Choose Your Regrets
Decide by comparing the regrets each path could create
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 5
- Confidence
- 99%
The model begins with the claim that regret is not proof of a bad decision; it is an unavoidable consequence of opportunity cost. Choosing one path means losing the experience of another, so even a sound choice can leave an open loop. Instead of trying to eliminate regret, list the available paths and imagine the regret associated with each one. Ask which regret you could live with and which missed possibility would remain unbearable. This reframes a decision from predicting an unknowable outcome to choosing an acceptable cost. Chris uses his move to America as an example: failure and returning home would have been bearable, while never testing whether he could pursue the podcast there would not.
Origin
Chris says Douglas Murray relayed Christopher Hitchens's line, 'In life we must choose our regrets,' then develops it into a decision model on The Diary of a CEO.
Core principles
- 01Opportunity cost makes some regret inevitable
- 02A good decision can still leave an open loop
- 03The bearable regret is a useful decision criterion
- 04Trying can close uncertainty even when it fails
How to run it
- 1
List the real paths
Write the choices that are genuinely available, including deliberate inaction. Remove options that are fantasies rather than executable paths.
Watch out Not choosing is still a choice with consequences.
- 2
Expose the opportunity cost
For each path, state what you cannot do, keep, or experience because you chose it. Accept that no option preserves everything.
- 3
Forecast both regrets
Imagine the chosen path failing and imagine never taking it. Describe the regret in each scenario without assuming a favorable outcome.
Pro tip Use a future date to make each scenario concrete.
Watch out Do not use hindsight from an already-known outcome to judge an earlier decision.
- 4
Choose the bearable regret
Select the path whose downside you could accept and whose abandoned alternative would not haunt you more. Make the trade-off explicit.
Pro tip Ask which possibility you could not bear never testing.
- 5
Judge the choice fairly
After acting, distinguish the quality of the decision from the result. A failed experiment can still close an important open loop.
Watch out Post-hoc rationalization can make any outcome look inevitable.
In the wild
Chris says he could have lived with selling his UK events business, trying to build his podcast in America, failing, and returning home. He could not have lived with never testing whether he had the conviction to pursue that opportunity.
→ The comparison made taking the risk easier even though success was not guaranteed.
At about 22, Chris chose a season in Ibiza over staying home to earn and save because he believed the opportunity might not return before further study and full-time business commitments.
→ He closed the open loop and retained fond memories of the choice.
Common mistakes
Trying to eliminate regret
Every meaningful choice excludes alternatives, so the demand for a regret-free option can prevent a decision.
Confusing outcome with process
A lucky result does not prove a choice was sound, and an unsuccessful attempt does not automatically make it wrong.
Is it for you?
Best for
It is best for major life or career forks where inaction also has a lasting cost.
Not ideal for
It is not ideal as the sole test for routine, reversible, or data-rich business decisions.
From the transcript
“In life we must choose our regrets.”
“Regrets aren't a bug, they're a feature.”
“Which regret could I live with?”
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