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Following the Rules

Placing Little Bets and turning them into work you actually like doing

The idea of little bets, also known as doing a bunch of things at once hoping one of them will pay off, is something used by a lot of entrepreneurs and artists to make sure they create their best work, but it can also be used to find projects you actually like doing.

Cal Newport in his book So Good They Can’t Ignore You introduces the concept of “career capital.” He discovered, by talking with hundreds of successful people, that in order to have a company where clients come to you and you both make a bunch of money, the first step is to get a real job to learn the ropes, then specialize in something awesome.

Beard braiding

Like beard braiding

Might as well let Cal explain it:

Don’t obsess over discovering your true calling. Instead, master rare and valuable skills. Once you build up the career capital that these skills generate, invest it wisely. Use it to acquire control over what you do and how you do it, and to identify and act on a life-changing mission. This philosophy is less sexy than the fantasy of dropping everything to go live among the monks in the mountains, but it’s also a philosophy that has been shown time and again to actually work.

At my last startup I would approach the CEO at the beginning of each week with a list of ideas on new directions we could take the company. Some of these ended up paying off, while other ones did nothing.

Check out this video about little bets, and look for the challenge at the end:

I’m slowly learning that if you try 100 different things and fail at 99 of them, it won’t matter because once that one major success happens, people will only focus on that.

Nobody talked about NeXT computer after Steve Jobs turned Apple into a behemoth, and nobody is talking about Thomas Edison’s foray into concrete houses. They focus on the success because that’s the interesting part.

Go out there and try a lot of things. Fail a lot, and you’ll be surprised at what you create. I’m not even close to being done failing, and I’ve already learned guitar, lived on the street, worked in a startup and traveled around the world.

How close are you to doing what you want to do?


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