3 Things I’ve learned from Ryan Holiday

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lessonsfrom / Monday

Welcome to week 2 of A Summer of Learning! There are some great posts lined up for this week and I’m really excited to get started with today’s post on someone who has inspired and influenced my thinking for the past 4 years. On to the post:


Ryan Holiday is one of my favorite authors. After Robert Caro (author of the LBJ biographies which I found through Ryan’s reading list), he is probably the author I have read the most words of. I started with his articles, then read Growth Hacker Marketing. Then read Trust Me, I’m Lying and wrote about it for one of my monthly book notes. Started reading a lot more using the frameworks in this article. Made a system to remember and use what I am reading inspired by his commonplace book. Then read The Obstacle is the Way. Started journaling using the Daily Stoic Journal. I finished reading Conspiracy last week.

I’ve obviously learned a lot from his books. But I’ve also learned a few core meta-lessons. Let’s talk about them.

Say it like it is

Cut to the core of the issue. When Ryan writes about how Lyndon B. Johnson used older men around him to climb the ladders of power by being a “professional son”, he doesn’t sugar coat it in wishy-washy terminology like ‘mentorship’ or ‘networking’. He says it like it is – a symbiotic relationship that is titled to one side – and offers advice on how to navigate the nuances of such a relationship. Like most of Ryan’s advice, you can choose to use it for good or bad. But just because there is a possibility that someone might it towards their own ends doesn’t mean that he’s going to mince words. I think this ability to cut to the chase has personally made me a much better writer and increased the authenticity of my conversations.

Don’t believe your own bullshit

You always need to tell stories. Narratives about why you want this job or that internship, how you got to where you are, etc. But a lot of events that shape your life happen to you. You don’t really have a part in causing them. But you need to tell these stories anyways – stories stick with people and make you memorable. That’s a dichotomy – there is a need for stories yet often they are untrue. So how do you reconcile the two?

I didn’t know the answer to that and I had read Ryan’s articles about the danger in believing in your own stories. So I sent him an email:

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Hi Ryan,

I’m Sid, a freshman at Northwestern University studying Industrial Engineering.

Everywhere I go, people tell me to focus on the narrative – how I got to where I am, why I want this internship, etc. I see many of my peers make up narratives when it’s obviously just a string of random co-incidences. I’ve read your posts on the narrative fallacy and so I don’t want to make this mistake. But it seems really hard to answer these identity-based questions otherwise – people are more attracted to stories and once you tell stories to others, you start believing in it yourself.

How do I balance the two parts – not fooling myself into a narrative fallacy but at the same time being able to adequately describe my background and motivations? Thanks for considering the request and I completely understand if you’re not able to answer. Thanks for the great work!

Best,

Sid

This was his reply:

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Every marketer tells a story. The key is that you can’t buy your own bullshit.

I’ve been following this advice ever since.

Read what you can, use what you read

Before I read Ryan’s thoughts on reading, I thought of books as a passing exercise. You pick up a book, you learn something, you feel smarter, you soon forget most things from the book. Maybe you remember the central thesis.

Ryan’s framework around reading involved treating it like serious work. Some of the tenants of this framework? Read widely. Read at the edge of your knowledge. Look at the bibliography or appendix, find source material on the topic, read that (it’s very similar to Elon Musk’s tree of knowledge analogy). Mark the page, take out clippings, write your thoughts on the margins – it’s your book! It’s not some precious thing. Never be afraid to buy a book because of its price (it’s one of the most favorable bets you can make – $15-20 for a completely different view on something). Squeeze as much value as you can out of it. Then use the quotes and anecdotes in conversations, emails, and essays (this has been a big one for me). This not only helps with retention but improves understanding as well. Pull it together into a system (my system is much more simplistic than Ryan’s).


If I could recommend an author (meaning anything from them is good), it would be Ryan. His work is accessible and important – not a common mix. If you want to get started, I recommend his latest book, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue. Will be back tomorrow with a great book on how a fish ate a whale. 

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