Ryan Holiday's Advice on Writing: Note Cards, Stoic Discipline, and Writing a Book a Year

Ryan Holiday wrote The Obstacle Is the Way, Ego Is the Enemy, Stillness Is the Key, The Daily Stoic, Discipline Is Destiny, and more than a dozen other books. Roughly a book a year. His newsletter reaches over 700,000 subscribers. Before all of this, he was Director of Marketing for American Apparel at 21, and before that, a research assistant to Robert Greene.

His writing advice comes from David Perell's conversations, his notecard system essay, a Writing Routines interview, and Medium breakdowns of his method.

The Note Card System

Holiday's process begins not at the keyboard but in a box of 4x6 index cards.

When reading, he underlines passages and writes thoughts in the margins. Then he waits several weeks. The ideas that survive the cooling-off period are worth keeping.

He transfers surviving highlights onto 4x6 notecards. One idea per card. Category label in the upper right corner: Stoicism, Life, Strategy, Writing, or a specific project. Cards go into storage boxes. Each book gets its own box. By the time he starts writing, a book is thousands of physical cards organized by chapter and subsection.

The system came from Robert Greene, who taught it when Holiday was his research assistant. Greene reads 300 to 400 books per project and generates 3,000 to 4,000 cards. "This is not 'my' notecard system. I use a perverted version of a system taught to me by the genius Robert Greene."

Writing by hand forces you to digest ideas rather than passively highlight them. Shuffling physical cards reveals connections digital notes miss. The box is "a backup hard drive of your brain."

2,000 Words by Noon

Holiday treats writing like a job with set hours. Journals first, then assigned writing by 8 or 9 a.m. On a productive day, 2,000 words by noon. Afternoons are for reading, research, and email.

"I don't cram. I don't do spurts when inspiration strikes." His approach to writer's block is the same as his approach to running: you simply do it.

Before writing, he avoids email. Pulls out his notecards. Turns on a single song and plays it on repeat until it stops working - a Pavlovian trigger for focus.

You cannot control whether the writing goes well on any given day. You can control whether you show up. Steven Pressfield calls this the war of art. Holiday fights it with routine rather than willpower.

Separate Research from Writing

Holiday keeps research and writing as distinct phases. Months, sometimes a year, accumulating material before writing a single sentence.

"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."

He arrives at the page already knowing his argument. The writing phase is compression and sequence, not discovery.

He continues reading during writing, but about different topics. Cross-pollination produces unexpected connections. He found material for Trust Me, I'm Lying while reading Ender's Game.

The Distillation Test

Before starting a book, Holiday distills: the core idea in one sentence, then one paragraph, then one page. If you cannot do this, you are not ready to write.

He outlines on notecards, organized by part and subsection. The physical layout shows the entire architecture at once. Cards can be moved, removed, or regrouped without rewriting anything.

One Model Per Book

For each book, Holiday selects a style model - a single work that represents the tone he is aiming for. Trust Me, I'm Lying: Upton Sinclair's The Brass Check. Perennial Seller: Cyril Connolly's Enemies of Promise.

He pins inspirational quotes at his workspace. Cicero's translator: "A sustained interest, a constant variety, a consummate blend of humor and pathos, of narrative and argument." Machiavelli: "I have not adorned this work with fine phrases, with swelling, pompous words, or with any of those blandishments."

When you are deep in chapter seven and have lost the thread, the model reminds you what the book is supposed to feel like.

Environment Shapes the Work

Holiday moved to a new city for each of his first three books: New Orleans, Los Angeles, New York. "Writing a book is really a series of long walks." New Orleans proved ideal.

He considers writing in coffee shops insane. "You need space to pace, stare, organize materials, and control your environment." Cards spread across desks. Boxes stacked by project. Books piled in reading order. The environment is infrastructure.

The Recursive Edit

Holiday's editing is recursive. Write the introduction, edit it. Write chapter one, edit introduction and chapter one together. Write the first third, edit as a unit. By the time he finishes, early chapters have been revised many times.

If a 60,000-word draft becomes 55,000 published words, that is a success. The notecards already eliminated irrelevant material.

This is closer to Eric Roth's page-one method than it might seem. Both reject the "vomit draft." Both prefer to get it right as they go.

The Stoic Writer's Life

Holiday's books about Stoicism describe his own writing practice.

The Obstacle Is the Way: the obstacle is the blank page. Face it. Ego Is the Enemy: ego is the voice that says this sentence is too good to cut. Cut it anyway. Discipline Is Destiny: discipline is the daily 2,000 words by noon. The freedom is a book a year.

Holiday lives what he writes. That coherence is why his audience trusts him.

Key Takeaways

• Use a physical notecard system. One idea per card, categorized by theme or project.
• Wait weeks before transferring notes. Let time filter what matters.
• Write 2,000 words by noon. Treat writing as a job with set hours.
• Separate research from writing. Arrive at the page knowing what you want to say.
• Distill the book to one sentence, one paragraph, one page before starting.
• Choose a style model for each book. Pin it to your wall.
• Edit recursively. Each new chapter triggers a re-edit of everything before it.
• Control your environment. You need space to pace, stare, and spread cards.
• Live the philosophy you write about. Coherence between life and work builds trust.

Holiday's method is the industrial version of Robert Greene's research system. Greene spends five years per book. Holiday spends roughly one. Both prove that physical, manual, disciplined processes produce books that last.

Sources: Holiday's notecard system essay, his Writing Routines interview, and David Perell's conversations. Athens is an AI writing editor.