Most investment writing focuses on optimization—how to get the greatest returns, how to outperform benchmarks and earn so-called alpha. And why not? Who doesn’t want beat the market? Who doesn’t want to win? However, many articulate and persuasive writers have pointed out that investing should focus less on winning and more on not screwing up.1 When such a strategy is followed, your short-term highs may not be as high (as those who take on greater risk), but your aggregate gains over the long-term will be enviable.
I never took a class on economics or personal finance in high school or college.1 I believe this more a reflection on the American educational system than own leaning prejudices, but I also believe that schools should teach children how to swim and teenagers how to drive stick shift. Until my mid-twenties, my formal financial education consisting of learning how to write a check in home economics in middle school; informally, it consisted of my father instilling in me with the idea that so long as one spent less than they made they’d get along just fine in life.