Ryan Holiday

Ryan Holiday joined Shane Parrish to talk about his (newest) book Ego is the Enemy. Holiday has been on this blog twice before, back when these posts had numbers; #18, #108.

This post will be all about how Ryan Holiday works.

Holiday started out by dropping out. Kinda. He told Parrish that he left college  because the opportunity cost was too high.  He was working on three things where, “if you told me when I was graduating that I could choose one of them, college was worth it.” He left college.

Life was busy, but worth it. Holiday said the work was exhausting, but also a compulsion. One of those jobs was as a researcher for Robert Green. This job was “transcribing interviews and reading books he (Greene) didn’t want to read.” It paid off. Greene taught Holiday how book indexes are constructed and how he wrote books.

This reminded me of how Louis C.K. approached his new show Horace and Pete. Louis, like Holiday, collected skills. Louis explained it using The Matrix as a metaphor.

“When there is a helicopter and he says to her, you know how to play helicopter. And she goes wait a minute and she loads the program. Now I do. Well, anyone can do that. It just takes longer. You can just load a program. So, now I know how to create a multi-camera drama and mount it the same week that I shot it. And how to direct many great actors which I had never done before.”

One of Holiday’s merit badges was the notecard method. He’s explained the system before, but what he emphasized to Parrish was that it’s not Evernote. “It’s physical notecards for a reason.” Holiday works better with a tangible, non-searchable system. “People overestimate the perfect optimized thing,” Holiday said, “not having it searchable has not held me back.”

What matters? Doing the work.

What doesn’t matter? The perfect system or gear.

Casey Neistat makes awesome movies and preaches that the gear doesn’t matter. B.J. Novak writes on notebooks and in Microsoft Word. You don’t need RED cameras or fancy software. You just need to do the work. That’s what Holiday has done.

Holiday guessed that this work for Greene and others compressed his 10,000 hours of practice into four years. In choosing the work options over school Holiday recognized opportunity cost.

This can be hard to weigh in our decisions. Dan Ariely studied our (error-prone) mental calculations. The XMBA requires you understand opportunity cost. John Nagl studied the opportunity cost in war. Whatever the domain, understand there’s something on the other side of each choice.

Holiday told Parrish that eventually this got out of control. He used to take every opportunity. Eventually though he realized that all the energy he put out wasn’t coming back in one form or another. “I never asked ‘what’s the opportunity cost’ and sometimes you have to touch the stove and get burned.” So Holiday scaled back.

He changed how he works with clients. He’s focused his business. He realized, much like Brad Feld that you don’t need to get on every flight and put out every fire.

Scaling back and making changes doesn’t necessarily mean Holiday works less. “I couldn’t turn off my brain,” he told Parrish. His typical routine is to wake at 7, write from 8-11 and then work with clients until 3. After that Holiday runs or swims where ideas “come loose” in his head. He stops official work at 5 or 6, except for email.

Both Holiday and Parrish say that writing “is draining,” and Holiday can pivot to working on something else. Successful people have something to work on. Holiday shifts from writing to consulting to running Brass Check. Nate Silver does this. Casey Neistat does it too. When they get exhausted in one area, they switch to something that draws on a different reservoir of effort.

Holiday’s schedule reflects deliberate choices. It means swimming next to your goats.


Your choices should be intentional, he warned Parrish. “My whole life was about not showing up to an office,” yet he was saying yes to everything and kept ending up in offices. So he cut back. “If you don’t make the decisions about what’s important to you will end up very far from what makes you happy,” Holiday said.

Part of Holiday’s designed life is writing and he looks to his readers for ideas. Holiday treats emails like “frequently asked questions, a sign that someone wants to know something.” Other writers have done this too; Jocko Willink, Austin Kleon, and Steven Kotler all turned audience questions into books.

As Holiday (and Parrish) have succeeded, so have solicitations. If you reach out to them, don’t offer to buy coffee. The five bucks isn’t worth it. The obstacle for busy people, Tyler Cowen noted, isn’t the money but the time. Cowen said that he doesn’t take another research assistant because it would be too much work to supervise them.

Thanks for reading, I’m @mikedariano on Twitter.

16 thoughts on “Ryan Holiday”

  1. […] Different isn’t a Silver Bullet. The thing still has to be excellent. Jenn Hyman tested the Rent the Runway idea on her sister and friends in college. Scott Galloway tells his NYU Stern students – and anyone else who listens – to build a great product before you worry about marketing. So does Ryan Holiday. […]


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