408: James Frey – Breaking The Rules, Writing & Becoming Yourself Again

James Frey failed at writing for 12 years.

Then he wrote “A Million Little Pieces.”

Oprah blessed it. He went on her show. Everyone was reading the book. She built Frey up. And then tore him down when it wasn’t 100% a memoir.

Then she apologized.

“What was it like to get yelled at by Oprah?”

“I don’t really care,” James Frey said. “People always ask me about Oprah. And my response is that it was an hour of my life, right? Somebody yelled at me for an hour of my life…. That happened before I ever went on Oprah, it certainly happened since. And so be it. I wrote a book that was designed to break rules, to defy conventions, to not fit into places people wanted to put it…”

“What do you mean by that?”

I’ve read all of James Frey’s books. His latest is “Katerina.” My favorite is “The Final Testament of the Holy Bible.” Every creative person should read this book.

I’ve read it over a dozen times.

“Wow, that makes me happy,” he said.

We’ve talked a lot on social media before he came on. And he listens to the podcast. So it’s nice to have that mutual respect for each other’s work.

But people don’t want to be writers anymore.

Kids don’t.

When James Frey was growing up he idolized Ernest Hemingway, Jack Kerouac, Kurt Vonnegut, Norman Mailer.

But novelists aren’t the hero’s of artists anymore. YouTubers and Instagrammers are.

Frey called this “the death of the novel.” It’s scary to see what you’ve poured your soul into disappear.

Because a broken industry either evolve or fails. And everyone in the industry has to decide what side they’re on.

James chose evolution.

James Frey the writer became James Frey the entrepreneur/founder/CEO.

He had two offices.

One for writing and one for business.

Business took over.

He worked with companies like DreamWorks, Warner Brothers, Disney, HarperCollins, Simon & Schuster, HBO and more.

The idea was to digital create content.

The iPad was about to come out. James read a lot about it. And started thinking about how it was going to function. He realized you can read a book, watch a movie, play a video game AND by merchandise all from the same place.

“It worked,” he said. “The model worked.”

“How did you make the switch from literary to young adult?”

“It’s just storytelling,” he said. “It was fun.”

But then he got depressed.

“I felt awful,” he said.

“Despite whatever success I had, despite having a family I loved and friends I loved… I just wanted to die. I would wake up everyday and get in my car and think about driving it into a tree.”

He told me how he got help.

“I have this therapist who I think I have a pretty unconventional relationship with. The first time I saw him I said, ‘Listen, I’m not here to talk to a f—ing wall. I expect this to be a conversation. I want to hear your thoughts. I want to hear your opinion. And I want your advice.’”

“I called him and I told him basically what I just told you, ‘I wake up everyday and I want to f—ing die.’”

The therapist laughed. And he said, “Well, I have a couple questions for you.”

He asked, “Do you have your earrings in?”

“What kind of clothes are you wearing right now?”

“Where are you?”

James didn’t have his earrings in. He was wearing khakis and a polo shirt. And he was at his office.

Then the therapist asked, “How Connecticut? You like that big house of yours? It’s ok?”

James answered the questions. “Yeah, it’s ok.” And then he heard this…

“The reason you want to f—ing die is because you forgot who the f— you are. And you miss who you are. Go home and put your earrings back in. Take off that polo and put on a t-shirt. Stop going to the office of the company and go to the office where you write. And write a f—ing book.” He said, “The version of you I knew would make fun of the version of you that exists today.”

James knew he was right.

He started writing. He blasted his music. And the book came through.

He sold his company. And he has ideas for his own movies and miniseries.

That’s all part of reinventing.

There’s steps to it.

1. First you have to build your skillset.

James Frey failed at writing for 12 years, that means he spent 12 years developing his skill set.

2. Then apply that skillset to a different areas of life.

He hit peak performance with a bestselling book. Then he wrote another. And another.

He created his own writing style that anyone could look at and say, “That’s James Frey.” He got international recognition. And became the most controversial writer of our time.

Then he built his business. He transferred his storytelling skills from one medium to ten others.

I don’t know what step three is. It depends on the person. It depends on the reinvention.


Links and Resources: 

Read James’ books:

“A Million Little Pieces”


“My Friend Leonard”

“Bright Shiny Morning”

“The Final Testament of the Holy Bible”

“Endgame: The Complete Training Diaries: Volumes 1, 2, and 3 (Endgame: The Training Diaries)”

“Endgame: Sky Key”

“Endgame: Rules of the Game”

“Endgame: The Calling”

“Endgame: The Complete Zero Line Chronicles (Endgame: The Zero Line Chronicles)”

  • #1 is just it James; build your skills guys! I implore bloggers to practice writing daily. Goodness knows authors need to do the same. What a fascinating dude James is, and what a story.

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  • Hi James,

    Failure means that you have tried. This also means that you have the chance to learn from the failure and try hard again. Everything that you learn from failure help you to become a better person or skilled person. The story touches the various points of James Frey’s life.

    Glad you have shared this.

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  • Fascinating. I must meet this guy.

  • James Buechler

    Had never heard of him before. Maybe he has just said all that he wanted to say.

  • James Buechler

    Wow. What a true human being.

  • Ann

    Maybe Frey felt like dying because he was exploiting all those young writers for $250 a book at that fiction farm of his. I know I would.

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