Ryan Holiday is the author of Trust Me I'm Lying, Growth Hacker Marketing, and The Obstacle is the Way. In Trust Me I'm Lying, he exposed how simple it was to manipulate the media for your own aims. He was the director of internet marketing for American Apparel. And he has helped Robert Greene research for The 48 Laws of Power and The 50th Law. And now he works as editor and contributor for the Observer.
Not bad for a 28 year old.
I mainly know him for his writing on Stoicism, an ancient Greek philosophy, which has had a huge impact on my life.
In this part of the interview, we spoke about his views on developing empathy and doing what you love for a living.
In the first part of the interview we spoke about how we delude ourselves and how we can prevent this natural instinct.
Hope you guys enjoy.
"When a person realizes he has been deeply heard, his eyes moisten. I think in some real sense he is weeping for joy. It is as though he were saying, 'Thank God, somebody heard me. Someone knows what it’s like to be me.'"– Carl Rogers
I wanted to talk about developing empathy. What has been your process for becoming more empathetic?
I think that empathy is one of those things that as you grow older, you become more capable of. It also becomes increasingly more important.
I think that as you get older you start to understand your own issues. Once you’ve understood yourself, it’s easier for you to understand other people.
Therapy has been really good for me in the empathy department. I realized the source of my personal issues. I try to combine ancient philosophy with the modern techniques and discoveries about empathy.
I grew up as a very independent kid who wasn’t very well understood. When you’re in that situation, it’s very hard to be empathetic because you’re sort of thrust into being solely responsible for yourself. You channel your very limited capabilities into understanding yourself and fighting for your own little bit of space. It’s an adaptive strategy for self-preservation. Ideally, parents are supposed to be there explaining why you feel the way that you feel. If you don’t have that, you never develop it.
As you get older you end up perpetuating the same cycle onto other people. Since you were never understood, and no one cared about how you felt, you do that to other people. You have no ability to understand any other perspective other than your own. Nor do you have time or sympathy to understand other people.
For me therapy and my writing have been about developing that capacity. I’m never going to be as good at it as someone who grew up that way. It’s hard to be a boss, a communicator, a boyfriend if you’re not empathetic.
In the "The Next Step" you talk about two principles in developing empathy. Could you summarize them?
"People hurt. People are messed up. People are stuck in patterns and don’t even know they are pattens. Most of what we do is not malicious, not stupid, not selfish or ignorant. It is, instead, a response to events whose significance we often don’t even recall." - Ryan Holiday in The Next Step
There are two kinds of empathy. A self-sufficient kid is going to get very good at understanding what makes people do what they do. It’s not because he cares about them. It's because he wants to get something out of it. I would say that I’m probably above average in that department. I’m pretty good at feeling my way around different situations and intuitively knowing what the right attack is. Inherently, I think there is something manipulative about that approach.
The next step is not just finding out what these things can do for you, but what they mean and how they can help you to understand someone better and relate to them. Instead of seeing them as a means to an end, you learn to see them as a vehicle for understanding and relating to people.
I'm a big fan of Joe Rogan's podcast. On it he talks a lot about this idea of trying to see people as babies. Since he has kids, he realizes that most issues that people develop come from how they were raised.
Let's say a kid is being a brat. People rarely go ‘Oh, that kid’s a fucking brat, I hate that kid.’ They say, ‘He’s just tired. He needs a nap.’
They understand that this specific behaviour doesn’t say anything about the kid. There is a reason why they’re acting this way. They’re very forgiving and understanding. They see it as an aberration.
We don’t treat adults that way. Of course when you’re an adult, you’re responsible for your own actions, while a child is not. But we would dramatically reduce the amount of conflict and disagreement, if we could just chalk things up to aberrations. We would say to ourselves: ‘Look, they’re acting this way because of this. It doesn’t say anything about them. Maybe they just need a vacation.’
"Before you approach your partner with a grievance, take a mental peek into the mirror. What aspect of yourself, what issues or ‘stuff,’ either past or present, are you bringing to the discussion about this problem?" - Dr. Rob Dobrenski in Why Marriages Fail
I think it’s similar to what we were just talking about.
Let's say you and your girlfriend are fighting about where to go to dinner. You’re not actually fighting because of dinner. You’re fighting about that thing plus a bunch of other issues. Neither of you is being honest enough to admit that. If you can introduce those things and talk about them, then you’re not having an insane and irrational discussion about dinner. You’re having a fair and honest discussion about a variety of different issues.
One of the problems is that we see everything as being self-contained when in reality everything is very much related.
It’s when you see what issues you're bringing to the table, but also being able to be empathetic to what theirs are, and why they might be feeling the way they’re feeling.
"When you find your path, you must not be afraid. You need to have sufficient courage to make mistakes. Disappointment, defeat, and despair are the tools God uses to show us the way." – Paulo Coelho in Brida
Another important theme on your blog is doing what you love for a living. Do you any advice for people who are trying to figure out what they want in life?
I think everyone knows what they want to do with their life. The problem is admitting it. Who just sits around and doesn’t do anything because they don’t know what they like. I think it’s more likely that people know what they like, but they don’t think that it could be a job. The real obstacle then is opening your mind to the fact that the things that you do for fun could be turned into an occupation.
In your blog, you also spoke about your issues with self-doubt. Can you elaborate?
I think betting on yourself can be very scary.
It’s very critical that you have people surrounding you that believe in you. I think it's important to counterbalance your own natural self-doubt.
Self-confidence doesn’t come naturally to me. It took a lot of work. For some people confidence comes naturally, but there are downsides to it. Having a lack of self-confidence can be beneficial in that you don't make overly ambitious mistakes. But it also has its downsides. You're less likely to take risks.
I wanted to talk about one of the main principles that you write about for maneuvering systems to get what you want out of them. Which is important if you want to do something that you enjoy for a living. I think one of them is not getting caught up in the game.
For me, when I was in university I got caught up with getting good grades and thinking that my self-worth was tied to them.
How do you avoid getting caught up in these external incentives?
It’s about deciding what incentives matter to you. I think that it’s a matter of focusing on the important metrics.
Say you want to become a politician. So you break down what it takes to be successful. You might have do a certain amount of military service. You might have to have some success in the private sector. You have to be good at networking and making contacts.
"We have this instinct where if have a number in front of us, we try to make that number as big as we can."
So it’s important to remember that these are just boxes that you’re trying to check off. Let's say you're in the military, and your boss is an asshole. You might try to ruin him for fucking with you. But you have to remember that the end game is leaving the military in three years. So none of this matters.
It’s the same thing for university. You’re going to school to learn, to meet people, and get a degree. If you remember that it’s part of a larger cohesive strategy, you don’t need to get that obsessed about grades. It's only a part of why you’re there.
We have this instinct where if have a number in front of us, we try to make that number as big as possible. It’s important to remember that sometimes a win is not the thing right in front of you. It’s part of a larger whole.
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.
If you'd like to find out when new interviews are available, sign up for my newsletter here. Don't worry I won't bombard you with emails.