🌼36 Lessons on the Way to 36 Years Old

The amount of times I had to do the math to see how old I was this year was alarming. Even as I wrote this piece, I had to check, 36, right? Wait, did I accidentally do 36 last year? I don’t know why, because this is definitely not old enough for senior moments, but I’d like to think that this is a sign that I’m living my life the right way.

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Seneca had a great line. At the end of your life, he said, you should have more to show for it than just a number. My view is that if you love what you do, you lose track of time. That’s how I know I’m really in the zone on a book — the hours fly by, the days follow. 36 isn’t a big enough number that I should lose track of it, but then again, if I have packed a lot of living into those years, if they’ve all blurred together, maybe it is.

Anyway, today on my birthday, which also happens to be the 16th or 17th year I have written one of these birthday posts, I thought I would put together some lessons (or in some case, observations) I have picked up on the way to 36. Doing my best to pack a lot of living into these years, I’ve learned a lot — through both mistakes and experiences, successes and failures, by original discovery as well as by the experiences of others. (You can also check out/track the evolution of these lessons from my collections at 35, 34, 33, 32, 31, 30, 29, 28, 27, and 26).

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–The word of the year for my wife Samatha and I has been LESS. Less stuff. Less distractions. Less screentime. Less commitments. Less so we can have more — more presence, more peace.

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–As part of that, I made the difficult decision to call my publisher to push my next book a year or so. This was a massive clearance on my schedule — several hours a day did not have to be spent researching and writing on a project. Yet it was remarkable how little my life changed. Because tasks expand to fill the space, because it is so easy to say yes to other things. Less demands vigilance and discipline, perhaps even more effort than actually doing stuff.

–Which is to say that less is actually harder to do than more.

–I’ve caught myself several times, after getting out of the cold plunge, waiting for the shower to warm up before I jump in. I just got out of 38 degree water…and I’m waiting for the shower to be the perfect temp? It’s like when I take the elevator three floors down at the hotel…to go outside and go for a run. Challenging yourself is great. Exercise, cold plunges, whatever — but don’t be so focused on them that you miss yourself of the ordinary, always accessible challenges of life that are right there. They might be small, but they add up too.

–I was talking to a financial advisor a couple years ago and I was talking about how, you know, I have a very unpredictable career, that I didn’t know how much longer it would keep going as well as it has been — you know, typical artistic insecurity. He stopped me and said, “But have you put any thought into what happens if it gets even better?” He was right. I was only planning/worrying about the wheels coming off. I wasn’t thinking, “What if I keep getting better? What if my hard work keeps paying off?”

–Related to that…My business has grown year over year for many years. My book sales have grown year over year for many years. This is wonderful, but I’ve also taken to telling myself: It doesn’t have to be this way. You don’t always have to top what you did before. You can be happy with what you have.

–It isn’t that assholes never succeed — just look around. It’s that if you look closer, you see all the ways that being an asshole holds them back. The way it moves what they really want just a little bit outside their grasp, the way it prevents them from ever really enjoying or appreciating what they’ve done.

–Literally from the first doctor’s visit with your newborn, they are telling you how your kid stacks up against other kids — their height and weight percentile, etc etc. It never stops…unless you stop it. You are not raising the average child, you are raising YOUR child. How many of the things you’re worried about as a parent would worry you if you didn’t know or didn’t look at what other families were doing?

–I’d like to think I am more open minded, more caring, more patient, more aware than I was a year ago. If that’s not the direction you’re going, where are you headed?

–There is a quote from the physicist John Wheeler about how as your island of knowledge grows, so does the shoreline of ignorance. To me, that’s not only about being a perpetual student but also realizing, as you go, just how limited your experience of the world is. One of the beautiful things about reading is that it opens you up. I was reading this memoir of the high school experience of the musicians Tegan and Sara this year — what the hell did I know about being a gay Canadian teenager in the early 90s before that? But like I said, my heart and mind are more open now than it was before.

–As a public speaker, your agent has as your “fee” which they “quote” to people who inquire about hiring you. These numbers can get preposterously large, especially when you consider how not that long ago you’d have gladly done it for free (as many other people still would). There is another important term though, it’s called “fee integrity” and it has to do with whether you actually mean that quote, or if you regularly accept much less. Fee integrity is important in life. You have to know what you’re worth (both to yourself and according to the market) and you should not accept less. It’s not just bad business, it’s also sort of shady.

–We had to put our 16-year-old dog down in May. The last few years had involved a lot of clean up and ruined carpets/floors etc. Of course, the second she was gone this all felt very unimportant. I try to remember this with my kids: Paint is cheap. Even sheetrock itself is easy to replaced. Where is the car my own parents were so worried about getting dirty when I was a kid? It’s in a junkyard somewhere…which by the way, is where all your stuff will end up someday.

–People like to say that facts aren’t feelings, which is true BUT one thing I have come to understand is that other people’s feelings are facts to them. The irony of the ‘facts aren’t feelings’ crowd is that they spend all this time trying to argue other people out of their feelings… as if that has ever worked. As if that’s not a super emotional and irrational thing in and of itself. The sooner you accept that a person feels a certain way and meet them there (or just let it go), the sooner you can come to a resolution and an understanding (or just move on with your life).

–I heard of a great rule from many writers that pertains to this: When someone tells you something is wrong (with your writing), they’re right. It’s not working for them. Does that mean they know how to fix it? No. Or even that you should fix it? No, it may well be that they’re not the audience you’re aiming for. But you cannot — with your writing, with your kids, with anyone — tell them actually their reaction is incorrect. Hear what they are saying, respect it, then decide what you’re going to do about it (which may well just be letting them know that you heard them and you appreciate the time they took to say it).

–All success is a lagging indicator…all the good stuff (and bad stuff) is downstream from choices made long before.

–I have trouble wrapping my head around the fact that Free Fallin’ by Tom Petty came out in 1989. Like it’s only a couple years older than Smells Like Teen Spirit? I remember hearing someone play it by a campfire at a Boy Scout camp when I was in elementary school and thinking that it was from the 60s or something…in fact, it was still new! Great art is like that, timeless and timeless — really, it’s out of time, apart from time (If you told me that The Night They Drove Old Dixie Down was actually from the the Civil War, I’d believe you…and to many people Kate Bush’s Running Up That Hill felt like a new release)

–There’s a funny clip of Theo Von on Rogan recently, where he says something like, “There’s nothing better than peeing in the pool while you’re having a conversation with someone.” Rogan laughed but says, “what are you talking about? — that doesn’t even make the top one thousand great things”. The smell of fresh baked bread is better, he says, even if you don’t get to eat it. Anyway, I think the point is that there is a list of a thousand tiny, absurd, weird things that really are great (Neil Pasricha has a whole book of awesome stuff like that). Most of it is cheap. Most of it is accessible to you in an instant. If you want to be happier and live a richer life, seek these things out, appreciate them as much as the big things.

–You look back at the things you took very seriously earlier in your life — the things you fretted about, fought about, took personally, held onto — and now you laugh. Chances are, most of the things you’re fretting, fighting, taking personally, holding onto today will fall into the same category in the future.

–Several years ago, a business partner and I had a falling out and went in different directions. They were very public about all their successes as time went on, and even though I believed what they were doing was largely a hustle and something I wanted nothing to do with it, it was hard not to feel insecure, not to compare myself against it. Then more recently, it was revealed that the whole thing was basically a house of cards and it all came crashing down (harming quite a few people in the process). It’s just another reminder, first off, not to compare yourself to other people, because they are often lying or exaggerating. Second, it’s Seneca’s reminder to stay on the path you’ve chosen for yourself and to not be distracted by those that criss cross yours, especially when those people are hopelessly lost.

–A decade and a half ago, Tyler Cowen first told me about the idea of “quake books” — books that shake your whole view of the world. At the time, I asked him if he’d read any recently and he said, “There just aren’t books like that left for me anymore. So I read many more, to learn bits, but haven’t in years experienced a ‘view quake.’ That is sad, to me at least, but I don’t know how to avoid how that has turned out.” At 20, I could not relate. At 36, I understand more.

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–In fact, I noticed a version of that as I wrote this very post. After I finished, I went back and looked at last year’s and noticed I had written many of the same lessons! Maybe my rate of new ideas/breakthroughs is slowing down…Or a more positive way to think about it is that I am still chewing on and working my way through bigger insights, and that as I get older and wiser, it’s not such a fast or instantaneous process. There’s more to integrate now, more to integrate into now.l

–I’m not saying going for a walk will solve all your problems, I’m just saying there’s no problem that’s going to be made worse by going for a walk. (I put that on an Instagram reel this year…and somehow like 15,000 people have made their own versions of it. Insane).

–The thing I’ve learned about leveling up in your career, or breaking through different ceilings, is that you really only realize that it happened in retrospect. Just like you don’t notice your hair growing or your face aging, you can’t really feel it as it’s happening. Be patient — evaluate later. Don’t kick yourself now because you think you’re stuck. You might be the opposite of stuck and just not know it.

–My wife and I have been going back and forth a lot about how we want to educate our kids. Home school? Private school? Public schools, like we did? Some combination of all three? Should we move somewhere with better schools? Anyway, my editor Adrian Zackheim said something to us that was quite helpful: Everyone who cares about their kids’ education has these same issues…and always have. I took from this that there is no perfect solution and that we shouldn’t fool ourselves (or feel guilty) thinking that other parents have it all figured out.

–Sometimes just as I am about to fall asleep, some bit of current events will slip into my mind and make me so angry I can’t sleep — book bannings, groups that smear gay people with the word ‘groomer,’ cowards who have enabled Trump, anti-vaxxers, etc. Then I try to remember the arc of American history — there were the oligarchs who controlled the levers of power to until the Civil War, then fought social reformers of the Gilded Age, then resisted the social safety net during the Great Depression, that fought tooth and nail to preserve segregation…it’s a dark energy that forms in opposite of the progress or justice of the day, that attacks or persecutes, that becomes reactionary and obstinate often in regards to issues that neither picks one’s pocket nor breaks their legs. The big test on any issue is what does the dark energy think about it? Start forming your own views at the opposite. Don’t let them suck you in.

–Even more than not just getting infected by their toxic beliefs though, you can’t let them make you bitter either. You have to find a way to process the anger and the frustration and the disappointment before it curdles into cynicism. Basically, you can’t let the sonsofbitches turn you into a sonuvabitch.

–Another constant: Being able to adapt and make use of new tools. I have no idea what the long term implications of artificial technology will be, all I know is that the best approach as an individual is to find a way to use it to get better at what you do.

–Having now been in pro locker rooms and board rooms and briefing rooms with special forces operators and the Senate dining room etc etc — all very different worlds, I have come to believe that elite performance is elite performance is elite performance. That while these folks all do very different jobs at very different levels of fame or fortune, they’re all basically thinking about the same handful of things, accessing the same core mental skills: Resilience. Creativity. Focus. Collaboration.

–Oh, related to that: I’ve had the privilege of doing a fellowship for the Stockdale Center at the U.S Naval Academy this last year and have done a series of lectures (you can see some of them here). Some right wing critics have tried to claim that the armed forces are becoming ‘woke,’ but when I look out into the audience, I see what it is: The cream of the crop of American talent is incredibly diverse. And as your population gets diverse, particularly a diverse population of talent that can choose to be or do anything they want, an elite organization has to figure out how to meet the needs of that talent. If you want to know why they’re taking the names of Confederate generals off of bases, or doing really anything that pisses off old white dudes, it’s because they — the military, Wall Street, etc etc — is for the first time seriously having to cater to constituency that is not old white dudes. [For the Navy, you can plug in a bunch of industries/companies here]

–Funny thing related to that too: I talked about Stockdale the last time I was there, particularly in regards to these attempts to ban certain books (like where I live in Texas). When Stockdale was in the Hanoi Hilton, he would get in long debates with his captors about Marxism…and he would win. Why? Because he had actually read Marx. While he was at Stanford (where the Navy sent him), he had done a whole course on the original communist texts. Most of his captors had only been given propaganda, sometimes second or third hand. You build strong, resilient people by exposing them to information, not hiding it from them.

–And then finally, a couple weeks ago, I interviewed Dave Carey, a POW who went to the Academy and was locked up with Stockdale. He told me the secret to parenting/life/negotiation is to remember that the main goal in every conversation is to have the next conversation. He was saying that you never want to behave in a way that shuts the door for good, never want to say things that end things. I love that.

–When we were getting off a plane the other day, my oldest son was sort of misbehaving and causing trouble. I asked what was up. My youngest looked up and said, “Clarkie is tired and he’s having trouble making good decisions.” Then a couple days later, we were in the car and my youngest was upset and yelling. I asked what was going on and my oldest said, “I think Jonesie is overstimulated right now.” I say this not to celebrate our parenting but to say that I wish I could get better at having that kind of awareness — of myself and of what/why other people are doing.

–I looked out into my garage at some point this year and had this feeling that I was looking out into a graveyard. Strollers we don’t use anymore, a crib we won’t use again, toys they’ve outgrown. But this only has to be a sad scene if you didn’t use the shit out of the stuff when you had it, if the stroller doesn’t remind you all the wonderful time (and walks) you spent together, if you regret how not present you were for the periods the stuff all represents.

–I don’t know many smart people who watch cable television news. Just as I would get up and move away from someone who was smoking, when I see it on at the airport or a waiting room or whatever, I go wait somewhere else.

–Speaking of waiting rooms, sometimes something as jarring as a pandemic helps you see differently, but the idea that all the sick people wait in the same windowless room at the doctor’s office or urgent care or whatever is completely insane. Yet when I politely told the receptionist as urgent care earlier this year I was going to go sit on the bench outside (where the weather was wonderful), she — the person getting breathed on by sick people 40 hours a week — looked at me like I was the weird one.

–We did this course for Daily Stoic about money and as I built out the marketing/messaging, I was very sensitive about not wanting to have anything in it that seemed scammy or hustle culture-esque, I certainly didn’t want to present Stoicism has being a get-rich-quick kind of a thing. And the nine week course we wrote is very much the opposite of any of that vibe too. But you know what happened? People still accused me of doing exactly that…meanwhile, because I bent over backwards to not offend, we found that the marketing didn’t land with some people who otherwise would have bought it. Every time I pull my punches because I am worried somebody who already doesn’t like me won’t like me, I regret it.

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I mentioned Seneca above, and I’ll close with my favorite insight of his. “This is our big mistake,” he wrote, “to think we look forward to death. Most of death is already gone. Whatever time has passed is owned by death.” He’s right — we are dying every day. No day, once dead, can be revived. So the question, I try to round out each of my birthdays with is a quick thought of the fact that I’ve just lived/died XX years. Did I spend them well? Did I live it while I was in it?

I wish you the same.

Contributed by Ryan Holiday

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