Ryan Holiday dropped out of college at 19 to work with controversial author, Tucker Max.
He knew that Tucker used to link to just about every article written about him. So he decided to write a review of Tucker's work. He was blown away by Ryan's writing. He wrote in an email, "Seriously, I am awed by your grasp of me and my material." Eventually Tucker offered him an internship.
Since then, he's helped Robert Greene with The 48 Laws of Power and The 50th Law. He also became the director of marketing at American Apparel. And now he works as editor and contributor for the Observer.
He wrote Trust Me I'm Lying, a description of how he used online media to manipulate mainstream media. And he recently released his first book on philosophy called The Obstacle is the Way. In it, he outlines how we can use philosophy to take difficult times and turn them into an experience that we can grow from.
He's accomplished all this before the age of 30.
The main reason why I decided to interview Ryan is because he introduced me to Stoic philosophy. His blog has deeply influenced how I live and think.
In a world where people are focused on creating an image of themselves, Ryan has spent years trying to break his down. His blog has been his journey trying to see things as they are. We all deceive ourselves. That's a part of being human. But how do we combat these instincts? In this part of the interview, Ryan tells me how he's learned to do so.
In the second part of the interview, we spoke about his views on developing empathy and doing what you love for a living.
I hope you guys enjoy.
"Like seeing roasted meat and other dishes in front of you and suddenly realizing: This is a dead fish. A dead bird. A dead pig. Or that this noble vintage is grape juice, and the purple robes are sheep wool dyed with shellfish blood. Or making love—something rubbing against your penis, a brief seizure and a little cloudy liquid.
Perceptions like that—latching onto things and piercing through them, so we see what they really are. That’s what we need to do all the time—all through our lives when things lay claim to our trust—to lay them bare and see how pointless they are, to strip away the legend that encrusts them.
Pride is a master of deception: when you think you’re occupied in the weightiest business, that’s when he has you in his spell." – Marcus Aurelius in Meditations
A major theme that you write about on your blog is your process of developing humility.
Could you talk about about some of the biggest obstacles on the way?
I think that the more successful you become, the more work and dedication you have to channel towards humility. The more responsibility you take on, the more you think that you deserve it. The more money you make, the more important you think you are.
In psychology there's a concept called the Fundamental Attribution Error. When you watch Tiger Woods play golf, you see that he’s very controlled, dedicated, and looks like a good guy. You assume that because he’s a nice guy here, that he must be a nice guy everywhere. It works the other way around. You find out that he’s a sex addict. Now he’s a bad guy. It’s an extrapolation.
Part of humility is not letting anything be anything other than what it is. If you make a lot of money, all that means is that you make a lot of money. It doesn’t say anything about you. It doesn’t even say that you necessarily deserve to make that money. Say you become a celebrity. That doesn’t say anything about you. All it says is that a lot of people know who you are.
The Stoics practice an exercise called Contemptuous Expressions to remind themselves of what things actually are. For example, instead of thinking that you're important because you have a lot of employees, you might actually look at it like a burden. If you’re eating a fancy dinner, you might look at your food like a pile of dead animals. It’s a reminder of what things really are.
Probably some of the biggest obstacles to humility are extrapolation and seeing things for more than what they are. Since our instincts tell us to do both of these things, it’s a good idea to have exercises to counteract our instincts.
If someone who is overconfident does something 'good', they might think that they’re a good person. Whereas if someone who struggles with self-confidence, does something 'bad', they might they're a bad person.
Something that psychologists talk a lot about is this idea of permanence. If something bad happens to depressed people, they tell themselves that it’s going to be like this forever. More resilient people don’t make those kind of extrapolations.
I also noticed that a lot of religions and life philosophies try to help people see themselves as part of a whole. I think that helps to develop humility in some way. Do you have any practices that help to maintain that perspective
I think it’s a lot easier to be normal and grounded if you can think that way.
But of course there are things that you can do that help develop this. You can go to a beach at night and stare out into the ocean. You are reminded of the immensity of the world that surrounds you.
It's important to remind yourself of how tiny and utterly fragile utterly you are.
Michel de Montaigne
"I shall put myself under observation straight away and undertake a review of my day--a course which is of the utmost benefit. What really ruins our characters is the fact that none of us looks back over his life. We think about what we are going to do, and only rarely of that, and fail to think about what we have done, yet any plans for the future are dependent on the past." - Seneca in Letters from a Stoic
Another major theme on your blog is your struggle with self-examination. What tools do you use to help you with self-examination?
I don’t know if it’s ever as laid out as that but my website is one of them.
I think everything is a vehicle for self-awareness and examination. Everything is an opportunity to look at things from new angles and learn about yourself. I read, I write, I talk to smart people.
Montaigne had that exercise of using an outsider’s perspective to examine yourself. Do you use that too?
Contrast and comparison are very helpful.
I don’t think there’s anything better than reading a book that wakes you up and expresses a perspective that you didn’t know before. You can internalize, borrow, and apply it to your own life.
It’s easy for me to read books that are just entertainment.
But I think it’s really important to read books with the right sort of weight and substance that forces you to ask questions.
If you enjoyed this interview, try out my interview with Nick Denis, retired UFC fighter and former biochemist. He cut his career short in his prime because he was worried about head trauma. He weighed the glory, money, and fame and chose another path. We spoke about many things, one of those things being why it was easy for him to completely change paths.
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