In the chess endgame, the king stops hiding and starts fighting. Know when the phase of the game has changed.

A king that spent the whole game hiding becomes one of the strongest pieces once most of the board has cleared, and players lose endgames by continuing to play carefully long after careful stopped being correct. The rules did not change. The situation did, and the habits built for the earlier situation quietly became the wrong ones.

Ask whether the thing you are being cautious about still needs caution: a friendship that is steadier than it was, a subject you are now good at, a job you have outgrown. If the phase has changed, change with it rather than waiting for permission.