Hey Dad,

Our relationship is strained.

It feels like it has been for a while. For the last four years, there has been an elephant in the room—I’d joke and call it an orange elephant, but I’m nervous that might end this earnest conversation before it even begins.

Have I changed? I mean, yes, of course I have. I’ve gotten older. I’ve had two children. I’ve tried to read and learn as much as possible, just as you taught me.

In fact, that’s sort of the weirdest thing. I don’t think I’ve changed much. I still believe, deep in my bones, all the fundamental things you not only talked to me about, but showed me when I was little.

I believe in character.

I believe in competence.

I believe in treating people decently.

I believe in moderation.

I believe in a better future and I believe in American exceptionalism, the idea that the system we were given by the Founding Fathers, although imperfect, has been an incredible vehicle for progress, moral improvement, and greatness, unlike any other system of government or country yet conceived.

I believe this exceptionalism comes with responsibilities.

Politically, I’m pretty much the same, too. Government is best when limited, but it’s nonetheless necessary. Fair but low taxes grow the economy. Rights must be protected, privacy respected. Partisanship stops at the water’s edge. No law can make people virtuous—that obligation rests on every individual.

So how is it even possible that we’re here? Unable to travel, banned from entry by countless nations. The laughingstock of the developed world for our woeful response to a pandemic. 200,000 dead. It hasn’t been safe to see you guys or grandma for months, despite being just a plane ride away. My children—your grandchildren—are deprived of their friends and school.

Meanwhile, the U.S., which was built on immigration—grandma being one who fled the ravages of war in Europe for a better life here—is now a bastion of anti-immigrant hysteria. Our relatives on your side fought for the Union in the Civil War. Great-grandpa fought against the Russians in WWI, and granddad landed at Normandy to stop the rise of fascism. And now people are marching with tiki-torches shouting, “the Jews will not replace us.” What is happening?! Black men are shot down in the streets? Foreign nations are offering bounties on American soldiers?

And the President of the United States defends, rationalizes, or does nothing to stop this?

I’d say that’s insane, but I’m too heartbroken. Because every step of the way, I’ve heard you defend, rationalize, or enable him and the politicians around him. Not since I was a kid have I craved to hear your strong voice more, to hear you say anything reassuring, inspiring, morally cogent. If not for me, then for the world that will be left to your grandchildren. This does not feel like a good road we are going down…

Look, I know you’re not to blame for this. You hold no position of power besides the one we all have as voters, but I guess I just always thought you believed in the lessons you taught me, and the things we used to listen to on talk radio on our drives home from the lake. All those conversations about American dignity, the power of private enterprise, the sacredness of the Oval Office, the primacy of the rule of law.

Now Donald Trump gushes over foreign strongmen. He cheats on his wife with porn stars (and bribes them with illegal campaign funds). He attacks whistleblowers (career army officers, that is). He lies blatantly and habitually, about both the smallest and largest of things. He enriches himself, his family members, and his business with expenditures straight from the public treasury. And that’s just the stuff we know about. God knows what else has happened these last four years that executive privilege has allowed him to obscure from public view.

I still think about the joke you made when we walked past Trump Tower in New York when I was kid. Tacky, you said. A reality show fool. Now that fool has his finger on the nuclear button—which I think he thinks is an actual button—and I can’t understand why you’re OK with this. I mean, the guy can’t even spell! You demanded better of me in the papers I turned in when I was in middle school.

I know you don’t like any of it. If you’d have had your choice, any other Republican would have been elected but Trump. You’re not an extremist, and you’ve never once said anything as repulsive as what people now seem comfortable saying on TV and social media (and in emails to your son, I might add). Four years ago, I wrote to you to ask you not to vote for Donald Trump. But this time around, that’s no longer enough.

At some point, just finding it all unpleasant and shaking your head at the tweets, while saying or doing nothing more about it, is moral complicity. You told me that as a kid! That the bad prevail when good people do nothing.

A while back I emailed a friend of mine who is an advisor to the administration. I said to him, why do you think my dad’s support of Trump bothers me so much more than yours? Because it does. This is someone who helped put Trump in office and wants to keep him there, but we’re still friends. Talking to him doesn’t hurt my heart the way it does when politics come up over family meals.

The man’s answer was telling, and I am quoting. He said, “Because I am irredeemable, but your dad ought to know better.”

Does that register with you at all?

One of the things you taught me well was how to spot a scam. Double check everything, you said. Do your research. Look at what the people around them say. Look at their history. Remember when you used to quote Reagan’s line to me, “Trust, but verify”?

I’ve been lucky enough to make a few trips to Washington the last few years. I’ve sat across from Senators and Congressmen. I’ve talked to generals who have briefed the president, and business leaders who worked with him before the election. This is a guy who doesn’t read, they said, a guy with the attention span of a child. Everybody avoided doing business with him. Because he didn’t listen, because he stiffed people on bills, because he was clueless. He treated women horribly. He’s awful, they said. I thought this was a particularly damning line: If Donald Trump were even half-competent, one elected official told me, he could probably rule this country for 20 years. I have trouble figuring what’s worse—that he wants to, or that he wants to but isn’t competent enough to pull it off. Instead, Washington is so broken and so filled with cowards that Trump just spent the last four years breaking stuff and embarrassing himself.

I learned from you how to recognize a dangerous or unreliable person. If you don’t trust the news, could you trust what I’m bringing you, right from the source? Let’s trust our gut, not our political sensibility. Based on what I’ve told you, and what you’ve seen: Would you let him manage your money? Would you want your wife or daughter to work for him without supervision? I’m not even sure I would stay in one of his hotels, after what I’ve read.

Watching the RNC a few weeks ago, I wondered what planet I was on. What’s with all the yelling? How is this happening on the White House lawn? Why are his loser kids on the bill? His kid’s girlfriend??? And what is this picture of America they are painting? They are the ones in charge! Yet they choose to campaign against the dystopian nightmare that is 2020… which is to say, they are campaigning against themselves.

Look, I agree there is crazy stuff happening in the world. The civil unrest is palpable, violence is on the rise, and Americans have never been so openly divided. Sure, rioting and looting are bad. But who is to blame for all the chaos? The President. Remember what you told me about the sign on Truman’s desk? The buck stops here. (May we contrast that with: “I don’t take responsibility at all.”)

In any case, what some crazy people in Portland are doing is not ours to repeatedly disavow. What the president does? The citizens are complicit in that. Especially if we endorse it at the ballot box come November 3rd.

Besides, what credibility do we have to insist on the ‘rule of law’ when eight of the president’s associates have faced criminal charges? His former lawyer went to jail, too! And then the president commutes their sentences, dangles pardons to keep them quiet, or tries to prevent them from cooperating with authorities? When he’s fined millions of dollars for illegally using his charity as a slush fund? When he cheats on his taxes? When he helped his parents avoid taxes, too?

I remember you once told me the story of a police officer in your department who was caught filling up his personal car with gas paid for by the city. The problem, you said, wasn’t just the mistake. It was that when he was confronted by it, he lied. But the cameras showed the proof and so he was fired, for being untrustworthy most of all.

Would you fire Trump if he worked for you? What kind of culture do you think your work would have had if the boss acted like Trump?

As for the lying, that’s the craziest part, because we can, as the kids say, check the receipts: Was it bad enough to call John McCain a loser? Yes, but then, of course, Trump lied and claimed he didn’t. Bad enough to cheat on his wife? Yes, but of course, he lied about it, and committed crimes covering it up (which he also lied about). Was it bad enough to solicit help from Russia and Wikileaks in the election? Yes, but then he, his son, and his campaign have lied about it so many times, in so many forums, that some of them went to jail over it. Was it stupid that, in February, Trump was tweeting about how Covid-19 was like the flu and that we didn’t need to worry? Yes, but it takes on a different color when you listen to him tell Bob Woodward that in January he knew how bad it was, how much worse it was than even the worst flu, and that he was deliberately going to downplay the virus for political purposes.

I’m sure we could quibble over some, but The Fact Checker database currently tallies over 20,000 lies since he took office. Even if we cut it in half, that’s insane! It’s impossible to deny: Trump lied, and Americans have died because of it.

A friend of mine had a one-on-one dinner with Trump at the White House a while back. It was actually amazing, he said. Half the evening was spent telling lies about the size of his inaugural address. This was in private—not even for public relations purposes, and years after the controversy had died down. That’s when he realized: The lying is pathological. It can’t be helped. Which is to say, it makes a person unfit to lead.

Politics should not come before family. I don’t want you to think this affects how I feel about you. But it does make it harder for us to spend time together—not just literally so, since Trump’s bumbling response to the pandemic has crippled America and made travel difficult.

It’s that I feel grief.

I feel real grief—were the lessons you taught me as a kid not true? Did you not mean them? Was it self-serving stuff to make sure I behaved? Was I a fool for listening?

Or is it worse, that my own father cares more about his retirement accounts—and I’ll grant, the runup of the market has been nice for me, too—than the future he is leaving for his children? Are you so afraid of change, of that liberal boogeyman Limbaugh and Hannity and these other folks have concocted, that you’d rather entrust the country to a degenerate carnival barker than anyone else? I see all this anger, what is it that you’re so angry about? You’ve won. Society has worked for you. My own success is proof.

So what is it? Because it can’t possibly be that you think this guy is trustworthy, decent, or kind. It’s definitely not about his policies… because almost every single one is anathema to what Republicans—and you—have talked about my entire life.

The one thing I hold onto is hope. I believe in America. I believe in the goodness of hardworking people like you and Mom. I know that this is not what you wanted to happen, that this is not the America you grew up in nor the one you would like for me and my kids to grow up in.

I hold onto hope that you’re tired enough to draw the line. That you are not irredeemable as that Trump advisor allowed himself to become. The right thing is always the right thing, you’ve said. Even when it’s hard. Even when it goes against what your friends think, or what you’ve done in the past.

The right thing is obviously to end this. To cancel this horrendous experiment with its cavalcade of daily horrors and vulgarities and stupidities and historical humiliations.

America is a great nation. The world depends on us being great. Your grandchildren deserve that greatness.

You know this has not been it. You know this goes against everything you’ve ever asked or expected of yourself, and your children, and anyone you’ve ever led or worked for.

I need you not just to not vote for Trump this year, Dad. I need you to speak up. I need you to do something.

Your loving son,

Ryan

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Something went wrong for Kyrie Irving in Cleveland, despite three trips to the Finals and one championship. 

Then, what could have been a great team fell apart in Boston.

So far, Brooklyn has been a dud. One coach has already been driven away. Now the most recent, just hired, is already being set up to fail, with heavy handed assertions about who is actually in charge.

Who could have seen this coming? 

Well, Kyrie could have… by looking in the mirror. 

Indeed, just about any casual observer knows what to expect at this point. 

The secret is explained by an old Greek saying, popular with the Stoics: ἦθος ἀνθρώπῳ δαίμων. 

Character is fate.

Not simply that good people do well and bad people fail—we know life is more complicated than that. The proverb means that character traits predict the kind of actions we’ll see. 

The selfish person may succeed… but it will be a lonely, isolated success. The corrupt will end up corrupting the institutions and people around them. The ignorant will end up missing some critical piece of information that costs them. The paranoid will create the enemies they worry are out to get them. The egotistical will ignore the warnings that could have saved them.  

Who we are, what we believe, the standard we hold ourselves to, the things we do regularly, our personality traits—ultimately these are all better predictors of the trajectory of our lives than talent, resources, or anything else. 

Kyrie is, from all reports, sweet and serious and often generous. It’s just also not surprising that a guy who at one point believed the world was flat—despite literally all evidence and information to the contrary—would be a difficult guy to coach. The impulse that broke apart a relationship with the maybe greatest basketball player of all time is not a singular one, it’s one that will repeat itself again and again. 

What should surprise us is how many people failed to see this, or managed to convince themselves that it would be different this time. 

It’s a phenomenon we see play out in the market, in politics, in relationships all the time. We want to see the best in someone, so we ignore the obvious. We really want something, so we deny the contrary evidence or the risk factors. Sports is such a great example of this, Antonio Brown being the most recent bit of proof. 

When people show you who they are, Maya Angelou said, believe them.

But we don’t… and it bites us in the end. 

I remember at American Apparel being amazed that these financiers kept giving the company money, expecting it to be different, thinking that their investment would be the lone exception, believing the CEO when he explained that he’d changed. At the same time, I stayed longer than I should have, because I often blamed fate or circumstances for problems at the company that were, in retrospect, obviously rooted in character and cultural flaws. I kept my stock longer than I should have, too…and it cost me. 

It was funny, I was right in the middle of researching Ego Is the Enemy and I didn’t quite get it. But Cyril Connolly was correct: Ego sucks us down like the law of gravity. 

Character is fate. 

But it’s important that we don’t use this rule just to judge other people. 

As Seneca said, the purpose of philosophy was to scrub off your own faults, not the faults of others. 

The bad news is we are all like Kyrie. The good news is we also have the ability to determine our own character—to address our traits and change them—and therefore chart the course of our destiny. 

Are you going to be someone that values the right thing? Are you going to be honest with yourself? Are you going to keep your ego in check? Are you going to respect your fellow human beings? Are you going to take responsibility? Are you going to be someone others can depend on, trust, believe? Or are you only going to look out for number one? Are you going to make excuses for liars and cheats and egomaniacs because they agree with you, or might benefit your business or help your cause in the short term? Are you going to blame fate or the gods or the Chinese when things don’t go your way?  

The answers to these questions influence more than just whether you’re pleasant to be around. If you get them correct, you’ll be resilient, reliable, adaptable; you’ll learn, you’ll grow, you’ll be able to collaborate with others. If you get them wrong, you’ll be fragile, stupid, and selfish, incapable of integrating feedback, shifting course or generating sympathy. 

One gives you a chance at success. One guarantees—on a long enough timeline—that you’ll fail. 

Quite possibly in a catastrophic way.  

My new book Lives of the Stoics is out now!

Small events—a single moment, a simple exchange, an unremarkable decision—are what change the world.

On a fateful day late in the fourth century BCE, after a disastrous voyage on the Mediterranean, the Phoenician merchant Zeno washed up penniless in Athens. He could have despaired. Instead, he studied philosophy and ended up founding a school known as Stoicism. “I made a prosperous voyage,” Zeno would later say, “when I suffered a shipwreck.”

In the first century BCE, Pompey tried to corrupt Marcus Porcius Cato by dangling a marriage alliance. “Go and tell Pompey,” he instructed the go-between, that “Cato is not to be captured by way of the women’s apartments.” A few years later, his daughter, collaborating in an attempt to overthrow Julius Caesar, would stab herself in the leg to test her ability to withstand torture. Able to successfully bear the pain, she and her husband Brutus went ahead with the conspiracy. Several generations would pass and eventually place Marcus Aurelius at the head of the Roman empire. A friend stopped Marcus as he was leaving his home one morning. Where are you going? To handle business? No, Marcus was on his way to attend a philosophy lecture. “Learning is a good thing, even for one who is growing old,” Marcus told the stunned man. “From Sextus the philosopher I shall learn what I do not yet know.”

These little moments—these are insights into the lives of what made the greats great. 

This, the great moral biographer Plutarch said, is why you can often learn more from a single anecdote than a sweeping historical portrait. Unlike the biographers of our time, who publish big, thick books filled with footnotes and postmodern digressions, Plutarch included only the essence of great men and women, so that he might inspire us to follow in their footsteps. He was obsessed by what we could learn from the figures he wrote about. 

“It is not histories I am writing,” Plutarch would write, “but lives; and in the most glorious deeds there is not always an indication of virtue or vice, indeed a small thing like a phrase or a jest often makes a greater revelation of a character than battles where thousands die.”

This distinction is core to Stoicism. Study the philosopher, they said, not the philosophy. Unlike the so-called “pen-and-ink philosophers”—as the type was derisively known even 2000 years ago—the Stoics said not to pay so much attention to what philosophers have thought or written because what counts is what they do. The choices they made, the causes they served, the principles they adhered to in the face of adversity. They cared about what you did, not what you said. 

“Don’t talk about your philosophy,” Epictetus would say, “embody it.” That’s why he would become so frustrated with his students who congratulated themselves on being able to read the obscure writings of Chrysippus: they were missing the point. Philosophy wasn’t about big words or complicated texts. It was about applying concepts to the real world. It was about living a happy and resilient and purposeful life. 

“I know,” Seneca wrote in 55 CE in a book on mercy written for the young emperor Nero, “that the Stoics have a bad reputation among the uninformed for being too callous and therefore unlikely to give good advice to kings and princes: they’re blamed for asserting that the wise man does not feel pity and does not forgive… In fact, no philosophical school is kinder and gentler, nor more loving of humankind and more attentive to the common good, to the degree that its very purpose is to be useful, bring assistance and consider the interests not only of itself as a school but of all people, individually and collectively.” 

It’s on these models that my latest book is written: Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius. With Stephen Hanselman, my co-author on The Daily Stoic, we pored over hundreds of ancient texts and modern scholarship to bring you 26 biographies of the most important—and most interesting—Stoics from history. Inspired by Plutarch, we wrote Lives of the Stoics with an eye towards practical application and advice. We wanted to leave you not only with some facts about these figures, but with a fuller sense of their essence and the aspects of their lives that teach us the most about the art of living. 

That’s the only reason to study philosophy—to become a better person. 

Anything else, as Nietzsche said, is merely a “critique of words by means of other words.” It’s empty talk. Schopenhauer called it “fencing in the mirror.”

This is, unfortunately, the role philosophy plays in the modern world. Today it’s about what smart people say, what big words they use, what paradoxes and riddles they can baffle us with. 

No wonder we dismiss it as impractical. It is!

 “To be a philosopher is not merely to have subtle thoughts, nor even to found a school,” Thoreau said. “It is to solve some of the problems of life, not theoretically, but practically.”

That’s what the Stoics were after, what we remain interested in to this day: lights to illuminate the path in life. They wanted to know, as we want to know, how to find tranquility, purpose, self-control, and happiness. This journey, whether it begins in ancient Greece or modern America, is timeless. It is essential. It is difficult. Which is why we ask, as the Stoics asked: Who can help me? What is right? Where is true north? 

“You’ve wandered all over,” Marcus Aurelius wrote to himself in Meditations, “and finally realized that you never found what you were after: how to live. Not in syllogisms, not in money, or fame, or self-indulgence. Nowhere.” 

If philosophy is anything, it’s an answer to that question—how to live. It’s what we have been looking for. “Would you really know what philosophy offers to humanity?” Seneca asks in his Letters from a Stoic. “Philosophy offers counsel.” Seneca said that was the most powerful lesson he learned from his childhood tutor, Attalus the Stoic. The purpose of studying philosophy, of reading about the great men and women who lived and died before you, of learning about that simple question Zeno asked, that small decision Cato made, that one passage that guided Marcus was to “take away with him some one good thing every day: he should return home a sounder man, or on the way to becoming sounder.”

You must heed this counsel and struggle with what Seneca described as the most important job of a philosopher—the act of turning words into works in the real world. To study the lives of the men and women who came before us for the same reason Plutarch (who wrote about many of the Stoics as well) did: to turn the lessons of the lives, their living and their dying, their succeeding and their failing, into actions in the real world. 

For it is this, and nothing else, that earns one the title: Philosopher.

My new book Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius is finally out. I can’t wait for you to read it. If you’ve gotten anything out of these emails over the years, it would mean a lot to me if you could support this book, which I have been working on for a long time. It’s worth your time, I promise. 

If you do, I’ll still send over these pre-order bonuses which include three extra chapters I couldn’t fit in the book. 

Thank you!