You can spend so much effort avoiding regret that caution itself becomes the regret.

Choosing safely every time to avoid future regret produces a specific and heavy regret of its own: the accumulation of things not attempted, which arrives late and cannot be acted on. Caution feels costless because its price is invisible until much later, and by then the alternatives have expired.

When you are weighing a risk, ask what the cautious version will look like from twenty years out. Some risks are genuinely unwise. But if your answer to everything has been no for a long time, the pattern is worth examining, because it is producing its own bill.