I’ve been playing a lot of backgammon, recently.

If you’re not familiar with the game, the description, per Wikipedia is as follows:

“Backgammon is a two-player game where each player has fifteen pieces that move between twenty-four points on the board according to the roll of two dice. The objective of the game is to be first to move all fifteen checkers off the board.”​

The other key element of the game worth noting is that a stack of two or more pieces is protected, blocking the opposing player from placing their own piece(s) on that point. A single piece, however, is unprotected, meaning the opposing player can place their own piece(s) on that point, sending your piece home, Sorry! style.

The thing to understand about Backgammon is that while there is certainly a level of strategy involved, the strategy can be learned quickly, at which point, two experienced players are simply playing a game of pure chance.

In cases such as this, whoever rolls higher-scoring dice over the course of the game is going to win.

Or at least, they should.

As simple as the strategy of Backgammon is to understand, there is one trap that even experienced players fall prey to.

The trap? Themselves.

You see, each dice roll presents you with a series of available moves, some of which will be risky, and some safe. In my experience, the strategy that wins most consistently is to default to the safest move, taking smart risks to leave pieces exposed only when necessary.

We can think of sticking to this strategy as the “disciplined” approach to the game.

When both players take a disciplined approach to the game, the outcome will almost certainly be determined by chance alone. While it might make for a boring game, it also provides the best odds of winning.

As a game of chance between two players, those odds are 50%, meaning that if you simply follow this strategy, you can guarantee yourself victory in half the matches you play.

The trap, however, is when one or both players get greedy, believing that they can beat the 50/50 odds and straying from the disciplined approach to the game.

This departure from discipline almost always takes the form of a ratchet, with one unnecessarily risky move being punished, now requiring a further risky move in order to make up the lost ground.

This cycle perpetuates until all semblance of discipline has been thrown out the window.

When both players fall into this style of play, games can turn into wide-open free-for-alls with multiple lead changes that are exhilarating to play and heartbreaking to lose.

If only one player opts for this style of play, however, while the other maintains their discipline… The undisciplined player is likely to have their clock cleaned.

If this is the case, why then, would an experienced player who knows the disciplined approach will give them the best chance of winning, ever abandon it?

The answer is almost always emotion.

Once emotion enters into the decision-making process, probability is no longer the only determinant of the outcome. Over the long run, this can only decrease your odds of winning.

If a disciplined game is about assessing the odds and making the most rational move available, allowing emotion to affect your decision-making can by definition only lead to more irrational moves.

Soon enough, frustration, anger, revenge, spite, hope, desperation, and more all take a turn at the wheel, driving you to make riskier and riskier moves based only loosely on any assessment of the odds.

I won’t lie, the victories earned by playing with emotion are often the sweetest. But they’re also much harder to come by.

What’s more, the lows after losing an emotion-fueled game are much lower.

When you lose a disciplined game, you can take solace in the fact that for the most part, you made the right choices and luck just wasn’t on your side this time around.

Lose a game driven by emotion, however, and you’re left to beat yourself up about all the (in hindsight) stupid mistakes you made that lead to the loss.

What this all means, is that Backgammon is not the simple game of pure chance it appears to be on the surface, but a game about mastering your emotions and playing with discipline.

The same concept applies to our creative work.

​

Don’t Let Emotion Drive Your Creative Decisions

Much like with Backgammon, we can choose to take either a disciplined or emotional approach to our creative work.

Unlike Backgammon, however–a closed system comprised of a limited number of available moves and outcomes, all of which controlled by the roll of two dice–the potential moves, and the odds and risks associated with our creative work are harder to calculate.

This lack of clarity makes it easier for us to rely solely on emotion to guide our decision-making.

Sure, we’ll often dress our reasoning up in stories about why our choices are the most rational or strategic, but underneath it all, emotion is in the driver’s seat. As with Backgammon, with emotion at the wheel, our chances of success drop sharply.

When it comes to navigating the terrain of our creative work, the feelings most likely to drive our decision-making are negative emotions like doubt, impatience, fear, and inadequacy, as well as positive emotions like inspiration, purpose, desire, and excitement.

Our challenge, when faced with any of these emotions, is to not let them sway us from playing a disciplined game.

Much like Backgammon, playing with emotion in our work can lead us to put ourselves in risky positions.

More often, however, emotion in our work leads to inconsistency, causing us to jump from strategy to strategy, tactic to tactic, never giving any of them enough time or attention to actually begin to work for us.

In Backgammon, the strategy of playing a disciplined game is clear: assess the odds and make the least risky move.

But what does discipline look like for creative work?

​

Disciplined Creative Work

The core of the disciplined approach to creative work is the same as the disciplined approach to Backgammon: Default to the moves that in the long run, give you the highest probability of success, taking a sprinkling of smart, calculated risks along the way.

This raises the question, however, what are the moves that give the highest probability of success in the long run?

There are a number of practices, habits, tasks and mindsets that fall into this category, but I want to focus on two.

​

Focus On the Long Game

The first is to make the decision to play the long game in the first place. Playing with discipline requires you to ride out the surges of emotion, positive and negative, that might otherwise compel you to jump from strategy to strategy at the first sign of frustration.

Think of your work as an acorn.

While it has the potential to one day grow into a towering oak, it must first be planted in fertile soil, and then be given a steady supply of sunshine and water for months before the first signs of growth become even the tiniest bit visible above the soil.

Any strategy worth pursuing will require the same patience, attention, and nourishment in order to succeed.

Adopting the long view from the beginning and helps you ride the waves of emotion and make wiser decisions, even when the first signs of growth have yet to appear

Once you’ve adopted the long view, the second practice central to disciplined creative work is to consistently ship new work.

​

Ship More Work

Imagine for a moment that you knew that with every podcast episode, newsletter issue, or YouTube video you published, you would get 25 new subscribers.

Knowing this, you would likely never stop publishing new content.

Now imagine you knew that you would get 2,500 new subscribers at the moment you published your 100th piece of content, but not one before that.

With this guarantee, you would likely still feel confident as you published those first 99 episodes, even without the steady signals of progress along the way.

With the guaranteed influx of subscribers after your hundredth iteration, you might even choose to speed up the process, compressing the requisite number of reps into less time in order to get the resulting subscribers more quickly.

While we like to think that growth happens in a linear fashion, it more often resembles an exponential curve, similar to the second scenario, with long periods of slow, incremental (maybe even imperceptible) growth and improvement that then–suddenly and unexpectedly–gives way to a surge of progress.

While the surge always takes time to materialize, time itself is not the factor leading to it.

We can’t simply wait it out. The only way to arrive at the surge is to ship a lot of work.

There are a few reasons why.

​

Shipping With Discipline Improves Your Luck

First, our early work just isn’t that all that good, at least not compared to what it will be 50, or 100, or 500, or 1,000 reps from now.

We can learn and read and study all we want, but nothing improves our work like creating, publishing, and getting real-time feedback (even if that feedback is crickets).

Secondly, each time we ship our work is an opportunity to experiment.

If we only publish 4 pieces of content a year, for example, it will be hard to draw conclusions on what’s resonating, and thus worth doubling down on, and what’s not.

Publish 100, however, and you’ve got a significant sample size from which to draw conclusions.

Finally, as with Backgammon, there is an element of luck to doing successful creative work.

In Backgammon, our opportunities to get lucky are constrained by the number of turns in the game. When it comes to our work, however, our opportunities to get lucky are constrained only by the number of times we choose to ship.

The more work we ship, the more opportunity we give luck to find us.

Playing a disciplined game helps us level the odds when it comes to our creative work.

By taking the long view and continually shipping our work, we can put ourselves in a position where it’s only a matter of time before we catch a break and we ride the surge upward.

---

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.

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.

Subscribe

---