Whenever I have had a major life decision to make, it has always struck me as of central – indeed, definitive – importance to think about whether I would regret my decision, if things turned out in one way rather than another. But I find this a bit puzzling. I’m going to try out one way of saying why.
We can think of my current expectation for what I will regret in the future as a weighted average of what I will regret in different states of the world, weighted by my confidence that those states of the world will result from my decision. And we can break down the regrets that I will experience in each state of the world into rational regrets and irrational regrets.
Irrational regrets may matter for what decision I should make – after all, regretting something is one way of feeling bad, and how I feel after making a choice is one among many things that may be relevant for which choice I should make. But it is hard for me to get my head around the idea that this makes good on the centrality that I feel that considerations about regret ought to have for me, when I am making a major life choice such as where to go to graduate school, which job to take, or who to join with as a life partner. So let’s screen them out.
The expectation for my rational regret we can then regard as a weighted average of what I will rationally regret in different states of the world.
But it is plausible that it is rational to regret something if and only if you believe that you ought not to have done it. So this is an expectation about what I will, in the future when I am better informed, believe about what I ought to have done at this time.
Now of course I can see why this would correlate with my expectation about what I ought to do. But I’m not sure how it would help me to decide what I ought to do. If my expectation of what I will rationally regret in different worldstates depends on what I will rationally believe that I should have done, in those worldstates, then how does it help me to decide what I ought to do, rather than just being a reflection of what I think I ought to do?