One useful tool I use when I want to make a hard decision easy: I picture myself at 80 years old and ask, will I regret not doing this? If the answer is yes, I have to try it. If the answer is no, I can let it go and move on without losing sleep over it.
I learned about this reading The Everything Store by Brad Stone. The idea is called the Regret Minimization Framework. When Jeff Bezos was deciding whether to leave his job and start Amazon, he used this exact exercise. He imagined himself at 80 and realized he would regret not trying, even if it failed. The potential regret of not trying was worse than the potential regret of trying and failing.
I think this works because it cuts through the noise. When you’re in the middle of a decision, there are a million factors pulling you in different directions. Fear, comfort, what other people think, the risk of looking dumb. But when you fast-forward to 80, most of that noise disappears. What’s left is what actually matters to you.
I’ve used this for career decisions, for hard conversations I was avoiding, and for things that scared me. It doesn’t make the decision painless, but it makes it clear.
The trick is being honest with yourself. It’s easy to convince yourself that you won’t regret something just because the alternative is uncomfortable right now. But if you sit with it, really sit with it, the answer usually shows up.
-JV