I’m fascinated by the notion of regret. If you want to understand someone, you should understand their regrets. People are more honest and insightful when talking about regret than when sharing life experiences about which they have pride.
On the topic, I often invoke the Mark Twain line “We regret the things we don’t do more than the things we do.” In other words, looking back and wondering “I wonder what would have happened if I had done…” hurts more than looking back at something that didn’t work out and regretting having taken the action.
Vaughan Bell over at Mindhacks has a good post on a recent study of Americans’ regrets. The sources regret are predictable — romance, career, education, family. The interesting part has to do with whether inaction actually leads to more regret than action. Sounds like it depends whether you want short term and acute pain or softer, more lasting pain:
The study also found that regrets about things you haven’t done were equally as common as regrets about things you have, no matter how old the person.
The difference between the two is often a psychological one, because we can frame the same regret either way – as regret about an action: ‘If only I had not dropped out of school’; or as a regret about an inaction: ‘If only I had stayed in school’.
Despite the fact that they are practically equivalent, regrets framed as laments about actions were more common and more intense than regrets about inactions, although inaction regrets tended to be longer lasting.
So the question of whether it is better to regret something you haven’t done than regret something you have, might actually be answerable for some people, but we still don’t know how much choice we have over adopting the different views of regrets or whether this is largely determined by the situation.