I’ve been a big sports fan since childhood, and I watched many times on TV during high school and college as John Wooden coached UCLA to college basketball glory. He is one of the most successful coaches in any sport, of all time. And at age 98, he has done quite well writing books, and in public speaking. Michel Hiltzik’s column, John Wooden’s still Coach, even in the investment game, in the Los Angeles Times is a highly interesting interview with Wooden about his investing principles. Hiltzik points out that Wooden coached in an era (the 1940s through the mid-1970s) when coaches weren’t paid particularly well. A big takeaway from this column, besides Wooden’s thoughts on investing, is how he dealt with uncertainty in life after retiring from UCLA at 65. Besides seeking prudent professional advice for getting his finances and estate in order, he transitioned into what became a lucrative career writing and speaking about not only his coaching principles, but more importantly, his principles for leadership and living a successful, meaningful life. In 1975, it was much less prevalent for people to reinvent themselves after retirement. Wooden is still going strong, 34 years later. And he didn’t dwell on how he possibly could have had more money when he retired from coaching (partly because of a decision revealed in the lead of the column). “But if you always think things will be better with more money,” he tells Hiltzik, “your life’s not going to be that good.” Regarding the concept of initiative, one of the 15 building blocks of his “Pyramid of Success,” Wooden gives a great quote that can be applied well beyond the world of investing: “Don’t be afraid to fail. We’re all imperfect. We’re going to fail at times. If you’re worried about temporary reversals, you’ll be afraid to make a decision.”