I try to never ever ever ever think like that. I believe there are only two feelings that a stock market is capable of producing. You can either go "omg why was I so bearish? Obviously this was going to blow up. All the signs were there. I should have bet the house!" or "How could I have been so bullish? I shouldn't have put one bloody damn cent into that ponzi scheme. I'm such a fool." I don't believe there is such a thing as being satisfied with your choice of investment. The people who are often making life changing money are people with 100x that much money to begin with - I think a societally agreed upon mortal who invests and makes life changing money has succeeded the same way they might have succeeded in a casino.