Nassim Taleb is most famous for his books on radical uncertainty and randomness, but he made his money in the options market. For the unfamiliar with options, the short version is that you only make money on a put option when a stock goes down to a certain price, and you only make money on a call option when a stock goes up to a certain price. The options themselves are priced based on the probability that the market has assigned the event of getting up or down to those particular prices.
Taleb employed a “barbell strategy”—that is, two risk extremes with no medium level. He put a big majority of his money in the safest assets he could find, such as treasury bills or cash. The rest he put into what are called way out of the money options—put options that are massively below the current market price of the stock, or call options that are massively above, and are priced as being extremely improbable events. The strategy is to make sure you could lose all of your money each time without getting wiped out, because you only need to be right once. And indeed, in the 1987 crash Taleb made tens of millions of dollars, and in the 2008 crash he did it again.
There is a similar strategy available to those who would devote themselves to a craft. The heart of Taleb’s philosophy is that you should minimize the downside risk to yourself, while maximizing the potential upside. When it comes to a craft, the best way to accomplish this is to prepare yourself for the possibility that all you will get out of it is the enjoyment of doing something well. Meanwhile, you should be putting your work out on the public web in order to make it possible for it to get a lot of attention—but again, only if you can emotionally prepare yourself for the fact that it probably won’t.
The first part should not be hard. As Richard Sennett eloquently describes, craft work has long been about devotion to doing good work for it’s own sake. There is a big cognitive payoff from putting in a lot of upfront effort to hone a set of skills over a period of years, and finally arriving at a point of tangible progress. The feeling of flow, in which one has the sensation of working right at the peak of what they’re capable of, is a sensation that craft workers are able to earn by taking on increasingly ambitious projects and developing their skills to a point where they can see those projects through.
The problem comes in when people think that doing good work by itself is something that translates into business success. That is not the case. If you’re a writer, for instance, you may be able to find work writing, but it’s unlikely to pay well and it’s probably not going to be doing the kind of writing that you’re interested in. Moreover, if you think simply putting yourself out there on a blog or elsewhere is going to allow you to do what you love and get an audience, you’ve probably got another thing coming. The vast majority of people who try to get into writing, fail. An enormous supermajority of people who post online end up getting, on average, maybe a few dozen pageviews. Writing is a power law industry, where a tiny minority dominates the entire business landscape.
Those at the top all started at the bottom at some point, of course. But the odds of making it to the very top are vanishingly small; if we could assign it an option value it would be as far out of the money as it gets.
The point is, if you start blogging thinking that you’re well on your way to achieving Malcolm Gladwell’s career, you are setting yourself for disappointment. It will suck the enjoyment out of writing. Every completed post will be saddled with a lot of time staring at traffic stats that refuse to go up. It’s depressing.
Instead, the perfect balance is committing to only those crafts that you can perform with satisfaction even if you have to do so in utter obscurity. Then, put your work out in public as part of the process itself—if you’re making homebrew beer or an Arduino hack, make a video or write about the process as a means to think harder about the details of it. If you’re a writer, think of putting it online as simply having the work backed up in one more place.
In this way, you open yourself up to the spectrum of possibilities, ranging from utter obscurity at one end to global fame at the other. Far more likely is something closer to the obscurity end but much more satisfying—that you will draw the attention of a relative few who share your interests.
In my mind, this is the best way to take advantage of modernity while minimizing its costs. We are an affluent enough society that we’re able to make enough money as individuals to have time to devote to doing something we love for its own sake. We are also an interconnected society where some artisans are able to rise to sudden prominence and make a living doing what they love. A satisfying life will focus on the former while keeping the door open to the latter possibility.