The business of creative work is the business of riding randomness. If you want to write a bestselling book or launch a revolutionary company, you’re going to need luck. You’re navigating Extremistan, not Mediocristan, as I talked about in episode 253. How do you increase your chances of having a hit without risking everything? You do it with “The Barbell Strategy.” You can use the Barbell Strategy in many areas of life and work. The Barbell Strategy defined The Barbell Strategy is introduced in Nassim Taleb’s The Black Swan, which I summarized on episode 244. The Barbell Strategy protects you from catastrophic losses that can take you out of the game. Meanwhile, it gives you chances to make big gains. Why “barbell”? Think of a barbell – a very lopsided barbell. On one side of the barbell is a big weight. On the other side of the barbell is a small weight. In the middle is the thin bar that connects the two. The Barbell Strategy is an investment strategy Taleb introduces The Barbell Strategy in an investing context. This is the strategy Taleb has used as a financial trader. As we’ll see, you can apply it to other areas as well. Taleb says: If you know that you are vulnerable to prediction errors, and if you accept that most “risk measures” are flawed, because of the Black Swan, then your strategy is to be as hyperconservative and hyperaggressive as you can be instead of being mildly aggressive or conservative. (emphasis mine) In other words, you have to accept that the world is full of Black Swans. As a review, Black Swans are outlier events with extreme impact. We think we can explain Black Swans after the fact, but we really have no idea. They can be positive, or negative. Things like financial market crashes or mega-best-selling books. By being hyperconservative, you avoid the negative Black Swans. By being hyperagressive, you expose yourself to positive Black Swans. 85% hyperconservative investments, 15% hyperaggressive investments Most people go with the “safe” investment. I’m not a financial advisor, and nothing I’m saying is investment advice, but for most people, that’s the index fund: Keep putting money in an S&P 500 ETF. Expect to get a 7% return over your lifetime. The strategy Taleb espouses is to avoid so-called “medium risk” investments. Instead, put 85% of your portfolio in hyperconservative investments – places where you won’t lose money. Invest the other 15% of your portfolio in hyperaggressive investments – places where you might lose your money, but where there’s also no limit to how much money you could make. When you’re invested in the index fund, your entire portfolio is exposed to Black Swans. The stock market dropped nearly 90% during the Great Depression, and swift drops of 30 or 40% are not uncommon. If 85% of your portfolio is spread across hyperconservative investments, you’re unlikely to need to weather such storms. With 15% of your portfolio in hyperaggressive investments, you can only lose 15% of your money. Meanwhile, there’s no limit to how high those hyperaggressive investments can go. Imagine you put 1% of your net worth in Bitcoin five years ago. Multiply that by 100, and that’s your current return. Even if you lost all the other 14% of your net worth in hyperaggressive investments, you would have nearly doubled your money, with little downside risk. The Barbell Strategy in creative work As you learned in episode 253 about Mediocristan vs. Extremistan, creative success is unpredictable. As award-winning screenwriter William Goldman said, “Nobody knows anything.” Most creatives expect their success to go “up and to the right.” When someone suggests they take some chances, to justify not taking those chances they abuse survivorship bias – as I talked about on episode 251. So they stick to “the middle.” They do the thing they feel will get them a little success. For authors, this is the strategy of cranking out a formulaic novel every month that’s sure to sell some copies – but for which nob