One of the greatest temptations published authors face is to repeat themselves. You\u2019ve written a successful book? Great! Write the same book again, just as a sequel!<\/i> It\u2019s hard to face this pressure down, if only because making a living out of writing books can be hit-or-miss.<\/p>\n
Ryan Holiday has written on the media<\/a>, marketing<\/a>, ancient philosophy<\/a>\u2014and in spite of selling hundreds of thousands of books and earning devoted fans in the arenas of sports<\/a> and Silicon Valley, he\u2019s managed to do it without falling into the trap of repeating himself. He\u2019s also been on all sides of the writing game: as an author<\/a>, a ghost-writer<\/a>, a columnist<\/a>, an essayist<\/a>, a Grammy-award winning producer, a book marketer<\/a>, and a book connoisseur, providing monthly reading recommendations<\/a> going on 8 years.<\/p>\n How does he get it all done? He tells us in this thought-provoking and thoughtful look at his writing routine<\/a>\u2026<\/p>\n To me writing is a job, a profession, and the best way to be a professional is to set professional hours. So I don\u2019t cram, I don\u2019t do spurts when inspiration strikes, I don\u2019t 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\u2019s 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\u20149 at the latest\u2014and 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\u2019s ever been dark outside\u2014unless because it\u2019s that early\u2014that 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.<\/span><\/p>\n I\u2019m weird about tools and they\u2019ve sort of become merged into my rituals. For instance, <\/span>my books<\/span><\/a> 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\u2014so TOITW-Working-Draft-5-22.) During my research phase, <\/span>my favorite tools are 4×6 notecards<\/span><\/a> 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\u2019ve read, interviews I\u2019ve done, random thoughts I\u2019ve had and so on. The cards are done by hand\u2014pen, 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\u2014<\/span>Hey, this is starting to become something\u2014<\/span><\/i>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\u2014almost as much as whatever I am saying. I am obsessed with that symmetry and progress. <\/span><\/p>\n Music definitely. I use the music not only to shut out outside noise but to shut off parts of my conscious mind. I\u2019ve found that picking one song\u2014usually <\/span>something I am not proud to say I am listening to<\/span><\/a>\u2014and listening to it on repeat, over and over and over again is the best way to get into a rhythm and flow. There\u2019s very few albums I\u2019ve ever been able to do this to. Bon Iver\u2019s <\/span>22, A Million<\/span><\/i> is maybe the only one (and that\u2019s because it\u2019s better as an album than singles\u2014if there was one standout song, I\u2019d just do that)<\/span>.<\/span><\/i> 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 <\/span>when I run later<\/span><\/a>, or if I go for a walk. It\u2019s just creating a continuity to the creative process. The only song I love that I\u2019ve never listened to on repeat, mostly because I love it too much and feel like it would ruin it, is Alice in Chains\u2019 <\/span>Nutshell. <\/span><\/i><\/p>\n 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\u2014it\u2019s got all my books <\/span>and these floor to ceiling bookcases<\/span><\/a> filled with them, it just feels right. If I drive there, it\u2019s sort of like <\/span>going to work.<\/span><\/i> I wrote all of <\/span>Trust Me, I\u2019m Lying<\/span><\/i><\/a> at the Tulane Library in New Orleans (and <\/span>just finished the updated version there<\/span><\/a>, 6 years later) and at the Tom\u00e1s Rivera Library at UC Riverside. I wrote <\/span>The Obstacle Is the Way<\/span><\/i><\/a> and <\/span>Growth Hacker Marketing <\/span><\/i><\/a>in a small apartment in New York and the New York Public Library. <\/span>Ego is the Enemy <\/span><\/i><\/a>was at the U.T library. <\/span>Perennial Seller <\/span><\/i><\/a>was at the ranch, and this next book has been at the ranch and the place in the city. <\/span><\/p>\n 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 \u2018professionally.\u2019 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. <\/span><\/p>\n I don\u2019t know if I have an answer to that. I definitely try to eliminate wasteful writing preemptively. That is, I\u2019m 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\u2019s 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\u2014not 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\u2019ve had like maybe one \u201cbonus\u201d chapter I didn\u2019t know what to do with after.<\/span><\/p>\n A really good day for me is maybe 2,000 words. But I suppose if I didn\u2019t have my approach, I could write a lot more. It\u2019s much easier to vomit words on the page, it\u2019s harder to spit out polished prose\u2014but that\u2019s 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 <\/span>Power Broker<\/span><\/i><\/a> (written by hand no less!). He could have given us another edition <\/span>in the LBJ series<\/span><\/a>! But to each their own, to each their own. <\/span><\/p>\n What\u2019s the first sentence? What am I trying to say here? What\u2019s 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\u2019ll just start in the middle and work my way outwards. <\/span><\/p>\n Take <\/span>Obstacle<\/span><\/i> and <\/span>Ego<\/span><\/i>\u2014and 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 <\/span>what this book is going to be<\/span><\/i> 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\u2019s 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\u2019ve finished I\u2019ve gone through the book dozens and dozens of times. I spent close to a year on <\/span>Ego<\/span><\/i> this way. Over a year this way with <\/span>Perennial Seller<\/span><\/i>. By the time I am recording the audiobook, I almost never want to see or hear these words ever again. <\/span><\/p>\n The law of diminishing returns is your friend. It will tell you when it\u2019s time to call it a day. I am somewhat bewildered and impressed by writers who write the whole day. I don\u2019t know how that works. I\u2019m spent after an hour sometimes. But it\u2019s been a productive hour, you know? I like to leave enough that I am beginning the next day with some confidence. I don\u2019t like to wake up and not know what I am starting with tomorrow. Again a book is a long hard slog\u2014so the more ways you can create momentum, or really the <\/span>illusion<\/span><\/i> of momentum, the better. Because otherwise you\u2019re going to feel like you\u2019re not making progress. You want to feel like you are making progress.<\/span><\/p>\n Do most of the research first. Treat writing as something separate. That\u2019s how I think about it. I might spent several months or a year accumulating stuff\u2014and then one day you start WRITING.<\/span> That\u2019s a big day, and it\u2019s 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 <\/span>Trust Me, I\u2019m Lying<\/span><\/i><\/a> for a long time and was almost finished with it and happened to be reading <\/span>Ender\u2019s Game<\/span><\/i><\/a>\u2014I found things to add in from what was seemingly a totally unrelated piece of material. You can\u2019t put yourself in a position to do that if you\u2019re still scrambling to catch up on the fundamentals or basics of the topic you\u2019re writing about. <\/span><\/p>\n I don\u2019t think I am, but of course we always are. I do like to have a model for each book. For <\/span>Trust Me, I\u2019m Lying<\/span><\/i><\/a>, it was Upton Sinclair\u2019s <\/span>The Brass Check<\/span><\/i><\/a>. For <\/span>Perennial Seller<\/span><\/i><\/a> it was Cyril Connolly\u2019s <\/span>Enemies of Promise<\/span><\/i><\/a>. The books are nothing like each other but they helped inform it in a big way. Or I\u2019ll 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: <\/span><\/p>\n \u201cI 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.\u201d<\/span><\/i><\/p><\/blockquote>\n For <\/span>Trust Me I\u2019m Lying<\/span><\/i><\/a>, 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\u2019s translators in the Loeb\/Harvard series.<\/span><\/p>\n \u201cA 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.\u201d<\/span><\/i><\/p><\/blockquote>\n Cicero\u2019s <\/span>defense of Cluentius<\/span><\/a> (accused of parricide) checks about every box that a writer or a speaker must check and H. Grose Hodge\u2019s 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 <\/span>stays on the wall<\/span><\/a> because I\u2019m not sure I\u2019ll ever really master it.<\/span><\/p>\n 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\u2019t 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\u2019s 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. <\/span><\/p>\n I\u2019ve thought about this quite a bit and I don\u2019t have a good answer. I don\u2019t know when I started wanting to be a writer and since I\u2019ve written a bit about <\/span>the danger of telling yourself stories<\/span><\/a>, I try not to just pick a date or make one up. I <\/span>started my blog<\/span><\/a> in 2006. My first book deal was in 2011\u2014but in 2009 or so someone at a small publisher <\/span>had reached out to see if I was interested<\/span><\/a> in doing one. I got an offer to ghostwrite something at one point. So it was around then that I started to think, \u201cOk one day, if I go all in on this, there might be something here.\u201d For me, the hesitation was less <\/span>if<\/span><\/i> I could do it at that point, it was <\/span>when<\/span><\/i> and with <\/span>what<\/span><\/i> 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. <\/span><\/p>\n Each was miserable in its own way, each had some pleasurable moments in its own way. I agree with the saying \u201cPainters like painting. Writers like <\/span>having<\/span><\/i> written.<\/span><\/i>\u201d Now that I am done, I think I am proudest of <\/span>Ego is the Enemy<\/span><\/i><\/a>. <\/span>The Daily Stoic<\/span><\/i><\/a> was written in such a rush and there were so many little pieces\u2014366\u2014that sometimes I\u2019ll see someone <\/span>share a page from it<\/span><\/a> on social media and forget that I made that for a second. That\u2019s something I love. It\u2019s like catching a glimpse of your wife from far away and thinking \u201cWow, they\u2019re really pretty\u201d in the split second before you realized who it was. <\/span><\/p>\n Bird by Bird<\/span><\/i><\/a> of course. <\/span>Enemies of Promise<\/span><\/i><\/a> is another. It\u2019s hard to do better than <\/span>The War of Art<\/span><\/i><\/a> though. Really a perfect book. <\/span><\/p>\n 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\u2014it 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\u2019s not a better city to walk in in America. It\u2019s old and beautiful and slow. There\u2019s a history of great writers there\u2014<\/span>a connectedness to the past that was inspiring<\/span><\/a>. I was having trouble finishing this book I\u2019ve been working on and I actually just went and spent 10 days there to recapture it. Worked like a charm. <\/span><\/p>\n 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 <\/span>Fight Club<\/span><\/i><\/a>.<\/span><\/i> 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 <\/span>liked New York least<\/span><\/a>. I tend to break up my afternoons with a long run and running in Manhattan is overrated. In Austin it\u2019s wonderful. New Orleans is unbeatable. <\/span><\/p>\nLet\u2019s start with the basics: What time of day do you start writing? Is it easier for you to write early in the morning? Late at night?<\/b><\/h3>\n
What\u2019s your preferred tool for writing\u2014a word processor like Microsoft Word, Google Docs, etc.? A pen and paper?<\/b><\/h3>\n
Do you listen to music when you write, or do you prefer silence, or something else in the background?<\/b><\/h3>\n
Do you have a writing space\u2014an office, kitchen table, etc.? Or do you move around? Change locations? How does your physical environment affect your writing process?<\/b><\/h3>\n
Do you have any pre-writing rituals or habits?<\/b><\/h3>\n
How many words a day do you produce, or try to produce? How much of that ever sees the light of day?<\/b><\/h3>\n
When you first sit down to write, how do you begin?<\/b><\/h3>\n
What\u2019s your process for editing your work?<\/b><\/h3>\n
How do you finish out a day of writing? Do you have a process, or is it just that you know you\u2019ve hit a natural stopping point?<\/b><\/h3>\n
How much of a day for you is spent in research versus writing, or are you doing both at the same time?<\/b><\/h3>\n
Are you consciously trying to emulate the style of another author or authors? Do you have people who you look to as models for your writing?<\/b><\/h3>\n
Do you consider writing to be easy? Would you say it comes to you naturally?<\/b><\/h3>\n
When did your aspirations to become a writer begin?<\/b><\/h3>\n
Which book would you say was your favorite to write?<\/b><\/h3>\n
What are your favorite books on writing if you have any?<\/b><\/h3>\n
You\u2019ve written in different places\u2014among others, New Orleans, Los Angeles, New York, and now, Austin. Did your surroundings affect the work, and if so, how did they?<\/b><\/h3>\n
You\u2019re a new dad. What\u2019s it been like writing while also caring for an infant? Any surprises that you didn\u2019t expect?<\/b><\/h3>\n