Play the life game with least regret
“This is my penultimate day as a Vodafone employee.”
That’s how I started my closing email to colleagues. This signalled the end of my 32 year career in telecoms.
No drama. No grand list of achievements. Just a door gently closing.
However, beneath it sat something bigger for me. A decision. Should I go back into the corporate world or strike out on my own?
Every significant decision raises a question: How to choose? I turned to the regret minimisation framework.
We regret inaction more than action
>I knew that when I was 80, I was not going to regret having tried this. - Jeff Bezos
Before founding Amazon, Jeff Bezos had a comfortable, well-paid job. He didn’t leave because he was failing. On the contrary, things were going well. That’s what made the decision hard.
He created a mental model to help decide: the regret minimisation framework. Project forward to age 80. Which choice would you regret more? Trying and failing or never trying at all? The answer, for him, was obvious. The risk wasn’t leaving. The risk was staying.
The default path often carries hidden regret
>When you choose not to decide, you still have made a choice. - Tim Urban
On the Radio 4 programme “Unspeakable,” comedian Sara Pascoe coined a new word that perfectly captures a state many of us recognise.
“Fokay.” It means: I’m sort of OK, but not really.
There’s a pattern I’ve noticed:
Three situations:
- Things are great → we don’t change
- Things are okay → we stay stuck
- Things are terrible → we’re forced to change
The middle is the dangerous one. Because “okay” is comfortable enough to tolerate and uncomfortable enough to regret. That’s where most long-term regret lives. Not in failure. In lingering.
Decisions are games we choose to play
>Life is a game, play it. - Mother Teresa
This quote struck me profoundly. I decided to reflect upon it in my parting email to Vodafone colleagues:
"This is my penultimate day as a Vodafone employee. I close the door on 32 years trying to persuade myself and others that I know something about telecoms.
Rather than boring you with an account of what I loosely refer to as my corporate career (not that I can remember much of it), I’d like to leave you with a way of thinking that has helped me and may help you too.
Charlie Munger (Warren Buffett’s business partner) talked about building a latticework of mental models (ways of thinking). Then picking the right one for a given situation.
Here’s one I’ve found particularly useful:
Think of life as a series of games.
We tend to think of games narrowly: football, bingo, board games. These are finite games. Clear rules. Known players. A defined end. But most of life is made up of different kinds of games. Multi-player games: school, career, status, relationships. There are also Single-player games, e.g. learning, reflection, creativity.
Some of these games are incredibly rewarding while others can induce anxiety. The tricky ones are the status games with no obvious end. We earn more… and then want more. We get promotion… and then compare ourselves to someone further ahead. The finish line moves. At that point, we’re no longer playing the game, the game is playing us.
As Naval Ravikant put it: “The reason to win the game is so we can be free of it.”
That idea stuck with me. There seem to be two ways to deal with this.
One is to play very few games. Want less. A peaceful path, but not one most of us naturally take.
The other is more practical:
Choose our games carefully. Define what “winning” looks like. Then stop playing when we get there.
For me, I’ve played a number of games which I feel I’ve won. These include: Living in a beautiful place (Bath). Being a good parent (my kids still want to talk to me). Using my skills to build useful business tools (Bid model and the Fixed cost benchmarking tool).
So now I’ve reached the end of my corporate career game which I’ve enjoyed playing a lot.
Now I’m stepping into a different kind of game. One with fewer rules, more uncertainty and (hopefully) a lot of learning. I’m off to be a solo creator/startup founder. If you want to see how that unfolds then (if you have not done so) please register for my free weekly A Bit Gamey blog (https://abitgamey.substack.com/about).
Thank you for allowing me to play on the same pitch as you.
Bye for now.
Phil…"
My email wasn’t just a farewell, it reflected a decision I’d made. Like all decisions, it was a bet that carried opportunity and risk.
Play the game with the least regret
>Life is about making choices that minimise future regret. - Daniel Kahneman
We don’t control outcomes. We do control the games we choose to play. And the biggest risk isn’t failure. It’s staying in a game that’s no longer worth playing. So when you reach a fork in the road, ask: At 80 which path would I regret not taking? Then take it.
Want more?
Seven Ways to Spend Our 4000 Weeks Well post by Phil Martin
How Three Tech Titan Make Decisions post by Phil Martin
When I am in my 80s, looking back, I’m sure I will not regret my decision to try my hand as a solo creator.
Game on.
Phil…
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