Creative Wayfinding For Ambitious Optimists.

Toss & Catch: The Simple Practice to Develop Creative Confidence

January, 29, 2022

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

Within minutes of leaving my front door for a walk, it’s almost inevitable that I’ll have stooped down to pick up something off the ground.

Most often it’s a small, interesting (at least to me) stone or pebble–when I’m walking along the coast my pockets will end up literally overflowing with such stones–but any vaguely spherical object will do, including various forms of nuts, seeds, fruits, or other naturally occurring orbs.

While in Texas a couple of months ago, I picked up a collection of acorns that are now apparently accompanying me around the world.

Acorns are wonderful metaphors for the value of patience, persistence and how great things can grow from small beginnings, and I keep them on my desk as a reminder.

This isn’t an article about acorns, however.

See the picking up of the object, in this case, an acorn, is only the starting point. Once I have it in my hand, it’s only a matter of time before I begin tossing it to myself.

Toss. Catch. Toss. Catch.

I’ll start with low tosses and easy catches, all the while continuing to walk, but as I become more comfortable with the size and weight of the object, understanding how it arcs through the air in the current conditions, I’ll begin to throw higher.

Soon, I’ll attempt throwing it over tree branches, through gaps in the foliage, throwing higher and higher as my confidence increases.

Toss. Catch. Toss. Catch. Toss. Bounce. Drop. Stoop. Retrieve. Toss. Catch.

I originally thought this habit was some kind of boyish male compulsion born of a love of sports and competition.

How many groups of guys have I been around, who, when pulled over at a road trip rest stop for example, within five minutes have, without speaking or explicit organization, found a target at which to collectively throw rocks in tacit competition?

But the more I thought about it, the more I realized there was something else going on and that this habit had further reaching implications than the simple tossing and catching of an acorn might initially suggest.

In the end, I realized that this tossing and catching was a small, subtle form of confidence building, that, silly as though it may seem, extended into the rest of my life, including my creative work.

Confidence Is Fluid

We often think of confidence as being domain-specific.

We might be confident in our ability to prepare a delicious meal, for example, without having any confidence in being able to run a 10k race.

The truth, however, is that confidence is more transferrable than we often think and can bleed over from one domain to another.

This is especially true of pursuits that share some common denominator.

Take sports for example.

While you might be a novice soccer player, if you’ve been playing hockey your whole life you likely have a level of confidence and comfort in your physical abilities, an understanding of the how team sports work, and your ability to to pick up the nuances of the game fairly quickly.

Confidence is especially fluid and transferable when the activities in question fall under a domain we hold as a core part of our identity.

In the example above, if we see ourselves as athletes we’re likely to have confidence in our ability to understand and excel at any type of athletic endeavour, regardless of whether or not we have any current experience with it.

This type of identity-based confidence is a powerful tool to acquire.

If we hold the idea of being “creative” as being a core part of our identity for example, and have confidence in it, we’re far more likely to excel at any (and perhaps all) creative pursuits we encounter.

But what if we don’t yet have confidence in our abilities as a creator?

Is it possible to transfer confidence over from somewhere else?

Finding Your Common Denominator

It turns out that confidence built up in one area is, in fact, transferrable to pursuits in unrelated domains.

The trick is we just need to work a little harder to find the common denominator tying them together.

I’ve written before about how there’s a lot we can learn as creators from the word game Wordle, for example.

By most definitions, Wordle and creative work fall into entirely unrelated domains.

One is a short, sweet, fun diversion that takes 5-10 minutes a day while the other is the work that many of us pour our hearts, souls, fears, and hopes into for years, decades, or even a lifetime with the goal of earning a living and creating an impact off of it.

And yet, when we shift our categorizations of each of these pursuits from “game” and “work” to the common denominator of “puzzle” all of a sudden the link between the two becomes a whole lot clearer.

With the link now established, the confidence that comes from competence in one area almost naturally begins to flow into the other.

I’ve experienced this exact boost in puzzle and problem-solving confidence in my creative work by regularly playing games like Wordle, crosswords, learning how to solve a Rubik’s Cube, board games, card games, and more.

When you find the link and then approach two pursuits as fundamentally the same thing, the gains made in either of them apply to the other.

Which brings us back to tossing and catching acorns.

Confidence is a Common Denominator Unto Itself

As I walked and tossed and caught and dropped and tossed and thought about the possible common denominators between tossing and catching and any other more… shall we say, useful pursuits, I cycled through possibilities.

The obvious one was the physicality of the activity.

The accuracy and timing required of the toss and the hand-eye coordination required of the catch both feel fairly broadly applicable to other physical activities.

Then I pushed a level deeper and thought about so much of creative work is essentially tossing an idea up to our audience and hoping they catch it. At the same time, we ourselves are constantly trying to catch the subtle cues our audience and the market are sending our way in order to inform our work.

Toss. Catch. Toss. Miss. Stoop. Retrieve. Toss. Catch. Toss. Catch.

It’s a tenuous connection, I’ll admit, when it comes to how much creative confidence can possibly be built by tossing acorns over tree branches.

And yet, it provides an interesting lens to think about the process of doing creative work.

The unexpected gusts of wind, caroms off tree branches from poorly aimed tosses, and simple misjudgments that might cause us to miss catching an acorn all exist in some form or another in creative work.

As do the ways in which we might account for and manage these potential disruptions.

As too does the thrill in our gut of aiming an ambitious toss and pulling out the catch on the far side of its arc.

Perhaps the more fundamental form of confidence we gain stand to gain from tossing and catching, however, is the belief in ourselves to envision an action and have it work out successfully.

Whether it’s tossing and catching an acorn or planning and executing a product launch, establishing a vision and following through on it is how confidence builds.

The more ambitious the toss we’re able to snag, the more confidence we gain for the next one.

That’s not to say every toss we make will be perfect, or that we’ll make every catch. But as long as we keep tossing, we find that the confidence gained from a successful toss and catch is greater than the amount lost by missing.

And in the end, in my experience, at least, confidence built up in any area of our lives is additive.

Even if we can’t make a direct connection about how confidence built up in one area might flow into and serve us in another area of our lives, our overall, master level of confidence in ourselves is informed by all the domain-specific confidence we possess.

And in the end, that master level of confidence has a way of finding its way into every single thing we do.

Confidence is confidence.

Which means any chance we have to increase it–be it tossing up an acorn or an idea–is worth taking.


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.