This is only anecdotal, but with a couple of rare exceptions, the only people I knew who made real money on Wall Street were professionals–traders, bond issuers, analysts, and actuaries. Each of them has at least one story where they were down (with their own money) six figures or more. It takes serious stones (or a huge trust fund) to weather those moments. On the plus side, they get paid to follow the investing world, so it isn’t hard for them to spend a bit extra time for their own portfolios–BUT when your job and your investments are that related, watch out for the busts! I know one woman who lost a mint (I think is was $100’s of Millions) of client money in ’89–it was Black Tuesday or something like that. The kicker is, she lost her entire bonus that year, which is most of her income, she lost a huge part of her own portfolio AND almost lost her job…
Almost twenty years later she owns real estate in NYC, Park City, Vancover, and Hawaii–so I guess it pays to stick with it. IF you can afford the Malox!
I stick with boring buy and hold. I probably will never buy my own island, but I should be making as much or more in dividends when I retire as I do now.
In stocks like real estate, it is easy to look smart and make money in a bull market, but it is the professionals, die-hards, and lucky SOB’s that can keep it in a downturn.