Thriving Amidst Chaos: An Interview About Stoicism With Former New York Observer Editor Ken Kurson

Most people know Ken Kurson as a political strategist or a newspaper editor. He is rather famous for these things. He was Rudy Giuliani’s Chief Operating Officer (and ghostwriter) during his 2008 campaign for the Republican presidential nomination. He was the editor of the New York Observer from 2013 to 2017 (and a friend of the Kushners and Trumps). Because of these roles he’s appeared hundreds of times on television and radio, including NPR, CNN, FOX, FOXNews, CNBC, MSNBC, ABC, and countless others. But I first met him as a simple fan of the Stoics. He sent me a friendly email about Tom Wolfe’s A Man in Full and we chatted—and then in the random way that life can go, he ended up as my editor and boss at the Observer.

We didn’t always agree (especially on politics—in fact quite publicly on politics) but we were always friends. Because Ken is not only one of the friendliest and kindest people on the planet, even when you disagree with him, you cannot think that he is anything but sincere and well-intentioned in his beliefs. Ken’s leadership at the Observer took the site from 1.1 million monthly unique users doing 3 million pageviews to 6 million unique users doing 20 million pageviews, and that’s certainly impressive. He also used the site to publish a number of interesting writers on Stoicism, and made a home for my own writing on the topic as well. Many millions of people were exposed to philosophy because of his advocacy.

I wanted to interview him here about that, and also about the role of philosophy in his own life and in his political life. How did he handle running a newsroom that was divided by the divisive politics of the day? How did he handle the scrutiny and criticism that came his way? How did he separate friendship and disagreement and the public intersection of those two things? (something I certainly didn’t make easy for him)? How does he see the role of Stoicism in politics today?

These were some of the questions I asked and Ken was nice enough to put an incredible amount of time and honesty into answering them. He didn’t need to do that but we’re grateful that he did. Hopefully you are too.


Tell us the story about how you were first introduced to Stoicism. Do you remember your initial reaction?

Well, of course I remember having a vague awareness of the Stoics from Intro to Philosophy type courses in college. But I think that like most people, when they hear the word ‘stoic’ even when it’s taught at a college level, it’s almost impossible to overcome the vernacular usage of the word. You have written about how misunderstood Stoicism is when people conclude that it’s about enduring pain wordlessly, or showing no emotion. That’s exactly what my understanding of Stoicism was until I read Tom Wolfe’s greatest book—and I say “greatest” advisedly because I love virtually every single word the guy has ever written, and he’s written a lot of them—but I think his master work is A Man in Full. In it, one of the characters, Conrad, is unfairly imprisoned through a catastrophic series of bad coincidences, and he tries to order an adventure novel called The Stoic’s Game, but instead, after waiting many weeks (this was before Amazon), he gets a book called The Stoics, and discovers the philosophy, and through it the reader also discovers it, including me.

I remember my initial reaction being exactly that of the character, Conrad, realizing that this was about truly freeing yourself from the prison of others’ perceptions. And for me, as a Jew, there were parallels that I had never imagined. For example, there’s a rabbinical idea that no one else can embarrass you. You can only embarrass yourself. That’s so powerful to me, because I have spent so much of my career being hated by so many people whose opinion I value and respect. I’m a conservative who travels in Manhattan media and social circles. And worse, from their point of view, I’m not just that guy who says, “Well I’m fiscally conservative and socially liberal.” I’m actually pretty awful on most of the social stuff too.

So, by virtue of that, I spend a lot of time basically being gutted. A writer from Gawker emailed me after the election and said, “I hope you feel a great sense of ownership for all of our new president’s actions.” I’ve always been comfortable without the approval of the people around me. But it can be a lonely place to be, and Stoicism put into a philosophical framework all of these random feelings I had had, but had never managed to coalesce into a coherent philosophical framework until I started studying.

Who is your favorite Stoic and why? Do you have a favorite quote from them (the one from Epictetus right)?

Well, as you recall, Ryan, you and I first met over email a year before I became your editor at the Observer because I had been so powerfully moved, especially by Epictetus. But the one story in particular that resonates with me stars the Stoic philosopher Agrippinus. His student Florus comes to him and says, “Oh no, a terrible thing has happened. I have been summoned to perform for the enjoyment of the Emperor. If I do it I will be humiliated, and if I don’t do it I will be put to death. What should I do?” Agrippinus answers him and says, “Well, of course you should perform in the play.” And the student says, “But Agrippinus, surely you would not have performed in the play,” and Agrippinus tells him, “No, I would not.” And the student says, “Well then why should I?” And Agrippinus says, “Because you have considered it.”

That just completely says everything to me.

During the heat of the 2016 presidential campaign, when literally every move I made was worthy of scrutiny and often criticism (you can google stories detailing where I sat at the Republican National Convention), I made the decision to help then-candidate Trump with an important speech he was to deliver to AIPAC. I of course knew that that would create controversy were it revealed, and I also knew that some of my own staff at the Observer might have trouble getting their head around my decision. Because I believed Trump would likely be the next President, and because the safety and security of the State of Israel is of paramount importance to me, I decided I would help Trump on his speech.

We worked on it together. Practiced it, and he delivered it beautifully in what many considered something of a turning point, because it revealed that he was capable not just of devastating one-liners and put-downs, but of a thoughtful serious delivery on an important topic. It helped people envision him as President.

So, a couple of months later, I was running around the reservoir and my phone rang from an unidentified number. It was Gabe Sherman, the very tough reporter who was then at New York Magazine, and is now at NBC. He said, “I have it on good authority that you helped Donald Trump with his AIPAC speech. Is that true?” I immediately answered him, “Yes, it’s true,” and that was that. He printed it. It caused a lot of hysteria from the news media, which I expected, and at the Observer as well, where our smart, dedicated staff worked hard to produce a non-biased coverage that was tough on all candidates. And I supported them in that mission, and can cite dozens of examples of news coverage, as well as opinion coverage that was very tough on candidate Trump. But yes, the Editor-in-Chief helping a candidate on a speech certainly created much concern among my peers.

I thought about that Agrippinus quote, because I hadn’t even considered spinning it to Gabe or worse, lying to him. Not just because I had no idea whether he really knew it for a fact or was just fishing, but because I made my decision when I agreed to help on the speech. I didn’t regret it and I thought back to the Stoic notion that all I really have in life is what Epictetus called “this vessel of clay and a quart of blood.” And people are going to make their conclusions about my integrity and my judgement, and I get some stuff wrong and some stuff right, but I really didn’t regret what I had done in writing that speech. And I was willing to face the consequences of my action.

A similar thing happened when Dana Schwartz contacted me to tell me she was thinking about writing a strong piece condemning what she perceived as Trump’s anti-Semitism and her thought that Jared had failed to sufficiently condemn it. I remember that moment precisely because I was driving on a particularly beautiful stretch in upstate New York on July 5, which would have been my dad’s 86th birthday. I didn’t hesitate or have to think it over or check with anyone. I told her “go.” I knew it might cause an uproar, and it certainly did – Dana is a writer of uncommon power and of course the topic is irresistible. But I was prepared to deal with any consequences because I knew it was the right thing to do. Jared has never received the credit he deserves for his response. As our publisher, he could have fired Dana or me, or worse just been aggrieved and miffed. Instead, he responded with his own powerful take on the situation, which is exactly how media is supposed to work.

An interesting side note to this that I don’t think anyone has ever written about, is that a few months later almost the exact same thing happened again with Gabe Sherman. Gabe emailed me and said, “I have it on good authority and I’m going to print it, that you write all of Ivanka Trump’s speeches and that Donald Trump calls you for advice all the time.” And I emailed back and said, “That’s not true. When you called me earlier about the AIPAC speech, I told you the truth, even knowing it would create a hassle for me. Now I’m telling you the truth again. Whoever told you that is mistaken. I hope I have some credibility with you because I told you the truth the first time and I’m telling you the truth now.” And to Sherman’s credit—and he can be very tough on me and on Jared and on all things Trump-related—he didn’t print that. So, it’s sort of a corollary to a Stoic idea, that you tell the truth not just because it’s the right thing to do in some abstract, but because no one else can embarrass you, you can only embarrass yourself. And although people can certainly write things about you that create a hassle in your life, if you stay true to what you believe, you’re going to do okay. I think I benefit in my life from having been dirt poor and having been widely hated. Both are survivable, so it’s hard to threaten me with “you’re fired” or whatever – I know I’ll be ok.

One of your (many) careers has been in politics. The Stoics were certainly no strangers to politics. Cato was a Senator. Marcus was chief executive essentially. Seneca was the highest of the high in terms of political consultants in Rome. Yet politics is also a dirty business and one could argue that Cato did poorly at it because he was unable to compromise and make deals. How have you thought about the principles of the philosophy and the complicated world of local and national politics?

I think that there is suddenly room for Stoicism in politics. Maybe for the first time in American politics, because the value of “telling it like it is” is so strong right now. So, we’ve got a guy in the White House right now whose chief attribute is his excellence as a communicator, and his willingness to say things that giant swaths of the population are unhappy to hear. That’s a major asset. In this particular case, it’s not maximized in a Stoic sense because he’s not super careful with facts and doesn’t have the sort of philosophical coherence that Stoic scholars and readers would prefer. But I think Donald Trump’s great underestimated strength is how quickly and violently he cleared out this notion that had developed over hundreds of years, that you had to be all things to all people to succeed electorally. That’s just not true, and he proved it, and I think you’re seeing the value on all sides of the political spectrum, from Bernie Sanders to Roy Moore. I would put Donald Trump almost in the exact center of those two extremes, but you’re seeing the value of politicians enjoying massive success for the first time in so long on the outskirts of the ideological spectrum, as well as nearer to the center. And I’m sure there will be objections at my characterizing Donald Trump as nearer the center, but the fact is, on issue after issue he has favored the center position, including in the Alabama primary itself. You’ve got a guy who is willing to say unpopular things and people responding in ways that are shocking the pundit class.

An example is Trump takes on the NFL, and instantaneously every journalist in New York City, every pundit in Washington, DC thinks that Trump has called it wrong. The instant he said that I communicated to the White House that Trump is right and I hope he doubles down, and he has, and we’ve seen little by little people realize, even people who dislike Trump, that he was right. That it is a disgrace to refuse to honor the flag. We would never tolerate that kind of disrespect if during the Olympics or some other international event some foreign athlete showed an intentionally disrespectful gesture to the American flag. Can you imagine at an Expos-Mets game if some Quebec-born player at Shea Stadium stood for the Canadian anthem and then refused to stand during the American anthem? It would be a disgrace, as it would be if an American athlete dishonored some other country’s flag.

So the idea that these owners—who are in some cases the most reprehensible characters around, I mean they look like slaveowners when the camera cuts to them suffering after their property has fumbled or celebrating after a touchdown, it’s disgusting—here they are creating a system where it is now beyond a doubt that reward only awaits you after decades of having the shit pounded out of your head in a way that is now certain to cause CTE. Here are these owners watching their employees deepen their permanent brain damage, and they are the populist heroes in the eyes of the New York City media and the Washington, DC pundit class.

All that tells me is that after all the hand-ringing on November 9th, and all of the assertions that we have to learn more about what America is thinking, these guys have learned nothing. They don’t understand America and Trump does, and that’s why he won and that’s why he’s probably going to win again, and that’s why the journalists who all wrung their hands and said, “We have to learn more about why America elected this lunatic,” they’ve actually done nothing. All they’ve done is further insult him, doubled-down on their lecturing hectoring tone, and they’ve revealed that he is a master politician and they are way behind him in understanding and explaining the American people. He’s actually a better journalist. Trump is actually a better journalist than a great majority of the journalists who cover him, because he does a better job of explaining America than they do, and that’s the job.

So, I think this is a unique opportunity for Stoicism to make a stand, because it’s much harder to shame politicians and to manipulate them when they don’t really believe that they have to impress everyone to enjoy electoral success. When they finally begin to believe that they can have electoral success despite speaking their minds, I think you will get a lot closer to what the Stoics envision, which is the ability to stick to your guns.

Being an editor of a media outlet is not the easiest gig out there either. We can only imagine how much the stress increases during an election, especially when it comes to one that was as contested as our last and one where there was such an intense magnifying glass on you personally. Can you talk to us about how you managed and dealt with that? What got you through it?

First, I will take issue with the “what got you through it?” portion of your question. There were dicey moments, to be sure, but being paid a ton of money to work for people I consider family, all while being treated well and fixed up with gorgeous friends of Jared and Ivanka … that’s not exactly hard labor. But yeah, Ryan, you saw firsthand how close the scrutiny could get. I was under a microscope while editing the Observer. Literally where I sat at the Republican National Convention was deemed worthy of news coverage. It was ridiculous, but that’s the hand I was dealt. I would also point out that I was going through a divorce at that exact time, so my personal life was a fucking mess. And then you’ve got my closest friend leading this campaign —the first campaign he ever worked on was a presidential campaign, and he won, defeating a murderer’s row of governors and senators in the primary and then vanquishing a shoo-in during the general—so it was a stunning, strange and surreal time to be the editor of the Observer.

I managed by using a lot of the Stoic principles. I basically got up every day and I said my morning prayers and thought, you know, my job is not to be the greatest editor in the world. I don’t even know if I can be the greater editor of the New York Observer, which has been lucky enough to have editors like Peter Kaplan and Graydon Carter and Susan Morrison. My job was to be the best editor that Ken Kurson can be. That’s all I owe the Kushner family. It’s all I owe the world and the media, and it’s all I owe myself. I think I got that right just about every day.

There are some things I would have done differently in retrospect. I think my original thesis, which was that we would not opine on Trump because of the obvious conflicts and only cover him from a news point of view, was a mistake. I think it was a bad idea not just because he winded up winning and sticking around longer than anyone predicated, but because it automatically imposed a double-standard. In fact, I was trying to be fair, but the net effect is that we were treating one candidate differently from how we were treating other candidates, and that’s not a defensible position. So when other smart journalists weighed-in—and I sought advice from the beginning from yourself (you might remember you and I had a passionate disagreement, and you are a true Stoic, so you never raise your voice or even let your pulse climb above 60 beats a minute, but you will probably remember that I was yelling and screaming), so I sought advice from people like yourself and from the other great journalists at the Observer, and people like Jill Jorgensen and Will Bredderman were very helpful to my thinking, and from different journalism professors and other people I respect. Time and time again it kept coming up with well, there’s no real precedent on how to handle this. And the closest we would get is something like William Randolph Hearst running a million years ago. There wasn’t a great roadmap for this, so I did my best. I made some mistakes, but overall, with the benefit of hindsight I think I got it right a lot more than I got it wrong, and I’m very proud of the journalism that the Observer created during my entire five years there. And I think our finest hour was 2016.

You are a father of three kids. Do you think about Stoicism in a parenting context? Are there any lessons you actively try to pass on to your kids? Or changing your behavior as a dad inspired by the Stoics?

You know, I don’t think there is a lot that can be learned about parenting from what little I know about Stoicism, with the exception of the value Stoics place on honesty. I have tried my whole time as a parent, even before I thought of myself as a Stoic to be very honest with my children. I was influenced a lot by Charlie Kushner in this regard, who I consider an amazing father. But you know, things like my kids know my salary. When our family has had difficult times financially they’ve known about it, and we’ve had easier times they’ve known about that too. And you know, you have to be responsible with this stuff and you can’t… When your children are too young to sort through complicated material emotionally you can’t just for your own benefit of being true to the stoic philosophy of brutal honesty, it’s not kind to share with children all of the details behind say a tough divorce or the reason a year ago we lived in a mansion with a pool and now we live in a shoe. So those are considerations that … this is why I am a flawed Stoic to the degree I’m a Stoic at all, considerations of the heart and sort of my natural inability to disappoint my kids has sometimes trumped my intellectual understanding that blunt force honesty is always the best policy. So you do the best you can, but yes, in general, being honest with my children and trying to raise them in a way that places fidelity to one’s self even when it’s tough has helped them emerge as strong individuals.

One of my daughters found herself in a difficult social situation and I was so proud when at a very young age, and I’m not sharing the name or the exact age because I’m trying to allow for a little bit of privacy here, when this child said to herself, ‘I’m okay not being in that group of friends. I’ll find a new group,” and she did. And the beauty of that is that the original group that sort of cast her aside, they respected her for it too and have come back to her looking to restart the friendship.

So I think that some of these principles do apply to parenting, but they’ve made me a better person and that makes me a better father, so there’s that too. You know you might not say “I’m doing this as a father because it’s consistent with Stoic philosophy,” but if you as a human being and a man are okay with yourself, compared to the anxiety and smallifying that comes from constantly seeking the approbation of others, your kids can see that in the way you model it too. It’s not only what you tell them or how you instruct them, it’s how you carry yourself.

And we are always curious for all of our guests: Do you have a Stoic routine in your day-to-day life? Friends of yours know of your famous Shabbos message each Friday, which is often about gratitude and compassion and the absurdity of modern life. Is that sort of a journaling thing for you?

Thank you for praising my “famous Shabbos message” – that’s really nice to hear. You know, that message has nothing to do with journalism. One of the things that disgusted me most during my time as editor of the Observer – and it’s the reason I’m not on Twitter — was the way in which journalists audition constantly for the praise and approbation of their fellow journalists. To me, being a journalist is about serving the public. Because the interests of journalists are not only different, but often contrary to the interests of the public, I think if you’re too concerned about the esteem in which your fellow journalists hold you, you are probably not doing your job well.

And then there’s just the fact that it turns me off as a punk rocker for people to so nakedly audition for each other. Who can think of the funniest anti-Trump quip that will get me more likes and more followers. That’s the wrong impulse when you’re sitting down to tell a story, not only because it off-limits your product to the half of the country that approves of Trump and voted for him, but because it disqualifies you as an unbiased observer of whatever is in front of you.

So, you know, I go on these panel shows and they usually cast me as like the lunatic who has yet to figure out that Trump is some combination of too foolish to sit in the Oval Office, but also the most sinister and diabolical evil mastermind who ever lived. It often turns somewhat confrontational because invariably the host of the show represents what 99% of journalists think, which is, you know, I’m positive without having polled it that Hillary Clinton got in the high 90s of journalists’ votes and probably Bernie Sanders did in the 60-70% range during the primary. So naturally, the tenor of these interviews pits the host who pretends to be neutral, against me, who is either delusional, stupid, or evil for continuing to support this guy. And during the commercial breaks the hosts actually go onto their own Twitter to try to solicit the praise of all the people who are at that moment on Twitter, you know, beating the shit out of me for supporting the president.

So, like if that’s in their head while they’re interviewing me, if they are sitting there thinking, “I will get some kind of reward” for antagonizing Trump, then they’re not performing their job properly. And as you know Ryan, you have written about it more eloquently than anybody in the world, this constant auditioning and the building of personal brands as journalists is toxic to the job of journalism. So if they are rewarded for a particular vicious one-liner about Trump, or an especially confrontational interview with a Trump supporter then we’ve created an incentive program that is completely contrary to any of journalism’s higher values.

Ever journalists I generally respect have embarrassed themselves by walking into this trap. Brian Lehrer on WNYC has become virtually unlistenable because he cannot describe even the most innocuous event of the president’s day without using the phrase “white nationalist.” Which is not only untrue, but worse, such an inflammatory thing to say because no one can possibly continue the conversation with that in the air. Yesterday in the aftermath of the horrible incomprehensible Las Vegas shooting, Lehrer told his audience that he was cringing in anticipation of Trump’s statement before Trump even spoke. Reaching conclusions about things before they occur is not how I was taught to commit journalism. And he’s guilty of the same schtick that CNN and the New York Times do – in order to be “balanced,” they have on a Republican, but it always, 100% of the time, an anti-Trump Republican – Ross Douthat and Bret Stephens in the Times, Charlie Sykes on WNYC, Ana Navarro on CNN. These are all fine people, but the delusion that they represent the half of the country that voted for Trump is absurd. It’s a tautology. WNYC’s producers are looking for “reasonable Republicans” and they’ve concluded that it’s unreasonable to support Trump so the only Republican they will welcome onto their air is one who opposes Trump. I am invited on CNN frequently but mostly when I’m outnumbered by other panelists who are prepared to denounce Trump in lockstep with the host.

You just started as a senior managing director at Teneo Strategy. Can you tell us a bit about that? There’s sort of a Stoic connection there too, right?

You know, I’m not in the leadership hierarchy at Teneo, so it’s not my place to speak for the philosophy of the company. But I will say that one of the things that attracted me to joining the firm at a time when my profile was high and I had a lot of offers and was sort of sifting through my next move following Jared’s leaving the Observer, one of the things that attracted me was that Teneo philosophy has a lot to do with truth telling. So the word ‘Teneo’ is Latin for ‘to guide.’ Our firm is engaged in strategic advising of the leaders of the biggest and most complex organizations in the world, including an amazing percentage of the Fortune 100 companies.

So, something that attracted me to the leaders of this company and to our firm in general is our willingness to be blunt. I’m a blunt person. I think I’m agreeable, and I hope someone like you who has been my close friend for a lot of years would not consider it off-putting, but I’m the type of person where somebody is truly looking for… You know, sometimes I think that bluntness, people think that that’s like a way of saying, “Does my ass look fat in this dress?” that the brave person says, “Yes it does.” Well that’s where Stoicism and Judaism disagree. In Judaism, a white lie out of kindness is not only permissible, it’s encouraged. And on this question, I’m with the Jews. Ryan, your ass does not look fat in that dress. I don’t think there’s any need to be unnecessarily cruel, especially on that sample question when there’s really nothing somebody can do about it right at that minute.

But when it comes to advising companies, these CEOs are surrounded by yes men. Of course they are. The livelihood of their lieutenants, and too often even the board, depends on the CEO’s approbation. If the CEO says, “I just worked very hard on this brilliant strategy, what do you think of it?” it’s hard as hell if your success depends on that CEO’s approval, for you to say, “Well boss I think that plan is terrible and whoever came up with it is a moron and here’s what you should do instead.” I was attracted to Teneo’s reputation for a willingness to say, “Hey, you know what, you pay me a lot of money each month and I would like for that arrangement to continue, but not at the cost of leading you on.” And I’ve seen that in practice during my four months at the firm. I think being strategic and kind in the delivery of that message is important, but I’ve already seen instances in which my blunt advice has been welcomed and just as importantly that of my colleagues. My colleagues have been encouraged to be frank with our clients.

And do you have any message for the Daily Stoic community that you’d like to share that we didn’t ask you?

Well, my final message would be that a key tenet of Stoicism is that one of the reasons you don’t get overly emotional about setbacks or overjoyed about successes is that there is some sort of master plan. The book I mentioned in describing my real introduction to Stoicism, A Man in Full, the crux of the way the three different storylines comes together has to do with an unbelievable coincidence. This guy in Oakland who is imprisoned and accidentally gets the book winds up being the personal assistant to the millionaire in Georgia whose random decision caused the chain of events that landed the first guy in prison in the first place. So it’s the kind of ridiculous coincidence that you would see in Curb Your Enthusiasm or something like that.

But, in real life, that’s basically what happened to me, because you and I met before I ever worked at the Observer. Because of my interest in stoicism, you and I started emailing and then miraculously I winded up being your editor and forming a close friendship, where we’ve visited each other’s homes and become real friends outside of work. And meanwhile, the way I got this job is practically a miracle along those same lines. I was on a red eye flying from San Francisco home to New York. I do that thing of whenever I’m on a plane I put on the biggest most obnoxious headphones to send a signal to anyone near me that if you speak to me the penalty will be harsh. I’m a big advocate of not communicating on planes. And by the way, I will use this space to register my strong disagreement with you about leaning your seat back. I think you should lean your seat back totally, all the better if there’s some 6’8” giant behind you.

But anyway, so I’m on this plane about to snuggle in and go to sleep on the nice lie-flat seat they’ve got up there in United for the redeye, when all of a sudden, the guy next to me pulls out a book. I take off my headphones and I say to him, “Excuse me, I never speak to anyone on a plane and I will not speak to you and I will not answer you if you speak to me. But, the guy who wrote that book is a close friend of mine and I’m his editor.” And the book was your book, The Obstacle is the Way, and the guy reading it was Declan Kelly, the CEO of Teneo. A few weeks later we had come to terms on me leaving the Observer to work for Teneo, and that’s where I’m sitting as I answer these questions right now. So maybe there is a little bit of Stoicism at work right here on Park Avenue.

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