Coaching practices for I Just Made a Hard Call Under Real Uncertainty and I Keep Wondering Whether Someone with Genuinely Good Judgment Would Have Handled it Differently There's a Person I Imagine Who'd Have Seen What I Missed and I Want to Close the Gap Between How I Decided and How They Would Have
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Does this sound like the set of challenges you might be facing?
- I made a call that turned out badly and now I feel like an idiot for it
- I just made a hard call under real uncertainty and I keep wondering whether someone with genuinely good judgment would have handled it differently
- A choice I made blew up and I’m tearing into myself
- Now that I know how it ended, the whole thing feels like it was always going to land exactly here
- There’s a big, hard-to-undo choice in front of me
Practices that may help
- Judge decisions by the process, not the result
A good decision that produces a bad outcome is still a good decision.
Expected Value Thinking: Deciding Under Uncertainty - Developing phronesis: practical wisdom through reflection
After a significant decision, reflect on what a practically wise person would have done — and update your judgment for next time.
Aristotelian Eudaimonia: Flourishing Through Virtue - Evaluate decisions by process, not outcome
Judge a decision by the quality of the reasoning at the time, not by what happened.
Hindsight Bias: Why Everything Seems Obvious in Retrospect - Generate the counterfactual outcome
Deliberately imagine how the same decision could have gone differently with the same process.
Hindsight Bias: Why Everything Seems Obvious in Retrospect - Stay inside for high-stakes, irreversible decisions
Reserve your autonomous judgment for decisions within your circle; get help for the rest.
Circle of Competence - Log probability estimates before the outcome
Write down your confidence level and reasoning before you know how things turn out.
Hindsight Bias: Why Everything Seems Obvious in Retrospect - Score decision quality separately from outcome quality
Judge the process you used — not whether it worked — when you review a past decision.
Decision Journaling: Learning to Decide Better Over Time - Separate the quality of the decision from the outcome
A good decision can produce a bad outcome, and a bad decision can produce a good outcome — do not confuse them.
Thinking in Bets - Ask 'What am I missing?' before major decisions
Treat a confident feeling before a high-stakes decision as a cue to check what your competence map is omitting.
Circle of Competence - Move fast on two-way doors
On reversible decisions, decide with 70% of the information you wish you had — then adjust.
The Two-Way Door
Related concerns
- When Expected Value Thinking Separate Good Decisions From Good Outcomes
A good decision that produces a bad outcome is still a good decision.
Judge decisions by the process, not the result
- Decision Quality Vs Outcome
A good decision can produce a bad outcome, and a bad decision can produce a good outcome — do not confuse them.
Separate the quality of the decision from the outcome
- Good Decision Bad Outcome
A good decision that produces a bad outcome is still a good decision.
- How To Develop Good Judgment
After a consequential decision, reconstruct what you perceived, what you valued, and what you’d change.
Build wisdom through case-based reflection
- How To Evaluate Decisions Fairly
Judge the process you used — not whether it worked — when you review a past decision.
Score decision quality separately from outcome quality
- How To Judge Decisions Correctly
Judge the process you used — not whether it worked — when you review a past decision.
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