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Work & ambition

Are you even playing the game?

I was taking my kids to school the other day when a Ferrari with a personalised number plate roared past me.

(Well, it didn't really roar, so much as trundle. It was rush hour in London and traffic wasn't moving but Ferrari's usually roar so I'm gonna go with that image...)

I immediately thought, "What kind of dickhead would buy a Ferrari?"

Are they successful?

Famous?

Powerful even?

As someone who has previously been that dickhead, I often think about this.

There are lots of things you can do when you've achieved some success. One of those things is to buy something, which tells everyone else, that you've made some money. A Ferrari is a good choice for this.

But as a car, it's totally rubbish. Uncomfortable. Loud. Expensive (to run, to insure). It can't go over speed bumps...

...and it makes everyone hate you.

So if buying a Ferrari doesn't count as 'success', what does?

Have you ever thought about what success looks like?

If not, then you might be playing the wrong game.

And that’s bad.

Playing the Game

These two types of games in life - something I realised when I hit 40, had a mid life crisis and retired to become a hippy (still working on that...).

These games aren’t just about rules—they shape how we approach goals, relationships, and life itself.

Finite games we all know about.

They’re the ones with clear rules, measurable outcomes, and an endpoint.

Sports, board games, or even ticking off items on a to-do list fall into this category.

The goal of a finite game? To win.

Finite games are satisfying because they offer closure. You can declare victory, hang up your metaphorical shirt, and bask in the glory.

Think of the moment you finally finish a tough project or cross the marathon finish line.

But there’s a problem. The satisfaction is fleeting. Like buying a Ferrari.

Once the game ends, what’s next?

You’re often left searching for another contest to conquer.

Playing the Long Game

Infinite games, on the other hand, don’t have a finish line.

They aren’t about reaching the end, and defeating the level boss.

They're about sustaining the process, evolving, and discovering purpose along the way. Think of a lifelong commitment to learning, nurturing relationships, or pursuing personal growth.

The goal of an infinite game? To keep playing.

This approach taps into something deeper.

It fosters resilience because the payoff isn’t immediate or tangible—it’s found in the ongoing journey. Infinite games challenge us to adapt, redefine success, and think beyond short-term wins.

Why This Matters

At first glance, finite games seem more appealing. They’re measurable, structured, and come with that thrill of victory.

But infinite games hold the potential for profound satisfaction. They help us focus on what really matters, even when success can’t be neatly checked off a list.

This distinction forces us to ask a critical question:

Which game are you playing?

What Can You DO Today?

  1. Balance is Key: Life isn’t about choosing one type of game over the other. Finite games can provide motivation, while infinite games bring depth.
  2. Define Success Carefully: Are you chasing wins that will quickly fade, or are you investing in something that sustains you over time?
  3. Adopt an Infinite Mindset: When you face setbacks, ask yourself: How can I keep playing? Infinite games encourage resilience and long-term thinking.

In the end, these games we play get us to rethink not just how we play but why.

What would life look like if you focused less on winning and more on staying in the game?

I no longer have my Ferrari; I drive a Volvo now.

And I play fewer finite games - I find they just don't do it for me anymore. I mean, yes, if we meet on the golf course, I'm going to destroy you and feel good about it.

But career milestones, the next rung on the ladder, a faster car, a bigger house, they just don't fit with who I am these days.

Happy Saturday,

Jon "Really Wants to be a Hippy" Kaye

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Original newsletter disclosures

DISCLAIMERS & DISCLOSURES This content is for education and entertainment purposes only. Jon does not provide tax or investment advice. The information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. Past performance is not indicative of future results. All investing involves risk, including the possible loss of principal.