Ryan Holiday
“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:
- Be humble in your aspirations
- Be gracious in your success
- 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:
- Read Ryan Holiday’s books:
- Also mentioned, “The 48 Laws of Power” by Robert Greene
- Visit his website here and sign up for his newsletter
- Follow him on Facebook & Twitter
- Listen to my last interview with Ryan: