One of the most interesting pieces of advice on writing books comes from author Ryan Holiday, who advocates not writing a book. Unless…  “What matters more now than any other single thing is that what you’re saying is different–that it’s interesting, that it provokes some response from people. You’ll only accomplish this if you’ve got something you have to say. Better yet, you need to have something that you can’t NOT say.  If what you’re writing is a compulsion rather than a vehicle for your display how smart and well practiced you are.”

That’s a lot of pressure, but it’s also a good litmus test; if you don’t believe the thing you’re actually writing about is worth talking about to people and promoting, then it’s best not to write a book about it. Save your sweat for something more rewarding. 

Holiday’s definition is very practical and marketing-savvy, but there’s another perspective to having something you can’t not say; that you need to say something, and need to express yourself no matter what. If that’s the case, you’re going to read the rest of this post, shrug, and write a book anyway. Even if everyone else thinks it’s a bad idea. Even if agents and publishers won’t talk to you. Even if your heroes say they don’t think it’s a good idea to you. Perseverance is a positive signal in success, but only if you have other small bits of evidence that this could work. If everyone thinks it’s not a good idea, don’t be surprised it doesn’t work out, and don’t bet the farm on it.

I believe it was in one of Holiday’s books that he points out Mario Puzo’s motive to write The Godfather, which was to get himself out of debt. Puzo bet the farm and it worked. I wouldn’t have the stomach for it. 

Instead, I saved a bunch of money and gave myself four months to write a book. I just picked my most popular article and ran in that direction. The book emerged, I independently published it, I made a bit of money, I then signed a deal with Holloway to expand and revise it, then I got a full-time job. It’s going to come out in a month. 

I would’ve made more money working half a week at my job than I would have writing the book. But yes, it was totally worth it. I plan on writing many more.