Ryan Holiday [LIVE] – “Are You Doing Your Best Work?” / How I Celebrated 5 Years of “Choose Yourself”

Then Ryan Holiday told me about his pet donkeys.

He has two.

“They just stand there,” he said. “At first, I thought this was funny. Then I realized they were doing their job. As long as they don’t die, that’s a good day as a donkey.

Then he said, “Is a human not an animal? We somehow think we have to be doing and making and creating and earning and winning. And that if we don’t…”

I interrupted.

Because I needed to point out his huge career arc.

Ryan Holiday is 31 years old. He’s already worked with Robert Green, Tim Ferriss and Tucker Max. At age 22, he was the director of marketing for American Apparel.

He’s published six books, one journal and thousands of articles.

He sends a daily newsletter and has amassed a huge email list.

All of that is a second job. Surviving is his first.

“You’re main purpose as an animal is to not die and to have children,” he said. “That is your main purpose as an animal. That’s what your genes are here to do.”

So I made made this guide.

8 RULES TO HELP YOU FULFILL YOUR MAIN PURPOSE

 

RULE #1: Don’t get sick

Ryan did a fitness challenge with his Apple Watch: burn 1,000 calories a day.

He did it for 35 days.

“I didn’t get an award on the day I stopped. I got mono.” Then he couldn’t do anything for two months. He had to go back to job #1 (survive) before he could go back to job #2.

 

RULE #2: Do nothing

Like the donkeys.

 

RULE #3: Give yourself reasons NOT to do something

I’ve been writing at least one book a year for the last four years.

But I didn’t last year. Because I didn’t feel like it.

“Which is a great reason not to write a book,” Ryan said. “The best reason to write a book is that you HAVE to do it. You can’t not do it.”

He gave an example from Fight Club.

When new guys show up, the members tell them to leave. Day after day, they show up. And they’re told to leave

Finally, they show up long enough to stay. But some stopped showing up.

The ones who stopped showing up proved they belonged somewhere else.

 

RULE #4: Say “no”

If somebody says, “Hey, can you speak at a conference in Bulgaria?”

I’ll say, “Well, when is it?”

“February.”

“No problem. I’ll speak at it.”

And then when February comes, I won’t return their phone calls. Because I’m scared to tell them “no.”

So now I pretend the conference is happening tomorrow. I ask myself would I say “yes” or “no” tomorrow?If it’s a “no” tomorrow, it’s a “no” six months from tomorrow.

 

RULE #5: Don’t do what everyone else is doing

If I say, “I saw Jim do X and I want X so I’ll just do what Jim did,” then I’ll fail.

Because:

  1. It won’t work
  2. You won’t be good at it
  3. You’ll feel miserably even trying
  4. You’ll get stuck comparing yourself to the people succeeding
  5. You’ll lose money doing it
  6. You’ll waste energy
  7. You’ll waste time
  8. You’ll regret it
  9. You’ll get sick
  10. You’ll get stuck 

 

And then you’ll have to start over.

It’s just easier to work on things you want to work on. Even with the fear of “maybe this won’t work.” Rather than getting stuck in someone else’s story.

 

RULE #6: Do what you want for all the reasons you can think of EXCEPT one

I’ve been on a lot of podcasts. And it’s amazing to see how many people just use a printed list of generic questions. They don’t care about the art of the interview.

They see it as a get rich quick scheme.  

But that never works.

“I want to make a million dollars” is a bad reason to do anything. I do a podcast because I want to talk to Neil deGrasse Tyson, Mike Ovitz, Sara Blakely etc.

I have questions. And I want everyone to hear their answers. But I also want to be friends with my podcast guests.

And that’s OK, too. I can do what I love for all the reasons.

 

RULE #7:  Do what you want for all the reasons you can think of (part 2)

First Ryan wrote this article: “Whatever you Do, Don’t Start a Podcast.”

And I wrote, “Why You Must Absolutely Do a Podcast.”

Then we both wrote articles about books being the new business card.

He regrets writing it.

I don’t.

He says, “It’s filled the word with shitty books that shouldn’t exist.”

But I still say everyone should self-publish a book. Because you don’t know what it will lead to.

Speaking gigs, podcast interviews, business opportunities, a new network or tribe, letters from people who say “thank you.” And people who say “I needed this today.”

 

RULE #8: Choose Yourself

Ryan’s lucky. Because he has a good relationship with his publishers.

But most people don’t.

Most people lose 85-90% of their revenue to their publisher. It’s the price they pay to be picked.

And there are examples of this in every business. I remember asking Tyra Banks, “Why do the gatekeepers get it wrong?”

Because her TV show was rejected three times before she realized she was pitching the wrong people.

Her answer:  “They want to keep us in our place.”

So she went around the “they’s” and the “them’s” and found an “us.”

Ryan tattooed two of his book titles on his arms because the publishers kept trying to make changes. Whenever they had a new title idea, he’d send a picture of his arms.

And the conversation would drop.

I don’t want to fight that hard to be myself. Because I’d rather fight to be good at my first job. Surviving is hard work.

I don’t want to push back against the current. I want to get out of the water. And choose myself.


Links and Resources

Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue by Ryan Holiday

The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living & The Daily Stoic Journal

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday

Ego Is The Enemy by Ryan Holiday

Perennial Seller: The Art of Making and Marketing Work That Lasts by Ryan Holiday

Trust Me, I’m Lying: Confessions of a Media Manipulator by Ryan Holiday

Also Mentioned

Movie – China Town

WestWorld

Seneca

The time I threw everything out

My article on why you should quit your job

Tim Ferriss

Hunger Games

Stoicism

Transcendental Meditation

Viktor Frankl’s concept: The existential vacuum

My interview with The Fonz 

Fight Club

Billions

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