10 Things I Learned About Writing From Ryan Holiday

In August of 2016, I emailed Ryan Holiday and asked if he would help me write my first book proposal. I paid him $ 1,000 an hour for his time. He probably costs a lot more now.

Over the following three months, I would have a 1-hour phone call with him, once per month. And he would review what I developed. He started by helping me craft the idea, then helped me structure it.

After getting his help, I was able to get an agent and in January of 2017, a nearly quarter million dollar deal with one of the biggest publishers in the world. I then hired Ryan and his team to help me write and market the book itself.

Here’s some of the lessons I learned:

1. Write The Proposal For “Them” And The Book For “You”

If you want to go the “traditional” publishing route, you need to have a marketable concept. The publisher needs to trust that you can sell this thing, and that the book concept has merit.

  • The purpose of the proposal is to get the publisher to care.
  • The purpose of your book is to write the book you need to write, and that your audience needs to read.

2. The Book Proposal Has 3 Parts

There are three parts to a book proposal:

  1. What is this book?
  2. Who are you to write it?
  3. How can you sell it?

3. Get Blurbs For The Book Before It’s Even Written

For your proposal, you should get as many blurbs for the book as you can for the book that you are proposing… which hasn’t yet been written. 

Get people to provide testimonials of the book and about you as a writer. This can create extremely high expectations for the people reviewing your proposal, which is exactly what you want. You need to get them ready to have their minds blown. And then you need to make good on that built-in expectation.

4. Never Lower Your Standards For Your Work

It doesn’t matter how good of a publisher or editor you have, you need to hold yourself to the highest possible standard. More than that, you need to surround yourself with people who hold you to an even higher standard than you hold yourself. 

What blew me away during the writing process of WILLPOWER DOESN’T WORK  is that, every time I’d send a draft to Ryan, he’d rip it to shreds and say, “You can write so much better than this.”

I didn’t take it as an offense. It wasn’t even just about the writing. It was about the whole process. “Do I really care about what I’m doing?” was the question I had to ask myself after getting Ryan’s feedback. It was just what I needed.

5. The Title Of Your Book Really Matters

When I sold my book proposal, I had the idea and an initial title. But it wasn’t the right title. The book was originally going to be called, “The Proximity Effect.”

I couldn’t come up with a better title. For months, no one could. But Ryan would never let me settle. Even after I told him I was completely settled internally on the matter. He continued to push back. 

Eventually, with the help of Joe Polish and Joe’s copywriter, JR, I was able to get the right title for the book, WILLPOWER DOESN’T WORK. 

The title needs to stand on it’s own. It needs to create a statement or polarize or create an experience.

Ryan’s books are a great example of this. Some of his titles include:


6. Write Something Perennial

Don’t just write a book to write a book. Don’t just write a book to become a flash-in-the-pan bestseller.

Write something that can withstand the test of time. Write something that will continue to sell long into the future. 

I’m grateful Ryan held me to this standard throughout the writing process. Too many people write a book just for the sake of having a book. They don’t hold themselves to the standard of writing something they can be proud of… something that will be expected to sell and reach new audiences for decades.

7. Spend The First 3 Months Doing An Insane Amount Of Research (“Find stuff no one else has found.”)

When you first start writing, spend the first several months digging digging digging. Find stuff no one else has found. That’s what Ryan told me to do. And that’s what I did. 

I was able to find some fascinating stuff that I believe made WILLPOWER an innovative book. If you’re not pushing your own limits through the creation process, you’re probably not making new connections. Writing a book (or creating anything, for that matter) should change YOU in the process. The level of transformation you experience should reflect the level of transformation you hope your readers will experience. 

8. “If The Story Wasn’t About You, Would You Use It?”

In the first several drafts of my book, I had a ton of stories about myself. Ryan called me out on that.

“If this story was about someone else, would you use it?” he asked me.

“Probably not,” I responded.

Then don’t use it. Make this book worth reading. It’s much better to create something that’s amazing than to write about yourself. The content will always be king. 

9. Even After You Have Done Something Big, You Can Always Do Better (the student’s mindset)

After I finished the final draft of WILLPOWER, I got some humbling feedback from Ryan.

“You can do much better than this,” he told me.

I remember being somewhat put off. Then I thought about it for a day or two and knew exactly what he was saying. There is no such thing as a perfect book. And I know that, given this experience, I can absolutely write a better book than what I just created. 

Another friend and mentor of mine, Richard Paul Evans, who has written 38 New York Times Bestsellers, told me that every book he writes, he tries to make it the best book he’s ever written. 

I recently had dinner with Alice Cooper and he told me that he believes, after 50 years of making music, that his “best song” is still in him. He told me that if he believed he had already written his best song, he wouldn’t continue writing music.

10. The Best Way To Market A Book Is To Write The Next One

After WILLPOWER’s publication date, Ryan emailed and congratulated me. Then he swiftly said, “Write the next one.”

He told me the best marketing you could do for a book is write the next one. The success of every book spills-over into the success of the other books. I learned that writing several viral articles. When one’s doing well, you want to write more. The traffic compounds. 


Writing a book could change your life. It could change the way you see the world. And more than that, It could change the way you work. 

I now hold myself and my writing to a much higher standard. 

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