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.