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RyanHoliday.net - Meditations on strategy and life
Blog

24 Things I Wish I Had Done Sooner (or my biggest regrets)

Of all the things in life we don’t control, the past is the clearest. It already happened. It’s done. It’s set in stone. 

Perhaps we could have controlled and changed it, but the fact is, we didn’t. And now it is what it is, forever a was. 

For this reason, the Stoics were not big on regret. Neither am I. There’s no reason to whip yourself or be paralyzed by the “What Ifs” of life. Still, we can learn and grow, and in fact, we must. 

I once interviewed the peerless Dr. Edith Eger, Holocaust survivor and the author of one of my favorite books, The Choice. At the beginning of the podcast (you can listen here), I ask her about something I regretted, a relationship I had messed up. She looked at me and said she could give me a gift that would solve that guilt right now. “I give you a sentence,” she said, “One sentence—if I knew then what I know now, I would have done things differently.” That’s the end of that, she said. “Guilt is in the past, and the one thing you cannot change is the past.” 

So below are some things that, while I try not to regret, I do wish I had done differently or sooner or better. I think you might benefit from doing them sooner too…

-I look back at stuff I was so worked up about, things I fretted about, fought about, took personally, held onto, and now think, WHAT? If I had to go back and give a younger version of myself one word of advice it would be: “Relax.”

-This line from Bruce Springsteen captures, in retrospect, almost every argument or grudge I’ve held onto: We fought hard over nothin’ / We fought till nothin’ remained / I’ve carried that nothin’ for a long time. There are very few arguments I’ve had with my wife that I care that much about anymore.

-Writing Trust Me I’m Lying, I was 90% conscious about what other people might think and 10% following what was in my heart as an artist. The book I am most proud of is my book Conspiracy. The only parts of it I wish I could do differently are the few instances which, in retrospect, I was too conscious of what other people might think (particularly journalists). I’ve flipped the ratio by this point, but I wish I had gotten to that happier place sooner.

-I also should have fought harder on the title of my first book (I wanted to call it Confessions of a Media Manipulator, not Trust Me, I’m Lying), and I should have stuck to my guns about the prologue of Ego is the Enemy (I didn’t want to be in it, they wanted me in it). In creative disputes, the publisher/studio/investors/etc are not always wrong, but often they are. And even when they’re not, you have to remember, that whatever the decision, you have to live with it in a way they do not. I’ve regretted anytime I did not go with what was in my heart as an artist.

-As far as saving and investing money goes, there are so many different automatic transfers I should have set up earlier. I don’t know what my block was, but I stuck with doing things by hand for too long. Meanwhile, every account I have and did eventually set up scheduled transfers for–for my retirement, for my kids college, rainy day fund etc–constantly surprises me with how large the balances have been. Set it and forget it…the sooner you do it, the more you’ll have. You won’t regret compound interest. 

-Man, I ate like garbage for so long. When you’re young you can get away with it. Mostly, I just didn’t know any better. But when I started cutting stuff out? Soda, lots of carbs, most sugar, etc etc, I just felt incredible. I look at pictures of myself in my early twenties and even though I was a runner, I was just doughy. But mostly I think about how crappy I must have felt and not even knowing that I was feeling crappy or why I was feeling crappy. 

-There are many books I regret powering through, far fewer that I regret quitting. Life is too short to put up with bad writing—bad anything really. If the food sucks, don’t finish it. If the speaker is boring, get up and leave. If the party is no fun, go home. Stop powering through crap.

-Maybe it’s because I’m a 90s kid, but there’s a part of me that is instinctually a little bit skeptical of stuff that’s popular. If a book really pops or I hear a bunch of people tell me it’s a classic, part of me goes: “Well, I’m not going to read that!” Yet almost every time I have pushed through that, I’m more than pleasantly surprised: David McCollough’s biography of Truman is as good as everyone said it was. Malcolm Gladwell has sold millions of books for a reason. Erik Larson too. 

-People are waiting longer and longer to have kids. I wish we’d have done it earlier. Having kids at 29 has changed my life for the better in almost every single way…I’m glad I didn’t do it at 19. But there were a couple years there where I was ready, I was just telling myself I wasn’t. 

-I should have taken care of my skin more when I was younger. I should have worn sunscreen more. So should you. 

-Do I regret writing Trust Me I’m Lying? Like I said, regret is a tricky word. I wouldn’t be here if I hadn’t. It was the only first book I could have written. I don’t like all the ways it was received and used, but the main thing I wish is that I had been compelled to write it earlier–or more accurately, I wish I had been aware enough to question my life and my choices and my industry sooner. That might have actually made the book impossible, the stories less interesting, but I would have been a better person. I was just too blind, too caught up at being good at something to figure out it wasn’t a good thing to be good at. 

-I also distinctly remember as I sold that book to my publisher feeling so rushed. Like it had to come out right away, or I would miss the window, that the ideas wouldn’t hold true. Lol. It was a book about ‘fake news’ before that phrase even existed! I wasn’t late, I was early. I have since learned the importance of being patient, that taking your time, getting it right instead of first, is much less likely to be something that leads to regret than the alternative. 

-In the afterword of Courage is Calling, I tell the story about being asked to do something terrible at American Apparel. I didn’t do it, but I also didn’t take much of a stand about it. Why? I didn’t want to get fired. Only much later did it fully occur to me how ridiculous that is: A job where you have to be worried about getting fired for not wanting to do something wrong is not a job worth keeping!

-I’ve made a few very costly mistakes as an entrepreneur/business person. I noticed one trend: My wife was against them all at the time. It took me longer than it should have to notice this very illuminating signal. 

-I should have drawn better boundaries with my parents sooner. 

-It’s clear to me in retrospect that my desire for approval, for being seen, for being a part of something important or newsworthy or exciting, blinded me to the character of certain people I worked for. Of course, this was something those people understood and exploited in me and lots of other more vulnerable victims, but it’s still on me. You have to wake up to the ways that the wounds you experienced as a kid make you a mark, or create patterns in your life. It’s not your fault things happened to you, it is your fault if you don’t learn how to adjust accordingly.

-You know deep down that accomplishing things won’t make you happy, but I think I always fantasized that it would at least feel really good. I was so wrong. Hitting #1 for the first time as an author felt like…nothing. Being a “millionaire”…nothing. It’s a trick of evolution that drives us, and no one is immune from making this mistake. The mistake to really avoid though is the one that comes after the anti-climatic accomplishment, the one where you go: “Ah, it’s that I need to repeat this success, it’s that I didn’t get enough. More will do it.” You know this but then you act otherwise…

–In many interpersonal conflicts over the years I have come to rue acting quickly, responding emotionally or getting personal. I have never regretted taking my time, being firm but still understanding, and trying to give the other person a way out, a way to save face.

-With 36 years of data now, I can confidently say that I have never once lost my temper and afterwards said, “I’m so glad I did that.” 

-When I look back at my old writing, the main thing I regret is usually tone. Certainty does not age well. Life is complicated. Situations are nuanced. My books have gotten longer as I’ve gone on. I don’t think I’m being self-indulgent, I think I am being more fair, more compassionate, more truthful. 

-If you keep having to put down your horses, it’s because you’re riding them too hard. Unfortunately, I have lost a lot of otherwise great talent because I put too much on them. Just as athletes have to think about personal load management, coaches and GMs have to think about it for the whole team (and understand that every person has a different threshold).

-With the exception of the kind of people for whom no contact is a necessary strategy, I have never regretted the impulse to send someone a check-in text or call. And I have twice regretted neglecting the impulse to reply or reach out to my friends Seth and Bret, because I never got another chance, as I detailed here.

-Every repair or improvement I put off doing for my house, when necessity eventually came around and I had to do it anyway, I’ve thought: What did I put this off for? It cost the same and I deprived myself of the enjoyment in the interim. I’m trying to get better at not kicking cans down the road. 

-Most of all, I wish that I had enjoyed my work sooner. A few years ago, I was talking to a retired pro athlete and they were telling me how they regretted not enjoying the game as much when they played, that they hadn’t had more fun while they played. It wasn’t a particularly unique insight. I’ve heard it in a million speeches and interviews, but I was in the middle of a particularly hard writing project at the time and not having much fun. I remember thinking: I’ve made it. I’m a pro at this really cool job…why am I not enjoying myself? 

I’ve made a conscious effort since to consciously appreciate that I get to do this, to not let it turn into a grind or a slog. You don’t know if you’ll actually make it to publishing a book–you could die, the book could die–so why not have fun while you’re doing it? Why not make each day the win, the joy, the experience as opposed to the end result? 

As Marcus Aurelius said, it’s insane to tie your wellbeing to things outside of your control. Success, mastery, sanity, Marcus writes, comes from tying your wellbeing “to your own actions.” If you did your best, if you gave it your all, if you acted with your best judgment—you’ve won.

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July 25, 2023by Ryan Holiday
Blog

It Always Takes Longer Than You Expect (Even When You Take This Into Account)

When I finished my first book, I hired a publicist.

I was 25.

It cost $20,000 and was, to that point, the most money I had ever spent in my life.

As part of the scope of work, they had me put together a list of my top twenty or so media targets—–what I thought I had a reasonable shot of getting and what would be good platforms with the book.

Pretty much none of those opportunities happened. It wasn’t the publicist’s fault–they did a good job. It was that I had been preposterously unrealistic. You have these high hopes, you think this is my shot and of course, it turns out that the world has other plans.

You’re going to get everything you want when you want it?

GTFO.

If you really want something, you better be ready to hurry up and wait.

That was especially true for me then, since I was a kid, already getting to publish my first book far earlier than most people get to dream of.

All of this came back to me as I was flying home from New York from the launch of The Daily Dad. I had just done The Daily Show, CBS This Morning, and a daytime talk show in the span of a week. Which meant that 11 years and 14 books later, I was finally making a serious dent in the list that I had made back then. It had sometimes seemed like slow going, but then in the span of just a few days I had crossed off the best and hardest-to-get outlets.

There is this law called Hofstadter’s Law which says it always takes longer than you think it’s going to take. Even when you think it’s going to take a long time. Even when you take Hofstadter’s Law into account.

I started blogging in 2005. My first book came out in 2012. The Obstacle is the Way came out in 2014…and took six years for it to hit any bestseller list. I didn’t hit the New York Times Bestseller list until 2019, on my 13th book.

If you had told me that’s how long it would have taken, I might have been able to endure it. But Tom Petty was wrong. Waiting is not the hardest part. It’s the not knowing when the waiting is going to end.

But that’s life. That’s how success works.

It takes longer than you want. It takes longer than you expect. It takes longer than you’re willing to wait.

In any case, it takes however long it takes.

Talk to parents who had trouble conceiving. Talk to people waiting for their immigration papers to come through. Talk to scientists taking a drug through clinical trials and regulatory approvals.

This isn’t to say there isn’t good news along the way, that there aren’t trending signs and little hits that keep you going. There will be. I’m not sure I would have kept going if there hadn’t been.

But it’s going to take a while to get what you want.

Interminably longer.

It just will.

I thought opening my bookstore would take a few months…COVID delayed it a full year.

On February 25th, 138AD, the emperor Hadrian adopted a 51-year-old man named Antoninus Pius on the condition that he in turn adopt Marcus Aurelius. Given life-expectancy statistics of the time, Hadrian figured Marcus would be at the helm in three or four years, max. All was well, except Antoninus lived and ruled…for twenty three years.

In 1971, at the age of 26, Ed Catmull defined his dream: to make the first computer-animated feature film. He accomplished it when Toy Story was released…twenty-four years later.

The writer Steven Pressfield published his first novel, The Legend of Bagger Vance, in 1996…after twenty-seven years of trying to get a novel published.

I thought it was a matter of hiring the right publicist and having a good product. How entitled and naive. If that was all it took…there aren’t enough media slots in the world to satisfy all the people who satisfy that criteria.

No, I had to go out and earn my spot many times over. I had to prove that I had great stuff. I had to demonstrate that I had an audience. I had to prove that I wasn’t going away. I had to prove I was good on camera. I probably even had to reassure some skeptics or critics who I pissed off with my first book.

That took time, a lot of time. A decade!

We conceived and raised a six year old in less time than it took me to earn my spot.

Intersecting with Hofstadter’s Law. is Murphy’s Law. Things go wrong. There are delays. There are mistakes. Communication breaks down. The market shifts. Lucy yanks the football away right as you’re about to make contact. The outfielder robs you of a home run. They sell out right before your turn in line.

Are there exceptions to these rules? Are there people who get it all faster, quicker? Are there times when all the greenlights line up?

Maybe.

Sure.

OK.

But you are probably not that person. You are probably not on that path, and that will not be your fate.

Which means you’re going to have to buckle up.

You’re going to have to learn patience, humility, perseverance.

You’re going to have to find other ways to measure your progress and your success.

You’re going to have to put that energy into getting better, into understanding the game better.

You’re going to have to wait, and then wait some more…and then wait more after that.

 

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July 11, 2023by Ryan Holiday
Blog

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. 

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).

–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.

–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. 

–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. 

–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. 

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.

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June 16, 2023by Ryan Holiday
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