35 Lessons on the Way to 35 Years Old

Today, I turn 35 years old. This feels incredibly weird to me because I vividly remember writing a version of this article on my 25th birthday, on the eve of the release of what would be my first book. But that is the nature of life, as you get older, long periods of time—like the famous Hemingway line—slowly and then all at once, feel like short periods of time. And so here I am, entering the second half of my thirties, reflecting on what I’ve learned. 

In those ten years, I wrote more than 10 books. I got married. I had two kids. Bought a house. Then a farm. Then a 140-year old building to open a bookstore in. I’ve traveled all over the world. I’ve read a lot. I’ve made a lot of mistakes (as I wrote about last year). I’ve seen some shit (a pandemic?!?). I’ve learned some stuff, although not nearly enough. 

As always, that is what I wanted to talk about in this annual article (you can check out my pieces from 33, 32, 31, 30, 29, 28, 27, and 26). Rules, lessons, insights, trivia that I’ve learned in the last year…as well as the last thirty five years. You may agree with some and find others to be incomprehensible or outright wrong (but that’s why it’s my article). 


–Don’t compare yourself to other people. You never know who is taking steroids. You never know who is drowning in debt. You never know who is a liar. 

–There’s a sign by the track I run at in Austin, put there by Hollywood Henderson (who paid for the track). It says, “Leave This Place Better Than You Found It.” To me, that’s the meaning of life, in things big and small (but mostly small). 

–I’m continually surprised at how much even very famous, very rich, very powerful people appreciate a kind word about their latest TV appearance, accomplishment or project. The point of this isn’t that “celebrities are people too,” it’s that if praise from a friend/acquaintance still registers even at that level, what do you think it means to your kids or to your co-worker/employees or to your siblings and friends?

–You don’t have to explain yourself. I read one of Sandra Day O’Connor’s clerks say that what she most admired about the Supreme Court Justice was that she never said “sorry” before she said no. She just said “no” if she couldn’t or didn’t want to. So it goes for your boundaries or interests or choices. You can just say no. You can explain to your relatives they need to get a hotel instead of staying at your house. You can just live how you feel most comfortable. You don’t have to justify. You don’t have to explain. You definitely don’t need to apologize.

–You don’t have to be anywhere. You don’t have to do anything. All that pressure is in your head. It’s all made up.

–On your deathbed, you would do anything, pay anything for one more ordinary evening. For one more car ride to school with your children. For one more juicy peach. For one more hour on a park bench. Yet here you are, experiencing any number of those things, and rushing through it. Or brushing it off. Or complaining about it because it’s hot or there is traffic or because of some alert that just popped up on your phone. Or planning some special thing in the future as if that’s what will make you happy. You can’t add more at the end of your life…but you can not waste what’s in front of you right now. 

–The older you get, the harder it is to see how subpar—or outright crazy—the things you accepted as totally normal once were. You notice this trend when you have kids and people proudly (see: judgmentally) explain to you the insanely dangerous or cruel things they used to do to their kids. We used to let our kids…You see this with some of the COVID analogies people make (pointing out all the other dangers we accept as if it’s totally reasonable for so many people to die of heart disease or car accidents). It’s important to push back against this—to not let cognitive dissonance prevent you from enjoying a better, safer, different present/future. 

–Speaking of a process that happens when you get older, I absolutely hate that expression that says, “if you’re not liberal when you’re young, you have no heart, and if you’re not conservative when you’re older, you have no brain.” Put the dubious politics of that aside, the implication there is that you should stop listening to your heart as you get older. That’s the opposite of what you want. The goal should be to get kinder, more compassionate, more empathetic as you go. 

–Just drink more water. It’s very unlikely you’re drinking enough and a veritable certainty that you’re not drinking too much. Trust me, you’ll feel better. 

–Same goes with walking. Walks improve almost everything.

–One of my all-time favorite novels is What Makes Sammy Run? After spending the whole novel hoping that the main character “gets what’s coming to him,” the narrator finally realizes that the real punishment for Sammy is that he has to be Sammy. His life, having to live inside that head—even with all the trappings—that is the justice he was hoping would fall upon him. I have found that this observation held true with many of the people who have tried to hurt me or screw me over in my life. Comeuppance did not come in the form of some sudden event, but like Schulberg said, it was a subtle, insidious daily thing. 

–This backlash against “elites” is so preposterously dumb…and I say that as a proud college dropout. Everyone and everything I admire is elite. The way Steph Curry shoots. The way Robert Caro writes. What a Navy SEAL can do. This idea that we should celebrate average people and their average opinions about things is well…how you make everything worse than average. 

–Lengthen your timeline. Opening my bookstore, The Painted Porch (delayed a year by COVID) taught me that it always takes longer than you think it’s going to take. That’s Hofstadter’s law. And even when you take the law into account, you’re still surprised. 

–I have come to believe that inside the human species there is a kind of dark energy—some combination of fear, evil, ignorance, cruelty, mob-ness. This dark energy has always been with us. It was there when they burned witches. It was there when they sicced dogs on protestors who wanted their right to vote. It was there screaming slurs at gay people or telling women to go back to the kitchen. This energy can be blocked but never defeated—it’s like water, it just pools and then seeks a new outlet. The question always, in every political and social issue, is to ask whether you’ve been corrupted by or given yourself over to that dark energy.

–If you can’t walk away from the deal, it’s probably not a deal in the first place. 

Seneca said, “I pay the taxes of life gladly.” He doesn’t just mean from the government. Annoying people are a tax on being outside of your house. Delays are a tax on travel. Negative comments and haters are a tax on having a YouTube channel. If you become a famous person, they’ll make up rumors about you. If you do charitable work, people will question your intentions or your motivations. If you have kids, you will lose sleep. There’s a tax on everything in life. You can whine about it. Or you can pay the taxes of life gladly, as Seneca said, and then move on.

–My kids often nap in the car, usually for an hour or so. It’s strange, sometimes as I drive around while they sleep, I’ll look down at the speedometer and think, why am I going so fast? I have nowhere to go, I have nowhere to be…literally the whole point of the drive is waiting…yet here I am trying to hurry while I do it? 

–What if the most impressive thing was to be great at what you do and be a good parent, good spouse, good person? What if instead of trying to achieve one more thing or set some new record, you tried to prove it was possible to be elite and decent? Or better, elite and (relatively) normal? 

–A year or two ago, I made the decision to stop basically all the advertising that my business does. I decided to put that money into making content instead—videos, articles, etc. I did this because it occurred to me that the money I was spending on ads made basically no positive impact on the world (if any impact at all), but articles and videos could at least be enjoyed by people (for free no less), even if they didn’t drive the same amount of ROI. In the long run, this content will be around forever and have a bigger and more meaningful reach. This is a small-scale decision given the size of my business, but if people spend more time trying to maximize the positive externalities of what they did instead of optimizing for short term profits, I think they’d be happier…and ultimately do better. 

–I have a drawing on my desk that Hugh McLeod sent me. It just says, “Like an asshole, I took him/her/it for granted.” 

–The last few years are an important reminder that good leaders/correct ideas fail without good communication and bad leaders/abhorrent ideas can find serious traction with good communication. It’s not enough to be right. You have to be able to sell it. 

–Despair and cynicism only contribute to the problem. Hope, good faith, a belief in your own agency? These are the traits that drive the change that everyone else has declared to be impossible. 

–Modern life is hard. Just think of all the things people have to know how to do today—from technology to the unwritten rules of polite society. Think of all the information thrown at a person from the moment they wake up. Think of the emotional acuity required to operate in daily life today. When you understand this, and how incredibly unequipped many people (see: some whole generations) are for this, it should help you be a lot more patient. They just can’t handle it. That explains so much of their behavior. Doesn’t excuse but it exposes.

–When Seneca said that poverty wasn’t having too little, it was wanting more, he wasn’t talking about poor people. He was talking about rich people. Which brings me to something I have begun to understand: wealth is not having to think a lot about money very often. Sadly this means a lot of rich people choose to live very poorly.

–Bruce Springsteen has a lot of great lyrics but the one that I think about most is this:

We fought hard over nothing

We fought ’til nothing remained

I’ve carried that nothing for a long time

–The most important thing I’ve taken from the success of my books is an understanding that everything starts as an uncertain mess—one you often despair of ever coming together. At a low point during my last book, I found a note card that I’d written to myself that just said, “Do your notecards. The book will come together.” That’s how it goes with every project. The process will get you there…if you trust it. The more you’ve done it, the more trust you have. Because you know. 

–We tend to think of ego as a millionaires or billionaires disease—something that afflicts the successful. In fact, it does the most damage to promising people/teams/causes in the early phases. 

–I was reading a book recently and I could feel a part of my mind trying to find a way to blame the subjects of the book for their own problems. The reason I was doing this, I came to reflect, was that if it was their fault, then I wouldn’t really have to care. I wouldn’t have to do anything or change any of my beliefs. I think it is this impulse that explains so much of where we are in the world today. This headline here is one that I think about almost every single day for that reason. You have to fight that trick of the mind, the one that looks for reasons not to care. It’s the devil’s magic. 

–If you can afford to, delegate it. If you can’t yet afford to, automate it. Time is the most precious resource. 

–The best coaches and CEOs aren’t the ones who succeed just on the field or in the boardroom. The true greats are measured by their coaching tree—what the people who worked for them, who they mentored, who they inspired go on to do. 

–Most people would rather argue about reality than do something about reality. 

–When I get emails/comments from people who are mad that I said something political, I sometimes remind them that I didn’t build an audience by telling people what they want to hear. I built it by saying what I think needed to be said. And besides, how successful are you really if you censor yourself because you’re afraid it will cost you? 

–Peter Thiel, famously seen as a “contrarian,” once told me that being a contrarian is a bad way to go. You can’t just take what other people think/do and put a minus sign in front of it. The point is to think for yourself. So in fact, if you find yourself constantly in opposition to everyone and everything (or most consensuses) that’s probably a sign you’re not doing much thinking. You’re just being reactionary. 

–Everyone else has patterns. Has an ego. Follows trends. Is a product of their time. But not you, right?

I guess the final thought here, as it is in some form every year, is my favorite one from Seneca. It’s not that I am now one year closer to my death per some actuary table, it’s that I have now died one full year. Because Seneca is right, the time that passes is as good as dead. The question to ask yourself with every year, every month, every day, every minute is: Did I live it while I was in it?


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Written by Ryan Holiday