Ryan Holiday's Blog, page 7

These 14 Small Mindset Shifts Will Change Your Life

For the most part, we can���t change the world. We can���t change the fundamental facts of existence���like the fact that we���re going to die. We can���t change other people.

Does that mean that everything is hopeless and permanently broken?

No, because although we have that extreme powerlessness in one sense, we have an incredible superpower in another: We can change how we think about things. We can change how we view them, how we orient ourselves to them.

That���s the essence of Stoicism, by the way. The idea that we don���t control what happens, but we do control ourselves. When we respond to what happens, the main thing we control is our mind and the story we tell ourselves.

So one way to think about Stoicism itself then is as a collection of mindset shifts for the many situations that life seems to thrust us in. Indeed, Seneca���s Letters, Marcus Aurelius��� Meditations, and Epictetus��� Discourses are filled with passages, anecdotes, and quotes which force a shift in perspective.

Here are 14 that I have taken from the Stoics over the years that have changed my life. I think they���ll do the same for you.

Everything is an opportunity for excellence. The now famous passage from Marcus Aurelius is that the impediment to action advances action, that what stands in the way becomes the way. But do you know what he was talking about specifically? He was talking about difficult people! He was saying that difficult people are an opportunity to practice excellence and virtue���be it forgiveness or patience or cheerfulness. And so it goes for all the things that are not in our control in life. So when I find myself in situations big and small, positive or negative, I try to see each of them as an opportunity for me to be the best I���m capable of being in that moment. It doesn���t matter who we are, where we are, we can always do this.

Every event has two handles, Epictetus said: ���one by which it can be carried, and one by which it can���t. If your brother does you wrong, don���t grab it by his wronging, because this is the handle incapable of lifting it. Instead, use the other���that he is your brother, that you were raised together, and then you will have hold of the handle that carries.��� Another way to say that is that there are multiple ways to look at every situation, multiple ways to determine how you���re going to react. Some of them are sturdy and some of them are not. Some are kind and resilient, some are not. Which will you choose? Which handle will you grab?

The world is dyed by the color of your thoughts. Marcus said, ���The things you think about determine the quality of your mind. Your soul takes the color of your thoughts.��� He also said, ���Our life is what our thoughts make it.��� If you see the world as a negative, horrible place, you���re right. If you look for shittiness, you will see shittiness. If you believe that you were screwed, you���re right. But if you look for beauty in the mundane, you���ll see it. If you look for evidence of goodness in people, you���ll find it. If you decide to see the agency and power you do have over your life (which as we���ve said is largely in how we think), well, you���ll find you have quite a bit.

There is a tax on everything. Taxes aren���t just from the government. Seneca wrote to his friend Lucilius, ���All the things which cause complaint or dread are like the taxes of life���things from which, my dear Lucilius, you should never hope for exemption or seek escape.��� Annoying people are a tax on being outside your house. Delays are a tax on travel. Haters are a tax on having a YouTube channel. There���s a tax on money too���and the more successful you are, the more you pay. Seneca said he tried to pay the taxes gladly. I love that. After all, it’s usually a sign of a good problem. It means you had a killer year financially. It means you���re alive and breathing. You can whine about the cost. Or you can pay and move on.

Poverty isn���t only having too little. Of course, not having what you need to survive is insufficient. But what about people who have a lot���but are insatiable? Who are plagued by envy and comparison? Both Marcus Aurelius and Seneca talk about rich people who are not content with what they have and are thus quite poor. But feeling like you have ���enough������that���s rich no matter what your income is.

Alive time or Dead time? This isn���t from the Stoics exactly, but close enough. Robert Greene once told me there were two types of time in life: Alive time and Dead time. One is when you sit around, when you wait until things happen to you. The other is when you are using that time productively, actively. You���re stuck at the airport���you don���t control that. You decide whether it���s alive time or dead time (you read a book, you take a walk, you call your grandmother). I had a year left on a job when Robert gave me that advice. I could have just sat on my hands. Instead, it was an incredibly productive period of reading and researching and filling boxes of notecards that helped me write The Obstacle is the Way and Ego is the Enemy.

Anxiety isn���t escaped. It���s discarded. This was a breakthrough I had during the pandemic. Suddenly, I had a lot less to worry about. I wasn���t doing the things that, in the past, I told myself were the causes of my anxiety. I wasn���t having to get to a plane. I wasn���t battling traffic to get somewhere on time. I wasn���t having to prepare for this talk or that one. So you���d think that my anxiety would have gone way down. But it didn���t. And what I realized is that anxiety has nothing to do with any of these things. The airport isn���t the one to blame. I am! Marcus Aurelius actually talks about this in Meditations. ���Today I escaped from anxiety,��� he says. ���Or no, I discarded it, because it was within me, in my own perceptions���not outside.��� It���s not your parents that are frustrating you. They���re just doing what they do. You are the source of the frustration. That���s a little frustrating, but it���s also freeing. Because it means you can stop it! You can choose to discard it.

It���s the surprise that kills you. Stuff is going to happen, but what makes it harder is when it catches us off guard. The unexpected blow lands heaviest, Seneca said. That���s why we should practice the art of *premeditatio malorum���*essentially, a pre-mortem of the things that could happen in a day or a life. This takes the sting out of them in advance���it also lets us prepare and prevent. And for no one is this more important than parents and leaders. Seneca said that the one thing a leader is not allowed to say is, ���Wow, I didn���t think that was going to happen.���

You can���t learn what you think you already know. Conceit, Zeno said, was the enemy of wisdom and learning. This was the essential worldview of Socrates, the hero of the Stoics. Think of Socrates��� method. He didn���t go around telling people anything. He went around asking questions. That���s how he learned so much and ended up becoming so smart. If you want to get smarter, stop thinking you���re so smart. If you want to learn, focus on all the things you don���t know. Humility, admission of ignorance���these are the starting points. This is the attitude that gets you further in life.

What good is posthumous fame? Marcus Aurelius knew he was famous. He knew they were building statues of him. He knew he would have a legacy. He also knew this was basically worthless. What good is posthumous fame, he asks in Meditations, when you���re not around to enjoy it?! He reminded himself too that you know, it���s not like the people in the future were going to be way better than the people alive right now���there will be idiots in the future too. What do I care about how many people read my books in 100 years? What matters is if I am doing my best right now, if I am taking pleasure and pride from doing my best right now. So stop trying to live forever by achieving all this greatness, stop trying to get more than you need, stop trying to perform for history. Do the good you can do now. Stop chasing something you will never touch. Legacy is not for you. You���ll be dead. Leave it to others.

People are just doing their job. I don���t just mean at work. After bumping into a particularly frustrating person, Marcus Aurelius asks himself, ���Is a world without shamelessness possible?��� No, he answers. ���There have to be shameless people in the world. This is one of them.��� This is just someone fulfilling their role. Seeing things this way not only prevents me from being surprised, but it makes me sympathetic. This person has a crappy job. It���s not fun to be them���they have to be one of the jerks that exist in the world. And then I remind myself that I am lucky that my job is to try to be a good person.

They don���t want you to be miserable. It���s strange that Stoics have the reputation for being unfeeling when Seneca wrote three very beautiful essays on loss and grief called Consolations. I read these essays whenever I lose someone or miss someone who I loved. Anyway, one of the lessons that hit me the most is when he is writing to the daughter of a now-deceased friend. He brings up a great point, basically saying, look, your dad loved you so much. Of course, he would be honored that you miss him, but do you think he would want his death to make you miserable? Would he want the mere mention of his name to bring you pain? No, that would be his worst nightmare. He would want you to be happy. He would want you to go on with your life. He wouldn���t want his memory to haunt you like a ghost���he would want the thought of him to bring you joy and happiness. Of course, we���re always going to feel sad when we lose someone, but then we can remind ourselves of this and try to smile too.

Opinions are optional. ���Remember, you always have the power to have no opinion,��� Marcus says. Do you need to have an opinion about the weather today���is it changing anything? Do you need to have an opinion about the way your kid does their hair? So what if this person likes music that sounds weird to you? So what if that person is a vegetarian? ���These things are not asking to be judged by you,��� Marcus writes. ���Leave them alone.��� Especially because these opinions often make us miserable! ���It���s not things that upset us,��� Epictetus says, ���it���s our opinions about things.��� The less opinions you have, especially about other people and things outside your control, the happier you will be. The nicer you���ll be to be around too.

__

The last one is the most powerful one, I think. And it���s about the thing we have the least amount of power and control over: the fact that we���re all going to die.

But the Stoics want us to think about it differently���

Death isn���t in the future. It���s happening now. It���s easy to see death as this thing that lies off in the distant future. It���s a fixed event that happens to us once���at the end. This is literally true but it���s also incorrect. ���This is our big mistake,��� as Seneca points out, ���to think we look forward toward death. Most of death is already gone. Whatever time has passed is owned by death.���

It���s better to think of death as a process���something that is always happening. We are dying every day, he said. Even as you read this email, time is passing that you will never get back. That time, he said, belongs to death. Powerful, right? Death doesn���t lie off in the distance. It���s with us right now. It���s the second hand on the clock. It���s the setting sun. As the arrow of time moves, death follows, claiming every moment that has passed. What ought we do about it? The answer is live. Live while you can. Put nothing off. Leave nothing unfinished. Seize it while it still belongs to us.

24 Leadership Principles From The Greatest Business, Military, Political and Sports Leaders

People think that leadership is something that just happens. One is anointed a leader. One is promoted to leadership. One is born into leadership. And of course, this is not the case.

���Leadership,��� Eisenhower said, ���is the art of getting someone else to do something that you want done because he wants to do it.��� Which means that, like any art, leadership is something that has to be studied. No one comes out of the womb a leader. And yet we���re all leaders in one way or another���of families, of companies, of a team, of an audience, of a group of friends, of ourselves. So there���s no one who wouldn���t benefit from learning some essential leadership principles from some of history���s greatest leaders. These 24 by no means make a complete list���that���s why we built The Daily Stoic Leadership Challenge (registration is currently open for this year���s LIVE 9-week course) but if you implement even a couple of them, I���m comfortable guaranteeing you���ll be a better leader for it. But perhaps the first and most important lesson we learn from the leaders I talk about below is that leadership is a skill that one could refine over multiple lifetimes���so the sooner you start the better.

A Leader Is A Reader. Harry Truman famously said that not all readers are leaders but all leaders are readers���they have to be. And they certainly aren���t reading to impress people or for the mental gymnastics. It���s to get better! It���s to find things they can use. Not at the dinner table or on Twitter, but in their real lives. A leader must learn from the experiences of others. A leader must be challenged. A leader must prepare themselves for the things they���ll only be able to experience once, by learning from the experiences of others. To paraphrase the soldier-philosopher General James Mattis, it is unconscionable to fill up body bags while you get your education solely by experience, one mistake at a time. A leader must be a reader. It���s not just the best way, it���s the only way.

A Leader Puts Everything In The Calm and Mild Light. In Thomas Rick���s wonderful book Waging a Good War, he looks at what made Bob Moses one of the best (yet lesser known) of the civil rights leaders. Moses was quiet and calm. He did not seek out the spotlight. He did not make decisions out of emotion. Instead, Ricks says, quoting a colleague of Moses, he had a ������capacity for reflection and distance from the thing that you are very much in the midst of and even leading.������ The job of a leader, George Washington similarly said, is to look at all events, all opportunities, all people through the ���calm light of mild philosophy.��� As leaders, we will have good days and bad, moments of heartbreak and bad luck, as well as strokes of good fortune and good timing. What matters is how we respond to these swings of fate. (That���s why we dedicate week two of The Daily Stoic Leadership Challenge to mastering your emotions.)

A Leader Always Looks For Teachable Moments. In the 1960s, IBM CEO Tom Watson supposedly called an executive into his office after his venture lost $10 million. The man assumed he was being fired. Watson told him, ���Fired? Hell, I spent $10 million educating you. I just want to be sure you learned the right lessons.���

A Leader Finds A Teacher. Eisenhower was mentored by George Marshall and Fox Conner (and learned a lot about what not to do spending time under Douglas MacArthur). Marcus Aurelius spend two decades under Antoninus Pius (Hadrian had at best hoped Antoninus could offer Marcus a few years of tutoring). It was really an incredible and formative experience for him���it���s part of what we tried to distill down in the Daily Stoic Leadership Challenge, especially with the experts we brought in to talk to us. The idea is, as Marcus said of his own development as a leader, to go ���straight to the seat of intelligence.���

A Leader Is Imperfect. Bad leaders think that they have to appear perfect, that they have to have all the answers, that they have to cover up their weaknesses. Great leaders do the opposite. Gandhi, once being interviewed by a reporter, said, ���I am very imperfect. Before you are gone you will have discovered a hundred of my faults and if you don���t, I will help you to see them.��� Why would he do such a thing? Because he knew that as a leader, egotism and an outsized sense of one���s abilities is dangerous and destructive.

A Leader Seeks Out Advice And Feedback. ���It is impossible to learn that which one thinks one already knows,��� Epictetus says. When a leader lets their ego tell them that they have arrived and figured it all out, it prevents them from learning and it leads to mistakes. As Dwight D. Eisenhower, one of the best commanders of the last century, said of the necessity of listening to feedback: ���I have no sympathy with anyone, whatever his station, who will not brook criticism. We are here to get the best possible results.���

A Leader Doesn���t Tell People What To Do. Gandhi���s friends always appreciated the grace he gave them, not judging them for their choices or for the less-strict lives they led. In one of the deep dives in the Daily Stoic Leadership Challenge, General Dan Caine recounted that he has maybe given two direct orders in his entire 33 year career. Like Eisenhower said, a leader persuades, a leader motivates. A leader is a strong, inspiring example. They don���t bully and yell. They earn their authority. They are strict with themselves and tolerant with others.

A Leader Gets The Best Out of People. Lots of brilliant leaders and talented people have made the same mistake through the centuries: they expect of others what they expect of themselves, so they are constantly upset and let down. We know that Marcus Aurelius found a better way through. ���So long as a person did anything good,��� Cassius Dio wrote, ���he would praise him and use him for the service in which he excelled, but to his other conduct he paid no attention.��� That���s key for anyone in any position of leadership. Your standards are for you. You only control your behavior. You have to meet everyone else where they are. Get as much as you can from them and of them. See the good in them. Lean into their strengths rather than disdain their weaknesses. Focus on what is special and unique about them instead of zeroing in on the ways they are not as good as you. That���s not only the kind way to lead, it���s the only effective way.

A Leader Can Do Anything But Not Everything. In 1956, Harry Belafonte called Coretta Scott King. With her husband arrested once again, he wanted to check in with her and see how she was doing and what the movement might need. Except they could barely carry on a conversation, because Coretta kept being pulled away from the phone to attend to one of the children, to check on dinner, to answer the door. Belafonte politely asked why the Kings did not have any help at home. Because, Coretta said, Martin was worried other people would think he was enriching himself at the expense of the cause, living the high life while millions of blacks suffered. Belafonte was baffled, ���He���s here in the middle of this movement doing all of these things, and he���s going to get caught up in what people are going to think if he has somebody helping you?��� Then he said he was going to personally pay for staff���and that Martin had absolutely no say in the matter. This wasn���t just a nice gesture to an overworked family. It was also a strategic move. What Belafonte was buying Martin and Coretta was time, peace of mind, and more energy and more focus for the cause. “A leader,��� Plutarch said, ���should do anything but not everything.”

A Leader Prepares For The Inevitable Chaos. As the legendary coach Phil Jackson would explain, ���Once I had the Bulls practice in silence; on another occasion I made them scrimmage with the lights out. Not because I want to make their lives miserable but because I want to prepare them for the inevitable chaos that occurs the minute they step onto a basketball court.���

A Leader Thinks Long Term. In his 1997 letter to shareholders, Jeff Bezos said, ���We believe that a fundamental measure of our success will be the shareholder value we create over the long term.��� For companies���as is the case for individuals���there are always pressures to be narrow in our focus and vision. Bezos, unlike most business leaders, refused to play that game. ���Rather than short-term profitability considerations or short-term Wall Street reactions,��� Bezos said, the real value lies in thinking decades ahead. His maxim for business opportunities is also relevant here: ���Focus on the things that don���t change.���

A Leader Prioritizes Stillness. Randall Stutman has been a coach to some of Wall Street���s biggest CEOs for decades. His clients have included Goldman Sachs, Morgan Stanley and Bank of America. His consulting and advising agency, CRA, has worked with thousands of executives at hundreds of hedge funds and banks. These are people whose entire livelihood depends on them being perpetually ready to respond to the daily, hourly, sometimes even minute-by-minute volatility of the world���s financial markets. Stutman surprised me when he told me that he often asks these very busy executives how they recharge, given the all-consuming nature of their work. The best, he found, have at least one hobby that gives them peace ��� things like sailing, long-distance cycling, listening quietly to classical music, scuba diving, riding motorcycles, and fly fishing. There is a surprising commonality between all the hobbies: An absence of voices. For leaders, people who make countless high-stakes decisions in the course of a day, a couple hours without chatter, without other people in their ear, where they can simply think (or not think), is essential.

A Leader Has a Guiding Philosophy. Football coach Bill Walsh took the 49ers from the worst team in the league to Super Bowl champions in just three years thanks to his ���Standard of Performance��� philosophy. Seahawks coach Pete Carroll is known for his ���Win Forever��� philosophy���the winning mindset he aims to instill in his staff and players. The great coach John Wooden had his ���Pyramid of Success��� philosophy. These philosophies and frameworks are critical as they codify the principles and rules by which a team will make decisions and operate on a day-to-day basis. If you don���t have a philosophy, how do you expect to know what to do in tough situations? Or when things are confusing or complicated? Being reactive is never a position of strength. It is not a position a leader should find themselves in.

A Leader Always Keeps Their Cool. The journalist and author of The Chancellor: The Remarkable Odyssey of Angela Merkel, Kati Marton, told me on the Daily Stoic podcast that she once got to sneak into Merkel���s office. On her desk, there was a plexiglass cube with the words, In der ruhe liegt die kraft (���in calm, there is strength”) ���Which is truly her mantra,��� Marton said. ���That is among her superpowers: she does not lose her cool.��� Remaining cool-headed in times of crisis and adversity is one of the most critical skills. ���The first qualification of a general is a cool head,��� Napoleon once said. The worst that can happen is not the event itself, but the event and you losing your cool.

A Leader Stays Humble. Success, money and power can intoxicate a leader. Right before he destroyed his own billion-dollar company, Ty Warner, creator of Beanie Babies, overrode the objections of one of his employees and bragged, ���I could put the Ty heart on manure and they���d buy it!��� A leader benches the ego. A leader never believes they have the Midas touch.

A Leader Does The Right Thing. ���Just that you do the right thing,��� Marcus Aurelius told himself, ���the rest doesn���t matter.��� That would be his legacy, that would be his source of pride, not the buildings he erected or the conquests he made. A leader means making hard but costly decisions���like Marcus Aurelius making the decision to sell off palace jewels when the Antonine plague wiped out much of the Roman army. The people couldn���t afford to pay taxes for new troops. ���So Marcus held a vast auction of contents of the imperial palace, Brand Blanshard writes in Four Reasonable Men, ���and sold gold, crystal and myrrhine drinking vessels, even royal vases, his wife���s silk and gold-embroidered clothing, even certain jewels in fact, which he had discovered in some quantity in an inner sanctum of Hadrian���s.���

A Leader Seizes The Opportunity for Greatness. In early April 2020, Queen Elizabeth II gave a rare public speech with essentially that message. One of Britain���s last living links to World War II, the Queen compared it to the way she today can look back with admiration for those who acted bravely. ���I hope in the years to come, everyone will be able to take pride in how they responded to this challenge,��� the Queen said, ���and those who come after us will say that the Britons of this generation were as strong as any. That the attributes of self-discipline, of quiet good-humored resolve, and of fellow-feeling still characterize this country.��� When the Stoics say the obstacle is the way, this is what they were talking about���it���s an opportunity to be great.

A Leader Knows How to Prioritize. One of the great lessons from Eisenhower is his decision matrix that helps separate and distinguish immediate tasks from important ones. It asks you to group your tasks into a 2��2 grid deciding whether a task is either important or not and whether it is urgent. Most of us are distracted by what���s happening right now���even though it doesn���t matter���and as a result neglect what is critical but far in the future.

A Leader Makes People and Situations Better. Seneca said, ���Happy is the man who can make others better, not merely when he is in their company, but even when he is in their thoughts!��� That is the essence of being a great leader, a great Stoic, a great human being. As Randall Stutman told us in week one of the Daily Stoic Leadership Challenge. ���At the base of leadership, what all great leaders have in their heads and their expressions is the idea that they want to make people and situations better.���

A Leader Is Rarely Surprised. Seneca said every leader needs to regularly practice premeditatio malorum���a meditation on all that could go wrong���before it goes wrong. He liked to quote Fabius: the only inexcusable thing for a commander to say was, ���I did not think that could happen.��� And of course, he is right: The job of the leader is to be prepared, to have a plan, to anticipate all possible and probable outcomes. Whether it���s a military campaign, a creative project, or a business negotiation.

A Leader Keeps The Main Thing The Main Thing. John DeLorean was a brilliant engineer but a poor manager (of people and himself). One executive said he was always ���chasing colored balloons������he was constantly distracted and abandoning one project for another. It���s just not enough to be smart or right or a genius. Conversely, Jony Ive, the top designer at Apple would recount how Steve Jobs was always asking Ive and other Apple employees about what they were focused on and specifically, ���How many things have you said no to?��� because to focus on one thing requires not focusing on other, less important things. Jobs would have liked the motto of Los Angeles Rams GM Les Snead: keep the main thing the main thing.

A Leader Trusts, But Verifies. Samuel Zemurray���s line���per Rich Cohen���s amazing book The Fish That Ate the Whale���was ���Never trust the report.��� He went to South America or Boston or wherever the business was being done and saw the situation for himself. He wanted first hand knowledge so as a leader he could make the right decisions. A leader can���t simply accept whatever trickles up from below them���they have to see for themselves. They have to, as the Russian proverb goes, ���trust, but verify.���

A Leader Has The Courage To Stand Apart. The lesser known philosopher Agrippinus talked about how people are like threads in a garment. Most people see it as their job to match the other threads in color and style. They want to blend in, so the fabric will match. But ���I want to be the red,��� Agrippinus said, ���that small and brilliant portion which causes the rest to appear comely and beautiful������Be like the majority of people?��� And if I do that, how shall I any longer be the red?��� That���s the leader���s job. It is not to go along to get along. It is not to default to the status quo. It is not to be another replaceable thread in an otherwise unremarkable garment. The leader���s job is to stand up. To stand out. To speak the truth. As Sam Walker writes in his wonderful book The Captain Class about the unsung leaders who have taken their teams on incredible championship runs, one of the traits great leaders share is they have ���strong convictions and the courage to stand apart.���

A Leader Assumes Formlessness. Cato, one of the most vaunted and towering Stoics, built a reputation and a career out of his refusal to compromise his principles. But Cato���s inflexibility did not always best serve the public good. Indeed, no one did more than Cato to rage against his Republic���s fall, but few did more to bring that fall to pass. Cato���s refusal to compromise was driven by moral principles but ultimately hastened the end he so dreaded. A leader learns from Cato���s fatal mistake. A leader obeys Robert Greene���s 48th law of power: Assume Formlessness. ���Accept the fact that nothing is certain and no law is fixed,��� Robert writes. ���The best way to protect yourself is to be as fluid and formless as water.��� While we admire the high integrity and uprightness of the Catos of the world, the truth is that the inflexible, uncompromising, ���pure��� person who cannot adjust, who cannot conceive of doing things anyway but their own, is extremely fragile.

As I said, leadership can’t be distilled down into some list. It’s a process. It’s a mindset. It’s a lifelong commitment. That’s what we’ve been trying to do for the last few years now with the Daily Stoic Leadership Challenge, our most in-depth (and most popular) course.

We designed this 9-week challenge to mirror the kind of education that produced historically great leaders like Marcus Aurelius. Specifically, we built it around one of the key lessons from Marcus���s own development: the idea that leadership is less a position and more a process.

This is our first live version of this course since 2021, so we���ve got some great leadership experts lined up for FIVE Deep Dive sessions. It���s a great opportunity to hear from some of the best, and get your questions answered.

I really hope you join us for this leadership masterclass. Registration is now open, and the course begins on September 25. Head over to dailystoic.com/lead today to enroll!

These 38 Reading Rules Changed My Life

It’s a weird thing to say, but I guess I’m a professional reader. That’s really what authors are. A book is made of books. ���The greatest part of a writer���s time is spent in reading; a man will turn over half a library to make one book,��� Samuel Johnson said.

I���ve written 15 books now, which has meant reading many thousands of books in the process. Once a month for the last 15 years, I���ve recommended many of those books in the Reading List Email. And in 2021, I opened my own bookstore filled with my all-time favorites.

So the question I am asked most often is:

How do you read so much? What���s the secret?

The answer is not ���I���m a speedreader.��� As I���ve written before, speed reading is a scam. The answer is that I have a system, a process that helps me be a productive reader. It���s not my system exactly, as I���ve taken many strategies from history���s greatest readers. Nor is this a system designed around speed or quantity. Reading is wonderful in and of itself, why would I try to rush through it? No, I try to do it well. I try to enjoy it.

In this email, I thought I would detail some of the rules I���ve come to follow over the years. They don���t all make me faster, but they do make me better.

���Do it all the time. Bring a book with you everywhere. I���ve read at the Grammy���s and in the moments before going under for a surgery. I���ve read on planes and beaches, in cars and in cars while I waited for a tow truck. You take the pockets of time you can get.

���Physical books only.

-It���s not that I have a problem with audiobooks���if it gets you reading, I���m all for it. I just think there���s something very special about the physical form. I just read a great book about this actually called Proust and the Squid by Maryanne Wolf.

���Hardcover over paperback.

���Bring a pen with you too. Reading is better if you���re taking notes.

���Keep a commonplace book. As Seneca wrote: ���We should hunt out the helpful pieces of teaching and the spirited and noble-minded sayings which are capable of immediate practical application���not far far-fetched or archaic expressions or extravagant metaphors and figures of speech���and learn them so well that words become works.��� (Here���s a video on my commonplace book method).

���Err on the side of age. Classics are classics for a reason.

-Beat them up. Books are not precious things. As an author, I love it when people hand me a book to sign that has had real miles put on it. When people hand me a pristine copy and tell me it���s their favorite, I assume they are just flattering me. It���s obvious what my favorite books are���because they���re falling apart (here���s my copy of Meditations for instance).

���In every book you read, try to find your next one in its footnotes or bibliography. This is how you build a knowledge base in a subject���it���s how you trace a subject back to its core.

-Same goes when you find an author you love, read them ALL. I read Cecil Woodham-Smith���s book on the charge of the Light Brigade���only to find she had also written a biography of Florence Nightingale. It was that discovery that shaped a full third of my book Courage is Calling.

-That comment from (the disgraced and indicted FTX founder) Sam Bankman Fried about how every book could be a 900 word blog post is preposterously stupid. The whole point of reading is to really understand something. So if all you���re after is the ���gist,��� skip books and stick with blog posts.

���If you see a book you want, just buy it. Don���t worry about the price. Reading is not a luxury. It’s not something you splurge on. It’s a necessity. Even if all you get is one life-changing idea from a book, that���s still a pretty good ROI.

-That might sound privileged, but Warren Buffett considers the foundation of his multi-billion dollar empire to be a book. At 19-years-old, he bought a copy of The Intelligent Investor by Benjamin Graham. We don���t know exactly what he paid for it, but in the early 1950s, a hardcover typically went for $1.30���the best investment he ever made, he���s said. Today, Buffett���s worth $108.7 billion, having given away some $37 billion to charitable causes. Not a bad ROI!

���Some people might recoil at categorizing a book that way, but as a lover of literature, I have no problem with it. I myself wouldn���t be writing this to you today if I hadn���t bought a paperback of Meditations in 2006 for $8.25 on Amazon. That book of philosophy taught me not just about life, but also schooled me in the art of writing, in working with and managing people, and gave me the speciality which I now write my own books about. Again, not a bad ROI.

���Don���t just read books, re-read books. There’s a great line the Stoics loved���that we never step in the same river twice. The books don���t change, but you do.

���As I said, speed reading is a scam. You just have to spend a lot of time reading.

���If a book sucks, stop reading it. The best readers actually quit a lot of books. Life is too short to read books you don���t enjoy reading.

���The rule I like is ���one hundred pages minus your age.��� Say you’re 30 years old���if a book hasn’t captivated you by page 70, stop reading it. So as you age, you have less time to endure crap.

-Embrace serendipity. So many of my favorite books are just random things I grabbed at bookstores (this is why I say don���t sweat buying a book���just roll the dice). That���s what bookstores are for, what I���ve tried to build mine around. It���s a discovery engine better than any algorithm.

-Don���t just build a library, build an anti-library���a stack of unread books that humbles you and reminds you just how much there is still to learn. It���s a sign of what you don���t yet know. It���s also a resource there whenever you might need to do a deep dive into that topic.

���Emerson���s line was, ���If we encounter a man of rare intellect, we should ask him what books he reads.��� When I was a teenager, I got in the habit of doing this. Every time I would meet a successful or important person I admire, I would ask them: What���s a book that changed your life? And then I would read that book (in college, for instance, I was lucky enough to meet Dr. Drew, who was the one who turned me on to Stoicism).

���Speaking of Emerson���in his essay ���Reading,��� he put down his three rules: ���1. Never read a book that is not a year old [because only good books survive]. 2. Never read any but famed books [same reason]. 3. Never read any but what you like.���

���Whenever I���m in a reading funk/dry spell (most commonly, around book launches), I find I���m able to get back into a groove by re-reading some of my favorite novels. What Makes Sammy Run? The Great Gatsby. Ask the Dust. The Moviegoer.

-Speaking of Ask the Dust, I read that because my friend Neil Strauss said in an interview it was his all-time favorite novel. He also turned me onto Knut Hamsun���s Hunger, which he had also raved about. When people rave about something, don���t dismiss it. If someone says a book changed their life? Consider it seriously. They���re talking about something powerful.

-I find myself sometimes reluctant to read something that���s super popular. That snobbishness never serves me well. More often than not, when I get around to those bestsellers I kick myself���they were bestsellers for a reason! They���re great! Don���t be a book snob.

���You say you don���t have time to read but what does the screen time app on your phone say? What does your calendar say?

���If you want to understand current events, don���t rely on breaking news. Find a book about a similar event in the past. Read history. Read psychology. Read biographies. Go for information that has a long half-life, not something that���s going to be contradicted in the next bulletin.

-Examples: Read The Great Influenza to understand COVID. Read It Can���t Happen Here to understand modern threats to democracy. Read First Principles to understand American politics.

���Ruin the ending. I almost always go straight to Wikipedia and figure out the plot���especially if I am reading something tough like Shakespeare or Aeschylus. Who cares about spoilers? Your aim as a reader is to understand WHY something happened, the what is secondary.

���One of the things that people in publishing know is that readers tend to skip prefaces and forewords. This is crazy! Those things are there for a reason. They often have a ton of helpful and interesting stuff about the context around when the person was writing, who the work ended up influencing, and other tidbits that sometimes stick with you longer than even the work itself.

-���Don���t be satisfied just getting the ���gist��� of things,��� is what Marcus Aurelius learned from his philosophy teacher Rusticus. One of the reasons I try to spoil the plot, make my way through the intro and the preface, read reviews and articles about the books I���m reading, watch videos about them, and read other books on the topic is because I want to really understand what I���m dealing with. If I don���t, if I only want a surface take, why read a book at all?

���When intelligent people read, they ask themselves a simple question: What do I plan to do with this information?

-My favorite line from Harry Truman is, ���not all readers are leaders, but all leaders are readers.��� When we read, we aren���t learning to impress people, to win some game of mental gymnastics. It���s to get better, to find things you can use in your real life. If you���re looking to expand what you do with the books you���re reading, I highly recommend our Read to Lead course. It���s been taken by over 10,000 people, and is our most popular for a reason.

���Read widely and from people you disagree with. The Stoics believed that we should actively engage with anyone who can be a source of wisdom to us, regardless of their origin. If there is wisdom out there to be had, we���d be wise to avail ourselves of it.

-Pretentiousness is bullshit. Epictetus once heard a student talking proudly about having made their way through the dense works of Chryssipus. You know, Epictetus told him, if Chryssipus had been a better writer, you���d have less to brag about.

���Look for wisdom, not facts. We���re not reading to just find random pieces of information. What���s the point of that? We���re reading to accumulate a mass of true wisdom���that you can turn to and apply in your actual life.

-Another line from Seneca is about how people get too caught up in the facts and figures and they miss the message. I totally agree. On the literary snobs who speculate for hours about whether The Iliad or The Odyssey was written first, or who the real author was (a debate that rages on today), he said, ���Far too many good brains have been afflicted by the pointless enthusiasm for useless knowledge.���

���If a book is good, recommend it and pass it along to other people.

It���s the last one that I follow the most. I���m proud of the books I���ve been able to champion and turn people onto over the years. I feel like I am paying forward what the Gregory Hays translation of Meditations did for me (I loved it so much I put out my own edition you can grab here).

I love looking around my bookstore and seeing titles that I don���t see in other bookstores very often. Just recently, Ann Roe���s publisher of Pontius Pilate told us they had to do another printing because we���d raved about it too much. I heard something similar about William Seabrook���s Asylum. That���s the job of a reader and a writer���to find great stuff and suck everything you can out of it as you read it and re-read it.

And to help others do the same.

I hope these rules help you help yourself and help others.

No You Can���t Have It All (Especially as a Parent)

Parenting is all about discipline. It���s about being strict and firm and unrelenting.

Not with your kids, to be clear. That���s being a disciplinarian.

When I say parenting is all about discipline, I���m talking about the only form that matters: self-discipline.

There is a story about one of those legendary Beat parties in the early 1960s. Allen Ginsberg was hosting. Jack Kerouac was there holding court. There were drugs and ideas and romance. There was effortless cool and artistic genius on display. The kind of thing a young artist would dream of being invited to, and once in attendance, never wanted to leave.

Then all of a sudden a twenty-something poet named Diane di Prima got up to do just that, heading out right as things were getting started. The babysitter was waiting, she explained sheepishly.

���Unless you forget about your babysitter,��� Keroauc said to her in front of everyone, echoing the famous belief that the stroller in the hallway was the death knell of creativity, ���you���re never going to be a writer.��� Yet di Prima, not interested in being lectured to by a deadbeat father in the midst of drinking himself to death, left anyway.

���She believed she wouldn���t have been a writer if she���d stayed. To write and come home on time, she argued, required ���the same discipline throughout���: a practice of keeping her word,��� Julie Phillips writes about di Prima in her fascinating book on creatives and parenting, The Baby on the Fire Escape.

Before my two boys, now 4 and 6, were born, a writer gave me similar advice, much more succinctly. ���Work, family, scene,��� he said. ���Pick two.���

You cannot have it all. You have to choose.

These choices take discipline.��.��.��constantly.

In fact, hanging on the wall next to my desk, between two pictures of my kids, is a little sign that just says ���NO.��� It���s a reminder: when I say no���to a request to get coffee, to the offer to go speak somewhere across the country, to appear on the podcast (it���s always podcasts)���I am saying yes to the two most important people in the world to me. I���m saying yes to a moment in their childhood that won���t exist ever again. And the opposite is also sadly true: when I say yes���especially to things in the evening or things that involve getting on airplanes, I am by definition saying no to them, to the people I claim to put first.

The tragedy is that we all know this on some intellectual and emotional level. But it doesn���t make it easy.

There are invites in my inbox right now that I know I should pass on, but the best I can bring myself to do is ignore them and hope the silence will take care of it for me. It���s a certainty that at some point in the future I will undoubtedly be willing to trade anything for one more minute with my kids, yet here in the moment, they���re fighting against other people who are asking me if they can ���pick my brain.���

Love, I���ve heard it said, is best spelled T-I-M-E. So yes, we love our families, but who do we give our time to? Them? Or random impositions? And how much of it do we waste���out of a lack of self-control, out of insecurity?

One of my favorite bits from the comedian Tom Segura is the one where he says that since becoming a parent, he���s decided he has no time for arguing. Like most comedians, he���d always been opinionated, a conversational brawler, even with strangers. But not anymore. If he expresses an opinion to someone and they say, ���I disagree,��� he immediately changes his position and agrees with them���whatever it takes to avoid a pointless argument. To some this might sound weak, but actually it���s a strength that parents have to muster. His time, his energy, his patience belong to someone else. And nowhere, he says, is this truer than with his own parents���whose bait he now refuses to take.

I think about this when arguing with my own children. Is this actually something I need to be right about? Am I so insecure that I have to one-up a six-year-old? Do I really need to make him accept defeat in this discussion about whether dragons exist? ���If you say so��� is a magic phrase. So is ���Sure, suit yourself.��� My favorite is ���Alright,��� because it is. It���s alright if you let this go. It���s alright if they think that. It���s alright if they want to do it their way.

But man, it���ll test you. I sometimes look at the Twitter feeds of very important and busy people���people who I know have babies at home or teenagers in high school���and I wonder what they���re doing. Forget all the companies he runs, Elon Musk has 9 kids, ages 1 to 18, and he���s got time to tweet 30 times a day? He���s seeking out culture war issues to get sucked into?

Alright.

���Things are not asking to be judged by you,��� Marcus Aurelius writes in his Meditations. ���Remember, you always have the power to have no opinion,��� he says. That���s not just a philosopher and an emperor talking, it���s a man with a wife of 30 years and 14 children. He knew that the only way to make it through was to shut up. To let it go. Ignore it. Focus his energy where it had real impact, on his own behavior and his own choices.

So much of good parenting, like discipline itself, is about restraint���and you���ll find that the further upstream you go, the better you���ll be at it. The person who doesn���t fill up their pantry with junk food is less likely to grab it as a midnight snack. Deleting the app means you���ll spend less time on it. Setting up hard and fast rules means you don���t have to think about the decision. Hiring an assistant means some of the stress never even gets to you. Avoiding the provocation means you already won the argument.

These decisions help us be the person and the parent we aspire to be.

For instance, when I look back on a day that didn���t go well in our house���where tempers were lost, where things went sideways, when I wasn���t present enough, where we didn���t eat well or spent too much time on screens���they tend to all have one thing in common: I screwed up my morning. If I sleep well, wake up early, and get some exercise in, if I don���t get immediately sucked into my phone or some work issue that can wait, if I spend a few minutes with my journal, then it really doesn���t matter if the rest of the day blows up. I will have the capacity to deal with it. I can be what they need.

Yet again, discipline.

The other thing my wife, Samantha, and I are working on is just doing less. That was the word we set out as our intention for 2023: less. Less commitments. Less drama. Less busyness. Less screen time. Just less.

Part of the reason I want less is so I have room for more. More stillness. More presence.

The other day my family of four went into town for a children���s birthday party, and when we wrapped up, we decided to head down the street for dinner. It was going to be tight with bedtimes coming up, but it might be fun? Then we caught ourselves: less means trying to squeeze less stuff in. Discipline meant heading home, being content with the fun and relaxed day we���d already had. Especially when there were already signs of fatigue and the exhaustion of personal reservoirs. Discipline meant being fair to the kids, setting them (and us) up for success by not overdoing it, not trying to see how many straws the camel���s back can hold.

It���s easy to focus on the disciplinarian side of being a parent: These are the rules*. Listen to me.* In reality, we have so much less control than we think. What we truly have control over is ourselves, our choices, our decisions.

The most basic premise of Stoicism is the ���dichotomy of control,��� knowing what���s up to us and what isn���t. In fact, Epictetus, one of the great Stoic philosophers, would say that this is the chief task of the philosopher:coming to terms with what you have control over and what you don���t.

As the Stoics say, first you decide what you want to be. Then you need the discipline to make that happen.

This piece was originally published for The Free Press here. You can subscribe at thefp.com.

 

What To Do When War, Climate Change, And Other Global Threats Inevitably Hit Your Startup

I wouldn’t have thought that a book about an obscure school of ancient philosophy would put me in the manufacturing business, but life is full of surprises. Several years ago, after writing a book called The Daily Stoic, I started an email list that delivered one philosophical meditation each day. From there, I expanded the business into prints and then into an e-commerce company that sells all sorts of physical products���statues, coins, printed books���all over the world.

The Daily Stoic Store is a small business in the sense that there are only six or seven of us in the office every day���and yet it’s not really small at all, ranking in the top 1 percent of all Shopify stores. The result has been a surprising thrust into a world I had experienced before only from the outside. Labor practices, manufacturing practices, environmental practices–these were no longer abstract issues that other companies grappled with. They were things that I had to face, firsthand.

We all have opinions about big sweeping issues. We tell ourselves that if we were in charge, we would do things differently. If we were a multi��national conglomerate, we wouldn’t use chemicals that harm the environment. If we were the decision makers, we’d have a diverse workforce, we’d be family-friendly employers, we’d speak out on political issues. We would pay a living wage. We wouldn’t do business with an overseas company that uses child labor.

But then the order for company T-shirts comes across your desk and you suddenly have to choose between the $9 option from China and the $19 one manufactured in the U.S. The right thing is still obvious. It’s just harder.

I’ll give you an example: At Daily Stoic, we sell challenge coins inspired by philosophical concepts (one says Memento Mori, another Amor Fati). After receiving many bids, I learned that it would be significantly cheaper to manufacture those coins in China than in the United States. Although I might have previously nodded my head in agreement with people who criticized outsourcing, now the tradeoffs directly affected my own bottom line.

Suddenly, it was ethics versus expenses: It was out of my wallet that the higher cost per unit would come. I would be the one who would have to go to customers and ask them to pay a higher price. It was me they might balk at.

Eventually, I made the difficult decision to go with a U.S.-based company called Wendell’s (in business since 1882). Then, a few months later, I stumbled across something else I could not ignore. The coins were going straight from the manufacturer to the third-party shipping contractor and then to the customer. And it wasn’t until an order got shipped to me that I realized each coin came shrink-wrapped in its own plastic covering.

How much of this plastic was being produced for my company? How much ended up in the trash���or, worse, in the ocean?

Wendell’s explained the protective benefits of the plastic���and I’m sure 95 percent of the world’s excessive packaging exists for that reason. The company also explained the plastic bags weren’t really costing me anything; this was just the way it had been doing things for a very long time. But, in this case, the environmental footprint was on my conscience, and only I could make it go away.

In our inter��connected world, we entrepreneurs have more power than we think we do, and more than we might have had in earlier eras.

I say ���could��� because I wasn’t obligated to reduce the plastic my products were adding to the world. It’s not illegal to seek cheaper labor overseas. Most of my customers probably wouldn’t have noticed a change. But how could I have justified sorting my recycling at home if I was sending little plastic sheaths into thousands of homes every year? I asked Wendell’s to stop using the plastic. And if making that decision caused damage to a product during shipping, we’d deal with it. Nobody threw me a parade, but I, for one, felt better.

When John Mackey, co-founder of Whole Foods, espouses conscious capitalism���the idea that the purpose of business is creating value not simply for shareholders but also for employees, consumers, suppliers, and the planet���it’s easy to assume he’s talking to other powerful captains of industry. But, no, he’s talking to all of us.

As the great novelist and political theorist Leo Tolstoy once suggested, we all feel qualified to reform humanity’s issues���but we are less inclined to reform ourselves. The Stoic school of philosophy, the thinkers whose ideas are the foundation of my business, would say that talking about what you believe in is much less important than embodying that belief, filtering your basic daily actions and choices through your philosophy. We can despair at the enormity of the world’s problems, or we can get to work where we work.

The truth is that in our interconnected world, we entrepreneurs have more power than we think we do, and more than we might have had in earlier eras. With a click of a button, we have unprecedented reach. We can plug into international supply chains. We can access the kinds of resources that compel great powers to go to war.

Just over a year ago, I watched horrified as Vladimir Putin’s tanks rolled into Ukraine. And, as the geopolitical experts and military leaders explained Putin’s strategy, it wasn’t a bunch of unpronounceable words and distant places to me. I found myself understanding exactly what was happening, ��because I had recently purchased the rights to publish a leather-bound edition of one of my books and had begun working with a small company in Texas to do it���a company that had also been manufacturing Bibles in Belarus for decades.

Belarus sits above Ukraine, and the Dnipro River winds its way through the country and down through its southern neighbor, past Kyiv, entering the Black Sea not far from Crimea. Alexander Lukashenko, the leader of Belarus, is one of Russia’s closest allies, and in the early days of the war, Lukashenko seemed likely to get involved at any moment; both he and Putin hope to gain control of a valuable shipping route, which in turn would make their countries more attractive to businesses like mine and much bigger ones. For a year and a half, I had been using raw materials that came in through this area and then trucking finished books to a port to be shipped out. This meant the invasion mattered to me as an American not just from a logistics standpoint���how our goods might manage to get through a war zone from printer to customers���but also from an ethical standpoint.

I spoke with a handful of experts, including two members of Congress. Their answer was quite clear: It may not have been illegal to do business with Belarus, but it was effectively the same as doing business with Russia. Is that what I wanted to do? Is that what I should be doing?

This was not the answer I wanted to hear. Further, a solution to the problem was not exactly obvious. I liked the people I was working with in Belarus. The bids I got from manufacturers in the U.K. were as much as 200 percent higher. It struck me, however, that the very book I was printing included a relevant line from Marcus Aurelius, the great Stoic philosopher and Roman emperor: “Just that you do the right thing. The rest doesn’t matter.”

I decided I didn’t want any part of contributing to the economy of a country that does the bidding of China or Russia. I couldn’t change the world, but I could change this. I could get as far away as possible from something I found abhorrent.

Sure, it was more expensive. It would take long��er. Almost no one would have known if I had simply continued with what I’d been doing. But that doesn’t matter. I would have known.

In the end, it wasn’t a cost-benefit analysis that swayed me. The math wasn’t in my favor. I think you have to start with what you believe is right, and then try to make the math work from there.

I’m not McDonald’s or Apple or General Motors doing business overseas. And I’m not saying that I always make the right decisions, or that I have examined every inch of the supply chain and personally vetted every person or company involved. I haven’t. But, like many other entrepreneurs, what I’m doing is my best.

Each of us has the power to contribute to a problem or to be part of the solution. The decision to reform oneself is not an isolated one. It may matter only a tiny bit in the big scheme of things, but it does matter. All the decisions we make as business owners matter. We have agency, we have a say.

The question we all face, then, is obvious: How will we use it?

This piece was initially published in the May/June 2023 issue of Inc. Magazine and can be found on their website here .��

 

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.

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.

 

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.

31 Lessons I���ve Learned About Money

I remember learning how to play the recorder in elementary school. I remember square dancing. I remember cursive. I built a model of a Spanish mission out of sugar cubes.

Some of this was fun. Some of it wasn���t. Some of it probably contributed, in some indirect way, to my general ability to learn and function in the world. Most of it, I think it���s safe to say, did not.

Something I don���t remember learning about at all? Money. Even our math problems were mostly about potatoes and trains, not how to calculate the interest rate on credit cards or the return on an investment. There was the occasional���and now very politically incorrect���remark from teachers about how if you didn���t do well in school, you���d end up working at McDonalds. But even with all the pressure to go to college, school provided very little in the way of discussion about what kind of careers paid what, how to live within one���s means whatever that career was, let alone how one might create their own business and work for themselves.

This is sad and strange and hardly rare. We leave it to kids who become adults who then have kids to just figure it out for themselves. Not everyone does. I���ve since met high income earners who were terrible with money. I���ve met people who were quite rich by every financial metric but whose relationship with that money was quite terrible, (you���d never want to trade places with them). I���ve met people who have been the victims of scams and frauds because they lacked the basic knowledge needed to protect themselves.

To the Stoics, the solution to these timeless problems���the way to be better with money, to improve your relationship with money, to not fall for every smooth talker, Marcus Aurelius said���is the same: get smarter. Become better educated on the topic of money. ���Wisdom,��� as Seneca said, ���offers wealth in ready money.��� It���s something I���ve been thinking a lot about in my own journey���growing up with two civil servant parents, dropping out of college, succeeding in the corporate world until I dropped out of that as well to work for myself. I���ve been thinking about it a lot now that I have kids.

And I���ve been thinking about it a lot in researching and writing what is the most in-depth course ever built over at Daily Stoic: The Wealthy Stoic. It���s a 9-week course packed with the best wisdom from the Stoics, as well as today���s leading money experts, on how to be rich, free, and happy. Along with ~30,000 words of exclusive content, there will be 3 live video sessions where I���ll be joined by bestselling authors, pioneering businesswomen, and investing and finance experts. I���m really excited about this course. I think it���s going to be one of our best, and I would love to have you join us���you can learn more at thewealthystoic.com.

Here are 31 lessons I’ve learned about money���

���I’ve never met a person who ever reached ‘their number.’ You know, people say, ‘When I hit $Xm, I’ll be good.’ They say, ���Once I have X years salary in the bank, I’ll be good.’ No one ever seems to get to that number. We’re never ‘good’ because we move the goalposts…(or because we set a preposterous and unrealistic number to begin with).

���It’s important to remember what once seemed like a lot of money to you. When I dropped out of college to work as an assistant in Hollywood, I took a salary of $30,000. I remember saying to myself���no joke���”What am I going to do with all this money?” It was enough for an apartment and all the books I wanted to read. Remembering that as an anchor point has not only kept me humble, it’s kept me grateful. Think about what your parents made, think about what you used to get paid per hour to make smoothies or mow a lawn. People manage to live on that���you yourself once did.

���Seneca said that poverty wasn���t having too little, it was wanting more. He wasn���t talking about poor people. He was talking about rich people. He was talking about people who are insatiable. ���Rich��� is having enough���as this story illustrates.

���My work is unpredictable, and even success comes in the form of lump payments. So when it comes to savings and investing, I have always favored things that are dependable. My wife and I invested quite a bit in different real estate things over the years, with the idea being to eventually create enough annual income that we could be independent from my creative/entrepreneurial/artistic decisions. This strategy is not for everyone, but it worked for us. I could stop writing tomorrow and know the spigot isn’t going to be turned off.

-My parents did a good job modeling how to be responsible with money. They also taught me how to be savvy at investing and growing one���s money. I wish they had done a better job modeling generosity and the proper value of money (that is to say, that most things are more important than money). There have been lots of other opportunities since to learn the skills I got from them, the others much less so���

-Pick the low hanging fruit. I���ve had to remind the Daily Stoic employees several times to be sure to sign up for their 401k/matching we offer. I���ve left money for too long in checking accounts when the easiest of transfers would have significantly increased the interest I was earning. Don���t get overwhelmed by the whole of life, the Stoics would say, do easy things first.

���If you don���t take the money, they can���t tell you what to do. That���s what Bill Cunningham said: If they pay you, they get to tell you what to do. Remember his words: ���Money���s the cheapest thing. Liberty, freedom is the most expensive.���

���The trope that a day job takes away from your art or your hustle is stupid. There’s a great exhibition at the Blanton Museum right now about artists who had day jobs. I wrote 3.5 books while I was the Director of Marketing at American Apparel. I started my own marketing company while I was a writer. I have my bookstore. A job for someone coming up is like a trust fund you’ve earned. It helps.

���Learning is priceless. Robert Greene used to have to nag me to submit my hours when I worked for him. To me, the money was an afterthought, I knew the real return was my access to him, that he would answer my questions, that I could see how a real pro did the job.

���That doesn’t mean internships should be free. When you make it, you have an obligation to try to support the people coming up (which is why Robert insisted on paying me even though I didn’t care). It just means sometimes you have to accept a bad deal to learn what you know you need to learn…and also to walk away if you stop learning.

���I’ve had the privilege of talking to many, many extremely wealthy people. They are not that rare. Rarer is the one who actually likes what they do for a living (for instance, half the ones I meet all seem like they’d rather be writing books for some crazy reason). Rarest is the one you’d want to trade places with.

���When you’re building a business, salaries/staff can feel expensive. But if you succeed, you’ll regret giving up equity so cheaply.

���I had this idea that I wanted to be a millionaire by 25. Where this number came from, I don���t know. I made it up, it was ego, and I didn���t hit it. But you know what the difference of getting there a little later was? Nothing. No one throws you a party. Accomplishments don���t change who you are.

���I talked with Tim Ferriss when I was starting my marketing company. He asked me what I was working on and what I was trying to accomplish, and I gave your typical answer: I wanted to be financially successful. Then he asked me something I���ve never been asked. ���Ryan,��� he said, ���What do you do with your money?��� Basically, I just put it in the bank, I told him. ���Then why are you doing so many things you dislike to earn more of it?��� he replied. This insight changed the course of my business as well as my life. Making money is easier than most people think���knowing why and what for, and not being driven in the wrong direction to get it? Much harder.

���You work really hard to get money���and then once you have it you spend time worrying whether you���re putting it to work right. James Altucher once pointed out that you don���t have to make your money grow. You can just have it. It can just sit there. You can spend it. Whatever. You don���t have to whip yourself for not investing and carefully managing every penny. The reward for success should not be that you���re constantly stressed that you���re not doing enough to ���capitalize��� on that success.

���At the same time, I love Charlamagne���s ���Frugal Vandross.��� The less expensive stuff you have, the less there is to worry about.

���Be responsible. I have a life insurance policy. I have money saved. If something happens to me, people I care about will be taken care of.

���But not too responsible. The reason they will be taken care of and that I feel creatively and professionally satisfied, is that I have taken a lot of big risks. I dropped out of college (this gave me a two year head start on a lot of people). I left a good job. I bit off more than I could chew many times. Why could I take those risks? Because I had been responsible. I had money saved. I knew what was important to me. I had built a support network. I eliminated the tiny risks so I could take the right ones. If you cover your bases, then you can afford to bet on yourself.

���The best decision I ever made was taking a pay cut to write The Obstacle is The Way (less than half what I got for my first book). I knew it was what I wanted to write. I thought it could sell. I had my day job. It still seemed like a TON of money to me. Sometimes you have to take a step back to go forward,

���If you can, pick up the check. If you can, tip amply. It feels good, it���s nice, it also normalizes not sweating small amounts of money.

���As I wrote recently, a couple years ago, I made the decision to stop basically all the advertising that my business does. I decided to put that money into making content instead���videos, articles, etc. I did this because it occurred to me that the money I was spending on ads made basically no positive impact on the world (if any impact at all), but articles and videos could at least be enjoyed by people (for free no less), even if they didn���t drive the same amount of ROI. In the long run, this content will be around forever and have a bigger and more meaningful reach. This is a small-scale decision given the size of my business, but if people spend more time trying to maximize the positive externalities of what they did instead of optimizing for short-term profits, I think they���d be happier���and ultimately do better���and the world would be better.

���But if I am content with what I have, won���t I stop getting better? No. We play better with house money. Feel better too.

���A wise person once told me…if it’s a problem that can be solved by money, you don’t have a problem.

���If you never hear no from clients, if the other side in a negotiation has never balked to something you’ve asked for, then you are not pricing yourself high enough, you are not being aggressive enough.

���Anticipate the fact that maintaining discipline is hard. Automate. I���m always amazed when I check the balances of accounts where we���ve set up automatic transfers for investing, for our kids��� college, for our emergency reserves���things I set up a long time ago have been doing their job, a far better job that I would have done had I put it on my monthly to do list.

���Don���t compare yourself to other people. Caesar famously wept at the feet of a statue of Alexander the Great. ���Do you not think it is matter for sorrow that while Alexander, at my age, was already king of so many peoples, I have as yet achieved no brilliant success?��� he said. Um, you were both fucking terrible. And now you���re both gone. Who cares whether so-and-so did this or that earlier than you? Who cares that so-and-so had more?

���Acceptance is a difficult thing, but it’s an important skill as you become successful. Accepting that there will be a certain amount of your investments that fail, accepting that mistakes will cost you, there will be fees and other costs of doing business. Taxes are another thing you have to come to terms with. We must pay all this stuff gladly, the Stoics say, otherwise success will be a form of misery.

���If you live somewhere cheap, you’ve got a head start. Moving to an expensive, popular city ‘to make your start’ is a tough gamble. There is more opportunity…but less runway. I’m grateful to New Orleans in 2011 for giving me plenty of runway as well as friendships and inspiration.

���Yes, it���s true that money is better spent on experiences than material possessions. But, I will say that just because an experience presents itself doesn���t mean you have to feel obligated to do it. Remember, there is a cost to saying yes. And not just a monetary one, but it will take your most precious, non-renewable resource���your time.

���They say that if you think professionals are expensive, try hiring an amateur. This is true in the sense that being cheap or looking for a bargain on services has come back to bite me many times. HOWEVER, I have also been disappointed with how many professionals are actually amateurs. Sometimes, if you want a thing done well, you have to do it yourself. It’s very rare that you’ll just be able to hand stuff off���and don’t be fooled by high priced experts and consultants. You may end up still doing the job yourself in the end…after having shelled out for their fee.

���If it makes you a worse person (parent, neighbor, writer, whatever), it���s not success. If starting a business makes you a worse person���if it stresses you out, if it tears your relationships apart, if it makes you bitter or frustrated with people���then it doesn���t matter how much money it makes or external praise it receives. It���s not successful.

This Is Why You Can’t Wait Until Later

Before I dive into today���s post, I wanted to say thank you to everyone who preordered The Daily Dad! If you haven���t picked up a copy yet, I���ll be in New York City TONIGHT at the Barnes and Noble in Union Square at 6 p.m. with my buddy Casey Neistat (ticket includes a copy of The Daily Dad!). And if you���re in Austin on Monday May 8, I���ll be at the Barnes and Noble at the Arboretum with my buddy Austin Kleon at 7 p.m. Click the links for more details, and I hope to see you there!

***

At 6:45pm on Wednesday, April 23rd, 2014, I got an email from my friend Seth Roberts, the pioneering and peerless scientist.

I opened it, saw that it was to be the first of a long awaited column called ���Personal Science��� for the Observer, where I was then an editor. I assumed it was good���Seth���s work always was���so I marked it as unread and told myself it could wait until Monday.

On that Saturday, less than 72 hours later, Seth collapsed of a fatal heart attack while hiking in Berkeley. It would have been so easy for me to reply and and tell him how happy I was with what he had written. Or how much he���d helped me over the years and how excited I was to be working with him. How hard would it have been to give even the courtesy of acknowledging his email?

But I didn���t. And now I will never get to tell him anything ever again. This man who had mentored me, who had inspired me, who had made me rethink how I did so many things���I had left him on hold and now he was dead.

Of course, I was familiar with the Stoic concept of Memento Mori. In Meditations, Marcus Aurelius writes ���You could leave life right now. Let that determine what you do and say and think.��� Of course, I knew that any of us could go at any moment. Yet there is, as always, a difference between knowing something and knowing it. And there is nothing like losing someone you care about suddenly and unexpectedly to help you understand how fragile and ephemeral life is.

In an interview shortly after the death of the musician David Crosby, Crosby���s bandmate Graham Nash talked about the falling out they never got to resolve. ���He had sent me a voicemail saying that he wanted to talk to apologize,��� Nash said. ���I emailed him back and said, ���Okay, call me at 11 o���clock tomorrow your time, which is 2 o���clock on the East Coast.��� He never called, and then he was gone.���

You think you can do it tomorrow. You think you have tomorrow.

You very well may not.

The grudges we hold on to. The strange priorities we hold. The nonsense we get bogged down in.

There is a kind of arrogance in it. It takes tomorrow for granted.

This is the one thing all fools have in common, Seneca wrote. ���They are always getting ready to live.��� They are always thinking that they have plenty of time. They are always saying that they���ll be able to get to it later. They think that opportunities, that other people, that life can be deferred to the future.

They cannot.

These things exist, as Tolstoy wrote, only in the present.

Procrastination is egotistical. It is entitlement, embodied. I carried guilt about that with Seth for a long time���you can see I was still wrestling with it in the eulogy I gave for him a few months later (Tim Ferris gave a really good one too)���and it���s taken me almost ten years to even be able to write about it.

Meditation on our mortality is not a productivity hack. It���s more than that.

For me, I���ve tried to take from this experience a relatively simple lesson: I tell people how I feel about them when I have the chance.

It wasn���t just Seth that taught me this. I remember I was in O���Hare Airport a couple years ago, and I saw something on a TV I was passing that reminded me of my friend Bret Bearup. I remember thinking, ���Oh I should message him.��� Then I got distracted and boarded my flight. When I landed, I got a terrible bit of deja vu, more terrible news. He had died taking an afternoon nap.

If a friend pops into my head now, I take it as a sign: You need to reach out. Don���t do it later. Don���t leave them hanging. Don���t assume you���ll get another chance. Take the one that���s in front of you right now. Accept the gift in front of you���it is the present.

It���s very unlikely you���ll regret it. It may well be the last thing you get to do. For instance, in The Daily Dad (out now!) I tell the story of Bob Saget���legendary comedian, longtime host of ���America���s Funniest Home Videos,��� and Danny Tanner on ���Full House������who got a text from his daughter as he was about to go onstage to perform stand-up. We don���t know what she said, but it wasn���t urgent.

He could have easily said to himself, I���ll respond later. I���ll call her in the morning. We never want to consider that it���s our last chance. We tell ourselves that it���s nothing, that there will be other phone calls, other texts, more good-nights. But that���s not always true.

Saget took a second to send what neither of them could have known would be his last text. ���Thank u,��� he wrote. ���Love u. Showtime!��� Hours later, he was found dead, tragically, in his Orlando hotel room at age 65.

No one knows what their last words will be. No one knows how much time they have. So let���s use the time we have, before we lose the time we���re never guaranteed.

Let���s make sure we tell people that we care about them.

Let���s make sure we reply to the email, we return the call, we tell those we love how we feel about them while we can.