Ep. 171 – Ryan Holiday: The Powerful Enemy of Your Success

“You used to be arrogant,” I said.

He didn’t know.

I later decided it’s arrogant to call someone arrogant on your podcast. Or anywhere else.

I had a lot to learn.

It’s a good thing we had 90 minutes left in the studio. And dinner plans after.

“I’m sure other people must have told you that around that time,” I said, referring to when we first met a few years ago.

They didn’t.

My podcast guest, Ryan Holiday, dropped out of college at age 19. By age 22, he was the director of marketing for American Apparel. Twitter, YouTube, and Google all use his work as case studies.

Now he’s 28, a writer and owns his own business.

When I sold my first company, it completely destroyed me.

I know where I went wrong. Ryan’s new book, “Ego is the Enemy,” helped explain why.

This advice isn’t just for aspiring entrepreneurs or current business owners.

In this episode, I’ll tell you what I learned. And how you can avoid making the same common mistake.

Consider this interview a cheat sheet.

Listen now.

Or keep reading to learn 4 steps to avoiding the enemy of success

Step 1) Decide if it’s a “live time” or a “dead time”

Ryan Holiday had one year left at his job. He knew he was going to quit and start his own company.

He met with Robert Greene, his mentor and author of the national bestselling book, “The 48 Laws of Power.”

He told Ryan to make a decision.

“You can either be phoning it in at work, earning money and idly preparing, or this could be an active phase where you’re getting your research subsidized, you’re meeting people, (etc.),” he said.

Then he asked the one question that changed Ryan’s path for the next year: “Is this going to be live time for you or a dead time for you?”

Deciding is step one.

Step 2) Flip the switch

Ryan chose “live time.”

So I asked him, “How do you flip the switch? What’s the essence of making something a live time?”

He gave Malcolm X as an example. When people asked him, “What’s your alma mater?” he’d say, “Books.”

He didn’t just rot in jail. He invested in himself. And read everyday.

“He copied the dictionary by hand,” Ryan said. “That’s [why] he was such an articulate person.”

At every point in life, you can choose if it’s a “live time” or a “dead time.”

“You could call your friend and complain about how your other friend was rude, or you could call your friend and have a deep, provoking conversation about what you want to do with your life,” Ryan said.

It’s a choice.

Ryan gives you specific examples on how to maximize your time on today’s podcast. Jump to (1:24:00) to hear them now.

3) Be aware of the enemy

I sold my first company for millions of dollars. I just assumed, “Oh, I have money in the bank. I sold a business. I must be smart at everything.”

Sometimes, I can’t write about success because I don’t know if I’ve ever had any. I look at other people and don’t see success either.

I see people working. I see people with mixed priorities and broken hearts. You want to choose yourself. And do what you love. But then something says, “What if you fail?”

That’s the enemy.

“Ego says you are the car that you drive. It says you’re how much money you have in the bank… It takes all these things to heart or to head,” Ryan said.

And it stops you.

4) Understand the opposite

In his new book, Ryan says there’s one formula for true success: practice the opposite of ego. There are three parts to this:

  1. Be humble in your aspirations
  2. Be gracious in your success
  3. And be resilient in your failures

“Humility says, ‘This success doesn’t say anything about me as a person, but also when I fail it doesn’t say anything about me either,’” Ryan said.

I failed after every success because I wasn’t aware of the enemy.

Or the antidote.

Now I know a good life is made up of “live times.”

Laughing is “live time.” Being with people you love is “live time.”

Writing 10 ideas a day is “live time.”

Getting sleep is “live time.”

But let me warn you. If your “live time” means starting your own business, don’t let it destroy you… like I once did.

Listen to my podcast with Ryan Holiday. You’ll hear his choose yourself story and learn more about how to practice the opposite of ego.

Resources and Links:

  • The concept of being aware of the enemy is intriguing to me.

  • Virginia Reeves

    Ryan says there’s one formula for true success: practice the opposite of ego. There are three parts to this:

    Be humble in your aspirations
    Be gracious in your success
    And be resilient in your failures

    I like this description because it takes the pressure off ‘the big success’ that so many others push. I like to believe that anything you do of a positive nature is a small win. Gary Ryan Blair’s slogan is: Everything Counts.

  • Paul Marsland

    Hey James – would you consider having your podcasts transcribed and offering them in parallel with your audio versions? It would sort of be the long form to your show notes “Cliff Notes”

  • Ego is surely a mental trap that takes us away from happiness. And that is why “killing ego” is so very helpful – read more on this at https://random-reflections-thoughts-blog.blogspot.in/2012/07/killing-our-ego.html – and can help us retain a sense of balance at all times. Unfortunately, this is easier said than done!

  • Who was your old co host James?

  • Jordan

    I really enjoyed this interview and I took away a lot of good insights.

    One part that stood out for me, though, as a negative, was when James, comically, brought up at the beginning of the interview that he initially thought Ryan was arrogant. Ryan’s response was so defensive! He had this whole spiel about how it’s actually the other person’s issue because people don’t know what to do when a person (particularly, a young person) actually knows all the right answers. The solution, he later learned, is to explain how you are right…haha.

    Aside from that strange, and weirdly inconsistent exchange, I have already read half of the book and have enjoyed it immensely. Thanks for putting the work in!

  • Laura Trenton

    Faults Howard Hughes for a moral crusade against taxes. “Like taxes pay for stuff like you know?”

  • Anna Slyusareva

    To me, this idea is a restatement of Eckhart Tolle’s explanation of ego

  • Bob Lyle

    Funny when Altucher says the author (Holiday) used to be arrogant and is less so now, and this author gets thrown by it.
    Had a hard time staying with this one as they started going on and on about ego.

  • Dr. LaVigne

    So many gems in this discussion! Also, love that you take the time to write out many of the important points. I copy & paste them into an email that I send myself so they are easily accessible :)

  • philosogi

    What if nothing has felt like “Hell Yes” for a long time?