Over the past month, I’ve been playing tennis about three times a week.

These matches have largely been divided between two friends, Evan and Hamilton, with very different styles and experience levels.

In comparing how I play versus each of these different opponents, I’ve noticed an interesting trend that highlights a helpful lesson about the situations and environments we subject our creative work to.

A Tale of Two Opponents

Evan and I have both been playing tennis for years, albeit mainly against each other during the month or so I visit him in Winnipeg every summer.

Historically, he’s tended to win the majority of our games we play, although we’re very well matched and every point feels like a toss up.

Hamilton, on the other hand is essentially brand new to the sport.

This past month was the first time he’s played regularly, and while his improvement has been remarkable, his game is still highly inconsistent. When he’s on, he can make some great shots and carry extended rallies. When he’s off, however, he hits far too many shots either long or into the net to win sets consistently.

The stats tell the story.

Of the 50 or so head to head sets we’ve played over the past month, Hamilton probably won 3.

As a competitive person, I’d typically prefer to play tight, competitive games where I can test myself against a skilled opponent. And yet over the past month, I found myself enjoying my lopsided matches against Hamilton far more than the close ones with Evan.

But it wasn’t the feeling of winning that made me enjoy these matches more.

It was the feeling of improvement.

Which surprised me. Because I’d always imagined that the best way to improve your skill in any field was to play against others at or above your level.

Now, however, I’m not so sure.

The Problem with Competitive Games

While the matches I play with Evan are tight, competitively, they’re also tight stylistically.

Evan is as competitive as I am, and W\when we face off, it’s clear that we both care more about winning than improving.

As a result, we revert to safe shots we both know are well within our capabilities, preferring to simply keep the ball in play and wait for the other person to make a mistake, rather than attempting more aggressive (and difficult) shots that would test both ourselves to make and our opponents to return.

This approach leads to some extended, competitive rallies… but they’re not all that fun or interesting.

What’s more, because we’re not attempting many shots beyond our current skill level, it’s hard to say that we’re improving, despite the amount of time we spend playing.

Against Hamilton, however, things are different.

Because of the obvious skill differential, I have an overwhelming amount of confidence in my ability to come back if I fall a few points behind.

As a result, I feel the freedom to experiment with my game in a way I don’t against Evan.

Facing Hamilton, I’m aggressive, seeking the edges of the court and adding more speed to my swings than I necessarily have control over.

Most of those shots don’t actually work out.

Over the course of our games, however, the success percentage of those aggressive shots has steadily improved. With the increased level of comfort and competence, I’ve started working them into the games against Evan.

And I’ve started winning.

How Competition Stunts Our Growth

When it comes to our work, perhaps the most competitive environment of all is that of counting on our work to earn us an income.

And while this is the goal many of us are actively working toward, placing ourselves in this environment too early can ultimately stunt our growth and limit our potential.

When our work needs to deliver results, we tend to abandon the loose, experimental, explorative style we played with when the stakes were low.

Instead, we focus on a tighter, more measured style focused on limiting mistakes.

The problem is that mistakes are the most reliable path to growth.

Placing ourselves in environments without room for mistakes then, is a surefire way to remain stuck on the creative treadmill of constant exertion without significant improvement.

Ironically, it feels to us as though we’re playing the game the way it’s supposed to be played.

We’re running across every inch of the court and even getting ourselves into some extended rallies. But the rallies are characterized by safe shots to the center of the court, mimicking what we see the other players serving up. We rarely, if ever test ourselves by pushing shots to the fringes, testing the boundaries of our opponents, the court, and ourselves.

Play Games You Can Come Back From

There’s no doubt that if we want to reach our creative potential, sooner or later we’ve got to test our work in the most competitive environments.

But in order to get our work to the level where it has a chance to thrive in those environments, we need to spend much more time playing games we know we can come back from, with ample opportunity to make mistakes.

Then we need to take advantage of those opportunities and make the mistakes.

Most often, this is about testing the smallest viable version of an idea before landing on one that resonates, and only then going all in on it.

In practice, this might mean turning a particularly resonant Tweet into a blog post… into a workshop… before ultimately turning it into a course.

Keep in mind that there is almost certainly a time to focus on limiting mistakes.

Many a Wimbledon title is decided by which of the two world-class players makes just one fewer mistake than the other.

The thing is the way you win a Wimbledon title is far from the way you get to a Wimbledon final.

The path to Wimbledon, like the path to our potential is filled with countless low stakes games where we can test our ideas, refine our form, and build up our stamina, all with the knowledge that we can make our way back from any mistake we’re likely to make.

For every minute a champion spends soaking in the roar of the crowd under the primetime lights, they spend hundreds more on the practice court, without the fans, the glory, and the pressure.

Don’t forget to give yourself the same luxury.

---

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.

Subscribe

---