The version where you tried and failed makes a far better story than the version where you never tried.

Attempting and failing leaves you with something. Not attempting leaves you with a question that has no expiry date, and questions like that get heavier rather than lighter. Regret over effort fades because you learned things along the way, while regret over avoidance contains nothing that softens with time.

When you are weighing something, compare the two regrets rather than the two outcomes. Ask which one you would rather be carrying in ten years. That framing tends to make the decision obvious, and it is a more honest question than whether you will succeed.