Ep. 222: Ryan Holiday – The Essential Question: How To Live A Good Life

ryan holiday

I tried to ruin Ryan Holiday’s life. Fortunately, I failed. I told him to start an agency, build it up, sell it for 10 million dollars and THEN start writing books.

“It’s a good thing you didn’t listen to me,” I said.

But I was wrong. It turned out he took my advice.

“It made me super unhappy and it cost me a bunch of friendships,” he said. “But it’s not your fault. I know there are a lot of things that could make me money, but what I really like is writing. That’s what I want my life to be.”

“So what if you don’t know what you want your life to be?” I asked. “What should you do?”

“That’s the essential question,” he said…


Most writers die penniless. I can’t think of a profession where I can name as many suicides as writing.

I’m jealous of the people who don’t write actually. Making business deals and going to work is so much more profitable than trying to tear your soul apart and put words on a piece of paper most people won’t read.

There’s only one writer in history to become a billionaire. (J.K. Rowling, if you’re reading… come on my podcast!)

So why does anyone do it?

I don’t know. I do it because it’s what I would do if I had nothing again. It’s what I would do with everything. It’s the one thing that makes me feel like I am going places without moving.


Everyone wants to be the hero of their own story. I do. But I chose victim for years. I lost everything and I wanted the world to pick me back up.

I’m not mad at the world for leaving me on the floor. I’m grateful. Because it let me pick myself up. It let me choose myself.

“Stoicism is a practical philosophy and it works,” Ryan said.

“Define ‘works’.”

“At its core, it says you don’t control the world around you. You control how you respond to the world around you.”

He told me about the two most prominent practitioners of Stoicism. One was Marcus Aurelius, a Roman emperor. He had all the power in the world. His favorite Stoic was a slave, Epictetus, who was banished from Rome by a past emperor.

“You have extreme wealth and power using the philosophy, and it’s helping them,” Ryan said. “And then you have extreme adversity, difficulty and powerlessness using the philosophy and it’s helping them. To me, that’s working.”


People are losing their jobs. And they’re afraid. I asked Ryan if the Stoics have a practice for fear.

He said, “The Stoics call that amor fati, which in Latin means ‘a love of fate…’ You look forward to the bad things because they were made just for you.”


This is the key to all advancement in life. Make your job irrelevant. Burn the bridges behind you.

“You should be trying to make your job or your role irrelevant because what you’re actually proving is that you know how to do things, you know when something is working, and you’re able to come up with the next thing,” Ryan said.

“When an employee comes to you and says, ‘I know my job was to run this marketing department, but over the last 6 months I’ve automated X and Y. I’ve hired someone who’s incredibly talented, sales are up X percent and I don’t have that much to do.’ Your boss doesn’t go to their boss and say, ‘Well how do we get rid of James?” They go, “James is f**king killing it.’”

“That’s how you work through or up an organization,” he said. “No one says, ‘Your book was so amazing Ryan, we don’t need anymore books from you.’ They go, ‘What are you writing next?’”


I was listing the pillars of Stoicism. I wanted to know if I understood.

So I said,

  • Integrity, (universal integrity, for example: never lie to get what you want)
  • Fairness (Help the people around you. Even if it hurts you. If it helps someone more than it hurts you, it’s just.)

Then Ryan jumped in.

“Temperance,” he said, which means don’t be an addict to some other force. Don’t be an addict to anything.


“John Kennedy Toole killed himself because his book was rejected. That’s so sad to me because then the book won the pulitzer prize,” Ryan said.

I’m always happy when a friend says they like my writing. But I’m exceptionally happy when a complete stranger writes to me and says they like my writing. I don’t know why this is. There’s still a piece of me that craves validation.

So I asked Ryan, given that we still want people to like us, how can you be creative or if you don’t like your job, how can you persevere if you’re seeking other people’s approval?

He told me how he judges his own success. “I’m trying to shrink the amount of people whose approval matters to me.”

He gave an example.

A U.S. Senator wrote him. He said he reads “The Daily Stoic” everyday. “I really liked today’s entry,” the Senator said. “It’s exactly what I try to think about for my office.”

That’s the approval Ryan chose. He’s not after 10 million views on Facebook.

“I try to think less about if what I’m doing is popular and more about if what I’m doing is being proven right.”

It’s the same for entrepreneurs. You just need to attract a core group. And offer them real value. Because marketing won’t matter if your product sucks.

Know your scene, know how to help them, and ignore the rest.

The Roman Empire was declining. And Stoicism was rising. “Things were bad,” Ryan said. “But they learned how to accept it.”

They committed to high values and practiced self-reliance. I’ve become my own ruler a few times. Sometimes I was Marcus Aurelius, an emperor. And sometimes I was Epictetus, the slave.

I don’t know what I am now.

Maybe both.

Links and Resources:

Also mentioned:

  • Aren’t stoics the “bah humbug” guys in the corner no one wants to talk to?

    • bhobbs2008

      That’s a fairly common misconception about the stoic of old. The definition of the word stoic and the stoic philosophers are not synonymous. If I remember correctly, they got their name from the stoa that they originally taught under, which I believe was like a porch back then.

    • Stimpy

      You might be thinking of curmudgeons.

  • Sonia Garces

    Bottom line You got to Choose

  • Great interview !

  • Tolulope

    Nice one…”don’t be addicted to anything”

    • Stimpy

      Exactly. But easier said than done for too many of us.

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  • Mike Hren

    Hi James – You and your guests are always demonstrating and talking about a “growth mindset”. Choosing yourself is hard to do for most of us because our mental models, assumptions and beliefs were formed in families, schools and workplaces largely designed in the industrial economy where conformity and control were king. We need a new “system” to support and sustain the behavior needed to succeed in this new idea/innovation economy. Please watch my 7 min video to see what we are doing: https://youtu.be/guOwl_7Js48
    I am not a writer or famous like your normal guests. But, I am doing good work and would like to share it with you. Thanks for your time!

  • Derek Stark

    You are two of the best out there, James.

    In the process of writing my first book right now.

    Would love to chat with you about it sometime!

  • Make your job irrelevant – I love that advice.

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  • Doug Gibbs

    “Your reward for success should not be not being allowed to do what you want.” Did I get that right. Really enjoyed the podcast. Keep up the good work.

  • How to live a good life? How about living in the present than dwelling on the mistakes of the past or the worries of the future?

    Nick de Peyster

  • nekisha rolle (Lady of Change)

    Love, love your blog always this piece was written for me…that Ryan guy is absolutely wise…I needed this today!!!

  • Billy Williams

    I like the radical focus of not trying to appeal to get 10 million views but make one meaningful connection by adding real value. That’s strong.

  • Dr. LaVigne

    If you have the luxury of choice, always work on the project that has the strongest heartbeat. When you move on an idea that is already quite “alive” in your imagination, there is a natural energy and a certain ease that are ignited. It’s not the path of least resistance, it is working where the highest level of excitement already exists. Writing is certainly work, but it does not have to be tremendously difficult. Pain does not necessarily equal growth.
    As always, a tremendous conversation between you two. Love that it feels like natural, inquisitive conversation.
    James, I would challenge you about writing fiction and non-fiction on the same day…try it a few times and you may surprise yourself :)

  • James Buechler

    how come ryan uses foul language, and that that’s okay. i cut off the interview at that point.

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