You’d think that after 25 years of retirement, the hard questions would be behind you. But for Rich - a 79-year-old with a 12% average return over two and a half decades - the most important question is just now coming into focus. Is it time to pull back? This isn’t a story about someone who ran out of money or miscalculated their expenses. It’s a story about someone who did nearly everything right - built his own business, sold it, rode through the 2008 crash, and stayed aggressive enough to beat the market in most years since.