How many years of investing did it take you before you were sure you’d never fall below your principle?

Mid 2025 I invested $3k in my IRA for the first time and shortly after started thinking how much I’d need to gain to still be ahead after a 30%ish pull back but Ik never to time the market so stayed the course.

Ended up being lucky timing and have not even for 1 day dipped below principle but kept adding and maxed out around November and got $500 in this year. Due to later contributions I’m only up about 10% so the next bear market would still easily take me below principle.

Not like it really matters in the long run but feels like a milestone to me. A good 5ish years would do it for 1 lump sum investment but with new contributions it would be a lot longer. How long did it take you to get to the point where you were confident even a bad bear market would still leave you in the green overall?