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Mindset

Choose Your Regrets

Since regret is unavoidable, decide which regret you could live without

Difficulty
Moderate
Time to result
~days to results
Steps
4
Confidence
70%

From Christopher Hitchens' line 'in life, we must choose our regrets', relayed by Douglas Murray. Because doing one thing means sacrificing another, regret is baked into the fabric of a life of trade-offs; you can make the best possible choice and still regret the road not taken, and you never get to rerun it to know for sure. Rather than trying to find the decision you could live with, you flip the frame and imagine which decision you could not bear living without. You weigh the regret of each path and choose the one whose regret you could tolerate. This reframes the goal from an impossible regret-free life to becoming a regret-optimisation machine.

Origin

Christopher Hitchens told Douglas Murray 'in life, we must choose our regrets'; Murray recounted it to Chris Williamson over Manhattans in New York, who noted it echoes Thomas Sowell's 'there are no solutions, only trade-offs'.

Core principles

  • 01Regrets are features of a life of trade-offs, not bugs from bad decisions.
  • 02Every choice sacrifices an alternative you may always wonder about.
  • 03You cannot rerun a decision, so you never learn if it was truly optimal.
  • 04There are no solutions, only trade-offs.
  • 05Optimise for the regret you can bear, not for a regret-free life.

How to run it

  1. 1

    Accept regret is unavoidable

    Recognise that any meaningful choice sacrifices an alternative, so some regret is guaranteed regardless of how well you choose.

    Pro tip Treat regrets as features baked into trade-offs, not evidence of a mistake.

  2. 2

    Name the competing paths

    State the two real options honestly, for example a relationship that requires staying versus a job that requires leaving.

  3. 3

    Live inside each regret

    Imagine having chosen each path and vividly picture the regret that would follow.

    Pro tip Ask which decision you couldn't bear living without, not merely which you could live with.

  4. 4

    Choose the bearable regret

    Select the option whose regret you could put up with and forgive yourself for, and commit.

    Pro tip Aim to make every regret you carry an optimal, chosen one.

    Watch out Waiting for a regret-free option means never deciding, because none exists.

In the wild

Relationship versus new job

Facing a choice between a relationship that requires staying home and a job that requires leaving, both paths cause regret. Instead of asking which he could live with, the chooser imagines which regret he could never forgive himself for, and picks the path whose regret is bearable.

→ A hard, previously paralysing decision gains clarity and gets made.

Common mistakes

Chasing a regret-free choice

Believing the right decision avoids all regret leads to endless deliberation, because trade-offs guarantee regret either way.

Optimising the wrong question

Asking which choice you could tolerate is weaker than asking which loss you could never bear.

Is it for you?

Best for

Someone stuck between two meaningful options, each with painful opportunity cost.

Not ideal for

Low-stakes or easily reversible decisions where regret is trivial.

From the episode

16 Lessons From 2022 - Joe Rogan, Jordan Peterson & Jocko Willink - #565

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