If it was up to me, I’d always write at night, but that ends up wreaking havoc on my sleep schedule because business calls and a personal life aren’t as flexible. For the book, I wrote in the morning and while that doesn’t feel natural to me at all, as long as you take the time to make it a habit, it can work. The truth is, while book pages got done in the morning, the real guts of writing happen for me everywhere and anywhere. I’m thinking of ideas and taking notes on my phone whether I’m at the gym or out getting coffee. Some of what I jot down will later turn out to be critical, other bits will make me wonder, “What the hell was I thinking?”
Location isn’t very important to me. I usually work on the couch in my living room. But I can work at my desk or even in bed. Doesn’t matter. But I need to be alone and undisturbed. If people are running around and the phone is ringing, I can’t think straight and nothing of any substance gets accomplished. The idea of writing in an open plan office gives me nightmares.
I usually use Microsoft Word but any word-processing tool will work. I need to be able to easily move things around on the screen to properly structure the beats and get the piece flowing right. The days of typewriters would have been hell for me. If I type notes into my phone I can later easily cut and paste them into a doc.
When I’m brainstorming or playing with ideas, music is good. I’ll often go for a walk and the music helps me feel creative. When I’m actually writing sentences that people will read, I need silence. I really need to concentrate. I’d love to be one of those people who is so focused that they can write while in the middle of Mardi Gras, but I’m just not.
I usually start off by indulging in email and social media, and then I trick myself into starting. Yeah, I have to trick myself. I just start thinking about the material and focus in on something that makes me curious. Maybe it’s an unexplored part of the subject matter, maybe I’m wondering if what I was writing yesterday was clear enough, or if there was a way to make that one joke funny enough. Once I’m curious about something I’ll feel an OCD-style need to address it, and once that takes hold of me, there’s enough momentum to really get to work for a few hours.
I’m big on outlining and structuring. So I really can’t judge by words or pages. I don’t have anything readable until very late in the game. I wouldn’t necessarily recommend this to most people because many would just use it as an excuse to spin their wheels forever. That said, it makes my “first drafts” extremely tight because so much of the work has been front loaded. My first drafts aren’t really first drafts because I’ve spent so much time planning.
Writers are usually encouraged to write a “vomit draft” and just get something out, however terrible it is, in order to overcome The Fear, get some momentum, and move to more of an editing mindset, where’s it’s less scary to make progress. I don’t do that. I think that’s just a trick to try and lower the stakes so you can overcome procrastination and The Fear. And while it’s good for that, I think it’s bad in the long haul because you’re producing a lot of junk and that’s going to be hard to fully clean up.
I treat writing a lot more like architecture. You wouldn’t work without a blueprint, construct a crappy building, then knock it down and build a better one. That would be ridiculous. You’d put together a really tight blueprint, then construct the building once, the right way, and if it needs tweaks, they’re relatively small. As the old saying goes: “Measure twice, cut once.”
First I need to figure out what the heck it is I’m writing about and what angle I’m going to take. I want it to be something people can use and an issue they’re really dealing with. And I want to make sure I can contribute something new, counterintuitive or something that offers a fresh perspective. At first I’m focused on the ideas and the structure. I’ll collect my notes, form a structure and then start filling in the gaps. And I try to make sure everything is validated. We all read a lot of stuff that’s just some random theory the writer came up with over lunch. We don’t need more of that, so I want as much as possible to be backed by research or expert insight. If anything, I overdo it on this. You take a hit on readability but the tradeoff is legitimacy. I like to have a lot more content than I could possibly use when I’m heading into a post. It’s far better to have it and not need it than need it and not have it. Then I’m focused on making sure that the piece flows and draws the reader down the page. Then I’m thinking about relatability, a conversational tone, humor, taking the reader on an emotional journey, reversing expectations, simple and accessible language, etc.
Because I spend so much time in the outline stage, my first drafts are usually pretty tight and then I’ll just focus on what I can cut to make the read smoother. With blog posts, some people will complain about length but I rarely think that’s the real issue. Many people happily read longer stuff all the time—if they’re engaged. And if they’re not engaged they complain it was too long. Yeah, some people never read anything very long but, plain and simple, that’s not my audience. If you don’t draw hard lines like that you’ll end up serving random critics and not the people who really love your stuff.
Occasionally the transition from outline to actual blog post is rocky, and the final result doesn’t click like it should. It’s really just a matter of getting back in there and moving things around until you find the real through line and get a firm structure. The danger is that having to rework it at that level late in the game can be a blow to your confidence or enthusiasm about the piece. It’s best to keep your head down and not overthink it unless you discover there are deeper problems with what you’re writing, like you’re struggling to make something that’s tired into something fresh.
Finally, I’m rereading it over and over to make sure it both informs and entertains, that it’s conversational and that it flows. Finally, my friend Jason will proofread it because by that point I’m totally snow-blind and unable to see my own errors.
Reading good writing is essential. I find myself most drawn to writers with a distinctive voice because voice is one of the trickiest things. Some people have it immediately, others struggle with it forever, and for others it’s an ongoing evolution. Off the top of my head, big influences have been P.J. O’Rourke, Charles Bukowski and Chuck Klosterman.
It comes to me naturally but—good god—it’s not easy. If it’s easy, that’s a red flag. Sure, some ideas, sentences and sections may come out fully formed but if you’re not struggling, it’s not going to be all it could be. I don’t see writing as something smooth, elegant and effortless like a perfect golf swing. It’s a cognitively demanding exercise. Making writing simple and smooth is the hardest thing of all, yet often gets the least credit. Easy on the reader is hard on the writer, especially when you’re working with complex topics or potentially dull research.
I started writing stories in high school. I went on to produce sub-mediocre poems for my girlfriend sophomore year in college. (She still has them and makes a lot of blackmail jokes…I mean, I think they’re jokes.) But it wasn’t until I did a few internships in Hollywood after my junior year in college that it actually clicked in my head: Hey, people actually make a living as writers. By my senior year I finished my first screenplay. The second one I wrote got me an agent, sold, and was produced.
Stephen King’s book On Writing is excellent. William Zinsser’s On Writing Well is a classic. David Mamet’s little book about directing turns out to be one of the best books on writing. James B. Stewart has a solid book on writing nonfiction.
Overall, the toughest part of writing the book was learning how the hell to write a book. I’ve written movies, animation and blog posts but every medium is different and if you don’t respect that you’re in for a pummeling. It’s like an athlete changing sports. Some skills will carry over, others won’t, and you’re going to have to train some things you didn’t know before.
Screenwriting is excellent at teaching you structure, dialogue, how to be economical with your words, and how to move a reader emotionally. But you’re not going to know jack about describing or explaining concepts and you’ll find writing paragraphs longer than 3 sentences to be terrifying. Also, pacing in screenplays is utterly different than in books. Movies happen in real time. Books can spend 10 pages describing a kitchen table and that’s totally cool. My first chapter was tight as a snare drum but the pacing was so fast that my editor had to remind me, “You’re allowed to take a paragraph and really explain things. It’s okay. Really. They’re not going to throw the book against the wall because every sentence didn’t contain a counterintuitive revelation or a snarky joke.”
When I would interview authors I’d always take the time to ask them for advice. If I heard something more than once, I made note of it. I took a month to re-read my favorite nonfiction books and reverse engineer them to see what they all did, what they didn’t do, and what was in the middle. I wanted to learn “the rules.” Not that I intended to follow them, necessarily, but if I violated them, I wanted to make sure I had a good reason why. As Peter Guber said, “There are no rules. And you break them at your peril.”
Looking at how top performers get stuff done, what you consistently see is monomaniacal focus. Everything that is not the work gets jettisoned. So while writing the book, I absolutely 100% did that. And I ended up on the Wall Street Journal bestseller list. But that monomaniacal focus also made me incredibly depressed. In fact, while I was writing the 6th chapter—about work/life balance—things became horribly ironic. I saw these world class successful people who gave it all to their work, reached the pinnacle…and they screwed up their relationships beyond repair. I knew that I couldn’t keep working like this. I needed to follow what I’d written in that sixth chapter probably more than anyone who would buy the book. Luckily, I have a girlfriend who makes me step away from the computer and makes me actually take time to appreciate what I’ve accomplished. Back in early 2014, before I put the blinders on and went total workaholic, I wrote in the introduction: “By looking at the science behind what separates the extremely successful from the rest of us, we learn what we can do to be more like them—and find out in some cases why it’s good that we aren’t.” I had no idea how personally prescient those words would become. It’s your personal definition of success that matters, not being #1 on planet Earth. The research shows that over the long term, happiness leads to success more than success leads to happiness. Balance is essential.