That is a very nice story. This is how perhaps most people's life should be.
Only bet on things you can afford to lose and can do it for fun. That is the main learning I have taken from your story. I can't say I followed that with my life but majority of my academic research on geosciences is trying to understand the tail end of a log normal distribution, something that people call a black swan event. Later on when I got employed I was paid to take a bet. Thankfully it's other people's money so it's great. There is little emotion attached to what I do financially and that became a good thing for me.
You must be very bright for people to give you such responsibility, for people to believe that you can prepare for (or perhaps predict) such events.
Those of us who have the chance to grow older, have the opportunity to learn from our past. At least you learned. That's what age is for, isn't it?🍁