A small risk taken often beats a giant risk taken once. Build your nerve in reps.

One enormous risk puts everything on a single day, and whatever happens you learn very little from it, because you only get one result. Small risks repeated give you dozens of results and a body that has stopped treating a racing heart as an emergency. Nerve gets built the way strength does: often, in doses you recover from. A single heroic attempt is a bet; a habit is training.

Pick a weekly version rather than a someday version. One ask, one attempt, one unfamiliar room a week. Keep it small enough that you will genuinely do it again next week.