I will feel regret for the rest of my lives if I encountered even one of these 2 scenarios.

Luckily, I'm not encountering that financial regrets, and until now, I didn't encounter any financial regrets any. The first one isn't applicable for me because I started investing when I'm at my early 20's (just after I graduated from College), and I consider it still as early because when I'm still studying, I didn't even know that a thing called cryptocurrency exists, and I only knew it after I graduated.

The second one isn't applicable for me either because right now, I consider investing more than 75% of my investments in cryptocurrency as a risk already. Maybe the "tried more things" is where I feel a bit of regret, but I'm trying to learn some things that will help me earn more money thus, more money to risk for and invest. I'm at my mid 20's right now and I think I can still take risks because I consider myself young when it comes to investing compare to some others out there.

Playing it safe when you're young still isn't a good strategy. You got so many time to take risks and if you lose your money in your investments, you still have lots and lots of time to recover that money again. If you're still young, take risks and don't regret doing it. As for me, still I don't have every financial regret that I've ever made. Maybe I'm lucky.