Life Advice from Ryan Holiday
Few people use their birthday as an opportunity to give everyone else a gift. This is one of the many reasons I appreciate Ryan Holiday. Every year, he writes a birthday article sharing life advice and important realizations. You may scoff at life lessons offered by a man in his mid 30s, but Holiday has accomplished more in three decades than most do in seven or eight.
These annual articles are one of the best collections of life lessons I've ever encountered—and I’m a connoisseur of life advice. It’s a treasure trove from one of the most prolific writers of our time. Now you have them in a central location to revisit as often as you please.
I pulled out some of my favorite points from each year. If you enjoy them, go buy some of Ryan's books.
Age 36
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.
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.
There is a list of a thousand tiny, absurd, weird things that really are great. 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.
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.
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.
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.
Age 35
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.
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.
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.
Most people would rather argue about reality than do something about reality.
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?
Age 34
[*] 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.
[*] Needing things to be a certain way has continually prevented me from enjoying them as they are.
[*] 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.
[*] 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?
[*] 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. [Comment from Joe: This is exactly why I’m a proponent of compulsory national service.]
[*] 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.
Age 33
General James Mattis points out that if you haven’t read widely, you are functionally illiterate. That’s a great term, and one I wish I’d heard earlier.
When someone tells you something is wrong, they’re almost always right. When someone tells you how to fix it, they’re almost always wrong.
A few years ago I was exploring a book project with Lance Armstrong and he showed me some of the texts people had sent him when his world came crashing down. “Some people lean in when their friends take heat,” he said, “some people lean away.” I decided I wanted to be a lean-in type, even if I didn’t always agree, even if it was their fault.
Steve Kamb told me that the best and most polite excuse is just to say you have a rule. “I have a rule that I don’t decide on the phone.” “I have a rule that I don’t accept gifts.” “I have a rule that I don’t speak for free anymore.” “I have a rule that I am home for bath time with the kids every night.” People respect rules, and they accept that it’s not you rejecting the [offer, request, demand, opportunity] but that the rule allows you no choice.
“No man steps in the same river twice.” That’s Heraclitus. Thus the re-reading. The books are the same, but we’ve changed, the world has changed. So it goes for movies, walking your college campus or a Civil War battlefield, and so many of the things we do once and think we “got.”
“Your last book won’t write your next one.” Don’t remember who said it, but it’s true for writing and for all professions. You are constantly starting at zero. Every sale is a new sale. Every season is a new season. Every fight is a new fight. If you think your past success guarantees you anything, you’re in for a rude awakening. In fact, someone has already started to beat you.
Before we had kids, I was in the pool with my wife. “Do you want to do laps?” I said. “Should we fill up the rafts?” “Here help me dump out the filter.” There was a bunch of that from me. “You know you can just be in the pool,” she said. That thought had not occurred to me. Still, it rarely does. So I have to be intentional about it.
Age 32
Jerry Seinfeld once talked about how ‘quality time’ with your kids is nonsense. Time is time. In fact, he said garbage time — eating cereal together late at night, laying around on the couch — is actually the best time. I think that’s true of life as a whole. Forget chasing experiences. It’s all wonderful, if you so choose.
There is something special about re-reading, but something even better about listening to a song on repeat — like hundreds of times. Especially from an artist that towers and crashes (Bon Iver, Bruce Springstreen, The National). So many of my best insights or creative sessions have come from the state that helps induce.
Political correctness is dangerous, but so is being cruel and insensitive. People’s feelings do matter and the kinder we are, the better we all feel.
You gotta know what you want your day to look like. That’s how you build a life.
You need a philosophy and you need to write it down. And re-write it and go over it regularly. Life is too hard (and too complicated) to try to wing it and expect to do the right thing.
It’s always worth thinking about the things you believed very strongly and were now quite obviously wrong about. Because only an idiot would not see that that’s going to happen again and again.
Age 31
It always takes longer than you expect and this is a good thing because you’re growing and improving every day and thus are more prepared for whatever happens when it does happen.
It takes more self-discipline to say no than yes.
Age 30
Quit Dicking Around — The books I’ve been fortunate enough to write were not the result of mad sprints of intensity. I get up every day and work on them. One right after another. While I’m waiting for one to come back from the printer, I am hard at work on the next one. Basically, I’m not dicking around. 30 years is so much time. One year is so much time. Wake up every day and do a little more. Dick around a little less. See what happens.
Keep a Journal — Not for looking backward, but to force you to think about what you’re doing now. I should have done this earlier.
Have a Philosophy — Pete Carroll talks about his turning point as a coach, when he realized he was just winging it. So he stopped and wrote down his entire coaching philosophy. Now he has something to measure himself against. Well, what’s yours? Don’t wing it through your 20s. Focus. Live by something.
Exercise Every Single Day — Don’t let yourself get to the point where you feel like some day in the future you’d like to lose weight or be in shape. Be in shape. Make exercise part of your job, part of your duties as a human being. Let endorphins be something you give yourself every day.
Be Prematurely Old — When I hear someone say they are ‘adulting’ like it’s a funny exception to how they normally are, I think, “There is a person who is going to wake up one day and think about where all the years went.” But when you hear someone is an “old soul,” you think, “Man, they have their shit together.” Young people are stupid. Old people are wise. Which do you want to be?
Don’t Waste Time Being Offended — God, how much precious energy is spilled fighting online, shouting in other people’s faces. A well-ordered person never thinks, “How dare they?” because they don’t have those kind of expectations of other people and they don’t think their own feelings are other people’s problem.
Drive across the United States — No one should die before they have done this.
Design The Ideal Day — So many people have big goals for the future. I think it’s better to know what your perfect day looks like. Then you can ask yourself with each opportunity and choice: Is this getting me closer or further away? I know my ideal day and more importantly, I know when I have gotten too far from it. Life is too short to not live the way you want.
Age 29
“Sleep when you’re dead,” we say. Like it’s some badge of honor how little time we allot to it. I think it’s time to call bullshit. Because the myth is destructive. The benefits minimal. And the claims are dishonest. As Arthur Schopenhauer put it “Sleep is the interest we have to pay on the capital which is called in at death; and the higher the rate of interest and the more regularly it is paid, the further the date of redemption is postponed.”
Bismarck famously said that “fools say they learn by experience. I prefer to profit by other people’s experience.” Whatever is that we are doing and trying to accomplish, other people have already gone through that gauntlet and it’s all written down, often in the first person. People have been moving West, leaving school, investing their savings, getting dumped or filing for divorce, starting businesses, quitting their jobs, fighting, and dying for thousands of years. As Lord Chesterfield advised his son: “Surely it is of great use to a young man, before he sets out for that country, full of mazes, windings, and turnings, to have at least a general map of it, made by some experienced traveler.”
With success often comes the delusional belief that the good times will always last, that we will always ride that wave. As Hesiod reminds us, “Summer is not forever: now build barns.”
Author Steven Pressfield describes the meeting between Alexander the Great’s aide and the philosopher Diogenes: “This man has conquered the world! What have you done?” The philosopher replied without an instant’s hesitation, “I have conquered the need to conquer the world.” In a culture of more, more, more, this is one of the most enviable gifts that one can ever possess: the ability to kick one’s feet up—anywhere, at anytime—and think: “Ok, this is good enough for me.” This person, this thing, this present moment, this is enough.
On the Howard Stern show, Jerry Seinfeld was explaining how it never gets easier. How it is all work. He joked that “your blessing in life is when you find the torture you’re comfortable with.” For me, that’s writing—I’m grateful that it’s so hard.
Related to that, whether dealing with adversity or pushing through a creative project, one strategy has proven far more effective than others: endurance accompanied by determination and purpose. Roger Bannister, the first person to run a mile under four minutes knew a thing or two about that philosophy and summed it up as: “The man who can drive himself further once the effort gets painful is the man who will win.”
Age 28
When someone is rude to you or acts in an unfair way—that airport employee, that bank representative, the guy that is cheating the system—and you want to get even, you have to remember that it’s already happened. The punishment is working at an airport for the next 30 years. The punishment is being a fucking cheat. Would you trade places with them? No? Then there, you have your satisfaction and your justice. Move on.
Ego is the fundamental problem in almost everyone’s life. It’s what deprives them of reality and truth and connection.
Thinking you already know—whatever it is—is the most dangerous attitude. Because you probably don’t.
One of the hardest things in the world is for human beings to say no to making money. We’ll do it at any cost.
Learn to ask why you’re doing something. What your real goals are. Don’t wait until after to find out you didn’t know or had the wrong reasons.
Age 27
Some habits that have saved me a lot of money and only mildly inconvenienced me: fly coach, don’t drink much alcohol, don’t pay for premium cable, drive an older car… when I look at friends who make a lot more money than me and wonder where it all goes, I assume it’s these things.
Sometimes you have to be a dick. Don’t waver when the time comes for it. Just push through it and move on.
Pets are a reflection of their owners.
It doesn’t matter what age you are or how healthy you are: people die. They die unexpectedly. They die tragically. Sometimes they die violently. Never let this drift too far from your mind.
I never thought I would care about taking care of a lawn or running to Home Depot for some house project, but I do now…and I like it. These things are relaxing, welcome distractions. I get it now. I regret mocking it so much when I was younger.
Age 26
Public speaking is only hard or scary if you don’t think you know what you’re talking about. That’s relatively simple to fix.
When you’re traveling to a new city, the first thing you should do when you get to the hotel is change into your work out clothes and go for a long run. You get to see the sights, get a sense of the layout and then you won’t waste an hour of your life in a lame hotel gym either.
Be in the middle of a book at all times. Better still, carry one with you at all times–a physical one. You’ll be amazed at how impressed people are by this.
