Ryan Holiday’s Writing Routine

If you missed last week’s post which was all about Gretchen Rubin’s writing routine, then you may not realise that I am doing a mini-series on the creative practises of non-fiction authors. This week, I’m focussing on Ryan Holiday

Ryan Holiday is an American author whose books focus on bringing stoic philosophy into the modern-day. He is also a PR strategist, bookstore owner (yes!), and he is the host of The Daily Stoic podcast. 

Ryan takes his writing seriously, and for that reason, he has chosen to set professional work hours. He doesn’t work hurriedly to meet a deadline or wait until inspiration strikes and he doesn’t write in his pyjamas while working in bed. 

Instead, he writes every day and he treats it like work. Ryan is clearest and less likely to be interrupted in the morning so that’s when he writes. 

In treating it like a job, Ryan gets up, has a shower, gets dressed and then goes to his office, which is outside of the home, as though he were going to a conventional workplace. Ryan used to work at his home office but decided to relocate to a space above his bookstore, moving all of his books and work desk to the new location where he can write his books and blogs and recorded his podcast. 

In fact, he doesn’t even have a desk in his home anymore. 

Once he arrives at his office, he begins work on whatever writing task he has assigned himself that day, working from eight or nine until eleven or twelve. 

Three hours and he’s done. 

He finds the idea of working in a café bizarre as he values being able to stand up, pace, move around and stare. He needs to spread out his research materials, turn the music up or head out for a walk. 

In terms of structure, Ryan’s books are broken up into small sections. For each section, he creates a new Google Doc, but eventually, he joins them all together into one Word Doc, switching from writing online to offline for editing and re-writing. 

During his research phase, his favourite tool is 4×6 notecards which are stored in photo boxes. He outlines and organizes the entire book using these cards which are filed according to different parts of the project, or which subsection the thought or information is relevant to. 

Each of his books is made up of thousands of notecards which are based upon the books he’s read, interviews he has conducted, or his reflections, conclusions, or observations. 

Each card is done by hand unless the passage is especially lengthy. 

He knows that all of this research is actually starting to become something when he exports the documents from Google to Microsoft. 

Interesting, he uses music as a way to block outside noise and relax his mind. He will often pick one embarrassing song he’d never admit to listening to, and play that on repeat. There are few albums he’s been able to do this with that have the same effect as a single song to support him into getting into a state of flow. However, he considers some songs sacred. For example, he’d never use Alice in Chain’s Nutshell for this practice. (I LOVE that song!). He’ll stick with this one song until, for whatever reason, it stops working for him. 

His two pre-writing rituals include avoiding email and writing in his journal before switching over to professional writing. 

He says that he aims to figure out what he wants to say before he starts writing, rather than figuring his writing out on the page. A good day will see him write 2000 words, but because he aims to write clean content straight out the gate, it is often less than this. 

When he sits down to write, he begins by asking himself: how should this start? What is my argument? Where am I taking this? If this approach doesn’t work, he’ll start in the middle and work outwards. 

When editing, he takes a cycling approach, where he’ll write the first third, edited it, write the middle, then edit both sections together, and then write the final third.

 In this way, Ryan says, the beginning is constantly improving and by the time he gets to the end, he knows the first two thirds so well that the last comes together more easily and with less editing. 

Despite his rigorous approach, Ryan also knows when to call it quits. 

That may occur after only an hour, but he feels that it must have been a productive hour if that is how he feels exhausted. He aims to leave enough on the page that he has a beginning point the following day, stating that it’s vital to ensure you are creating as much momentum as possible for yourself, even if it’s only an illusion. In this way, he hopes to make writing as easy as possible. 

For Ryan, he says research is totally separate from writing. He may spend several months or years gathering material for a new project before he starts writing. Admittedly, he does conduct some research while writing as inconsistencies, gaps, or insufficiencies become apparent through writing. 

One of his favourite hacks is to read content that is totally different from what he is writing about as a way to forge new and unexpected connections. 

Interestingly, Ryan says that writing is easier than coming up with something to say and figuring out how best to present an argument, but he would never describe writing itself as easy. 


Follow-through_ How to complete a long-term writing project (1)

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