The risk you took and lost stings for a season. The one you didn’t take follows you around for years.

Losing something has an end to it. The pain is specific, and then it recedes, because your mind is good at processing things that really happened. The attempt you never made never resolves, since there is no result to absorb, so it stays available to be wondered about for years, usually at odd hours.

When you are weighing something, compare the two kinds of regret rather than the two outcomes. Ask which version you would still be turning over at thirty. That question tends to answer much faster than the pros and cons did.