I've been playing pool for five years now.

One of the first things you learn when you start taking pool seriously is that making the ball in front of you is almost never enough. In fact, recognising and integrating this in play is an unofficial milestone for a player's progress (and this reminds me that for a while now I've planned to codify pool training into a universally acceptable syllabus – I see no reason why this exists for "professional" fields like medicine or computer science, but not pool).

Anyway, beginners play one shot at a time. They play to pot balls.

There’s a ball. There’s a pocket. They make the ball, either by intention or by fluke.

Success.

Then they look up and realise they have absolutely nothing on the next one.

Perhaps the cue ball is frozen to a rail. Or the only available object ball is at the opposite end of the table. Or the angle is wrong. Or they’ve snookered themselves behind somebody else’s ball. Or they've left a cluster too long into the game. Or they’ve left a shot that technically exists, but requires the kind of precision that makes commentators say things like what a shot! – which is precisely the kind of precision a beginner simply doesn't have and might not even realise is possible, never mind having the experience to visualise it.

A better player is thinking about the next shot before they’ve played the current one. They aren't just thinking about whether this ball goes in, but where the cue ball ends up afterwards. Before they play, they create a plan – a path – for finishing the game. They handle clusters and problem balls early. And they duck when they need to. Impressive players force their opponents into playing the shots they want them to.

This is a valuable lesson about life.

Always leave yourself a shot.

That sounds obvious, but it isn’t. It took me a while to learn this and to begin to apply it to life itself.

Sometimes the spectacular pot is the wrong shot.

And sometimes the boring shot that leaves the cue ball three inches from where you need it is much better.

Sometimes you shouldn’t even be trying to pot anything at all. Like life, pool is about the long game, not the spectacular shots.

Position is part of the shot

In pool, the object ball disappearing into the pocket is only a third of the result.

The cue ball has to end up somewhere useful – and that's another third.

Being in position to execute the sequence is the final third.

Realising this changes how you think about everything.

It takes you from asking:

Can I make this?

To asking:

What happens after I do?

And it's a much better question outside pool too because a lot of bad decisions work perfectly well in isolation.

Taking on one more client might make you more money this month.

Building another feature might win one prospect.

Hiring somebody might solve the immediate bottleneck.

Quitting your job might give you more time.

Taking a job might give you more money.

None of those decisions can be evaluated properly without looking at what happens after you make them, and stepping back to weigh their place in the big picture.

Where does the cue ball end up?

If that client consumes half your week, prevents you from building your actual business and leaves you dependent on their revenue, you made the shot and lost position. Soon you've derailed your long term goal by three years.

If you spend three months building a technically impressive feature that teaches you nothing about whether anybody wants your product, same thing.

If you quit your job with three months of runway because you desperately want to work on your startup full-time, you may have bought yourself freedom today by creating desperation three months from now.

Nice pot. Terrible shot.

Good players preserve options

The best position in pool is rarely a single exact point.

Usually there is an area you want the cue ball to enter.

Land anywhere in that area and you still have a reasonable shot. Land outside and you'll either have no shot, or will have to work harder to repair your game. I like to call this the optimal landing area.

The optimal landing area matters so much because trying to put the cue ball on a coin-sized spot every time is fragile. It's too easy to lose position and damage a game. Slightly too much pace, slightly too little or too much spin, a dirty cloth, a bad contact, an unexpected bump, and the game immediately falls apart. That's not how games are won.

I've learned now that life works the same way. People spend a lot of time trying to optimise outcomes when they should be optimising optionality.

Cash in the bank is optionality.

A broad professional network is optionality.

Skills that transfer between industries are optionality.

Low fixed costs are optionality.

A product architecture you can change without rewriting everything is optionality.

A business with three acquisition channels is in a better position than one with a single extraordinarily efficient channel that disappears when Google changes an algorithm.

A product that relies on one critical third-party service is in a worse position than one with redundancies and optionality built in. (By the way, see the announcement by OpenAI regarding Cursor last week ).

Optionality is not indecision. It is position play.

You are deliberately trying to end each move with several reasonable next moves available.

Don't use more cue ball than you need

There’s another mistake weaker players make: doing too much.

Run three rails. Use maximum side. Huge draw. Playing too safe. A lot of power shots.

Although it looks impressive when it works, it also introduces multiple different ways to fuck up a shot that could have been played with more precision and intentionality.

And there is a version of this everywhere in life.

Businesses prematurely introduce complexity because complexity feels like progress.

Microservices for a product with forty users.

Sophisticated billing before anybody is even buying.

Hiring HR for a team of five.

AI where a cron job would work.

Three cars because you have money in the bank.

You can do all of these things, no question.

The question is why you would. What are you optimising for? How does this decision push you toward your long-term goal? Why wouldn't the boring choice work?

Good position play is often boring. Use the minimum amount of cue ball required to get where you need to go. Leave the fanciful shots for exhibition matches.

Sometimes the right shot is a safety

This took me longer to appreciate, and I'll tell you why.

Most pool players (like life players) fall into one of two broad categories: aggressive players and defensive players. I'm an aggressive player, both in the game of pool and in the game of life. When I come to the table, I'm often looking at running out (which is a pool term that means clearing all of your balls and winning the game, all in a single visit to the table). I take big risks, I plan for eventualities and work out how to still win the game if something goes wrong, then I take the shot, even if it's risky, with often very little doubt in my mind. In both pool and life, I often have multiple contingencies, and my contingencies have contingencies. These give me the confidence to take bold bets, and I have taken a lot of bold bets in my life. Like dropping out of medical school. Or walking away from N300M in 2022 (which I'll write about one of these days).

My mother (who doesn't play pool, and doesn't understand why I do it so much) is a defensive player. She is the wait and see kind of person. If there's non-trivial risk, she's unlikely to take that route. She is the don't stray from the well-beaten path kind of person. Where I'm make things happen, she is see how things unfold.

I've learned that neither of these are inherently bad approaches to either the game of life or pool. It's so much more important to clearly define your (not mine or your parents' or your partner's or your friends') long-term goal, recognise the strengths and inadequacies of your default approach, and adjust accordingly, always keeping your focus on your goal and your path to reaching that goal.

It's so much more important to know when to be aggressive and when to switch to defense.

Just yesterday I was playing a young lady. I had a single ball left to her six. She was on the table, about to make a really bad shot, and when someone asked, "why are you playing that shot?", she replied, "I want to pot the ball".

I glanced at her rail-side cluster that would have provided a really easy, really smart safety, and smiled because I knew I'd already won.

Pool is not a potting competition.

If there is no sensible attacking shot, you don't have to attack. You can leave your opponent nothing and watch them either foul outright, or fuck up their game and return the cue ball to you in a better position. You can force your opponent to play the exact shot you need them to.

A safety is not surrender. It is recognising that the table does not currently justify aggression, and switching your stance to defense instead.

And this is particularly useful in the startup world, where there is enormous cultural pressure to always be doing something: launch, hire, raise, expand, raise again, pivot, announce, ship, ship, ship.

But I've learned that sometimes the correct move is simply to reserve cash for 12 more months. Sometimes it is to keep the day job, or to kill the feature, or to decline the deal.

Sometimes the market is telling you that you don't have a shot.

You are not required to manufacture one: play safe, improve your position, wait for the table to change.

If you play defense right, there will be another visit.

Think in patterns

If you study pool long enough, it eventually stops looking like a collection of individual balls. It starts looking like chess. You start seeing patterns.

This one, then that one, leave an angle on the third to stun for the fourth, use the fourth to get onto the fifth with a bump on that cluster to open up the "eight ball", a 5-9 inch draw on the fifth to get on the sixth, stun forward on the seventh into the side pocket for an easy shot on the eight (not eighth) ball.

The current shot becomes part of a sequence. Your game becomes a map.

I've learned this is one of the biggest differences between people who consistently make good decisions and people who occasionally make brilliant ones. It's the difference between going forward a step at a time, and going forward three steps but regressing by five.

Bad players optimise for the shot. Good players optimise for the sequence.

The best career decision might not be the job with the highest salary; it might be the one that puts you in a market you want to understand, gives you access to people you want to know and teaches you something you can later turn into a company.

The best first version of a product might not be the one customers find most impressive. It might be the one that gets into their hands fastest and tells you what to build next.

Even knowledge works this way. You don't need to know everything. You only need to learn enough that the thing you learn today makes tomorrow's easier to understand.

Shot. Position. Shot. Position. Each shot is part of a sequence. Execute the sequence and you win the game.

You will get out of position

None of this means you can map an entire frame perfectly all the time. You simply can't.

Like life, pool surprises you. It's one of the reasons I love the sport.

Maybe you under-hit something. Or you over-hit something. Maybe you misjudge an angle. Or your opponent leaves you somewhere strange. Maybe you unexpectedly scratch and now your opponent has "ball in hand" and can suddenly clear four easy shots.

It's the same with the game of life. Plans fail. Markets change. People change. You change. Something will change.

Position play doesn't mean predicting every future move. It means making sure your current move does not unnecessarily (or even irreparably) destroy your ability to make another one.

Position play is about optionality, not clairvoyance.

When you do get out of position, don't compound the mistake by pretending you haven't. Reassess the table and see what options you have left.

Maybe the run is no longer possible. Accept that and move on.

Maybe you need to play safe. Switch focus to executing that perfectly and return to your seat.

Maybe the original plan is dead and there is another pattern available. Take that and adjust accordingly.

Strong players don't insist that the table still looks the way they wanted it to look. Strong players play the table that is actually there.

Leave yourself a shot

I think that this is a decent rule for making decisions generally.

You don't always need to make the optimal move, which is something I was reminded about last night after a chat with my partner about an administrative problem she'd experienced in her university days. I'd focused so much on proving that my mathematical solution was the optimal one while hers was only good, that I'd whipped out my iPad and stylus and made a diagram to explain.

Mine was taken directly from a load balancing strategy, which is a software engineering term I probably shouldn't go into detail about in this post. Hers came from common sense.

The optimal solution is often beautiful, but it's also often overkill unless context is taken into consideration.

Most of the time, it's good enough to make a good move that leaves another good move available.

Don't spend all the money. Don't burn every bridge. Don't build yourself into a corner. Don't take a risk whose failure eliminates you from the game. Don't optimise so aggressively for the present that the future becomes expensive. Don't take the shot just because it's there.

Sometimes playing safe is the best shot.

And wherever possible, when you get back up from the shot and look at the table again, make sure you've left yourself something to work with.