I’ve spent a lot of my life losing at things. In fact, I’ve lost at so many things that I’ve gotten really good at it. I’d say I am a proficient loser. Which, in a weird way has really helped me improve my winning percentage over time. It seems strange, but by getting really good at losing you can improve the way in which you win.

The reason why being a good loser makes you a better winner is counter-intuitive, but simple. Michael Maubboussin has described this concept as expected value:

“Expected value, in turn, is the weighted-average value for a distribution of possible outcomes. You calculate it by multiplying the payoff (i.e., stock price ) for a given outcome by the probability that the outcome materializes.”

For instance, a good gambler understands expected value. They know they’re involved in a negative sum game in the long-term, but by losing small and winning big they can improve the odds of having a positive outcome. Great gamblers are great losers. Investing is very similar (though different). We spend a lot of time losing as investors. But since the financial markets are a positive sum game over the long-term we can expect that our expected value will be positive over the appropriate time horizons. Dealing with how you lose in the short-term will very often determine whether you win.

Learning to lose well is arguably the most crucial element to good portfolio management. In fact, one could probably argue that learning to be a good loser is the most crucial element of living a good life. But I’ll spare you my philosophical ranting. You can get that from Donald Trump’s Twitter feed.

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