Ben Casnocha recently posted about the regrets of the dying, and Robin Hanson replied that in fact people on their deathbed do not spontaneously offer such regrets. Robin is technically correct, but he is taking the claim far too literally.
Indeed, there is broader data to suggest that the regrets of older people are quite different from the regrets of younger people. In particular, as time since a decision grows, people tend to shift their regrets towards not making the hedonistic decision.
An '06 study (link, pdf) shows how the intensity of regrets towards work or enjoyment changes as time passes. For events last week, people express slightly higher levels of regret towards enjoying instead of working (2.2 vs 2.0 out of 6). But for events five years ago, people feel more regret for working instead of enjoying (3.4 vs 1.4 out of 6). This change is even more pronounced for feelings of guilt vs missing out, and there's lots of replicating data (for example, see Ran Kivetz's other papers here).
This is part of what makes using the regret heuristic so complicated. One must not only project future regrets for a decision, weighted by the probability of each outcome, but also consider how those regrets might change in direction and strength over time, and integrate over all probabilistic future time points. If this computation were easy, there wouldn't be so much demand for strategies to get an approximate answer.
