29 Pieces Of Life Changing Advice I Collected By My 29th Birthday

Ryan Holiday
Ryan Holiday

Today I turn 29. For the fourth year in a row, I feel lucky enough to not only still be alive, but to still be working as a writer and thus able to share what I learned. But this year, I didn’t want to just look at new things I’ve picked up in the last 12 months.

I pulled down my commonplace book over the last few weeks and went through the little notes I have scribbled to myself over the years tagged with “Life” (for life advice) in the corner. As I poured through the hundreds of 4×6 cards, I was disappointed to see how many painful lessons I’ve learned over the last 12 months…when I had the perfect saying or reminder sitting right there that could have saved me the trouble.  

It’s safe to say that most of what I learned this year was stuff I thought I already knew. Or I should have already known. Yet I was forced to relearn it. As Daniele Bolelli has written, attaining wisdom is like sweeping the floor. Once is not enough. It should be swept every day (and certainly more than once a year).

Which is why for my 29th birthday, I am sharing with you 29 pieces of life-changing advice I’ve collected over the last decade. Hopefully you can learn, as Bismarck put it, from my foolish experience—instead of having to do it on your own time.


[*]The people you choose to surround yourself and spend time with is by far one of the most critical decisions you have to make. We seem to understand that a young kid who spends time with kids who don’t want to go anywhere in life, probably isn’t going to go anywhere in life. What we understand less is that an adult who spends time with other adults who tolerate crappy jobs, or unhappy lifestyles is going to find themselves making similar choices. Multiple authors have addressed this: from Lord Chesterfield “You are whatever the company you keep is,” to Goethe’s “Tell me with whom you consort with and I will tell you who you are.” Why? Because, as Walker Percy put it of those we spend time with: “one will pick up the worst of the other and lose the best of himself.”

[*]Sometimes it seems less fun to be the person who doesn’t drink or who lives a disciplined life. But on the other side of that—the benefit of control and self-sovereignty—is its own kind of freedom. Henry Flagler, one of John D. Rockefeller’s trusted partners would say the same thing, that it was hard to be disciplined and hold himself to high standards that there was a reason for it: “I would rather be my own tyrant,” he observed, “than have someone else tyrannize over me.”

[*]“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.”

[*]Jeff Bezos, the CEO of Amazon, likes to tell about the early advice he received from his grandfather: “Jeff, one day you’ll understand that it’s harder to be kind than clever.” Amazon may or may not be running a workplace contrary to that advice but it stands on its own. Be kind. As Kurt Vonnegut expressed it best: “There’s only one rule that I know of: Goddamn it, Joe, you’ve got to be kind!” Or if you prefer Elizabeth Gilbert’s version: “The golden rule is do unto others as you would have them do unto you, but the platinum rule is even higher: don’t be a dick.” Or how Cheryl Strayed, another amazing writer, summed it: “Because in your twenties you’re becoming who you’re going to be and so you might as well not be an asshole.”

[*]One of my favorite lines is from Heraclitus: “Character is fate.” Who you are and what you stand for will determine who you are and what you do.

[*]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.”

[*]It’s easy to take things at face value. The accountant says this is what you owe. Your employee says this is how things are. People say this is the only way it can be done. Accepting implicitly is a great way to find yourself in deep shit. Samuel Zemurray would say “Don’t trust the report.” Find out for yourself. Check the work. See it in person. Don’t take things at face value.

[*]At the same time, don’t over-think every damn thing. This is a recipe for a miserable life. As Nietzsche put it, the Greeks were often “superficial out of profundity. When you’re young fancy cars or big houses don’t seem that important—who needs all that, you think? When you get older and see your friends with them, your mind will start running circles in order to justify it. Stick with the simple justification. Stick with the contemptuous expression. It will make your life clearer.

[*]We often carelessly let fear, poor perception and our imagination magnify the obstacles and problems in our way. What we need is coolheadedness to unpack the source of our fear and anxiety. To really understand what is in front of us. As Civil War general Ulysses S. Grant put it best when he was talking about the haunting sounds of wolves on the prairie, “There are always more of them before they are counted.” (turned out there was just one wolf)

[*]“If you see fraud and do not say fraud, you are a fraud.” This little epigram from Nassim Taleb has been a driving force in my life. It fuels my writing, but mostly it has fueled difficult personal decisions. There’s another line in Shakespeare’s Julius Caesar. Caesar, returning from the conquest of Gaul, is reminded to tread lightly when speaking to the senators. He replies, “Have I accomplished so much in battle, but now I’m afraid to tell some old men the truth?” That what I think about with Nassim’s quote. What’s the point of working hard and being successful if it means biting your tongue (or declining to act) when you see something unfair or untoward? What do you care what everyone else thinks? As John Wycliffe put it, “If you do not object strenuously to a superior’s bad behavior, you are as bad, as guilty as he is of what happens.”

[*]As James Baldwin reflected on the death of his father, a man who he loved and hated, he realized that he only saw the man’s outsides. Yes, he had his problems but hidden behind those external manifestations was his own unique internal struggle which no other person is ever able to fully comprehend. The same is true for everyone–your parents, your boss, the person behind you in line. We can see their flaws but not their struggles. As James wrote, “Thou knowest this man’s fall; but thou knowest not his wrassling.” If we can focus on this, we’ll have so much more patience and so much less anger and resentment. You have no idea what other people are struggling with. You have no idea what their lives are like. Leave them alone. Judge them not. It reminds me of another line that means a lot to me from Pascal: “To understand is to forgive.” You don’t have to fully understand or know, but it does help to try.

[*]People are going to criticize you. They are going to resist or resent what you try to do. You’re going to face obstacles and a lot of those obstacles will be other human beings. As Heraclitus said, “Dogs bark at what they cannot understand.” People don’t like change. They don’t like to be confused. It’s also a fact that doing new things means forcing change and confusion on other people. So, if you’re looking for an explanation for all the barking you’re hearing, there it is. Let it go, keep working, do your job.

[*]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.”

[*]When I first started in Hollywood, one of the people a few years older than me cautioned me against being too good at being an assistant. What did he mean? I figured it out when I heard this old military maxim: “Never do a task too well, or you’ll be stuck with it forever.”

[*]“You’re two people, the scheming little bastard I saw so easily and the fine, intelligent boy underneath that your grandfather, bless him, saw. But you’re coming of age soon and you’ll have to choose. A boy can be two, three, four potential people, but a man is only one. He murders the others.” That’s what Duddy Kravitz, the ambitious young hustler, heard as advice in The Apprenticeship of Duddy Kravitz. It bears asking if you’re similarly young and ambitious, which potential person will you be? Which part of you will you allow to rule? The part that betrays your friends, family, principles to achieve success? Or are there other priorities?

[*]Funny but one of the reasons I have goats and bought some land and live in the country is this beautiful line from poet William Blake’s Auguries of Innocence: “The wild deer, wand’ring here & there /  Keeps the Human Soul from Care.”

[*]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.

[*]Don’t fake it ‘till you make it. Make it. Churchill: “Facts are better than dreams.” Related: there is an old jungle saying: “It is never safe to assume that a leopard is dead until it has been skinned.” Just a more dangerous way to express a timeless idea that you need to live in the real world, not one of hopes or assumptions.

[*]Instilling character in his players, legendary basketball coach John Wooden told his 1964 team (who were overall shorter relative to the other teams): “I don’t care how tall you are; I care how tall you play.” They couldn’t grow taller but they had control over one critical variable: how much effort they gave. The same goes for us, no matter what immovable obstacles stand in our way. We need to accept “reality on reality’s terms” and do our best regardless.

[*]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.”

[*]Remaining cool-headed in times of crisis and adversity is one of the most critical skills. The worst that can happen is not the event itself but the event and you losing your cool. Chris Hadfield, the astronaut, reminds us that there is “no problem so bad that we can’t make it worse” (and panicking is the best way to do that). Resolve, like John Adams did in a 1776 letter to his wife, that “the Panic may seize whom it will, it shall not seize me.”

[*]Stop lying to yourself about how much you need to work. Sleep is important, family is important, reflection is important. Pushing yourself past the point of diminishing returns is not. As Robert Louis Stevenson wrote “Perpetual devotion to what a man calls his business, is only to be sustained by perpetual neglect of many other things.” There is a great line from Goethe as well: “Absolute activity, of whatever kind, ultimately leads to bankruptcy.”

[*]There is a wonderful quote from Epictetus that I think of everytime I see someone get terribly upset (I try to think about it when I get upset about anything): “If someone succeeds in provoking you, realize that your mind is complicit in the provocation.” Eleanor Roosevelt similarly expressed the idea of having sovereignty over your mind: “No one can make you feel inferior without your consent.”

[*]Don’t read your reviews (whatever form they come in). I had to learn this the hard way as a writer. If I only I had seen this Hemingway quote earlier: “If they believe the critics when they say they are great then they must believe them when they say they are rotten and they lose confidence.”

[*]Alexander the Great, one of history’s greatest conquerors. Entire cities have been named in his honor. But once dead, to paraphrase Shakespeare, his dust is filling a beer barrel hole. From conquering to plugging holes. As the satirist Juvenal mocked Alexander, for whom the whole world wasn’t enough to satisfy his ambition but “a coffin was measure enough to contain him.” Let that thought center you and change your perspective. As Goethe wrote, “Man needs only a small patch of earth for his pleasures, and a smaller one still to rest beneath.”

[*]In a famous profile in The Atlantic on Saddam Hussein, Mark Bowden wrote that “one might think that the most powerful man has the most choices, but in reality he has the fewest. Too much depends on his every move.” When deciding on where you want to go in life it is worth reflecting if the success you’ve envisioned can become a form of slavery. How? One innocuous example is saying yes to more money can make you more trapped than you’ve imagined.  

[*]The writer Nicolas Chamfort once joked that “a man must swallow a toad every morning if he wishes to be sure of finding nothing still more disgusting before the day is over.” Meaning: People might suck today. It’s not going to feel great when that happens. But it’s far better to know that going in and to take your medicine up front, in the morning, than it is to dribble it out through the day. And who knows—maybe you’ll be pleasantly surprised sometimes. Better that than disappointed and pissed off.

[*]I often write that passion can be a form of insanity and dysfunction because it makes people selfish and emotional. It’s passion in the historical sense, which every culture—from the Greeks to the Christians—have always warned against. As Goethe wrote: “Great passions are maladies without hope.” It brings to mind W.B. Yeats: “The best lack all conviction, while the worst / Are full of passionate intensity.”

Anyway, happy birthday to me. Happy regular June 16th to you. Let’s hope we can talk again in 12 months. Thought Catalog Logo Mark

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