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Podcast No. 75: Ryan Holiday, Best-Selling Author

May 27, 2020

My guest today is the brilliant and deeply philosophical Ryan Holiday.

By Will Ahmed

Listen, review, subscribe.

Ryan is one of the most popular writers in the world and has authored bestsellers such as The Obstacle Is the WayEgo Is the Enemy, and Stillness Is the Key. His books have become wildly successful with high-performing people and teams, including Rory McIlroy and the New England Patriots.

Ryan and I discuss how he dropped out of college to pursue his dream of writing, as well as the difference between ego and confidence and why an unchecked ego will bring you down. We also explore cultivating stillness, the importance of patience, not letting external things define success, and how he uses WHOOP to optimize his life.

Ryan Holiday Podcast Show Notes:

3:15 – 10 Books by Age 32. “You definitely have to be in love with it to do it. I think writing is a bit like sports or the start-up world, there can be totally disproportionate and outsized rewards for it, but the risk is so high and so few people are able to do it that if you’re motivated by the outcome I think you’re in a bad spot.”

3:45 – His Calling. “Early in life I fell in love with books. I fell in love with the idea that there were these authors, these people who had wisdom or ideas and communicated them through books, but it was a longer journey for me to get to a place where I thought I could do that. It wasn’t like at age 7 I thought ‘I’m going to be a writer.’ That came much later, more towards college. I had a high school english teacher that opened my eyes to it at first.”

4:22 – Dropping Out of College. “I dropped out at the end of my sophomore year to be a research assistant for [non-fiction author Robert Greene] and to work with some other writers. Even then, it wasn’t like ‘Oh, I’m dropping out to write this novel that I have bouncing around in my head.’ It was more like, ‘I could sweep the floors of this recording studio and that’s at least getting me closer to the music.’ It was more like that. … It was an opportunity for me to go learn directly from the source of things.”

7:37 – Studying in the Real World. “The actual process of publishing [a book] is its own thing. In the way that being good at shooting a basketball is not the same as being a professional NBA player. You have to learn the ins and outs of the game, you have to learn how a season works, and you want to learn from people who have done that before. So with Robert, I worked on two books with him. … So before I wrote my first book, I had worked on those two books, plus several other books in a marketing capacity for other authors, so I had demystified the whole process. I had deconstructed it to a great degree. So when it was time for me to put out my first book, the whole thing was a lot less mysterious and intimidating.”

9:33 – A First Time for Everything. “Doing your first book is kind of like running your first marathon. It doesn’t really matter how you end up doing, even if you did quite well, a big part of that is just learning how you do it. At the outset of doing any difficult thing, you don’t actually know if you can do it. You think you can, but you don’t know.”

10:31 – The Next One. “With each one of my books, it’s still intimidating and scary [when I start writing]. Your last book doesn’t write your next one. But you are much more confident when you sit down that, ‘Hey, if I put in a certain number of hours and I don’t quit and I follow the process, I will get to the finish line. I don’t know how pretty it is, but I will get to the finish line.’ Having that belief lets you be a bit more flexible and creative.”

12:34 – Managing Ego. Ryan talks about his book, Ego is the Enemy. “I think a lot of people think ego is this sort of asset … but I actually am much more a proponent of confidence. It’s something you earn and you earn it from the work and you earn it from the results. … If you’re not getting more confident as you go, something’s probably wrong. It probably means that you’re not looking at the evidence that you’re compiling and getting the confidence that you’ve earned, or it means that you were way overconfident and delusional when you started.”

13:33 – Confidence vs. Arrogance. “Confidence, to me, is something you earn. It’s based on the work, it’s based on the evidence. But there also has to be a sense of the weaknesses, of the flaws, of the realities and the difficulty of what you’re doing. When we get into ego and when get into arrogance, we veer away from that. We get towards a sense of superiority, a sense of invincibility, a sense of entitlement. Even if in some cases these things are warranted, I just haven’t seen any evidence that they’re helpful.” Ryan cites the story of David and Goliath as a perfect example.

15:00 – Ego, Michael Jordan & 1990s Chicago Bulls. Will and Ryan discuss The Last Dance, the recently-released ESPN documentary on Michael Jordan. Ryan shares his thoughts on Jordan’s ego, confidence, and work ethic, and also how Scottie Pippen had to manage his ego while playing with Jordan and saw it get the best of him during Jordan’s retirement. “Ego makes us our own worst enemy. We mistake ego for confidence, but they are very different things. One is strong and the other is incredibly fragile. I think in some cases it has a death wish for us. It’s the source of so much failure and unnecessary conflict and pain.”

19:28 – Douglas MacArthur’s Downfall. Ryan cites General Douglas MacArthur as an example of ego bringing an otherwise talented person down. He wrote about MacAthur’s ego in a blog post earlier this month. “On a long enough timeline [ego] eventually brings us down.”

21:35 – Defining Stillness. Will and Ryan dive into Stillness is the Key. “To me, stillness is when things slow down, when you get into a zone, when things are clear, when you’re not distracted by external or internal things. It’s the ability to concentrate, the ability to focus, the ability to be at peace with oneself. Stillness comes in a lot of forms. I think we can more clearly define it by what it’s not: It’s not inactivity, but it’s also not needless activity. It’s when we get centered, when we get clear, when we get focused, and that can come in many forms for many people.”

22:53 – Stillness & Meditation. Will shares his stillness experiences through transcendental meditation. “I do it every day and the stillness that I get from that is quite profound and I would argue has really changed my life for the better.”

26:23 – When WHOOP Says to Rest. “I would like it always to be saying, ‘You have to workout super hard today.’ I’m in the middle of a 62-day [workout] streak because of the quarantine. I’ve just worked out every day, I’ve hit my exercise goal every day. The decision to break that streak is actually harder for me than the decision to go run 6 miles when it’s 90 degrees outside. I have much less problem working out than getting myself to not workout.”

30:03 – Patience. “When The Obstacle Is the Way came out, it did not sell particularly well at first. … It wasn’t until 9 or 10 months later that the growth began to accelerate and it’s been on an upward trajectory ever since then, almost 5 years now. There was a temptation to call it a failure, to say ‘That was a mistake, I should go in a different direction.’ Or to hear that feedback as evidence that I didn’t succeed. This is where that confidence comes in. Did you do what you set out to do? Do you know that the product is good? Do you have the patience?”

37:18 – Weighing Multiple Points of View. “I was the Director of Marketing at American Apparel for a long time and I watched a guy who everyone said was crazy, they said his ideas would never work, prove people wrong time and time again. What he took from that was, ‘Don’t listen to other people, everyone is a hater.’ So as he veered into more sensitive issues as the stakes got higher and higher he was, in a sense, a ticking time bomb. … When you escape consequences for your actions and for your arrogance time and time again, you’re not actually blessed. It’s setting you up for a much bigger fall.”

39:04 – Finding Stillness. “For me, it’s about cultivating habits and systems that create stillness that allow you to access stillness in the course of your day and the course of your life. The first thing I do in the morning is something I don’t do: I don’t check my phone. I do not want to start the day on my back foot. … I think exercise is a huge part of it. I do some form of strenuous exercise almost every day, whether it’s running or swimming or biking. I think reading is a big part of it. Journaling is a big part of it. Limiting the amount of distractions or inputs that you have. I don’t watch the news and I don’t read the news as much as possible. I don’t check my social media a ton. It’s about creating a space where you’re able to be focused.”

41:48 – What is Success? “To me, my definition of success is autonomy. Do I have autonomy over my day? Over my body? Over my habits? Over how things are done? If I’m moving towards autonomy then I’m becoming more successful, if I’m moving away from autonomy I’m becoming less successful, even if I’m making more or less money or achieving more or less recognition for my work or selling more or less books.”

42:59 – Stillness and Success. “This idea of stillness and this idea of being ego-free, I don’t think it’s antithetical to achievement, to success, or to great feats of prowess. … I actually think it’s more impressive to be successful and good and something and not a slave to it.”

43:39 – Goals. “I want to be a great writer. I want to be as good as I can possibly be as a writer. But, to me, that’s a distinct goal from being the most famous writer or selling the most books of any writer or making the most money of any writer. Those are goals that are outside of my control. But to fulfill the potential that I’ve been given to say all the things that I want to say the way that I want to say them, that is much more of my field to plow.”

46:38 – Internal Success vs. External Success. “Defining greatness by external things is a dangerous position to be in. I’m not saying that external things aren’t impressive, but what I’m saying is that what is truly impressive is to get there and then go beyond it and realize that there’s some other thing that’s motivating you. To me, it’s the love of the game that’s pure in a Michael Jordan. It’s the desire in a comedian to just get to what is funny and what is true more than the comedian who wants to sell the most seats or have the most famous special.”

48:32 – Relying on WHOOP Recovery. “The recovery almost has to be as conscious and deliberate as a workout. Being able to measure that has been really great. Sleep is obviously a big part of recovery. It’s easy to tell yourself, ‘I went to bed at this time therefore I got this amount of sleep.’ But the data is much less forgiving.

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Will Ahmed

Will Ahmed is the Founder and CEO of WHOOP, which has developed next generation wearable technology for optimizing human performance and health. WHOOP members include professional athletes, Fortune 500 CEOs, fitness enthusiasts, military personnel, frontline workers and a broad range of people looking to improve their performance. WHOOP has raised more than $400 million from top investors and is valued at $3.6 billion, making it the most valuable standalone wearables company in the world. Ahmed has recruited an active advisory board that consists of some of the world’s most notable cardiologists, technologists, marketers, and designers. Ahmed was recently named to the 2021 Sports Business Journal 40 under 40 list as well as 2020 Fortune 40 Under 40 Healthcare list and previously named to Forbes 30 Under 30 and Boston Business Journal’s 40 Under 40. Ahmed founded WHOOP as a student at Harvard, where he captained the Men’s Varsity Squash Team and graduated with an A.B. in government.