I am still too young and the things are just starting for me, but if I could go back in time, I will probably go when I broke my collarbone which made me sit out of sports for two years. It took ages to heal and more for me to know how to move my arm again.
When I got a divorce, my mother in law said to me "In your life you will make one mistake. A terrible mistake that will change the course of your life forever, everyone does. You will not be able to undo it. You will only suffer for it. I hope that this [getting a dvorce] isn't it."
Getting a divorce was not it. Going to law school was. I was a lawyer for 35 years, unwilling to give it up after all that work, unwilling to throw in the towel and admit I made a terrible mistake. 35 years of daily regret. Now I sit with my ex-colleagues as they cry about their own mistake and their own fear of getting out of the only way of making a decent living that they know. I encourage them to take a risk and blow it all on a roll of the dice, like I did. Get out. Do something else. They're too afraid. I know. I was too afraid for all those years. I justify it by remembering all those I was able to help. Sometime without payment at all. Sometimes with very little, thinking if I don't, who will? Too bad I did that, blinded by my own sense of self-righteousness and hubris. I ended up despising them all for their own foolishness and ignorance. 35 years is a lifetime, it's a lot of wasted time. There is a reason why pride is one of the seven deadly sins.
I would have stopped taking crap from people much earlier on in life because I got picked on so much in elementary/ middle school and it wasnt until 6th grade that I stood up for myself and I would have done it much much sooner
I would go back to the point when the lottery jackpot was the highest before anyone won it and play those numbers and retire early. That or go back and buy like 10,000 shares of Google stock back in the day when they were like 70cents each. Now they are well over 70 dollars each.