I was in my early 30s. My wife was pregnant and I had a good but very involving job.
I read an article in Forbes about successful money managers. One was a guy who happened to be local. He was interested in the detritus of the Penn Central Bankruptcy. I went to see him. Immediately I knew he was no bullshitter, and that he was on to what was likely a very big payday. I took half my savings and had him allocate it to various bankrupt Pennsy bonds. Overall, I think it worked out better than 10:1. This made me think that there was a lot of investment opportunity in really messed up stuff.
Although I continued to work 10 more years, my real vocation had become watching for money lying on the table.
I didn't keep parlaying, but I kept some in cash and continued to look for apparently crappy stuff that I thought might come to be seen differently. Some real estate opportunities came as Seattle started out of its massive early 70s depression.
My returns have slowed a lot, since neither stocks nor bonds nor property seem to be so mis-priced, or at least under priced. I have a very deep desire not to be the bagholder, so momentum or index or other passive investment schemes don't appeal at all to me.
I have made over 100 trades, but 3/4 of my net worth is due to no more than 10 situations that looked very good to me, so I made unbalanced bets.
One of my major goals is to be sure to have plenty capital to keep playing this game, as I enjoy it a lot.
Also, my responsibilities were lessened by my kids taking off early, and getting good jobs and putting themselves through school. I had mixed feelings about this. However, my Mom and Dad had operated an apartment in a university neighborhood, and I got to know a lot of co-op and GI bill and other self financed students. When I later went to college and compared the seriousness of those students with the drunks and wastrels at my "Daddy paid" school, I felt that not only would it be cheaper for me, but my kids would also get a lot more out of college if they were wholly in charge. I also completely missed the usual conflicts with older adolescent and post-adolescent children who are not yet truly independent. My sons could look at whatever I had to say, knowing that they could accept, partially accept, or reject it. Since I had no purse power, it was "FYI" only. There is an Arab proverb which I think applies-"Make your adult son your brother."
Mikey