(How to make big, tough decisions that you’ll never regret.)
I have, thus far in my life, made quite a few decisions for which —at the time and, then, in retrospect, even more so— the extensive counter-arguments were many and the sometimes-irreversible consequences were clear.
I quit high-school. I didn’t move to the US in my twenties. I got married. I accepted jobs I maybe shouldn’t have. I got divorced. I moved to the US in my thirties. I rejected jobs I maybe shouldn’t have.
Some of those decisions were the right call, some weren’t, some I’m still not sure about, and some I’ll never be sure about. But I regret none of them.
Whenever I’m faced with a big decision, I think about it. A lot. In fact, I think as hard as I’m able to, for as long as is feasible.
In exchange for consciously and deliberately forcing myself to agonize over the (big) decisions I make, I get to never regret those decisions. Because I know for sure that I did my best. Because I know for sure that, at that time, given those circumstances, knowing what I knew, I made the best decision I could’ve made.
PS:
(1) This only works properly if one keeps in mind three things: (a) not all decisions are “big” decisions; (b) “not regretting past decisions” isn’t in any way the same thing as “not learning from past mistakes”; (c) for most issues, most of the time, “I’m not going to make this decision right now” is a valid decision — we too often force ourselves to make definite, definitive decisions at times when we don’t, in fact, have to do so.
(2) I somehow stumbled across this idea when I was 15 or 16. Following it ever since has —I’m pretty sure— saved me from nearly-insurmountable amounts of regret.
Gabriel Coarna 