38 (Or So) Lessons On The Way To 38
There is something melancholic about birthdays. I’m not the first to notice this. Another year has gone by, a wise man once said, and we can’t help but note how little we’ve grown. “No matter how desperate we are that someday a better self will emerge,” he said, “with each flicker of the candles on the cake, we know it’s not to be, that for the rest of our sad, wretched pathetic lives…this is who we are to the bitter end…..inevitably, irrevocably. Happy birthday? No such thing.”
Marcus Aurelius?
Not quite, although Jerry Seinfeld is now a Marcus Aurelius fan, I am happy to report.
I’ve always loved that scene from Seinfeld (which happens when George tells Jerry to stop being his funny self). I’ve related to it on some birthdays but on others, like today, I don’t. I find I have grown quite a bit during most of my trips around the sun, to the point where I hardly recognize the person who first started these posts a decade ago (you can see my birthday posts for 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, and 37 here). I feel like I have changed a lot in the last year and that a better self has and is emerging.
Anyway, as always, here are 38 things I’ve learned in 38 years.
– I put up my first website a few days after I graduated from high school and I’ve been writing more or less every day since. It hit me recently that that means I’ve been doing this for two decades. And you know what? I’m just starting to feel like I’m getting the hang of it. If you told me twenty years ago that that’s how long real confidence would take, I don’t know if I could have handled it.
– This reminds me of an old Zen story. A student approaches a master: How long will it take? Ten years, he says. What if I work really hard? the student asks. Fifteen years, the teacher says. No, you don’t understand, the student says, I am in a hurry. Ok, then, the teacher replies, twenty years. Mastery is not something you can rush. Nor can you rush the opportunities you think you need. When I look back, that’s one thing I am struck by, how lucky I am that most of my biggest opportunities came later. If I had gotten them when I thought I wanted them, you know what would have happened? I would have blown them because I wasn’t ready.
– I’ve been a runner a long time and as I’ve talked about before, the one thing you get asked all the time as a runner is “Are you training for a marathon?” My answer has always been, “No, this is the marathon.” That is, the day-to-dayness, the doing it for no reason other than because, is the real challenge I’m tackling.
– Along those lines…I love the phrase from the college basketball coach Buzz Williams, be an every day guy. “You have to be Every Day,” he says. “There’s no, ‘We’ll do it tomorrow.’ No. We’re doing it today…You gotta do it every day. And if you can’t do it every day, then you’re going to struggle because it is every day.” I try to be an every day writer. An every day runner. An every day father. An every day spouse.
– Anyway, the last couple of months I have been training a little—I want to do the 26 miles from Marathon to Athens this summer. I haven’t done it yet, so I can’t be certain about anything, but I will say after looking at a lot of the training regimes, I haven’t had to change much. Which was my point all along: If you stay ready, you don’t have to get ready.
– A couple of years ago, my wife suggested I read this book called Fair Play by Eve Rodsky. It’s a great book and will definitely improve your marriage. The funny thing is I think the concept of mental load is equally essential in the workplace. If I give someone a task, I should be able to give them effectively all of it—meaning I shouldn’t have to worry about it or them, they should be updating and keeping me informed, if they run into problems they should come to me with the solutions etc. People who can manage themselves go far in life. People who can’t go nowhere.
– Again, it’s always shocking (and humbling) to discover just how hard it is to get good at something. I’ve been doing The Daily Stoic Podcast since 2018 and the long-form interviews since 2020. We’ve done hundreds of millions of downloads and it did well from the jump—so I think I can say people have always liked it—and yet I had a feeling doing an interview last week (approximately my 550th) that I was just getting the hang of it. But you know what? That sensation—that feeling of really being on the inside of something, finally, the clicking that happens after all that work? There is really nothing like it.
– Why am I rushing my kids? I’m rushing them (and me) where exactly? To the end of their childhood…precisely the thing I will soon enough miss desperately. What will I do with this time I am trying to save, what will I do with this time I get to myself after they go to bed? Watch Netflix?
– ‘Rich’ is how much you see your kids, I’ve been saying at Daily Dad. ‘Power’ is how much say you have over your own schedule.
-When I lived in New York, someone told me, “The thing you have to understand about New York is that things just cost what they cost.” This reminds me of Seneca’s famous line about “paying the taxes of life, gladly.” Things cost what they cost–travel costs delays, fame costs critics, kids cost noise, etc etc–and the sooner you learn to pay these taxes gladly, the happier you will be.
– You are what you won’t do for money. Your priorities and principles are demonstrated by what you say no to.
– I had the excruciating experience last year of updating The Obstacle is the Way for the 10th anniversary edition. Honestly, I would not wish re-reading (especially into a microphone for an audiobook) a book you wrote in your twenties on anyone. And again, that’s a book that has been loved by millions of people! There was so much I had to fix. So much I have gotten better at.
-That being said, if I envy anything about that younger version of myself, it’s that I didn’t have much of the self-consciousness I have now. I was freer. Things were simpler. I didn’t know what I didn’t know. I didn’t have the taste to properly judge or understand what I was doing. There is something to be said for that.
– There’s a line in The Great Gatsby where Jay asks Nick Carraway if he’d like to do a little job for him, a way to make some money on the side. Nick declines and says later, that had he answered differently, perhaps the whole course of his life might have been different. When I look at some of the people I used to work for or knew and I see where they ended up, I often think of how had I made even a few different decisions, I could have ended up on a very different trajectory.
– By very different, I mean very different. For instance, it occurs to me now that I was probably being vetted for something by Peter Thiel (I too had written a memoir he’d liked…). I could have gone to Washington in 2017. I’d like to think I was always just a little too independent to get fully sucked into anyone’s orbit. But maybe I just got lucky. The point is: Each of our choices adds up to who we are going to turn out to be.
– I am very ambitious as a writer. I no longer have any ambitions as an author. I’m not aiming at lists. I don’t think about deals. I rarely even look at sales numbers. I have stopped tracking how other people’s books are doing. What I’m saying is that I have locked into process and tuned out publishing. The funny thing is that my results have gotten better the more I have flipped this ratio. I have also gotten much more content.
– The people who are most successful in life, who accomplish the most, who dominate their professions—they don’t care that much about winning. They are obsessed, instead, with improving at the thing they love doing.
– Most labels are unhelpful, too—filmmaker, writer, investor, entrepreneur, executive. These are nouns. But what gets someone to that position? Verbs. Forget the nouns. Focus on the verbs.
– I don’t know what AI will mean or do over the long term. What I can say is that I have gotten a lot out of it. I mean that practically (for instance, it’s helped me fill out graphics and illustrations in my talks and in the Daily Stoic videos), but I also mean personally. As in, in figuring out how to use a new technology, I feel invigorated and improved. I’ve read books about it. Listened to podcasts about it. We talk about it in our weekly staff meetings. I’ve taught my kids about it. It is good to figure new things out. It is good to be a beginner at something again.
– You know what AI isn’t going to replace? Actually, what it will necessitate even more? A good bullshit detector. It may well turn out that the most valuable thing a person can have in this new era is a broad liberal arts education and a strong dose of common sense.
– As I waited at my gate at the airport for an extra hour or so the other day, it occurred to me: This is what anxiety steals from you. Or rather, this is what we steal from ourselves when we are anxious. I could have been at home with my kids, but I had let the remote possibility of traffic override my ability to do that. It occurs to me this is true not just for time, but for the present moments it takes from me and for the conflict it sucks me into. Anxiety is expensive.
– Related…I had an incredible conversation with Dr. Becky Kennedy that every parent—or really just any human—needs to listen to. (If you haven’t read her book, Good Inside, yet…what are you doing?!). In the episode, she defined anxiety as “some amount of uncertainty coupled with our underestimation of our ability to cope.” It reminded me of what Marcus Aurelius writes in Meditations: “Consider all that you’ve gone through, all that you’ve survived.” If these last five years haven’t given you a sense of your ability to cope…I don’t know what will.
– The less news I consume, the more informed I seem to get. “Read not the Times,” Thoreau wrote. “Read the Eternities.” Read old books. Read philosophy. Read history. Read biographies. Study psychology. Study the patterns of history. Read The Great Influenza to be informed about pandemics. Read All The King’s Men and It Can’t Happen Here to be informed about the demagogues of this moment. Read The Moviegoer to understand your listless teenager. Read The Years of Lyndon Johnson to study power and ambition. Read the Stoics. And definitely, definitely, definitely, read Zweig’s biography of Montaigne (which I talk about here).
– 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.”
– Conversely, I have never taken a walk without thinking, after, “I am so glad I did that.”
– I am always glad I jumped in the water. Even when—perhaps especially when—it’s really, really cold.
– It’s also rare that I have regretted asking for help. Sure, sometimes it can be more trouble than it’s worth, but at least I got some practice doing a thing that’s hard–being vulnerable, putting myself out there, connecting with someone.
– At least once a week, someone asks us if we’re going to open a second location of the bookstore. And at least three struggling bookstores have reached out about us acquiring them. The answer is usually a polite “no.” Sometimes it’s “Are you insane?” “Do Not Go Past The Mark You Aimed For” is one of the most important laws in The 48 Laws of Power. Know when you’ve won. Know what enough is. Know your limits.
– A couple of months ago I was working on something in a car from JFK to Manhattan. The car bounced and the Sharpie I was using made a little mark on the door. It was stupid for me to have been using a permanent marker in a moving car, but obviously, the driver didn’t see and I could have just gotten away with it. It was weird how much I had to work myself up in my head to tell the driver when I got out. “If you have to charge me for it, I understand,” I said. It was an uncomfortable little conversation, but I’m glad I had it. I honestly don’t even know if they ended up charging my card for anything, but if they did it was worth it. Calling fouls on yourself is not fun, but it’s a habit you need to build.
– A day or two before my ill-fated talk at the Naval Academy in April, as I was weighing whether I was going to speak up about the book bannings on campus in my remarks, I emailed someone who I really admire. They are a USNA graduate and someone who has served their country for many years with quiet, honorable leadership. I said, hey, I’m thinking about saying something but I don’t want to cause trouble for anyone and I definitely don’t want to get a good person fired (especially if they end up replaced by someone worse.) This is what they wrote back:
“I think you should just speak directly about what you truly believe. That is always a path.”
– I will say, in these deranged times we live in, one thing I have continually taken solace and inspiration from is when smart people or people whose work I respect, take a little time out of their day to say “Hey, I’m not OK with what’s happening,” or use their platform to reiterate basic values like decency, honesty, justice or kindness. Maybe this doesn’t feel like much to them or to you, but we are social creatures. We look around us, we look above and below us and we make our choices based on what we see other people doing. Deciding to stay silent breeds silence and complicity. Speaking up breeds courage and virtue.
– After a flight into LAX and a long drive to Palm Springs, I finally got my family into our hotel room. Then I started changing to go for a run. Are you out of your mind, my wife said. It was 4pm and 104 degrees out. “That’s not self-discipline,” she said, “that’s self-harm.” She’s probably right. It’s a fine line…and sometimes my problem is too much discipline, not too little.
– Something I’ve started saying all the time to employees: “Let’s start the clock on this.” If the bindery says it’ll take six weeks to make another run of the leatherbound Daily Stoic, I want to “start the clock” as soon as possible. I don’t want to add days or weeks by being indecisive, procrastinating, or slow to process an invoice. We don’t control how long others take, but we do control whether we waste time on our end. The project will take six months? Start the clock. You’re going to need a reply from someone else? Start the clock (send the email). Getting the two quotes from vendors will take a while? Start the clock (request it). It’s going to take 40 years for your retirement accounts to compound with enough interest to retire? Start the clock (by making the deposits). It’s going to take 10,000 hours to master something? Start the clock (by doing the work and the study).
– Whenever I go and do something with my kids (like a trip or an activity or an errand) I try to tell myself: Success is wanting to do this again. That is to say, it’s not about accomplishing anything or checking off certain boxes—did we see all the sights, did we get what we needed to get, did we arrive on time or whatever—it’s ultimately whether we got along well enough, enjoyed the experience enough, that at some point in the future they’ll say: “Hey, remember when we went to that concert? Can we do that again?” or “Oh, you’re driving across town to grab that thing? Can I come?”
– For a long time, my writing habit was all-or-nothing—either I wrote a lot of words or I didn’t. Over time, I’ve lowered the stakes: now the question is simply, “Did I make a positive contribution to my writing today?” Sometimes that means writing, sometimes editing, adding, deleting. Sometimes I’m home and it’s in my office, sometimes I’m on the road and it’s on a plane or in a hotel room. Sometimes it’s a big contribution, sometimes it’s a little contribution. The line from Zeno was that big things are realized by small steps. That’s what I try to remind myself: every day, just make a positive contribution.
– It’s important to realize that most of the time people are not playing three-dimensional chess. Most of the time they are slaves to their emotions and impulses. Most of the time they have no idea what they’re doing at all. I’ve been amazed at the degree to which smart people I know manage to convince themselves that what they’re seeing is part of some thought-out plan and thus rationalize what is obviously insane or explain away what would be otherwise deeply alarming. We forget Hanlon’s Razor at our peril.
– When we were working on What You’re Made For, George Raveling—who I think is one of the most remarkable people of the 20th century—said that when he wakes up in the morning, as he puts his feet on the floor but before he stands up, he says to himself, “George, you’ve got two choices today. You can be happy or very happy. Which will it be?” (Voltaire put it another way I love: The most important decision you make is to be in a good mood.)
– The basic most essential of responsibilities: Do not let assholes turn you into an asshole. To not let the cruelty harden you, to not let stupidity make you bitter, to not let outrage pull you down to its level, to not let the sonsofbitches turn me into a sonuvabitch. It is a timeless struggle, as Zweig put it in 1942 about Montaigne in 1562, saying that we must “remain human in an inhuman time.”
– 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.
—
I feel very lucky not just to be 38 but to be here at 38. I have been blessed in so many ways. I have been able to live so much. I’m good. If I get to do another one of these a year from now, I’ll be grateful, but it will be a bonus.
I spoke at a biohacking conference a few weeks ago where the stated purpose was all about living well into your hundreds. I teased them a little. Why? I said. So you can spend more time on your phone? So you can accumulate more stuff? So you can check more boxes off your to-do list? It’s not like these were researchers trying to cure cancer or engineers trying to bring clean water to communities that don’t have it, or scientists trying to solve the climate crisis—people whose services the world desperately needs…yet we all think we need to, deserve to, live forever.
I hope I get a lot more time with my kids and my spouse and my work, I do. But I also understand that I’ve gotten a lot of time on this already—and that too much of it I wasted or didn’t appreciate in the moment.
These 38 years have been good to me, better perhaps than could be reasonably expected. I think I’ve used them well. I hope you do, too.
