Regret Aversion

The best decision making tool I know of, and the framework within which I try to make most of my decisions, is the cost-benefit analysis.

The cost-benefit approach breaks down when you don’t have enough information to weigh all of the costs or benefits, or when the future costs or benefits are uncertain.

So my second framework is what I call “regret aversion.” My interest in the notion of regret started when I turned 18 and asked a few dozen adult friends what they regret not doing when they were 18. Interestingly, the #1 regret was not traveling more when they were younger. The regret question elicited an interesting set of responses and I followed up this idea with my post on asking questions in the negative.

Essentially, I have come to believe that many older people are haunted by the question “I wonder what would have happened if…” And that active 40 or 50 somethings regret not trying more things when they were younger. The regret can be as profound as “I regret not going to college” or as simple as “I wonder what would have happened had I mustered the courage to call that CEO I really respected and asked for help.”

While it’s no good being consumed with regret over a past you have no control over, it’s similarly no good to ignore the past and not try to learn from your decisions. Devoting an optimal amount of attention to the past is an elusive task indeed — I’m not convinced that complete detachment from the past is the best way to live. Most of the people I respect are reflective enough to have thought about their past and honest enough to harbor some regrets.

So, I regularly deploy the “regret aversion” rule of thumb: When in doubt, say yes. This will not eliminate regret from my life, nor is it a hard and fast rule (surely there are times when “No” is the right answer). But by doing more things, even relatively random things, if it doesn’t work out, at least I’ll know I tried (no “what if?”), and sometimes it actually does work out.

Let us remember in closing:

We regret the things we don’t do more than the things we do. – Mark Twain

20 Responses to Regret Aversion

  1. Flavio Rump says:

    Great post Ben.
    Have you read link to by Paul Arden?
    Great book centered around this life philosophy.

  2. Dave says:

    I don’t think the regret aversion approach really helps. Here’s why: every thing you say “yes” to necessarily closes off other things to which you must say “no.” You only have a finite amount of attention, time, and energy. Consequently, although the regrets you hear from people may often take the form of “I wish I had said yes to X”, often the reason they did not is that they said “yes” to something else.

    I do agree that *trying* things is a good idea – and that many people regret not trying more things when they were young that they could easily have tried without excluding anything else of interest. I’m talking about *committing* to things – that’s where the deep regrets come from.

  3. Krishna says:

    No regrets would also mean not having gained enough experience. Good judgment comes from experience and often experience comes from bad judgments. Sometimes your real life is the one you do not lead. If you realize that, you have a bundle to regret. Life can only be understood backward, while it has to be lived forward. Jog your memory and you’ll sure find the phrase `if only’ used as often; and if you don’t, then you haven’t tried enough and hence erred much less.

  4. Ben Casnocha says:


    Point taken. The question is whether the reason they did not say “yes” is because they did, in fact, say yes to something else. For some this may be true. For others I suspect there was a more passive approach.

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  5. Ian Graham says:

    Ben, I have also heard regret referred to as “the cancer of life”. Agree with Dave’s comment about living life forward. Taking the two previous points above (from my comment), if you live life forward and use regret as a catalyst to action in the future and lessons learned from the past I think you are on the right path. If you continue to ruminate about all the “what if’s” in your life you will be most unhappy.

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