Right now, I'm looking at something in my life like you did. But, I also think there was no predicting the future had I taken the other route, in your case, holding onto the shares. Either one of us could have died, lost loved ones, a child, had a terrible accident....or, those shares may not have accumulated as they had. We do not know. With the information I had at the time, I tried to think of each decision as right for that moment. I will never truly know what would have happened had I made a different decision. It may not have turned out as rosy as I imagined. That 2 million could have meant not having that first house and all that investment brought to you. Maybe never having a partner and children, etc. Eventually, I realize the good, get over it, move on, and make more decisions as best I can. You turned out great, from the sounds of it!