Probabilistic thinking:

Successfully thinking in shades of probability means roughly identifying what matters, coming up with a sense of the odds, doing a check on our assumptions, and then making a decision. We can act with a higher level of certainty in complex, unpredictable situations. We can never know the future with exact precision. Probabilistic thinking is an extremely useful tool to evaluate how the world will most likely look so that we can effectively strategize.

There are two ways to handle such a world: try to predict, or try to prepare. Prediction is tempting. For all of human history, seers and soothsayers have turned a comfortable trade. The problem is that nearly all studies of “expert” predictions in such complex real-world realms as the stock market, geopolitics, and global finance have proven again and again that, for the rare and impactful events in our world, predicting is impossible! It’s more efficient to prepare. What are some ways we can prepare—arm ourselves with antifragility—so we can benefit from the volatility of the world? The first one is what Wall Street traders would call “upside optionality”, that is, seeking out situations that we expect have good odds of offering us opportunities. Take the example of attending a cocktail party where a lot of people you might like to know are in attendance. While nothing is guaranteed to happen—you may not meet those people, and if you do, it may not go well— you give yourself the benefit of serendipity and randomness. The worst thing that can happen is...nothing. One thing you know for sure is that you’ll never meet them sitting at home. By going to the party, you improve your odds of encountering opportunity.

The second thing we can do is to learn how to fail properly. Failing properly has two major components. First, never take a risk that will do you in completely. (Never get taken out of the game completely.) Second, develop the personal resilience to learn from your failures and start again. With these two rules, you can only fail temporarily. No one likes to fail. It hurts. But failure carries with it one huge antifragile gift: learning. Those who are not afraid to fail (properly) have a huge advantage over the rest. What they learn makes them less vulnerable to the volatility of the world. They benefit from it, in true antifragile fashion. Let’s say you’d like to start a successful business, but you have no business experience. Do you attend business school or start a business that might fail? Business school has its benefits, but business itself— the rough, jagged real-world experience of it—teaches through rapid feedback loops of success and failure. In other words, trial and error carries the precious commodity of information. The Antifragile mindset is a unique one. Whenever possible, try to create scenarios where randomness and uncertainty are your friends, not your enemies.