Ryan Holiday: 37 (Or So) Lessons from a 37 Year Old
37 (Or So) Lessons From A 37 Year Old  - RyanHoliday.net




Earlier this month, I gave a talk in Colorado. I got in late, but it was OK because I knew they were putting me up in a really nice hotel, one I remembered staying in before. As I walked to my room, I was struck by how run down the hotel was. The furnishings seemed staid. The walls were scuffed. The decor was tired. Even the electronics in the room were old. 
Weird, I thought, this hotel used to be new and trendy. 
Then it hit me: It used to be. Time had passed. I might have been in my twenties the first time I stayed there! And then it really hit me: I used to be new and trendy. I’m pretty worn down myself! Those same years have been working on me, too. 
There is a similar observation from Seneca. He’s visiting the house he grew up in and is lamenting the poor state of the landscaping. All the trees that lined the road on the way in were dying. Then he realized, this wasn’t a maintenance issue. The trees, which he had planted himself were dying…of old age. And he himself was not in much better shape. 
I’m writing this birthday post—my 37th birthday and my 12th post in this series—in a COVID brain fog (I picked it up on my book tour). I’m not great at math, but when I was born, life expectancy was roughly 75 years…that puts me at the halfway point. I know medicine is better these days but that still hits me. It hits me like the vibe of that hotel hallway. 
Not that I feel old. If anything, I feel like I am at the height of my powers creatively. I love my life. I love my work. If you told me that this was the halfway point of my life, I’d be grateful. In fact, if you told me this was the end, I’d feel pretty good about that too—I have well more than 37 years to show for the 37 years I’ve gotten. 
So with that in mind, I thought I’d pass along some lessons I’ve learned this year (and beyond) as I have in previous years (check out 36, 35, 34, 33, 32, 31, 30, 29, 28, 27, and 26).
1. “We’ve got nowhere to be and nothing to do,” my seven-year-old said a couple of weekends ago when we tried to prod him to finish something up. He was right and I’m trying to make this a little bit of a mantra. It’s not exactly true but it’s a nice counterbalance to my more natural inclination of doing, doing, doing. 
2. I’m not sure I’ve ever opened a social media app and then after logging off thought, “Wow, I’m so glad I did that.” 
3. Conversely, I have never taken a walk without thinking, after, “I am so glad I did that.” 
4. George Raveling told me that when he wakes up in the morning, he says to himself, “George, you’ve got two choices today. You can be happy or very happy. Which will it be?”
4b. Voltaire put it another way I love: The most important decision you make is to be in a good mood.
5. I was talking to a friend and he said something I can’t stop thinking about: “Having a contrarian view that turns out to be correct can be a brain-destroying experience.” 
6. One more from George: he told me a story from when he was a kid—“George,” his grandmother asked him, “do you know why slave owners hid their money in their books?” “No, Grandma, why?” he said. “Because they knew the slaves would never open them,” she told him. To me, the moral of that story is not just that there is power in the written word (that’s why they made it illegal to teach slaves to read), but also that what’s inside them is very valuable. And the truth is that books still have money between the pages. My entire career has been made possible by what I read.
7. There is a fine line between complacency and using your success to be more deliberate and intentional. Or maybe it’s not such a fine line…that’s why I’m trying to use that advice from my 7-year-old to remind myself that if success doesn’t afford you the luxury of picking your shots (or some autonomy over your schedule), what good is it? 
8. Epictetus said that an athlete doesn’t think about whether a throw is good or bad. They just catch it and throw it back. This is life. Everything is a catchable throw. You gotta get there and then you gotta toss it back. 
9. Another sports analogy…the great ones tune out the crowd. It’s been a journey for me to wrap my head around tuning out not just the cheers but the reality of the fact that the bigger your audience is, by definition the bigger the amount of people who don’t like you also. (I shudder to think how many people out there think I suck…so I don’t think about it!)
10. “‘​Rich’​ is how much you see your kids,” I’ve been saying at Daily Dad. “‘​Power’​ is how much power you have over your own schedule.” 
11. I don’t have any goals. None. I have things I like doing—writing, running, etc—and I do them. My only goal is to keep doing those things. Results and accomplishments are the byproduct of this process. 
12. Gandhi was once asked what worried him most. His reply? “Hardness of heart of the educated.” When I look around right now, I think of this hardness of heart—the embrace of cruelty, ‘owning the libs,’ etc—as one of the big problems of our time. But that’s always been there. There has always been dark energy in human affairs. What is more alarming is the way that good people have become utterly exhausted and detached as a result of going on eight years of resisting this energy. 
13. By the way, that’s what the dark energy is after. They don’t actually hope to convince a majority of anything. They hope to exhaust a majority and then grab the steering wheel for a bit (again or for a bit longer). That’s what happened during Reconstruction. That was what Southern politicians hoped for during Civil Rights. That’s the movement afoot right now (both candidates are the same et al).
14. “You just have to keep going back,” the civil rights attorney John Doar said. You can’t let them wear you down. You can let them make you give up. 
15. If success—more knowledge, more ability, more money, a promotion, whatever—doesn’t make you a better person, it’s not success.
16. Along similar lines, a friend of mine was torn about leaving a very important job that a lot of people would kill for, but made him miserable. I told him, “If you can’t walk away, then you don’t have the job…the job has you.”
17. It’s amazing the amount of work we’ll put into humoring other people. It’s amazing what we’ll put up with from other people. It’s amazing how patient (or how many times we’ll repeat ourselves) we can be with a clueless colleague or client. Yet we just cannot bring ourselves to figure out how our own children can stand to watch YouTube videos of people playing video games. We can’t bear to ask them to do something a third time. We just cannot remember the names of our spouse’s friends or that thing they were telling us about. What the hell? 
18. Speaking of hotels, you know you can just leave when you’re ready to go. Checking out is for amateurs…
18b. What I’m really saying is figure out how the pros–the people who do whatever you’re doing, be it travel or banking or shopping for a car or whatever–do it and see what efficiencies you can pick up. See what assumptions can be questioned. 
19. I struggle with calibrating how to have high standards without hanging oneself on them. Of course, deciding willy-nilly what time you start each day is a recipe for slowly, steadily drifting towards starting later and later. On the other hand, sweating five minutes here or there—especially when what you’re rushing through is school dropoff or traffic that’s outside your control—is a recipe for misery and missing the point. A book, for instance, is a project that takes months and years. Pace yourself accordingly. 
19b. This is what John Steinbeck was talking about when he talked about the ‘indiscipline of overwork.’ It was, he said, the falsest of economies (​more about that here​).
20. Why did it take so long for me to get a water bottle to carry around? What percentage of my issues as a child–and arguments I’ve gotten into as an adult–were the result of mild dehydration? 
20b. The other day I had just enough ice in there that the water and the ice had sort of combined into a slush. It just hit me that this was the kind of pleasure that Epicurus was chasing. It’s not much…but it’s so wonderful. 
21. Like a lot of men of my generation, I’ve learned about this concept of “mental load” in relationships (the way, unthinkingly, a lot of responsibilities, emotional obligations and tasks are placed on women). This has necessitated a lot of changes in my life, not all of which have been easy. But I will say this concept has also helped me as a boss, realizing ways in which I was carrying mental loads for people/projects and allowed me to make changes in how I manage and what my expectations are for my employees. 
22. Which brings me to something I talked about in ​Ego Is The Enemy​. Almost invariably, making improvements in your personal life or your self-development will make you better professionally. The converse is less often true—getting better and better at what you do is not necessarily going to make you a better spouse, parent, citizen. 
23. At Per Se, Thomas Keller put up signs that say “A Sense of Urgency.” While I may need to work on slowing down a bit, I’d say most people could use a little speeding up. One of the things I say at work is ​“Start the clock”​ or sometimes, out of frustration, “Why the fuck have we not started the clock on this?” The point is: Stuff takes time. When you add time in front (by taking too long to start) or in the middle (by taking too long to reply) or at the end (by taking too long to process and start the next thing) you are making it take longer. How long other people take to do their parts is not up to you, how long you take to do your stuff is. 
24. All success (indeed all failure, too) ​is a lagging indicator​. What are the choices you’re making now to give you what you want later? 
25. Sometimes I’ll take a caffeine mint right before I go for a run or a bike ride. I have a lot of reasons to be glad I’m alive, but that right there is one of them. Epicurus would be jealous. 
26. How does this stop you? This was the question the Stoics asked. How does this situation stop you from acting with ​courage​, ​discipline​, ​justice​ and wisdom? How could it?
27. I am getting better at recognizing when my brain is not functioning optimally. So like, I can say, when someone tries to explain something to me, “Sorry, I am not in a position to understand this right now.” Or, I can recognize, hey, this is not a good time to have this discussion with my wife. I used to brute force everything, even when I was tired or burned out, but what you find is that this itself just requires more work later, when you have to undo the mistakes you made because you were too fried to think clearly. 
28. You are almost certainly not saying enough positive stuff. You’re not saying ‘good job’ enough. ‘Thank you’ enough. ‘I love you enough.’ You are not complimenting, congratulating, or appreciating enough. 
29. The fewer opinions you have, the happier you’ll be. Or at least, if you do have to have opinions about things that don’t really matter, hold them lightly and in good humor. 
30. Everybody thinks Jimmy Carter was a bad president because he was too nice or too idealistic or whatever, that he should have waited until reelection to do some of the things he did. Turns out the real reason he struggled (and why he wasn’t re-elected) was that he tried to get away with not having a Chief of Staff (read Chris Whipple’s book ​The Gatekeepers​). This is an important lesson, I think: At the end of the day, it comes down to how well-organized you are and how tight a ship you run. Most everything else is secondary. 
31. If you want to understand the present moment, go read about the past. Read something about a similar moment from a long time ago. ​The Great Influenza​ is an amazing book to understand the pandemic. ​It Can’t Happen Here​ and ​All The Kings’ Men​ are two great novels to understand the political moment. ​Invisible Man​ is a great way to understand the conversation about race. ​Jan Morris’ memoir​ from 1974 helped me understand what it means to be transgender. 
32. I posted ​a picture of my positive COVID test​ and a bunch of people got extremely upset. This struck me as really weird because one of the things I have learned as a parent is anything you can do to avoid getting your family sick, you should probably do.
33. But this is just a life lesson too: Not just, why should my kids have to miss out on things they were looking forward to this week because I picked up something on my book tour? Not just why should my wife be rewarded with a fever for holding down the fort while I was gone, but why should my employees have to take something home to their kids, why should an old person I stood next to at CVS end up in the hospital when I could have worked from home and gotten things delivered? And this has nothing to do with this very specific (and strangely controversial) virus but has to do with all colds, bugs, and illnesses, it has to do with how you choose to drive on the road, it has to do with all sorts of little choices we make. The ​virtue of justice​ is considering how your actions impact other people. The only positive we should take from the pandemic is how interconnected and interdependent we all are. 
34. And by the way, if you look back at COVID–something that killed more than 1.2 million Americans and at least 7 million people worldwide and you think we overreacted, I just don’t know what to say to you.
34b. Should we have done a bunch of things differently? Did the government make a bunch of indefensible mistakes? Did a lot of the assumptions turn out to be incorrect? Yes. But the indefensible reality is that we could have and should have done more, and when we look at this period as a historical moment, that’s what our children and grandchildren will say to us. 
35. At the beginning of 2023, I made the decision to push ​the book I was working on​ an extra year. It was the first time I’ve ever done that. I think maybe I thought that it would be a nice chill and easy year but if anything, it was much harder. This is a good reminder: We often work and stay busy as an excuse to not deal with harder problems at home and with ourselves. 
36. One of my favorite chapters in ​Right Thing, Right Now​ is the one on ​‘coaching trees.’​ A successful coach or leader should not just be judged on what they achieve, but also on what the people they discover, scout, hire, and develop are able to achieve. At the end of your life, you’re going to be most proud of the impact you’ve had on people.
36b. I can’t pay Robert Greene back for things he did and the doors he opened for me, but I can pay it forward.
37. Remember, you don’t die once at the end of your life. You are dying every second that passes. We are going in one direction. Don’t rush through it. Don’t miss it. Have something to show for it. 
