Choosing Your Regrets
Decide by asking which regret you can live with, not which option you want
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 4
- Confidence
- 78%
Christopher Hitchens' line 'in life we must choose our regrets' reframes decision-making entirely. Because opportunity cost is inescapable — doing one thing means not doing another — regret is a permanent feature of existence, not evidence of a bad decision. You will always carry the open loop of the road not taken, even when you chose correctly. So rather than asking 'which do I want?', ask 'which regret could I live with?' The regret of a hard conversation with a boss you're leaving is real but bearable; the regret of a decade wasted in a job you hate is far heavier. This frame also jump-starts your fear engine: instead of running toward a fuzzy 'want', you run away from a vivid regret, and loss-aversion makes that pull roughly three times stronger.
Origin
Christopher Hitchens told a young Douglas Murray 'in life we must choose our regrets'; Murray relayed it to Chris Williamson, who reflected on it for a year and shares the unpacked version with Alex Hormozi.
Core principles
- 01Regret is unavoidable because opportunity cost is baked into every choice
- 02You can't split-test life, so every path leaves an open loop of the road not taken
- 03Since regret is inevitable, the real choice is which regret you can bear
- 04Framing by regret activates loss-aversion, a stronger motivator than desire
How to run it
- 1
Accept regret is guaranteed
Recognise that any choice forecloses alternatives, so some regret is baked in no matter what you pick.
Watch out Don't chase the fantasy of a regret-free decision; it doesn't exist.
- 2
Name each option's regret
Spell out concretely what you'd regret about each path — the hard conversation, or the wasted decade.
Pro tip Make the regrets vivid and specific; vague regrets don't move you.
- 3
Ask which regret you can bear
Compare the regrets directly and identify which one you could genuinely live with.
- 4
Let the worse regret push you
Use the unbearable regret as your run-away-from engine, which loss-aversion makes far more motivating than running toward a want.
Pro tip Frame the stakes as what you'll lose, not what you'll gain — people feel losses about three times more strongly.
In the wild
A salesperson wants to leave a small business to start their own thing. One regret: sitting the owners down, watching them cry, feeling like a piece of shit. The other regret: looking back on a decade wasted in a job they hate. Framed as 'which regret can I live with?', the hard conversation is plainly the bearable one.
→ The decision that felt impossible becomes obvious once compared by regret rather than desire.
Common mistakes
Optimising for the perfect choice
Believing a better decision would eliminate regret keeps you paralysed, because regret is a byproduct of opportunity cost you can't remove.
Framing by desire instead of regret
Asking 'what do I want?' fails to engage loss-aversion, so the decision stays weak and easy to defer.
Is it for you?
Best for
People stuck between two hard options where no path is clearly 'right'.
Not ideal for
Low-stakes reversible choices where regret framing is overkill.
From the transcript
“if regrets are inevitable, if they're going to happen no matter what, an easy way to look at the decision is rather than which do…”
“In life, we must choose our regrets”
From the episode
23 Controversial Truths About Life - Alex Hormozi - #670
Alex Hormozi