34 Mistakes on the Way to 34 Years Old

The great Hyman Rickover used to say that success teaches nothing, only failure is educational. I don’t know if that’s completely true, but I will say that my own short time on this planet has had its share of teachable moments rooted in mistakes, usually of my own making. 

For going on ten years now, I have done a piece on my birthday around the idea of lessons learned, either from preceding twelve months or over the course of my life up to that point. This year, at 34, I thought I’d focus exclusively on my failures and what they’ve taught me. And I can assure you, ten years into my career as a published author, ten years into entrepreneurship, and going on fifteen years with my now wife, five years into having a family, I have made lots of mistakes. 

If I have been successful at all, it’s been through learning from these mistakes (painfully) and by benefiting from the mistakes of others (a less painful way to learn). With that, I share these things I learned the hard way…or continue to struggle with.

Also check out my pieces from 33, 32, 31, and however else long I have been writing this annual piece.

[*] If I had to go back and give a younger version of myself one word of advice it would be: “Relax.” It’s almost preposterous how intensely, passionately, anxiously I was worked up about certain things—how seriously I took things that, in retrospect, matter so little that I don’t even remember them. Of course, earnestness, commitment, and ambition are virtues (more so than their opposites, anyway) but taken too far they become liabilities, to happiness and objectivity most of all. 

[*] When I look back on my own writing, the stuff that makes me cringe isn’t necessarily even stuff I was wrong about. What disturbs me is the certainty. I thought I knew, but I didn’t really know. I wasn’t even close to knowing. Ego never ages well, even if it was correct in a narrow instance. As I get older, I’d like to think I am more open to nuance, less prone to black and white statements, and humbler in how I come off. 

[*] My first book was an exposé about media manipulation and fake news. I was convinced that if it didn’t come out right away, I’d get scooped, or miss my window of opportunity. This is what I was anxiously insisting to my publisher…in 2011! I thought I was out of time, in fact I was probably a half decade early (it’s second best sales week was in 2017!). Stuff is better when you don’t rush. If you think you have to rush, you’re either whipping yourself for no reason, or pursuing something too ephemeral to begin with. 

[*] 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 they often are. And even when they’re not, you have to remember, that whatever the decision, you have to live with it in a way that they do not. I’ve regretted anytime I did not go with 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 should have just played it exactly how I felt like playing it. Again, do what’s in your heart. 

[*] Why did I move to New York? I guess I thought I was supposed to. It wasn’t a mistake exactly, but it’s definitely not the right place for me to live—not permanently anyway. Life is too short to live somewhere that doesn’t make you happy

[*] As I explained on reddit a while back, I wish I had gotten married and had kids earlier. I wasn’t really late for my age bracket (29 and 30), but when I look back at the last few years—including even the pandemic—I’m not sure what I waited for. Elizabeth Bruenig’s New York Times piece on having kids at 25 expressed this better than I can, but I think I was worried I wasn’t ready, but the truth is you’re never ready. You learn by doing. You’re only putting off the thing that will provide you the most meaning and joy in your life. 

[*] In 2013, I started a business with a partner that my wife warned me against working with. I remember explaining to her why she was wrong and that I couldn’t possibly not do this because of some vague gut instinct of hers. It would turn out to share a commonality with almost all my mistakes and regrets: Not listening to my wife from the beginning. Anyway, this business turned into a nightmare, and it turned out that this partner was not someone I should have worked with. Who knew?

[*] Why have I so often expected differently of people who have already shown me who they are? Character is fate. Character is fate. 

[*] I bought my first bitcoin somewhere under $500. I’m still here working for a living, so that should tell you all you need to know about what kind of investor/gambler I am. It’s not that I’m afraid of risks, it’s that I have trouble putting the right amount behind risks when I take them. 

[*] Most of my regrets—things I wish I’d done, things I wish I’d said, stands I wish I’d taken—have one thing in common: Fear. We worry about what will happen if… But Marcus Aurelius has the answer: “You’ll meet tomorrow with the same weapons you have now.” I should have quit certain jobs sooner, I should have come out and said what I thought more clearly, I should have believed that I’d figure out how to get through it, even if things went wrong. 

[*] If you’d asked me in January 2020, if I could survive—professionally and personally—with no travel, no events, no dinners out, no get-togethers, I’d have said absolutely not. As it turns out, the last fifteen months have been not only rewarding but immensely productive in every sense. Why? Because clearly, those things I thought I had to do, I didn’t not actually have to do. I’m actually better and happier when I don’t. 

[*] That’s another lesson learned the hard way: Don’t say “Maybe” when you really want to say “no.” Just say no. The only person making a big deal about it is you. Just say no. How many events/meetings/wastes of time are you going to agree to and then regret before you learn this?

[*] It was sweetly painful over the fifteen months of the pandemic to get more than a year of consecutive bedtimes with my kids, to get an uninterrupted streak of morning walks and afternoons in the pool. It was sweet because I loved every minute of it. It was painful because I had chosen not to have this before, I had so often chosen the other things, the less important things we throw into that bucket of “work responsibilities.” It is intimidating to contemplate how easily it will be to slip back into the old way of doing things too. 

[*] 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. 

[*] Of all the people (or types of people) I’ve had strong negative opinions or judgements about from afar, only few turned out to be even close to as obnoxious or stupid or awful as I thought. In fact, more often than not, I ended up liking them quite a bit. The world works better when we get to know each other. 

[*] 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.”

[*] There have been a lot of problems I could have solved earlier if I’d been more willing to seek out experts on the topic. It’s funny, that’s clearly what sports teams and military leaders and politicians were doing when they emailed me after having read one of my books. How much growth have I left on the table, how much pain have I needlessly endured by not picking up the phone myself?

[*] Somewhat less related but still related: It’s good to be frugal, but if you don’t spend your money to make your life or your relationships or your work easier, what exactly are you going to spend it on? Actually, what I’ve found is that it is very expensive to be cheap. You just pay for it in the form of a frustrated spouse or a stressful life or with shit that never works and you have to end up replacing a bunch of times anyway. Don’t grit your teeth and bear it. You can only get so far white knuckling things. Remove the friction, improve the system—and money (not a lot usually) should help you do that. I thought of this just the other day as I reached for a Sharpie that was nearly dry, that I had clearly put back in the drawer in my desk for like the fifth time instead of buying a new one (and there was still a part of me that hated throwing it away). Replace your dull tools! Upgrade your workshop! Find quality help! You are expending energy in the wrong places.  

[*] There’s a great Kurt Vonnegut story about marriage. He realized, fighting one day with his wife, that what they were really both saying was, “You’re not enough people.” You can only expect so much from a person. They can only deliver so much. When I think of relationships that have not worked out, or near breaking points of others, at the root of them was that: Expecting them to be too many people. 

[*] With 34 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.” A corollary to this: I don’t recall the last time I spent time on social media and felt better after either. A corollary to this corollary: I regret almost every time I have expressed an opinion on social media. I don’t necessarily regret the opinion, I regret the lapse in self-control that culminated with me shouting into the void. 

[*] 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. 

[*] Needing things to be a certain way has continually prevented me from enjoying them as they are. 

[*] I’ve been lucky enough to sit across the table, literally, from some incredible people. Astronauts, musicians, athletes, entrepreneurs, politicians. The mistake I’ve made far too many times? Talking more than I listened. You get nervous, you want to impress, so you open your mouth. I tend to forget: Two ears, one mouth for a reason. In thirty years, are you going to want to look back on this chance encounter and think about what you said, or what you got them to say? So shut up!   

[*] I’ve done it so many times it’s now embarrassing but this is a pattern: I have an opinion or a frustration or a need that I don’t speak up about. It builds. By the time it finally does come to a head, the situation is past resolving. I’ve lost agents because of this, employees because of this, friends because of this. You have to speak to be heard. You can’t wait. You can’t let resentments pile up. Communication is not conflict. It preempts and prevents conflict. Everytime I forget this, it has cost me. 

[*] 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).

[*] Good enough is usually good enough…except when it’s not. When I was in high school, I ran a 5:04 mile in one of my last races senior year. I remember thinking, “Well, that’s pretty good!” No part of me (nor did anyone around me) pressed to see if I could shave those few extra seconds off. I was so close! Why did I settle? Only later did I come to regret it…and of course, every day that passed made it more difficult to ever get back there. In my mid-twenties, I did finally break five minutes but mostly as a reminder to myself: Don’t be satisfied with getting close enough. Go all the way. “Almosts” are the most painful regrets. Especially almosts where you didn’t do your best. 

[*] My anxiety has brought about exactly the kind of stress or frustration I was hoping to avoid infinitely more times than it has prevented it from happening. Don’t ride out to meet your ruin...

[*] Epictetus says, “You can’t learn that which you think you already know.” Evaluating my response to the early warning signs of the pandemic, or why I missed taking advantage of certain investing opportunities (see crypto and housing mistakes above, among others), invariably it was my certainty or smugness that blocked me from seeing what a more open, curious person would have seen. 

[*] Just because someone you don’t respect holds a certain position, doesn’t mean the position is incorrect. And vice versa. One of the toughest things to do in this life is to think for yourself, to come up with your own judgements on issues, stripped of bias or preconceived notions. Almost every time I have looked for a shortcut—whenever I have not done the work—I’ve come to regret my views. 

[*] I grew up in a mostly conservative household, one that internalized a lot of that Reagan-esque suspicion of governing. But of course, this suspicion—especially when widely held—contributes to poor governance. Government is not a thing, at least in America. We are the government, just as much as we are traffic, we are culture, we are media. A line I heard that changed my worldview: “Government is simply the name we give to the things we choose to do together.” I wasted a lot of time seeing politics as something you consume, when of course politics—going back to Aristotle—is always something we do. 

[*] Related, if success is not making your life easier—or at least, providing you more autonomy—what good is it? This was learned the hard way in our house. You’re not a beast of burden. Don’t treat yourself like one!

[*] This line from 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

[*] This idea of “Fuck Yes…or No” is far too simple and has caused me quite a lot of grief. Dropping out of college, I was maybe 51/49 on it. Leaving my corporate job to become a writer, maybe 60/40. Right now I’m about to do something big that I am both excited and terrified about. The point is: The certainty comes later. The truly life-changing decisions are never simple. If I had only ever done things I was absolutely certain about, I’d have missed out on experiences I love. Conversely, I regret a good chunk of my “Fuck yes’s” because I was caught up in a fit of passion or bias. The whole point of risk is that you don’t know.


So here I am at 34 with many more mistakes than these to my name. But the key to progress, I have found, is relatively simple. It’s not to avoid error…but to avoid making the same error more than once. Or, more realistically, fewer times than you might ordinarily be inclined to.

Because the only way to compound an error, to add to the suffering caused by its consequences, is to refuse to see them. To refuse to heed their lessons. 

And so, if I am lucky enough to make it another year, I hope to write to you again in 2022, a tad wiser and as always, grateful for the time and experiences I’ve been lucky enough to have. Even the not so glamorous ones. 

P.S. Seneca said a lot of people don’t have any proof for their age but a number of years. To avoid that mistake, I carry a coin that says “Memento Mori,” which is Latin for ”remember you will die.” On the back, it has one of my favorite quotes from Marcus Aurelius: “You could leave life right now.” That is how I try to go through life—not taking time for granted, not leaving anything undone, not wasting time on making the same mistake twice, not ever thinking tomorrow is a given. If you want to create more priority and appreciation in your life, get a Memento Mori coin and carry it in your pocket everywhere you go.

Written by Ryan Holiday
Ryan Holiday is the bestselling author of Trust Me, I’m Lying, The Obstacle Is The Way, Ego Is The Enemy, and other books about marketing, culture, and the human condition. His work has been translated into thirty languages and has appeared everywhere from the Columbia Journalism Review to Fast Company. His company, Brass Check, has advised companies such as Google, TASER, and Complex, as well as Grammy Award winning musicians and some of the biggest authors in the world. He lives in Austin, Texas.