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Choiceology · September 22, 2025 · 31m
The Road Not Taken: The Psychology of Regret
Explores the psychology of regret — why we regret inactions more than actions in the long run, how counterfactual thinking creates suffering, and how to use anticipated regret as a decision-making tool.
Canon
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Milkman: Jeff Bezos's 'regret minimization framework' is backed by psychological research. Imagining your future self looking back forces a long-term perspective that counteracts present bias and risk aversion, consistently nudging people toward bolder, more authentic choices.
Highlights
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Long-term regret is dominated by inaction — what we didn't do haunts us more than what we did
Milkman: research shows that in the short term, people regret actions more than inactions. But in the long term, the pattern reverses — our deepest regrets are about things we didn't do: risks not taken, feelings not expressed, adventures not pursued.