November 18

The Habits and Mindset That Made Ryan Holiday one of the Most Prolific Authors of Our Generation

Ryan Holiday is one of the most prolific authors of our generation. He averages one new book a year along with running a company and publishing new content monthly for a wide range of publications. There have been times when I’ve finished reading one of his new books and the next one arrives at my doorstep a week later.

The Most Important Lessons I’ve Learned from Ryan Holiday

I’ve had the good fortune of interviewing Ryan Holiday multiple times on the Unmistakable Creative Podcast. We also have the same publisher. In each of our interviews, he’s shared some of the essential habits and mindsets that have made him such a prolific writer.

1. Whatever You Do, It’s a Job

Ryan Holiday
Photographer: Aaron Burden | Source: Unsplash

“One of the things I definitely took from both my parents is that whatever you do, it’s a job. And that job requires you to show up and work on a daily basis. And I think that’s something you wouldn’t think would distinguish you from other writers, but it’s true,” said Ryan in one of our conversations.

The job of a writer is to write, focus on the process over the prize, sit in a quiet room, struggle through the pain of shitty first sentences and shitty first drafts. And if you want to succeed on any meaningful level, you go above and beyond the call of duty.

But many aspiring writers just want to see their finished books on the shelf with their name on the cover.

These types of people let their vanity get the best of them. They sign lousy contracts with terrible advances. And in one case, I even knew a writer who signed a contract where she paid the publisher.

Most aspiring creatives and people who want to make a living from their ideas dream about quitting their jobs to pursue their creative dreams. But whether you’re working for a company or writing a book, it’s still a job. And if most people approached their day jobs the way they approach creative work, they would be fired.

2. Never Talk About A Book Until it’s Finished

Photographer: Cupcake Media | Source: Unsplash

“Promotion is not how things are made great – only how they’re heard about” -Ryan Holiday, Perennial Seller

Ryan Hoiliday never talks about a book until it’s finished. You’ll never see a single Instagram post, Facebook status update or tweet from him about his latest book. The first time he ever shares something on social media about his latest book is when he submits the final manuscript to the publisher.

Every day people make announcements to the world about the book they’re going to write, the podcast they’re going to start, etc. As the comments, likes and praise roll in from strangers on the internet, they confuse attention with accomplishment even though they haven’t actually accomplished anything.

Remember, nobody gives a shit what you’re going to start. All that counts is what you finish.

3. Read Lots of Books and Take Notes

Photographer: Joel Muniz | Source: Unsplash

To say that Ryan Holiday reads a lot of books is an understatement. He has a monthly newsletter in which he shares the most recent books he’s read. And you’ll notice that often the books he’s reading have very little to do with the subjects he’s writing about.

Diversify Your Inputs and Read Lots of Books

If you want to be a prolific writer, you have to become a voracious reader. Reading is like oxygen for writers. The bulk of my of ideas for what to write about come from what I read. And you have to read a wide variety of books. The more diverse your inputs are, the more original your thinking will be.

Take Notes on the Books You Read

Learning how to take effective notes on the books you read will do wonders for your writing. It doesn’t matter whether you use Tiago Forte’s Progressive Summarization method or Ryan’s notecard system.

The notecard system has been so invaluable to Ryan’s writing career that when his house got robbed, the only thing he was afraid of losing was the notecards he’d accumulated over the years. When I asked him about the system, he said, “Many of the cards lead to nothing. But one of them is enough to build a career from.”

Ryan wrote down the idea for The Obstacle is The Way on a notecard four years before he wrote the book. The lesson is simple. Unless you capture your ideas, you’ll never be able to capitalize on them.

4. Maintain the Writing Habit

Antique Typewriter on Dark Wood
Photographer: Patrick Fore | Source: Unsplash

Even while he’s working on a book, Ryan Holiday writes several articles a month for publications like Forge, Thought Catalog and several others. This serves multiple purposes.


Momentum is the lifeblood of any startup or creative endeavor. Writing and publishing regularly helps you maintain momentum. It’s why I still write 1000 words a day even though I don’t have a contract for another book.

Accountability and Deadlines

When you write a book with a publisher, your first deadline is usually six months out. It’s on you to honor your commitments and hold yourself accountable. By writing for other publications, Ryan is able to reinforce accountability and meeting deadlines.


Ryan says most of his books are extensions of a chapter or idea in one of his previous books. The more you write about your ideas, the more ideas you’ll have to write about.


By writing other content throughout the book writing process, he also stays top of mind with his audience. If you disappear for a year, then suddenly announce to the world that you’ve written a book, most of the people in your audience will be long gone.

If you’re going to finish something you start, you can’t wait to be inspired. The work has to be a habit.

5. Longevity Over Fame

Back to school with a bullet journal
Photographer: Estée Janssens | Source: Unsplash

Many aspiring writers dream of being famous, but in a recent blog post about the downsides to fame, Tim Ferriss wrote the following:

If I’ve learned anything, it is this: fame will not fix your problems. Instead, fame is likely to magnify all of your insecurities and exaggerate all of your fears. It’s like picking up a fire extinguisher for your pain that ends up being a canister of gasoline.

Whatever degree of fame I’ve experienced with my books and my brief stint on a reality TV show validates most of what Tim has to say. It’s not all that it’s cracked up to be.

Longevity doesn’t come with the instant gratification of social media vanity metrics. It’s a commitment to mastery, deep work and creating work that stands the test of time. It’s commitment to what creating what Ryan Holiday calls a Perennial Seller.

Longevity is about building a career. Fame is about seeking attention. People who have lasting careers in the arts prioritize the latter.

Longevity might eventually lead to fame. But if you’re solely motivated by fame and you never become famous, you’ll think it was all a waste. If my niece who is a freshman in high school becomes a really talented piano player but doesn’t become famous, that’s hardly a waste. She’s developed a talent will have a positive impact on every other part of her life.

Most of Ryan’s books weren’t instant best-sellers. The Obstacle is the Way become a #1 best-seller on its 5-year anniversary. Today, it’s sold over a million copies and he’s had multiple books on the New York Times Best-Seller list at the same time.

6. Ego is the Enemy

Photographer: Taras Abbat | Source: Unsplash

When I had dinner with Ryan’s editor, she told me her boss thought giving him a book deal was a mistake. Now of course, with multiple best-sellers, he’s made them a fortune and they are eating their words.

Every author dreams of the day their book sells a million copies, they end up on Oprah, and hit some best-seller list. But most traditionally published books never sell more than 1000 copies or make any money for the publisher.

One of the hardest things to do is to separate your work and the effort that you put in from the results. An actor doesn’t control the movie around them. They don’t control what the other actors do. They don’t control the marketing budget. They don’t control the distribution. They could do the role of a lifetime, but the director or editor could mess it up in post-production. If your happiness with your job and your career is dependent on how the movie does at the box office or how the critics respond to your role, you have placed your happiness in the hands of other people, and that’s a recipe for profound disappointment. – Ryan Holiday, The Unmistakable Creative

While it’s easier said than done, if we don’t maintain that mindset, our creative work will become a source of misery instead of meaning.

7. The Next Level is a False Horizon

When you believe that you can only be happy when you reach some next level of success, you live in a conditional future.

In our interview about Stillness is the Key, Ryan shared this with me:

Whether it’s a successful career in the arts or any others career, there’s no such thing as an ‘I’ve made it’ moment. There’s always an eternal gap between who you are and who you want to be.

8. When You’re Finished, Start On What’s Next

Ready to Create
Photographer: Kelly Sikkema | Source: Unsplash

By the time Ryan Holiday finishes one book, he’s usually submitted a book proposal for his next one. When you’re finished with a project, the temptation is to sit around and bask in the glory of what you’ve accomplished.

But anybody who has been in the spotlight will tell you that it eventually fades. And their work eventually becomes an afterthought. Prolific writers don’t sit around waiting for applause. They get back to work and start on what’s next.

Most of us who write books probably won’t become the next Ryan Holiday, Elizabeth Gilbert, or Mark Manson. But that doesn’t change the fact that any writer has a lot to learn from the way that Ryan works.



You may also like