Erik Michielsen: How do you take collections of ideas and turn them into books?

Jon Kolko: The process is pretty simple. There's probably like a theoretical answer as well as a practical answer. The practical is a little easier but my process is typically to just write; to write with no directive, no outline, no goal in mind over a process of about nine months to a year, and I write when I'm at conferences, and I write when I'm in class, and I write when I'm on an airplane. The pro tip here is the more time you spend on an airplane, the more time you have to write. And so, there is sort of a weird relationship with being in extreme physical agony on an airplane, on an aircraft and being massively productive but whatever. And then at some point, the thoughts of all of these different conferences and conversations and writing start to congeal into a theme, and usually sort of in backwards looking. It's sort of like a retrospective. It makes sense, like of course it led to this book theme. But there's never any of that sort of central plan. I've set out to write a book about a certain topic like four or five times and I've never written that book. And so it's much more of an organic process. And then once that clicks and you're like, “Okay, cool. The next book is called Wicked Problems.” Then I deal with standard editing process and outline, here's the different points I want to hit and then revise it and tear it down and write it again, kind stuff. But before that point, it really is all over the place. I'm not even sure that I'm cognizant that I'm doing it when I'm doing it. And so, like on my laptop, I have all my nice little folders and stuff, then on my desktop I’ll have little notepad snippets of just random stuff, you know 500 words, 1,000 words. At some point it all starts to make sense. The tools for this suck. There's got to be a better way to structure that in a way that can start to draw the parallels between disparate ideas more closely. But anyway, that’s the practical way of how you set out and write a book. How I set out and write a book.

The theoretical way, there are points in the process where you're like, “I don’t know if I should write this book. I don’t know if I have this book inside of me.” I've had that over and over and over and it's right around 35,000 words usually, which is kind of weird. A book is 45 to 90,000 words depending on how big it is but right around 35,000 something kick in and you’re like… it's that same old voice, right? It's like you don’t what you're talking about or you're not good enough, or this book will never work, nobody wants to read this. You could squelch that voice, right? You can shut it up. It's weird how consistently that voice shows up and it ran right around at the same point in the process.