Good judgment improves when you stop making decisions solely to avoid regret.

Regret avoidance looks like prudence and behaves like fear. Decisions made to protect your future self from feeling bad tend toward whatever is most defensible rather than whatever is best, because the defensible option produces less self-blame if it fails. Over time this steers a life toward the conventional and the safe, not because you chose those things but because you were choosing against a feeling.

When you are weighing something, notice if your reasoning is mostly about how you would feel if it went wrong. Ask instead which option you actually want and what it would cost. You will still get some things wrong, but they will be your own mistakes rather than a series of defensive maneuvers.