter subscribers, and 30k Twitter followers, he’s also someone who has had much of the success I’d like to emulate.

After analyzing the historical newsletter, audience, and financial growth data that Jay shares in his Creator Science Lab (affiliate link), and comparing it to my own, I have a pretty good sense that I’m about 18 months behind him.

Knowing precisely where we are in relation to our destination helps inform the decisions we make as we continue to make progress.

But understanding our timeline is just as (if not more) valuable.

Plotting Your Progress

A few years ago, a study of the London Tube system conducted a study in an effort to boost rider satisfaction.

What they found was shocking.

Going in, the assumption had been that the best way to improve rider satisfaction was to improve the speed of the system through faster trains and increased frequency. This would have been a multi-billion dollar project resulting in only incremental gains in efficiency.

The result of their research, however, was that they could increase rider satisfaction with one simple fix, at a fraction of the cost of the larger renovation.

The fix?

Installing screens in the stations that displayed the upcoming trains’ ETAs.

It turns out, people cared less about the actual length of the journey than they did the uncertainty of it.

The same is true for our creative expeditions.

Most of us are willing to do the hard work required to build sustainable careers around our creative work. The root of our frustration, however, lies often in the uncertainty around how long it’s going to take to reach our destination.

This anxiety leads us to jump from shiny object to shiny object, abandoning projects and strategies that would have worked if we’d just given them more time, and severely stunting our progress.

Understanding where we are on the larger journey eases that uncertainty.

When we see clearly that each of our chosen guides spent years working hard for little result before finally something clicked, we feel infinitely better about our own situation.

We can see that the low results:effort ratio is simply a phase of the journey we all have to navigate through.

And most importantly, we can set our expectations around how long it will take to reach the end of this phase and what we’ll encounter on the other side.

Chart Your Course Wisely

Of course, we need to take this type of mapping with a grain of salt.

No one person has started from the exact same place as any of us. Nor are they moving toward the exact same destination or working with the exact same assets & liabilities.

The more roughly similar routes we can identify, then, the better we’re able to triangulate our position based on the landmarks found in their stories.

Once we‘ve roughly identified our location, though, we’re able to plot the most efficient course to our destination.

We’re also able to confidently ignore advice and route suggestions that don’t apply to us, which can save us years of time and effort.

It’s not much use, after all, following the creative path of someone who has previously sold a company and is now able to work full-time on their creative projects with no need for them to generate income in the short term.

At least not if we don’t have similar circumstances.

Nor is it worth attempting to follow the path of someone who has a set of innate skills, obsessions, or connections that we don’t possess ourselves.

Sure, we can attempt to emulate these paths.

At best, we spend months or years getting ourselves to someone else’s starting point, from which we can following their progress to our destination.

At worst, we spend the time attempting to meet up with their route, only to find it utterly impassible… or at least, impassible to us.

Better to understand clearly where we’re coming from, and base our route, landmarks, and timelines on those coming from the same neighborhood as us.

Our guides might be fewer, and we may have to look harder to find them.

But once we do, the map snaps into focus, the way becomes clear, and all that’s left for us to do is walk.


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.