One of the greatest temptations published authors face is to repeat themselves. You’ve written a successful book? Great! Write the same book again, just as a sequel! It’s hard to face this pressure down, if only because making a living out of writing books can be hit-or-miss.
Ryan Holiday has written on the media, marketing, ancient philosophy—and in spite of selling hundreds of thousands of books and earning devoted fans in the arenas of sports and Silicon Valley, he’s managed to do it without falling into the trap of repeating himself. He’s also been on all sides of the writing game: as an author, a ghost-writer, a columnist, an essayist, a Grammy-award winning producer, a book marketer, and a book connoisseur, providing monthly reading recommendations going on 8 years.
How does he get it all done? He tells us in this thought-provoking and thoughtful look at his writing routine…
To me writing is a job, a profession, and the best way to be a professional is to set professional hours. So I don’t cram, I don’t do spurts when inspiration strikes, I don’t do it in a bathrobe or from bed. I write every day and I treat it like work. I am sharpest and least imposed on in the morning so that’s when I write. I have a ritual: I get up, I shower, I get dressed as though I am going to a job and then I show up to work. I write in a journal first. I play with my son. And then I sit down and tackle whatever writing I have assigned for myself that day. I start at around 8—9 at the latest—and by 11 or 12, I am pretty much done. The rest of the day is for whatever other work I have and then the evening is for family, friends, hanging out, whatever. I can think of maybe a handful of times tops that it’s ever been dark outside—unless because it’s that early—that I have found myself writing. And those times were probably because I had jet lag or I was lightly editing something that was already in production.
I’m weird about tools and they’ve sort of become merged into my rituals. For instance, my books are all broken up in many small sections (I tend to have lots of short chapters instead of a few long ones). When writing these short chapters, I use separate Google Docs for each one but there comes an important inflection point in my progress, where I begin to combine these independent chapters into one Word Document. I basically go from online writing to offline editing and re-writing. (Each day I resave this Word Document in Dropbox with the an acronym of the title, the phrase working draft and the date—so TOITW-Working-Draft-5-22.) During my research phase, my favorite tools are 4×6 notecards and these photo storage boxes. The entire book is outlined and organized on these cards and filed accordingly to which part, which subsection the thoughts or research on that card will be put towards. So each book will literally be made up of thousands of these cards, which are often synthesis from books I’ve read, interviews I’ve done, random thoughts I’ve had and so on. The cards are done by hand—pen, pencil, whatever is close. Though I will occasionally type out very long quotes because my handwriting had gotten so atrocious. So that adds paper, scissors, and tape or a glue stick to the list of tools I guess. Anyway, my point is that this is all sort of a daily ritual or practice. Making cards, filing cards, picking out cards to write. One of the first times I start to feel optimistic about a book—Hey, this is starting to become something—is that transition from Google to Microsoft. I love looking at the file names tick the days off in Dropbox. All that is immensely pleasurable—almost as much as whatever I am saying. I am obsessed with that symmetry and progress.
Music definitely. I use the music not only to shut out outside noise but to shut off parts of my conscious mind. I’ve found that picking one song—usually something I am not proud to say I am listening to—and listening to it on repeat, over and over and over again is the best way to get into a rhythm and flow. There’s very few albums I’ve ever been able to do this to. Bon Iver’s 22, A Million is maybe the only one (and that’s because it’s better as an album than singles—if there was one standout song, I’d just do that). Basically I treat the music as sort of disposable, instant flow tool. I use it until it stops working, and then I move on to the next song. I use the same song that I am writing to when I run later, or if I go for a walk. It’s just creating a continuity to the creative process. The only song I love that I’ve never listened to on repeat, mostly because I love it too much and feel like it would ruin it, is Alice in Chains’ Nutshell.
My desk in my office either at my place in the city or on my farm, mostly. I tend to work better at my place at the city—it’s got all my books and these floor to ceiling bookcases filled with them, it just feels right. If I drive there, it’s sort of like going to work. I wrote all of Trust Me, I’m Lying at the Tulane Library in New Orleans (and just finished the updated version there, 6 years later) and at the Tomás Rivera Library at UC Riverside. I wrote The Obstacle Is the Way and Growth Hacker Marketing in a small apartment in New York and the New York Public Library. Ego is the Enemy was at the U.T library. Perennial Seller was at the ranch, and this next book has been at the ranch and the place in the city.
Two little ones: Try not to get sucked into email before sitting down to write. Write for a least a little bit in my journal before writing ‘professionally.’ But the rest of the rituals are the stuff I already mentioned. Getting out the notecards, pulling up the draft, turning on the music, etc.
I don’t know if I have an answer to that. I definitely try to eliminate wasteful writing preemptively. That is, I’m not writing to figure out what I have to say. I want to know what I am trying to say and writing is merely putting it down. If I write 60,000 words for a manuscript’s first draft, I want it to end up, in published form at, say 55,000 words. Meaning I am not having to cut a bunch of stuff that I could have avoided writing in the first place. I want editing to be a matter of tightening—not jettisoning. I definitely will re-write a big chunk of those 55,000 words, almost sentence by sentence, but I think of all my books I’ve had like maybe one “bonus” chapter I didn’t know what to do with after.
A really good day for me is maybe 2,000 words. But I suppose if I didn’t have my approach, I could write a lot more. It’s much easier to vomit words on the page, it’s harder to spit out polished prose—but that’s what I am trying to do. Writing to think is terribly inefficient, I think. I shudder at the fact that Robert Caro cut 250,000 words out of the Power Broker (written by hand no less!). He could have given us another edition in the LBJ series! But to each their own, to each their own.
What’s the first sentence? What am I trying to say here? What’s the most important point I am trying to make? Where am I hoping to end up? Then go. If I have trouble with that, then I’ll just start in the middle and work my way outwards.
Take Obstacle and Ego—and then the book I am working on. I would write the intro, print it out, and edit it. Get it passable and close to what I wanted. Then I wrote the first chapter, and did the same. Then once I had a clear sense of what this book is going to be I wrote the first third, edited and then wrote the second third. But here, I would combine Part I and II and edit them together. Then Part I, II and III. So it’s sort of recursive. The beginning is getting stronger and stronger and stronger. And as a result, I have interacted with the material so much at this point that the latter chapters need far less editing. By the time I’ve finished I’ve gone through the book dozens and dozens of times. I spent close to a year on Ego this way. Over a year this way with Perennial Seller. By the time I am recording the audiobook, I almost never want to see or hear these words ever again.
The law of diminishing returns is your friend. It will tell you when it’s time to call it a day. I am somewhat bewildered and impressed by writers who write the whole day. I don’t know how that works. I’m spent after an hour sometimes. But it’s been a productive hour, you know? I like to leave enough that I am beginning the next day with some confidence. I don’t like to wake up and not know what I am starting with tomorrow. Again a book is a long hard slog—so the more ways you can create momentum, or really the illusion of momentum, the better. Because otherwise you’re going to feel like you’re not making progress. You want to feel like you are making progress.
Do most of the research first. Treat writing as something separate. That’s how I think about it. I might spent several months or a year accumulating stuff—and then one day you start WRITING. That’s a big day, and it’s an important shift. Of course, you have to research while you write, because every day you are coming smack into all the insufficiencies you missed, and all the gaps you need to fill. But I like to be reading about totally different topics than the one I am writing about, it helps me find random connections and cool stuff. I had been researching Trust Me, I’m Lying for a long time and was almost finished with it and happened to be reading Ender’s Game—I found things to add in from what was seemingly a totally unrelated piece of material. You can’t put yourself in a position to do that if you’re still scrambling to catch up on the fundamentals or basics of the topic you’re writing about.
I don’t think I am, but of course we always are. I do like to have a model for each book. For Trust Me, I’m Lying, it was Upton Sinclair’s The Brass Check. For Perennial Seller it was Cyril Connolly’s Enemies of Promise. The books are nothing like each other but they helped inform it in a big way. Or I’ll have a single quote from an author that serves as sort of a touchstone. The book I am working on now is using this quote from Machiavelli to inspire its style and ethos:
“I have not adorned this work with fine phrases, with swelling, pompous words, or with any of those blandishments or external ornaments with which many set forth and decorate their matter. For I have chosen either that nothing at all should bring it honor or that the variety of its material and the gravity of its subject matter alone should make it welcome.”
For Trust Me I’m Lying, when I was struggling trying to figure out the tone and voice I wanted for the book, I printed out this quote from one of Cicero’s translators in the Loeb/Harvard series.
“A sustained interest, a constant variety, a consummate blend of humor and pathos, of narrative and argument, of description and declamation; while every part is subordinated to the purpose of the whole, and combines, despite its intricacy of deal, to form a dramatic and coherent unit.”
Cicero’s defense of Cluentius (accused of parricide) checks about every box that a writer or a speaker must check and H. Grose Hodge’s description of it provides a pithy summary of the duties of a writer. I still think of it often because it reminds me, as a writer, how to regard my audience, how to think about my style and my approach. This stays on the wall because I’m not sure I’ll ever really master it.
Writing is easier than coming up with having something to say and figuring out the best way to make your argument, certainly. Is it easy? I don’t think I would say that. More people would do it if it was. There would be less money in doing it well if it was. That’s what I tell myself when it gets hard: This is what they pay me for. Scarcity is good. The wall you hit is what keeps other people out.
I’ve thought about this quite a bit and I don’t have a good answer. I don’t know when I started wanting to be a writer and since I’ve written a bit about the danger of telling yourself stories, I try not to just pick a date or make one up. I started my blog in 2006. My first book deal was in 2011—but in 2009 or so someone at a small publisher had reached out to see if I was interested in doing one. I got an offer to ghostwrite something at one point. So it was around then that I started to think, “Ok one day, if I go all in on this, there might be something here.” For me, the hesitation was less if I could do it at that point, it was when and with what project. I was leaving a good corporate job, putting aside a pretty good career path so if I was going to do it, it had to be for real. I spent 6 months or so writing the manuscript for my first book and it sold about a month after that, for what was enough money that it suddenly felt very serious.
Each was miserable in its own way, each had some pleasurable moments in its own way. I agree with the saying “Painters like painting. Writers like having written.” Now that I am done, I think I am proudest of Ego is the Enemy. The Daily Stoic was written in such a rush and there were so many little pieces—366—that sometimes I’ll see someone share a page from it on social media and forget that I made that for a second. That’s something I love. It’s like catching a glimpse of your wife from far away and thinking “Wow, they’re really pretty” in the split second before you realized who it was.
For my first three books I literally moved to another city as I was starting it. Only the first time was that planned, the timing just happened for the others, but it worked very nicely. The newness of each city was an important ingredient I think—it added an energy. There were also fewer distractions, routines in each place so I could start fresh. New Orleans was really the perfect city to write in. I said at my first book signing that writing a book is really a series of long walks. There’s not a better city to walk in in America. It’s old and beautiful and slow. There’s a history of great writers there—a connectedness to the past that was inspiring. I was having trouble finishing this book I’ve been working on and I actually just went and spent 10 days there to recapture it. Worked like a charm.
We are a product of our environment I think. It seems to me like it would be very hard to write a book in a terrible office cubicle, unless that book was Fight Club. Writing in coffee shops seems crazy to me. I want to be able to get up and pace. I want to be able to stare. I want to be able to lay all my stuff out. I want to be able to turn the music up or get up and go for a walk. I actually liked New York least. I tend to break up my afternoons with a long run and running in Manhattan is overrated. In Austin it’s wonderful. New Orleans is unbeatable.
This is something I’ve been thinking about a lot. Cyril Connolly’s line is “there is no more somber enemy of good art than the pram in the hall.” I’d really like to prove that wrong. I don’t see how it could possibly be true—but it sounds true. I guess you have to really want both. I mean, on some afternoons I find myself feeling guilty, sitting there staring at the screen and thinking how much I would like to be playing with my son. I can see why people take long breaks—2-3 years or stop and never pick up a pen again.
Not that I have a ton of experience with it yet, but I think it comes down to adjusting and sticking to a routine. When Alexandra Alter at the New York Times was interviewing me for a story last year, we were talking about morning routines and I quoted the line from Tony Robbins where he says, “If you don’t have ten minutes to spare in the morning [to do a morning ritual] what kind of life is that?” And she said, “Wait ‘till you have kids.” She was right, I was underestimating how much things would change. But now most mornings, I take the baby for an hour or so while my wife catches up on sleep and one of the things we do is that my son sits on my lap and bangs on the desk while I write in my journal. So the routine is still there, it’s just different. Maybe better.
Beat it into submission. That’s the only way. How would you get rid of runner’s block? You go for a fucking run.