45. Nicholas Thompson - A Life of Long Form

·Operator, Writer, Athlete, Journalist
Nicholas Thompson - A Life of Long Form

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Description

Nicholas Thompson (Website, X, LinkedIn, Wikipedia) is the CEO of The Atlantic, an elite distance runner, and the author of The Running Ground*—*a memoir about his father, his life, and the sport of running.

Nick has led The Atlantic to tremendous subscriber growth and profitability since joining the then-money losing publication in early 2021. He was previously editor-in-chief of WIRED and editor of newyorker.com. He also co-founded The Atavist, wrote The Hawk and The Dove, and is a prolific interviewer, including his latest series, The Most Interesting Thing in AI*. *Nick is also the American record holder in the 50K, which he re-broke two days after we recorded this conversation (Exhales).

We talked about the future of words in the age of AI, what makes a journalist, why legacy media institutions like The Atlantic are worth fighting for, and what great editing and coaching have in common. Then we turned to running and life: the small tailwinds that compound beyond what we can imagine, Nick’s trajectory—through a prodigious start, early career failure and African kidnapping, cancer at 30, and wild success since—to name a few beats, the trials and blessings of inheritance, and the versions of himself he may no longer have time to find. To close, Nick honors Scott Thompson’s memory by sharing how we might all be more like him and reflects on what drives aliveness.

I hope you are inspired to get started, feel the wind at your back, clear unexpected hurdles, savor great words, raise your bar beyond what is reasonable, be grateful for those who came before and pay it forward to those who are next, and remember that there is always more waiting—for you, for me, for us.

P.S. It’s unrelated to this conversation, but please read The Atlantic’s latest cover story and one of my favorite (and funniest) things I’ve read in ages. Caity Weaver on The Best Free Restaurant Bread in America. Long live long form writing.

**Dialectic is presented by **Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic.

Timestamps

  • 0:00 Opening Highlights
  • 1:17 Intro to Nick
  • 2:24 Thanks to Notion
  • 3:30 Start: Words, Reading, and Writing in an Automated World
  • 18:39 Why Stories Matter and What Makes a Journalist
  • 28:22 Media Institutions, The Atlantic, Democracy, Tech, and Power
  • 44:21 Retaining Great Writers and The Virtues of Editors (and Coaches)
  • 57:44 Magazines and America
  • 1:05:57 Running, Motivation, Momentum, and Tailwinds
  • 1:16:08 Aging, Fathers and Sons, Inheritance, and a Mother's Grace
  • 1:31:00 Merging Machine-like Discipline and Wild Curiosity, The Boat that Never Touched Water, and Who We Might Still Become
  • 1:44:11 Gratitude, Stalin's Daughter, Scott Thompson's Verve, and Feeling Most Alive
  • 1:52:40 Closing and Thanks Again to Notion

Key Links & References

All Links & References

Transcript

(3:30) Start: Words, Reading, and Writing in an Automated World

Jackson: (3:30) Nicholas Thompson, thank you for being here.

Nick: (3:32) Thank you for inviting me on.

Jackson: (3:34) First, I should say I ran my first New York City marathon. It was my first race, my first marathon, my first anything.

Nick: (3:40) Wait, your first race was a marathon?

Jackson: (3:41) My first race was the New York City Marathon. The night before, I was listening to the first chapter of your book. It was meaningful. It's cool to do this.

Nick: (3:52) Amazing. You clearly weren't listening to the chapter on how to train for a marathon if you'd never run a race before. But whatever. I'm delighted you did it. That's awesome.

Jackson: (3:59) I'd run a lot. I just hadn't done a race.

Nick: (4:01) Okay. That's fine, actually.

Jackson: (4:02) I want to start somewhere else, though, which is words.

Nick: (4:06) Words. Okay.

Jackson: (4:08) I think this is a topic that Neil Postman, Walter Ong, McLuhan, and others were talking about years ago. You gave a really lovely written interview recently with Gaurav Ahuja for Timeless. You said this about the future of The Atlantic: "The big risks are real. Will AI search eat the web? Will Google stop sending people out? If so, what happens to us? What if we shift from screens to whatever Jony Ive is building, wristbands with no screen, all audio? We don't have as aggressive an audio operation as we do text. There will still be people who read words, but you can imagine words becoming less and less of the world. And we're really good at words." You wrote a lovely book mostly about running and what running has done for you. I'm curious what writing has done for you.

Nick: (4:55) What has writing done for me? Writing is a way of thinking and processing. The transition of taking thoughts from inside your head and putting them onto a page isn't just translation. It's bidirectional. Forcing yourself to write forces you to think more analytically and to process complicated things. Many of the things I've written have been ways of getting clarity on the things I've thought. It has also been a format and a mechanism for my most ambitious works. Both the book I wrote 17 years ago about the Cold War and this book that I wrote about running were seminal moments for me professionally: how I decided to write them and how I decided to do them. As you know from the book, I'm a journalist who wasn't really confident in his writing as a young person. In grade school, I was a math kid, not a writing kid. Learning to become confident in my writing was a very hard process that taught me a lot that I can apply to other parts of my life.

Jackson: (6:20) What about reading?

Nick: (6:22) I was a big reader as a child. I grew up in a family with books and bookshelves everywhere. If you had free time, you just read. You'd go out in the yard and play, toss the tennis ball up in the air, hit it with the baseball bat, and then go read. I loved it, and my mother read to me. Much of the best information in the world is stored in books. If you enjoy reading and can learn how to tell little stories in your head as you read, you can accumulate a lot of information. You can enter all kinds of different worlds. A lot of human knowledge can be passed down through books. One of the hardest things for me to watch is the culture of reading going away. Observing young people traveling on the subway or by train, I remember when I traveled by train as a young man. You just brought a paperback book. I remember traveling through Africa and taking buses everywhere. In trains, you just read everywhere. You stopped on the side of the road and read. Then you'd go to a new town, try to find a bookstore, and swap your book with someone at a hostel. It was this wonderful exchange of information. It's sad to see that dying because now everybody just uses Instagram. I can see it in myself, where I'm pulled into work and my phone. It's too bad, but it is what it is.

Jackson: (7:46) One implication in the quote and perhaps a counterargument to what you just said is that we aren't inherently losing depth of ideas. For example, we're doing a two-hour podcast, and there are lots of different formats now. What specifically about the written word, whether writing or reading, do you think is so important? What do young people or society as a whole gain from it?

Nick: (8:14) That's a great question, and I agree with you. I'm not one of those people who thinks we're all getting dumb because we don't read books. If you look at the complexity of the art and TV shows we create today versus 30 years ago, tell me they're not more sophisticated. Our ability to listen to books or podcasts while we're walking—we have this incredible capacity. I just mean that the amount of time people spend reading books, particularly younger generations, is significantly lower. Some of that time they substitute with really great stuff, like listening to your podcast. Some of it they substitute with useful social media content. They might watch YouTube videos that teach you how to bend a soccer kick so it curves into the corner of the goal, or how to fix your hair dryer. YouTube is incredible.

Jackson: (9:08) There are even video essays with incredible depth.

Nick: (9:11) Or videos explaining how quantum computing works. Some of it is just awesome. A lot of it is totally trivial, and a lot of it is negative. Back to your question. What's nice about reading: if you create a book or a magazine, everybody can read the same thing. In some ways, a conversation is better because I can react to you specifically. But a book is better in that we can read the exact same passage and I can share it with you. You just gave me this book, Not Fade Away. It means something to you, and the words I'll read are precisely the same as the words you read. It's a little different than if you had told me to type in a series of AI queries, where I would get different words. So the common ground we'll have... This is an artifact right here: Not Fade Away by Laurence Shames and Peter Barton. I've never read it and don't know anything about it, but I'll read it. You gave it to me, and it meant something to you, so I trust that it will mean something to me. It's this beautiful artifact that we can share. We can annotate and there's some value we can add to the page, but really, it's a physical thing that exists. I can tell somebody else about it, and they can go buy the exact same thing. There's also something wonderful about the image of going for a walk, putting a book in your bag, stopping to sit on a bench, and reading it. It's the same as it was in your bag, and it will be the same when you get back. If you go for a walk and have your phone, the information is constantly changing. You're probably going to get a bunch of notifications, and the whole experience will be much more complicated. If I take out my phone and look up Peter Barton's book, there's suddenly all this other stress attached to it. I know that elsewhere on this phone is my email, Signal, and WhatsApp. There's just something beautiful about the purity of sitting down and reading a physical book. It doesn't mean I'm reading a book a day, though I wish I was. But there's something great about the format and the cultural history. Obviously, we'll still be reading books in 50 years. I just don't know if we'll be reading as many as we are now.

Jackson: (11:27) That's a great answer. One last thread on this, which brings us a little closer to the work of The Atlantic. Written words have become incredibly cheap, if not infinite. There's a meta question here about how much we are going to care about who the words came from. Does it have to be Jackson plus AI, and so on? What remains scarce when you think specifically about words and building an institution around them?

Nick: (11:57) This is one of the existential issues at the core of my business problems. The things we can do right now that are scarce at The Atlantic—or ideally that I could do in The Running Ground—are writing with a certain kind of individualistic style and flair. I write in a very specific way that I can't quite describe. If you fed all of my essays into an AI, it still couldn't mimic it in a way that feels right. It might be closer than it was a year ago, but it simply can't do it. If you take an even better writer, like John McPhee, and ask AI to write like him, it won't produce anything like John McPhee. There's a distinct element of style that remains scarce. AI moves toward a homogenous style. It's a style that we like, obviously, but it's different from the best writers who have very distinct styles. The writers I love all sound very different. I used to play a game when I was at The New Yorker. I would read the Talk of the Town section, where the byline is at the end, and try to guess who wrote it based on their style. I don't know if there's a single sentence I've written in my life that is as good as any sentence Anthony Lane has written. There's a quality of writing that is distinct and that AI can't match. If we can maintain that at The Atlantic, we'll be in a great position.

Jackson: (13:23) Real quick: I feel pretty confident that Claude 5.5 will be able to write John McPhee-like writing based on the corpus of current John McPhee. That doesn't mean it can do whatever John would write next. Maybe you disagree. My sense is it will at the very least be able to write exactly how you write in the Running Ground.

Nick: (13:47) It might. It can't now, and it's not making as much progress as I would have thought.

Jackson: (13:53) Fair.

Nick: (13:54) But with 5.5, who knows? Number one is style, but you're right, that may go away. The second thing is reporting. Take any one of these issues of The Atlantic. There are people who made phone calls, talked to people who didn't want to talk to them, and doorstopped people. Adam Serwer on the courts here has many times talked to people who have absolutely no interest and probably shouldn't be talking to him. He has somehow gotten them to talk to him, and they've said interesting things that they're not going to say to Claude 5.5, even if it's got voice imitation. That's an important skill that is still scarce.

Jackson: (15:47) Agreed.

Nick: (15:48) People like to read other humans. They like to have a human connection. We put out this magazine, and we've got the names of 25 people. Each of them has a distinct personality. You probably like some, you probably don't like some, and you've probably never heard of some. Some of them I adore and I'll read anything they write. I have an intense emotional relationship, despite that—even though they work at The Atlantic—some of them I haven't met. There's a humanness that is really important, which is why I think even with Claude 15.5, there'll still be a demand for the Atlantic. What I worry about is when there's Claude 15.5, it would be pretty easy to write a good essay from scratch for anybody. Not only that, but at this point, there will be avatars created, and you'll have no idea what is real and what is false. You'll go on social media and you won't know whether anybody is human. People like to say it will all be slop, but it won't be slop them. It might be slop now, but it's going to be good.

Jackson: (15:50) It's going to be amazing. At least engaging.

Nick: (15:52) It's going to be engaging. There are going to be these infinitely beautiful people saying exactly what you want to say. Your social media feed is going to be filled with them, and I'm going to be competing with them with this print magazine. That's the future.

Jackson: (16:08) To go halfway there, there are probably a whole bunch of people currently who have a lot of humanity and maybe even interesting stories, but don't have the skillset or experience to write in the way that an Atlantic or a New Yorker writer might write. It's possible that this harness container might allow them to tell those human stories with a lot of AI help. The question is also, what will people tolerate? Are we going to need to know?

Nick: (16:41) This is a really interesting question. I love AI and use it all the time. I don't know how many tokens I've spent today, but it's a lot. I'm running agent farms, asking queries, and working in different models. Last thing I did: I have a race coming up on Saturday, so I snapped a photograph of a menu and asked what I should order for lunch based on what I ate for breakfast and my nutritional needs for Saturday. That's silly and stupid, but the agent farms are amazing. What I have not seen—and maybe it's because it's just not visible—is a journalist, whose work prior to 2023 or 2024 was mediocre, produce exceptional work. I've seen people who produced exceptional work use AI and produce exceptional work this year. I've seen people who produced bad work use AI and produce bad work. I haven't seen anybody...

Jackson: (17:38) Skip the jump.

Nick: (17:39) Surely that moment will come, and maybe that person is out there. Most of the stories you read about people using AI, they're producing garbage stories. You hear about AI being useful for good journalists doing investigative journalism. This AI helped us build this map, which helped us tell this story. Those are great journalists using the tools to further their great journalism. One of the most interesting moments for me will be when there's a mid-tier journalist or writer who produces exceptional work.

Jackson: (18:05) Who maybe could become a great journalist, but isn't a great writer.

Nick: (18:09) Or the other way around. Who knows? Most of the people here on this list have all the skills. There are ten things that make you great, and maybe they have eight of them. Maybe there's someone out there who has six and can use AI to fill the gaps. I just haven't seen it yet, but it will happen. You would have thought, given what you can code by now and how powerful and amazing these tools are, it would have happened already.

Jackson: (18:38) I agree.

(18:39) Why Stories Matter and What Makes a Journalist

Jackson: (18:39) I want to talk a little bit about stories and the other aspects of journalism and institutions. There's a quote from the same interview where you're talking about the rest of your career. You say: "That will be my North Star for the rest of my career." What is the thing I can do that will most increase good stories in the world? It's probably influenced by my grandfather. He spent his whole life trying to make America work. My role is to do that through journalism." Why do stories matter so much?

Nick: (19:08) I think having stories that people can agree on and discuss is one of the foundations of democracy. We make decisions on who should govern, what rules they should pass, and how we should treat each other in part based on stories. We hear the story of what happened to Renee Good, and it's very important to understand what actually happened. We need to understand why ICE was there, what ICE wants, what Renee wanted, what her family wanted, and what she was doing. There's a contentious question of what happened on that road, what she was doing in the car, what her intentions were, and if she actually hit the guy. Trying to get that right, make it accurate, and then tell the story helps the world and America understand what's happening in the country. You can make a decision once you've read it and understood it. Everybody discusses it, we have an argument, and you might think there should be more ICE agents, fewer ICE agents, or that ICE agents should act differently. Having accurate information and having people agree that this is the information we should discuss helps make society function. If there's no one to report on what happens to Renee Good and the benefits and costs of having ICE in Minnesota, then there's no feedback to the government. After that story came out, there was an understanding of what had happened. Even the Trump administration realized they had gone too far and changed the policies. Having good, accurate journalism matters. When I said that quote, I was describing a little bit of my career transition. I started as an editor, became a writer, went back to being an editor, became an editor-in-chief, and then took this job as CEO. The common thread was that at each moment, I was making a choice. In between, I also ran the website for the New Yorker and ran the product and engineering team there. Each choice was about finding the thing I could do that would increase the number of good stories because I think that's important. I can write one good story every few weeks or months. I can edit five, or I can build a business that allows us to publish hundreds. That was the fundamental logic behind why I took this job at The Atlantic. Many people asked why I, as a journalist and an artist, would go be a capitalist and CEO. Must just because I'm paid more. Well, no. If I'm good at it, I can have a very positive effect on the amount of journalism in the world.

Jackson: (21:52) The word story is interesting here. One of the things that has come up as I've been doing the podcast is I've had a few people ask me if I'm a journalist.

Nick: (22:01) What do you say?

Jackson: (22:02) I usually say I don't think so. You also use the word reporting, which is one end of the spectrum. Stories can mean a lot of things. Some of these amazing YouTube videos are amazing stories, but are they reported? I'm curious what the role of journalism is and what makes a journalist. More broadly, I would assume some of the things you guys have done over the years at all the publications skew more toward journalism and reporting in the way we were talking about with ICE. Some are just crazy stories, like your colleague vanishing. Is that journalism? I don't know.

Nick: (22:43) That's funny. I don't quite know how to define it, and the lines are changing. Are you a journalist? Is the first person who tweeted the Renee Good video or did a sophisticated Twitter thread a journalist? Is the first person who called two sources the journalist? Who is the first journalist? I don't know the answer to that. I know it when I see it, but I have a hard time defining it. Let's go back to that story of the guy disappearing because it's a fun story, and I think I can answer your question through it. We're talking about a story I did at Wired where I was an editor. My colleague Evan Ratliff wrote a story about how people disappear, fake their deaths, and start their lives over. He talked to a private investigator.

Jackson: (23:29) This was 2012, maybe?

Nick: (23:32) It was probably 2008 or 2009. It was early Twitter. When was Twitter founded?

Jackson: (23:38) 2007. (Correction: 2006).

Nick: (23:39) Right, so it was 2009. It was early Twitter. The first story ran in the spring, and the second story ran in the summer. The first story was about how it can be done. After that story ran, we decided to run an experiment. Evan was going to fake his death and go on the run. I was going to serve as a private investigator and release all the information a private investigator would have. I would have access to his credit cards, his E-ZPass, and I would be able to interview his family members.

Jackson: (24:10) By the way, this is a YouTube video. This is like a MrBeast video now.

Nick: (24:12) Totally, and it was so fun. I was going to post those details on Twitter, and people were going to hunt for him. If anybody found him in 30 days, they would get 5,000 bucks. If he could last 30 days, he would get 5,000 bucks. All these people started hunting, and he made a mistake. At one point, he was trying to use Tor and logged into the internet without using Tor. Somehow he got tracked. The person who tracked him didn't tip him off. They got an IP address, and from there, they found his burner Twitter account. One of his rules was that he was supposed to act like a person on the run. You don't go total cipher. You create a new identity and start posting and living as that person. He could have just hiked Mount Rainier and hidden in a hut, but that's no fun. The hunter followed the Twitter account as a fembot so Evan wouldn't recognize it. Then Evan tweeted something about being in New Orleans. I had previously put out that Evan was gluten-free, so they talked to all the gluten-free pizzerias. They eventually tracked him down in New Orleans. It was one of the most amazing things. The reason we did that story was twofold. First, it was fun, and Wired likes having fun. Second, there was this tension we were trying to understand. The internet makes it easier to start over, but it also makes it easier to get tracked. That's still a tension today with things like AI. You can create a new identity and persona, but you're also walking down the street with Ring cameras everywhere. Everyone's Tesla is tracking you too. Your phone is giving off information. Your heartbeat might be giving off information that some drone is collecting. You don't know. We were trying to get at that issue. You can just say, "Who knows about privacy? We have more, we have less." Or you can say, here's a story. That story was fun and weird, but it was also an interesting story about Twitter and how groups form. There were all these different elements that were ways of looking at things in the world that matter. It shaped perceptions and conversations about important issues.

Jackson: (26:24) Was it journalism?

Nick: (26:26) It's definitely journalism.

Jackson: (26:27) Am I a journalist? I'll tell you why I think I'm not. My entire goal—not in a fake way—is to make my guests shine and help the world see what I think is really special about them. I'm not trying to put a veneer on them.

Nick: (26:49) But are you trying to get the truth? If somebody was a jerk and a disreputable person, and you didn't realize that when you booked them, would you hide that or not while interviewing them?

Jackson: (27:07) I've run a variation of this thought experiment. People have asked me if I would interview Trump. One main reason I would be quite afraid to is that in almost every environment, he probably charms the socks off most people he meets. I put a lot of scrutiny into who I talk to. I try to talk to people who value truth, or whose trueness is something I'm attracted to. At the very least, if I saw that there were dark parts and light parts to them, I would try to point at the thing I thought was good in them.

Nick: (27:50) But would you let them hide? Is your primary commitment to your audience, or is your primary commitment to your guests?

Jackson: (27:59) That's a great question. I'm not sure I've been forced to answer that question yet.

Nick: (28:03) I don't know how to define a journalist. However, if your primary commitment is to your audience, you're a journalist. If your primary commitment is to the guest or to an advertiser, maybe you're not.

Jackson: (28:16) Food for thought. I like that a lot.

(28:22) Media Institutions, The Atlantic, Democracy, Tech, and Power

Jackson: (28:22) Media institutions. First and foremost, why are they worth preserving? Why do they matter so much?

Nick: (28:33) Media institutions?

Jackson: (28:34) At least ones like The Atlantic or The New Yorker. These publications have been around for a long time and could disappear since people aren't reading that much text.

Nick: (28:42) Some publications do disappear. There are amazing publications that don't matter as much as they used to, and there are new publications that do matter. There is something nice in the continuum that The Atlantic has played this role. We were founded by Ralph Waldo Emerson and Harriet Beecher Stowe. You look back and Abraham Lincoln wrote for The Atlantic. We were founded to help create conversations to prevent a civil war, and Martin Luther King published Letter from a Birmingham Jail. There is something important about keeping this publication going. In this long run of American history, on issues where for the most part, we've been right. We've gotten things wrong, but generally we've helped improve racial and intellectual progress in America. We wrote really smart stuff about the Iraq war. We did a lot of things right, and it's nice to be able to tie onto that history. That's one reason this is a very important institution you'd like to preserve and keep going forward. Secondly, it's just people who do good journalistic work. I think there should be more of it. Increasing the amount of truth increases the odds that you get democracy. One of the things that happens in dictatorships is they arrest the journalists, buy the media publications, or shut them down. Then the people in power say you have to write what we want you to write. That's one of the ways democracy dies. If you study the way autocracy comes about in many countries, look at what's happening in Hungary, Turkey, and or what happened in Russia. In countries where they have less democracy than they did ten or fifteen years ago, what was part of the playbook that Erdogan, Viktor Orban, and Putin ran? Arrest the journalists, buy the publications, and shut down the critical publications. That is part of the process of moving from democracy to autocracy. I am going to fight that because I believe in democracy. I will do my best to fight it, both by defending our rights in court if I have to, or protecting our journalists. If the White House were to come and say we're going to arrest your people because of what they say, I will fight it with everything I can. But I also want to create a thriving business model so that we don't go out of business. Sometimes good journalistic organizations go out of business not because the government tries to shut them down, but because they manage their finances wrong and spend too much on holiday parties. My goal is to make sure we fight the anti-democratic powers and stay as strong as possible to hire as many people as we can to do the best work we can.

Jackson: (31:32) You briefly hit on it. Why is Laurene enforcing a goal to profitability or sustainability actually a gift?

Nick: (31:42) I think it's totally a gift. Laurene Powell Jobs is very wealthy, which is obviously public knowledge, and she cares a lot. When I was hired, the mandate was that we were losing money then, but we were not going to continue losing money. Her reasons for mandating that are her own, but I do think it's a gift because it forces a kind of discipline. Excellence comes through discipline. If you are forced to make good decisions about how you run your business, what you pay for things, how you run your subscription models, and how you balance all these complicated math models that determine whether you're successful, it makes for a better publication. The discipline of being forced to make it profitable made it a better publication. The fact that it's an excellent publication also made it possible to become profitable.

Jackson: (32:34) You've been a good CEO so far, too.

Nick: (32:36) To some degree, but there's a lot that goes into this place's success. A couple of things were important to our transition from losing a lot of money to making money. One is the continued excellence of the reporting, which is top-notch every single day and has been since I've been here. The other is building a business model that is responsive and downstream of that. Instead of saying we're going to build a business model that depends on lots of output and covering particular topics where we think we can sell event sponsorships, we told the reporters to do what they're best at, and we would try to figure out a business model around that. We were working backwards. One thing I tried at the beginning was based on my time at Wired, where we ran an affiliate revenue business. We would review headphones, someone would buy them, and we'd get a cut. It was great.

Jackson: (33:33) That was probably a good fit for Wired.

Nick: (33:34) It was a great fit for Wired. I thought we should do that here, maybe on books or movies. One of the first things I did was build out the mechanism so we could get affiliate revenue. We built out the dashboard to track it and made sure we put in the tags. We ran it for a few months, and I'm not even kidding you, our affiliate revenue was $400. I was like, what are we doing? I realized this is not a publication for that. I'd rather have $400 than zero dollars, and I'd rather put an affiliate link than an Amazon link without one, but it was pretty clear that was trying to latch a business model onto The Atlantic that just didn't fit.

Jackson: (34:16) It's almost business model-product fit.

Nick: (34:18) Yeah.

Jackson: (34:18) On the note of your point about journalism defending democracy, I'm probably over-weighted from spending a lot of time in the tech world. Recently, there's a view among a lot of capitalists that journalists hate capitalists as much as they hate fascists, to use much more extreme language. Do you think this is a new phenomenon, or has it always been there? You've done amazing work on Facebook, among many other things. To what extent is the journalist's job to check increasingly powerful capitalists as much as it is the government?

Nick: (35:08) This is a really big story in Silicon Valley. Journalists are skeptical of power. That's part of the personality. People in Silicon Valley went from not having power to having power, so they went from being treated with less skepticism to being treated with more skepticism. A journalist will look at Elon Musk when he's just a scrappy guy making Tesla differently from when he's the richest man in the world with an empire. Most of the coverage of him when he was a scrappy guy just starting Tesla had a different hinge. He's also a different person, and he acts in different ways.

Jackson: (35:48) He sees himself similarly, though, which I think is one of the critical reasons he's so upset with all of this. He asks, Why are you treating me so differently?

Nick: (35:55) The answer would be, "You're different." Power changes people. You influence the world in different ways. This was a constant conversation with Musk in particular when I was at Wired. Part of it is, there is skepticism of power. You take an organization that goes from not being powerful to being powerful. Another interesting thing is that Silicon Valley in particular saw that it could counter journalism and no longer needed it. Part of what happened is they felt they could express feelings they may have bottled up before. A tech leader in 2015 may not have yelled at the New York Times publicly, A, because they didn't have a Twitter account with 100,000 followers, and B, because they wanted the New York Times coverage. Now they know they can start a Substack, so they feel they can go around them. They may be expressing things they felt before. Those are a couple of the factors at play. There's this very important key moment when I think the media and the tech industry diverged, which is after the election of Trump. There was this notion that technology tools would bring the world together and make the world more open and connected, as Facebook said. Suddenly, these technology tools had clearly been used to help elect a president—whose ideology you may or may not like; I try to be entirely nonpartisan—whose ideology is certainly not to make the world more open and connected. Journalists look at that and realize the tech industry is not what it says it was. These things don't work the way we've been told they work. We have this person who most of the industry was quite clearly highly skeptical of for lots of reasons. I think that was a real turning point, too.

Jackson: (38:01) I think there's an element—

Nick: (38:03) Can I say one other thing?

Jackson: (38:04) Please.

Nick: (38:05) Journalism is an interesting industry where it over-indexes on influence versus its financial status in the world. If you were to add up the market cap of all companies in journalism, it's a fraction of one tech startup. If you take the social influence that journalists have in setting the agenda, and then you take the influence they have on Twitter, it's massive. It's one-tenth of one percent of the financial influence in the world, and then seven percent of the influence on Twitter. There is just this massive gap. Maybe that's a positive thing in some ways because it helps distribute stories. But then journalists start saying things on Twitter criticizing individual venture capitalists. They say things they wouldn't say inside their institution. Suddenly you have these people who have more attention than one might expect, and they're saying things that clash with the overall views of their brand. Because of the way Twitter works, the dumbest thing that anybody in any organization says is what gets seen. It's seen as a stand-in for the whole thought of the organization. You can have a publication... let's take a random one like Politico. Politico publishes all these stories, and they're balanced, thoughtful, and respectful. Then one person at Politico tweets one crazy thing, and it goes viral. It's seen and shared by everybody, and suddenly that becomes the stand-in for what Politico thinks. Someone might say, Well, Politico is balanced. They give equal attention to multiple sides. They write these really thoughtful stories. But the response is, No, they're crazy. Did you see that tweet? The tweet is true, and the person did tweet that. That happens to every organization, but it happened more to journalism than anybody else. The perception of the way journalists saw the world became seen as actively trying to take down... Andreessen Horowitz. It was really just one journalist at one publication tweeting a dumb thing. There was this imbalance—that doesn't explain it all—between the reality of journalism, which is a lot of thoughtful people trying to do their best work to explain things, and the perception, which was shaped by some dumb tweets from people who probably shouldn't have been given access to their phones on those days. I don't want to overstate it; that's not all of it. I think it's underappreciated because people don't recognize the delta between the influence on social media platforms versus power in the world.

Jackson: (40:57) I was going to bring up a moment recently where Wired did a story on the gay tech mafia in San Francisco. My version of Twitter was wildly frustrated, saying Wired used to be optimistic. There's an element of what you were just describing. The technology world has recently come into a lot of power, and they have a view that more technology is good. Technology is basically value-neutral, and more technology is good.

Nick: (41:55) Right.

Jackson: (41:57) Your root point around plurality makes sense in a vacuum or even in reality. The challenge is how does speaking truth to power... I even struggle with—you brought up Elon. I really struggle with Elon because I have some people in my life who worship him, and I have some people in my life who think the fact that you would drive a Tesla means you're evil. I don't know how to think about him. This guy probably pulled us forward on EVs and space five to ten years alone. He also clearly can't sit with the fact that anyone is speaking truth to his power. It doesn't seem that we're headed towards this getting better.

Nick: (42:19) I think that's true.

Jackson: (42:20) There's a lot there.

Nick: (42:21) He's a great example. If you look at Elon in totality, it's a combination of this amazing man. Sometimes you listen to a podcast with him, particularly if you listen to the podcast of old Elon, and it's incredible. Even when he talked at Davos this year, he's so smart and sensible. Take climate change. Do I want to go to Mars? I don't want to go to Mars, but do I think humans should explore Mars? Sure. What he did with SpaceX and Tesla is absolutely amazing. Do I want solar walls? I do. Do I think he has always done the right thing? Maybe not. But he has both the intelligence and the dream, generally pointed in the right direction on society's biggest challenges.

Jackson: (43:02) And he believes in something very clearly, which not every technologist does.

Nick: (43:05) But he has also weaponized a platform against civil discourse in America. He has made it almost impossible to have good conversations in the town square. He has totally polarized it politically. He has very little conception of what is true and what is not true. He is the biggest spreader of misinformation on that platform. So you have this mess of Elon Musk. Everyone who knows him says the same thing asks what we do with this. Part of the problem of why it is hard to have a thoughtful conversation... You and I can have a thoughtful conversation. You can't do that on Musk's social media platform because it has been engineered for toxicity. Part of the reason we can't have good conversations about Elon is because of what Elon did to the town square. That is not the only reason. There's lots of reasons. There is partisanship in America, and maybe television has pushed us into more partisan ways. It is not like Bluesky is this site of beautiful civil discourse where people respectfully disagree with each other and reach consensus. But part of the reason it is hard to talk about Elon is because of what Elon did.

(44:21) Retaining Great Writers and The Virtues of Editors (and Coaches)

Jackson: (44:21) Changing gears slightly, but still in the broader bucket. Why should really talented writers want to join or remain part of an institution like this one?

Nick: (44:36) Yeah. Why would they not go to Substack, right? Part of it is that you get value from the institution. We edit, copy edit, fact-check, promote, and help put you on TV. We have the best editors in the world, and they are amazing. If you have never gone through the process of working with a great editor, it is transformative. A lot of people listening to this do not understand exactly what an editor does.

Jackson: (45:11) People haven't really been edited.

Nick: (45:12) It is not just that they make sure the apostrophe is in the right place. They are often a little bit like what I said about Elon, breaking things down to first principles and helping you resort them. Take this book. I worked with a bunch of great editors. They changed sentences, emphasis, and ideas. But they also—one of the notes that I think is so interesting: This book is mostly about my life and my father's life. It's also about running. In the early versions, it started with an introduction and the ideas of the book. Then it went back to the beginning to show my dad as a child. One of the readers pointed out that you can't do that. Nobody cares about your dad as a child at this point, and they don't care about you as a child. Nobody cares about anyone as a child unless they have an emotional relationship with them, and you are not famous enough. If you are Leonardo DiCaprio, start your book when you are a child because people buy the book and care about Leonardo DiCaprio. Nobody cares about Nick Thompson. You have to make them care about you. You are not going to be able to do that unless there is an incredible story from your childhood. But there isn't. Your childhood is setting up the things that are interesting. Very good point. So now what do I do? So I added a chapter where I describe everything that happens in your mind while you run a race from beginning to end. That explains what is most interesting about the book, which is the ability to give the feeling and emotions of running. It shows what it actually means to run while being aware of the world around you—while also including little set pieces that explain your crazy father and your pivotal story about cancer. That was an amazing edit that made the book much better. That is what great editing does. Somebody sees the fundamental structural or chronological weakness in what you have written. They see the character you need to add or subtract. Great work does not happen without great editing. You might have a writer who decides they don't like their editor and wants to go do it by themselves on Substack. Often, the work is much worse. That is not true of everybody, but you get a lot of value being here from the institution. We pay you a regular salary. You get a check every two weeks, and you know what it is. If you want more, you ask for more. There is value to being at a stable place with predictable income, great editing, and good promotion. For a certain class of writer, they can get paid a lot more at Substack. They have a far smaller reach and audience, but they can make a lot more money. If you have a huge enough audience, you can reach equal numbers of people. But because of the way the gating works and all those mechanisms. So... We've lost. Derek Thompson went to Substack. Guy was amazing, but he was a number one best-selling author. He is friends with the top people on Substack, which allows him to get in the recommendation engine and build an audience.

Jackson: (48:32) Why would someone like Derek stay?

Nick: (48:34) Someone like Derek would stay because you ideally get the best editing, the best ideas for your stories, the best copy editing, the best fact-checking, and the best social promotion. You're getting all of that, and ideally, there's also a brand association.

Jackson: (48:48) Do you think this model could work for media outside of writing?

Nick: (48:53) I do, actually. I've sometimes wondered whether we could build a network of YouTubers who aren't famous enough to be making tons of money on their own, but are great. We could create a network of them. We have an awesome ad sales team, so we can sell ads more efficiently than presumably they can as individuals. They can get more money if we sell their ads than if they just sell into the YouTube ad network. We could create a bundle of YouTubers who are on brand for The Atlantic. We bring them in, they make more money, they get a larger audience, and we get more content out there. It's good for us. I just haven't figured out who they are or how the real economics would work.

Jackson: (49:31) A lot of people do a version of that, but they're not a brand like The Atlantic.

Nick: (49:35) Yeah.

Jackson: (49:35) You have Cleo Abram at Vox, and she leaves. In video, overwhelmingly they start somewhere and then they leave. I'm almost more curious specifically about the editor-writer relationship.

Nick: (49:51) Take Cleo. Her work is awesome. Cleo is probably so successful that she wouldn't need us and likely makes more money than we could pay her. But you can imagine someone like her who is maybe a little less successful but exceptionally good. You can imagine an incredible video producer or video editor who can think through her next project. They could tell her, When you're doing your next piece on quantum computing, you should do it this way.

Jackson: (50:22) The difference now is they just go work for her.

Nick: (50:25) Right.

Jackson: (50:26) Writers don't hire editors. I guess you just don't get to that level of scale.

Nick: (50:35) They're different. I don't know the career path for great videographers, but I know the career path for great writing editors. They tend to end up at places like The Atlantic, not working as individuals for folks on Substack. I think they sometimes go the other way. Maybe they leave a book company and then go work for people on Substack. I don't know.

Jackson: (50:54) What makes a really great editor?

Nick: (50:56) Okay. I've spent a lot of time thinking about this. A couple of things make a great editor. One, they understand what the writer is good at. Their job is to get the best out of the writer. The fundamental mistake many editors make is trying to make the story the best version of the story they want, not the best version of the story the writer wants. Your job is to work with the writer, figure out what they're good at, figure out what they're bad at, and support them in everything they're bad at. Maybe they're a bad stylist but a great thinker, so your job is to help the writing. Maybe they're a great stylist but a bad thinker, so your job is to help the structure and the thinking. Maybe they're the kind of person who needs to really be pushed. It's almost like you're a coach. Maybe they need to be yelled at, maybe they need to be given a firm deadline, or maybe they just need to be loved. With each different writer, you need to develop a different kind of relationship, but you always need to be there for them. When I was an editor—which I was for a long time—the relationship with the writer was absolutely essential. I would make sure I always got back to them within an hour. No matter the situation, I'm going to try to get back to you. Even if it's just to say, I've got your story, and I'm thinking about it, or I'll get back to you in three days, or I'll get back to you in four hours. It's about never disrespecting them, always working with them, and promoting them by tweeting out their story and trying to get them read. You're always trying to find the thing you can do that's best for them, but the most important thing is helping them do the best work they can do. Remnick used to say this when I worked at The New Yorker. He would say, If the writer can only jump over a six-foot bar, your job is not to try to get them over a seven-foot bar. Your job is to get them over that six-foot bar. That's what the story is going to be. We're going to get it done, and we're going to get the best version of the story we can. We're not going to make them feel bad for not getting over the seven-foot bar or try to hold out this impossible standard. You have to figure out the best version of the story given their skills, the idea, and the time. You have to get them there, and that's the goal.

Jackson: (53:15) You brought up coaching. You talk about this in the book, and how you were working with other people, and then you started working with Steve Finley. He was just so fit to you, as you just described.

Nick: (53:22) Yeah.

Jackson: (53:27) It sounds like a huge part of that was that he was really good at giving you a system you could buy into. Is that relationship almost exactly the same? What is different, if anything?

Nick: (53:42) Yes, they're pretty similar. You can imagine a coach coming to me, and I came to Finley when I was the editor of Wired, a busy guy. Finley would give me the schedule and say, I don't care what you do on Monday, Wednesday, Friday, or Saturday. Here's a schedule, and on Monday it says run option. You can do whatever you want. Ideally, you'll run five or six miles, but I do care what you do on Tuesday and Thursday. He would then give me very specific things to do a couple of times a week. This is a good schedule for a busy guy like Nick. You can imagine another coach who says, On Monday I want you to run seven miles at a 7:30 pace, and I want you to do three 30-second hill sprints. On Tuesday we'll do this. I also want you to do a core workout and ride the bike. For other people, you can add way more structure and details. Finley thought, You can't do that because it's not going to fit with Nick's life and his other goals and ambitions. Running is not the most important thing. Finley was doing what I do with writers. What is Nick's skill? What is Nick good at? What are Nick's weaknesses? Where can we improve him? How can we do that without breaking him? There's that similarity. What is the difference? There's some differences in that there's way more back and forth with a writer. With Finley we were talking every three weeks.

Jackson: (55:06) How often were you running together?

Nick: (55:07) Twice a year.

Jackson: (55:08) Oh, wow.

Nick: (55:10) Yeah. I would physically see him five times a year. It wasn't that often. Whereas with an editor, you're on the phone with them six times a day sometimes.

Jackson: (55:24) How would you evaluate this outside the context of just a running coach or an editor? You're looking for somebody to help you, a therapist or a coach. Increasingly, we have coaches of different kinds. How would you test for this thing you just described? Maybe on both ends but especially on the side of the person seeking the editor or the coach.

Nick: (55:46) Well, I guess you'd ask them at the beginning and hold this in your mind. What do you think of this work that I've done? How would you have changed this story? What do you think I could do differently? You really listen. But I think the only way you can tell is by working with them. It's like a job interview. You can get something from the job interview, but you work with them for a little while and you get a lot more.

Jackson: (56:13) Imagine you start working with an editor. They're not overly negative, so you don't have that problem. How do you know if they're a 6 out of 10? Meaning they're nice and give you some good notes, versus a 10 out of 10. If you think about collaboration in general, Steve Jobs and Jony Ive were a 10 out of 10. I've never had a relationship with anyone like that, so I can't imagine what it would be like. Maybe part of it is you have to go work at The Atlantic or The New Yorker and truly see a great editor. Or work with Steve Finley...

Nick: (56:48) It's true. Sometimes people who haven't had great editing will see something and say, That was an amazing edit. Those are such good notes. Meanwhile, I know that person's not a good editor because I've gone through the intensive process with them. I think you have to go through it. It's such an interesting question. I had never been coached that intensively. I had been coached in high school by people who were wonderful, but they were coaching a whole team. I was coached in college by a guy who was perhaps the most successful track and cross-country coach in American history. He didn't know my name and still doesn't quite know who I am, so I wasn't getting a lot there. It took a long time until I realized Finley actually tapped into something in me that I didn't know was there.

(57:44) Magazines and America

Jackson: (57:44) Why do you love magazines?

Nick: (57:45) There are a couple of things. I don't think I could work in the publishing industry because it's just not enough.

Jackson: (57:58) It's not enough frequency or volume.

Nick: (57:59) It's not a frequency or a volume. I like the adrenaline and the speed, but I also like depth and complexity. There's something about the format. It's not a newspaper, so it's not just fighting for your attention at the moment. You're not trying to write something a person can read on the subway in four minutes. You're writing something a person can spend a couple of hours with, but there's enough of it. That middle ground has been great for me. It also happens to be where I started. I didn't plan my career. I stumbled through it like most of us. I didn't even plan to be a journalist, and I stumbled into a magazine job. You turn the ship five degrees north in the harbor, or you turn it five degrees south, and you end up in Greenland or South Africa. I guess that's not quite true. But you end up in Greenland or Spain? I don't quite know how you would turn the ship in the harbor.

Jackson: (58:57) How have the stories themselves changed? To be clear, you still make amazing physical magazines and ship a lot of them. But you ran newyorker.com and took it from being nothing to being very substantial. I don't know the data but I would guess that a whole bunch of people have no relationship with The Atlantic through anything physical anymore. Critically, this is also a curatory container. Now the stories live on their own. I'm curious how that is... Maybe it also speaks to the way the website can evolve over time.

Nick: (59:40) It's one of the hardest things for us. You get a copy of The Atlantic, you open it up, and here we go: "Women Will Be Targets" by Sophie Gilbert. Your perception of this story, whether it's good, whether you agree with it, and your sense of the writing quality is shaped by the fact that it's inside of this magazine. It's shaped by the fact that there's a Hauser and Wirth ad on the back. You have an emotional relationship with it. Then you go to the website and see the same story, and you have no idea where you are. Maybe you do because you came in through the homepage, but you probably came in through a link on social media. We try to make it so you know where you are. We have a distinct font and coloring, and there's the red A. We do all the things. A good eye test is if you can identify what website you're on from across the room, it's been branded well. We do all we can, but most people don't know where they are.

Jackson: (1:00:33) Sometimes I read it in a read-it-later app, it's a great story, but it's totally abstracted.

Nick: (1:00:37) People are often like, "I love that story in The Atlantic," and you ask, "Which story?" You lose a lot of the brand association. The advantage is you have infinite distribution at zero marginal cost, which is amazing. You just weigh those things against each other. The challenge for the folks running the editorial operation of the website is how to get the most brand value into those web views. How do you make it so that people who like the story develop a relationship and move down the funnel to become subscribers? And how do you make it so that people who you have no chance of ever seeing again at least see an ad?

Jackson: (1:01:23) What makes a good cover?

Nick: (1:01:25) It's something that captures the spirit of the moment and the spirit of the story. This is a weird cover. It's just a list of names for those of you listening, but it was an amazing cover. It was one of our most successful covers of the last year because it conveyed the drama of the moment: this is what's going to happen if Trump wins. Some covers convey these big ideas. This is an amazing cover, too: Derek's "The Antisocial Century." It's a beautiful, gripping visual, but it's not women in bikinis. We do put people on the cover. Look at Seamus Heaney right there.

Jackson: (1:02:10) Or maybe even comparing it to The New Yorker, they are famous for their covers. It's almost like an artifact now. I've had plenty of New Yorker covers stacked in my apartment before without ever opening them.

Nick: (1:02:27) The New Yorker cover is interesting because it's amazing for subscribers, but it makes no sense on the newsstand. The newsstand is less and less important every year. We used to put that flap on it where you at least list the names and the stories so you'd have some idea. There'd be a picture of a cat drawing graffiti, or whatever the cover is, that has nothing to do with anything, and then you at least have a list of the people inside. A cover is a beautiful work of art. It signals a moment in time and can sometimes convey the core of a story. When I was at Wired, I wrote this very intense piece with Fred Vogelstein about Facebook. This was the moment where Facebook was finally reckoning with its role in the world, having a hard time, and making a bunch of mistakes. After months of reporting, the picture was Mark Zuckerberg, slightly bloodied. There was no text on the cover, but it conveyed this incredibly important idea. It was a classic cover that people remembered even if they don't remember the details of that story. When the art director, Thabo, came up with that, we just thought, "Wow, that's it. That nailed it."

Jackson: (1:03:43) I think this is a line from you. You said you were doing events in every state, having writers across every spectrum, "doing our best to be a magazine about America." One thing that says a lot and is really important is what myth you believe about America. Is there anything that immediately comes to mind for you?

Nick: (1:04:11) Myth as in an idea, or myth as in a falsehood?

Jackson: (1:04:15) Not as in a falsehood, the opposite. A myth that would theoretically become true.

Nick: (1:04:26) America, unlike any other country, is built on an idea. We're not a nationalist group that all speaks the same language. We're people who came together, freed ourselves from the colonialists, moved west, and welcomed people from around the world. Because of that, you have different cultures, ideas, languages, thoughts, and opinions. We also have things that hold us together. We all love Sunday afternoon football, and we all celebrate the Fourth of July. We don't have to rely on a sense of nationalism and in-groups and out-groups. The thing I'd like to believe about America is that it's a place where you can find interesting people to talk to about big ideas. One of my dreams is to run across America. I have this belief that you would learn things in every little town you visit. You'd run twenty miles a day and cross the country in six months. Every day along the way, you'd find stories, meet people, and learn things. You'd get little cultural tidbits because everybody comes from somewhere else and has a different background. Everybody has a little thing that nobody else in the country has. I would love to do that. I have to figure out when I'm going to do it, but we'll see.

Jackson: (1:05:45) I've had a guest who cycled across, a guy I used to work for Chris Sacca, but running is a different level. You have the distance ability. It's a matter of making the time.

Nick: (1:05:54) I'll probably end up driving across, which is less fun.

(1:05:57) Running, Motivation, Momentum, and Tailwinds

Jackson: (1:05:57) Let's talk a little about running. First, to set the scene, here is a little excerpt from an old McPhee piece:

Nick: (1:06:05) Oh, wow.

Jackson: (1:06:06) *"Travel by your canoe is not a necessity and will never more be the most efficient way to get from one region to another or even from one lake to another, anywhere. A canoe trip has become simply a rite of oneness with a certain terrain. A diversion of the field, an act performed not because it is necessary, but because there is value in the act itself." I know the bark canoe piece was an important one for you, but I was reading that and it sounded a lot like running. As a very serious runner—I talked to a couple of people while preparing for this interview, and I used the word "freak runner" because I didn't have better language for it—and a serious racer and striver, how do you keep the autotelic part of running in mind?

Nick: (1:06:55) Tell me more about what you mean by that.

Jackson: (1:06:56) Doing it for its own sake. To use his language, finding value in the act itself.

Nick: (1:07:01) It's a hard balance because obviously I still strive. It's not just that I enter races and try to win them. I actually sometimes check my Strava segments, so I'm not...

Jackson: (1:07:16) You're also literally a world record holder in the 50-mile for your age group?

Nick: (1:07:20) I'm an American record holder in the 50K. I wish I was the world record holder. I was the top-ranked runner in the world in the 50-mile for most of last year, and then I lost it. It's a real balance. In a way, I wish I was totally pure and just ran for the joy without entering any races. If I did enter races, I'd not care about my time but still run fast. That would be the ultimate state. I feel like that's where Kilian Jornet is. He's the world's greatest mountain runner. People who race him hate it because they're trying to win, and he's just having fun in the mountains. Then he wins. I balance it in a couple of ways. I try not to focus too much on the goals. I'm running a big race on Saturday, and I mentioned last night that I needed to start carbo-loading. My wife asked if I had a race coming up. I was at least able to compartmentalize. My wife doesn't know? Either we have bad communication, or I'm compartmentalizing pretty well. I don't focus and obsess. If the race goes well, that's great. If it goes badly, I'll move on the next day and won't worry about it. I also try to make sure that a lot of my running is spiritual and disconnected. I'll run in the mountains without listening to music. I just try to meditate while I run, listen to the birds, and get as deep into the purity of the surroundings as I can. I look forward to those runs. If I'm going to a place where that's a possibility, I'll make sure I have time to do that. I'm not on the clock, rushing to run up and down a mountain quickly. I make sure I have time to go explore, see, and feel. Sometimes when I'm running here in Brooklyn across the Manhattan Bridge, I try to get into that deeper mental state. I'm constantly trying to use running as a form of reflection and spirituality, as opposed to just a mechanism for expressing ambition.

Jackson: (1:09:32) And then on race days, you show up.

Nick: (1:09:35) On race days, I show up and go really hard. Sometimes I do well, and sometimes I do poorly. I try to train as hard and methodically as I can. I try to optimize as best I can in the limited amount of time I have.

Jackson: (1:09:51) What is the biggest difference between running often and running daily?

Nick: (1:09:57) There are physiological differences and benefits to running daily. I don't actually know whether it's better to run seven days a week than six. What's good is that if you set it as an automatic habit, you don't have to think about whether today is an off day or an on day. If you can simplify the number of decisions you make in your life, you make better ones. One decision I've made is that I run every day. I don't take off days unless something's wrong or it's impossible because I have a 19-hour flight. Once you've decided you're going to run, it's simpler. Mostly I just run to work. There's no moment where I decide not to run to work because I'm tired, it's raining, or it's hot. I just run to work. You do have a second decision. If it's raining, you wear a rain jacket. If it's hot, you wear a thinner shirt. You make decisions after that, but it's very helpful to have a stoic philosophy of just doing it. I do it every day, and usually, I do it twice a day.

Jackson: (1:11:05) You have a line where you say that's the beautiful thing about a marathon: any finishing time can be a tragedy or a triumph. How do you remember to only compete with yourself?

Nick: (1:11:16) That line comes from a hilarious moment when I was running the Boston Marathon. It was 2004, and I really wanted to break three hours. I got sick beforehand, fell apart, and ran terribly. I ended up walking 10 miles and finished in 3 hours and 43 minutes.

Jackson: (1:11:44) With walking? That's crazy.

Nick: (1:11:46) You walk at a 12-minute mile pace. If you're running at a seven-minute pace, walking adds five minutes extra per mile. If you walk for nine miles, that's 45 minutes extra. You can do the math. It's not that hard. I crossed the finish line looking like death. There was a woman next to me who was probably trying to break 3:45, and we finished in 3:43. She was celebrating, and it made for a great photograph. It's a good reminder. Even when I ran my best marathon in 2:29, there was probably a guy who finished right behind me or ahead of me who wanted to run 2:15. You don't know. You're competing with all these people who might care a lot or might not care at all. They might be there for entirely different reasons, so you really are just running for yourself. It is useful sometimes to try and catch the guy ahead of you because it can motivate you to go faster and harder. I like looking at people in the distance and trying to figure out if I can catch up to them, or if I sprint at the end, can I get them? However, it hasn't mattered whether I finished ahead of or behind anybody in any race I've run since high school. It's been 33 years since I cared even one-millionth of a percent about whether I was ahead or behind anybody in a race. There was a five-mile race I won in Northeast Harbor that I wrote about where I was glad I beat the kid behind me because I wanted to win in front of my kids. But almost always, you don't win. I remember talking to Jeff Goldberg, the editor-in-chief, and he said it was surprising that I've been an elite runner for 30 years and have only won three races. Usually, you come in seventh or eighth. You sprint at the end and maybe you come in sixth, but you just don't win. There are 40,000 people in a marathon; one wins, and 39,999 don't. There are 500 people in a race in Prospect Park; one wins, and 499 don't. Your winning percentage is quite low.

Jackson: (1:13:47) A little bit on momentum. In the book you talk about your dad often talking about momentum in life. Sometimes you have it. Successes and losses compound. Use it when you have it and try to get it back. This idea goes in both directions. Specifically you say, "Every time we do something right, we create a tiny, imperceptible tailwind for the future. To have run during the day is to at least have done that." Somewhere else you said, "I had just done a hard thing of running up a mountain, and it convinced me I could do a much harder thing: betting on myself." You are somebody who shows up. You clearly have internalized this momentum thing and you have a lot of tailwinds. Do you have any advice for running, but more broadly for getting started or getting things to turn in the right direction?

Nick: (1:14:35) Yeah. Choose something simple that you can do right. When my kids are in despair over their homework, I try to help them reset. I actually do this myself sometimes when I'm wondering where I am and what is going on right now. I spend the next ten minutes doing whatever the hard thing is. That sets me up to do it for the rest of the time. Just choose something that you can get right.

Jackson: (1:15:05) Just to feel the positive momentum.

Nick: (1:15:07) Do ten push-ups. Just reset, and you'll be glad you did the ten push-ups. Then you can try something a little harder, like sending that email you didn't want to send. Now you've done that. Write that thank you letter you didn't want to write. Now you've done that. Go do that damn PowerPoint that you screwed up and your boss is mad about that has sent you spiraling. Figure out whatever the pattern is where you can just sort of reset. Sometimes I'll do other things where I take some time to reset, but I'm going to do something. I'm going to go water the plants and weed the plants.

Jackson: (1:15:47) Get a win.

Nick: (1:15:49) I'm just going to do it for five minutes. I'm going to get the W, and then I'm going to go do this hard thing. I just think that's a useful tactic.

Jackson: (1:15:56) Yeah. You also talk a lot about how it's heavily implied that running is a form of anti-aging or life extension.

Nick: (1:16:06) It might be, might not be.

(1:16:08) Aging, Fathers and Sons, Inheritance, and a Mother's Grace

Jackson: (1:16:08) You care a lot about being... and even being able to play soccer with your kids. How have you gotten better with age?

Nick: (1:16:18) How do I improve as a runner? How I got faster?

Jackson: (1:16:20) Open-ended, maybe. Specifically in the context of running, your peak marathon wasn't when you were 30.

Nick: (1:16:29) No, it was 44. But now I'm clearly going the other way.

Jackson: (1:16:32) More open-ended, how have you liked yourself more?

Nick: (1:16:36) I feel very similar to how I felt when I was 30. There are things that are different. You turn an ankle and it heals more slowly. It takes a lot longer to warm up. I've been very fortunate because I've been very disciplined about running, recovery, and diet. Aging hasn't affected me in the same way I probably expected it to when I was 30. I feel like the same person. I've got more wrinkles and gray hair, but I feel fairly similar. My marathon is about the same and I can probably do the same number of pull-ups. I can still run fast and I still can't do a lot of pull-ups. I'm very fortunate about that. The reason why I've committed to that is A, I want to be there for my kids. I've wanted to be able to play games with them, and I'm reaping the benefits. I run track workouts with my son. On Saturday, we were at a track running 800s together side by side, and that is a beautiful memory. On my 50th birthday this past summer, he paced me to a sub-five-minute mile. That's incredible. He's soon going to be significantly faster than me. The fifteen year-old is. On a Monday, I went and coached my son's soccer team, doing the fitness training for them after track. When I inevitably and soon begin declining physically, they'll have these very intense memories. I have memories of my father from when I was seven. What will my son Zachary think when he's 40? Maybe I'll be here, maybe I won't be. In 25 years, I'll be 75. I hope so, but who knows? What will he think about that day where we ran that five-minute mile when he was 15 and I was 50? I think that will be an amazing memory. I'm glad I made this commitment to combat my physical decline. Professionally, yeah I'm probably doing better. Maybe as with all people, you get more crystallized intelligence. You have more knowledge and you've seen more stuff. You're probably better at pattern recognition and less creative as your brain changes. I'm in a job where that stuff matters probably more. My job is not to figure out the brilliant insight. It's to systematically look at the strategic options for The Atlantic, choose one, and make the right partnerships. I'm in a job that matches where I am in my life and cognitive decline (laughs). I didn't do that strategically; it just happened how it worked out.

Jackson: (1:19:29) You mentioned your son. This is also heavily a book about your dad. I have a few quotes. First you say, "You can always lose a best friend or a spouse. Your father will always be your father. This creates different obligations, frustrations, and kinds of love." Separately, you say, "One of my central goals in life is to break the long string of Thompson fathers who have caused deep psychic angst for their children." Finally, "We give our children our genes and our love, and we don't have any idea what in the end they will do with them." Do you think that we have a choice over what we inherit?

Nick: (1:20:12) Yes, we have a choice over what we inherit. It's not a simple or easy choice. I inherited a lot from my dad. I kind look like him physically, and my career... intellectually I'm a lot like him. My strength, which is the ability to do lots of things at the same time, is also my weakness, which is the difficulty in doing one thing at any given time. That was the same for him. I had a pretty interesting moment at a restaurant in San Francisco. I was having lunch with one of his college roommates, and another one of his dorm mates walked in. His roommate brought me up to that guy and said, Hey, this kid here is the son of somebody we went to college with. The guy looked at me and said, "Scotty's son." I am very much his son, and there are lots of things I've directly inherited. But I also watched this man decline, in part through a lack of discipline and susceptibility to addiction of different kinds, like sexual and alcohol addiction. I committed to not being that. I almost inherited the antithesis, and that was a choice and an awareness. You watch your dad struggle with alcoholism, and you know it's genetic. You know you're susceptible to it. In some ways, you can inherit the alcoholism and fall into that trap, or you can fight it because you are scarred by having watched it. To some degree, I obviously made choices over what I inherited, but to some degree, I didn't. Maybe that's the right way to answer that question.

Jackson: (1:22:14) Was there a point where you were... at least on some of this stuff, you alluded to it: your dad was somebody who succumbed to passion, basically. I want to talk a little bit more about this later, but you're someone who is really consistent and disciplined. Maybe that just happened over time, and it wasn't a moment when you were 21 where you were just like, I can't go this direction. But I am curious to what extent that was conscious. Did you think, I have to build this up because I know exactly what that looks like, and I can see it happening?

Nick: (1:22:47) It's interesting. There was a degree of consciousness in the choice, but it didn't happen when I was 21 because I wasn't aware of it. It happened in my 30s, and I had watched him—

Jackson: (1:23:02) This is post-cancer.

Nick: (1:23:03) It's post-cancer. Three things happen to me between 30 and 33. One is I get cancer and I survive it, which is very important for changing your perspective on life. You start to care about things more. There's post-traumatic growth. It's a very important thing that happens. Secondly, I have children. My first son is born when I'm 32. You have a kid and life is totally different because what you do matters so much more. They're going to watch you, and you're either going to be able to build a good world for them or not. In fact, your obligation to the world outside of your life matters more because now you have someone you're attached to genetically, emotionally, and every other way who's going to live in it. My last child was born in 2014, and maybe they'll live to 2114. The world up to 2114 is partly my responsibility. Your whole responsibilities shift, and that's the second thing that happens. The third thing is I was in a professional rut where I wasn't able to get hired in my 20s. You could look from the outside... I've had people say, Nick, what are you talking about? You wrote stories for the New York Times. But I was a mid-tier freelancer, which is fine and good, but it wasn't what I wanted. I probably applied and was interviewed for six jobs at the New York Times at different times, and I got zero. I just wasn't getting on track. If you were to ask about my career trajectory and whether I was doing the things people in their early 20s wanted to do in journalism, I wouldn't be close. I had worked for this amazing man in New Haven, but I didn't want to live in New Haven. I got hired into my first really good job as an editor at Wired right after I turned 30. It was six months after that Boston Marathon race. I guess the other thing that happens is I start running fast. Those four things all happen at about age 30, where I go from being a guy who can't break three hours to a guy who runs 2:43. All those things happen in this very short period of time, and I wasn't quite aware of all that was changing in my life. I didn't know that when I got that Wired job, it would be the beginning of lots of great jobs.

Jackson: (1:25:39) It kind of goes back to the momentum thing.

Nick: (1:25:40) Right. It's where the momentum shifts in Nick's life. The question is, why did the momentum shift? Did it shift because I got that first great job? Did it shift because of post-traumatic growth after cancer? Did it shift because I had a response to becoming a father? Did it shift because I understood that I had these capabilities as a runner? I don't know. It's not like I went and ran a 2:10 marathon, and it's not like I got a Nobel Prize. I don't do that much. But the trajectory changed. If you had asked me at 29 where I would be at 50, I would like... this probably better than what I expected. In lots of different metrics.

Jackson: (1:26:19) I don't know if it was in the book or in the interview, but you were talking about how one of the core curses of Scott's life was being so prodigious. JFK tells him he's going to be president, all this stuff.

Nick: (1:26:29) Yeah.

Jackson: (1:26:29) You went to Stanford for running and then ultimately stopped. It wasn't all success, but you were also on track.

Nick: (1:26:41) Yeah.

Jackson: (1:26:42) Against the backdrop of what you were just talking about, I'm curious how you didn't succumb to the perils of being a prodigious person who then got off the rails. Maybe that would be the difference. You were both really trending up, and then you both went off the rails a little bit, or at least stopped being on the ascent, and then your dad never...

Nick: (1:27:02) This is maybe a very important difference. I'm a star at Stanford, I'm vice president of the student government, I win all these awards, and then I get punched in the face when I'm 22.

Jackson: (1:27:16) This is the first job?

Nick: (1:27:17) I get fired from my first job. I get kidnapped after I go to Africa. I come back and I can't get hired as an intern. I apply for an internship at 100 organizations and I can't get one.

Jackson: (1:27:28) You got fully yanked back to earth.

Nick: (1:27:30) I'm a subway musician. I hunt for a year and then I get hired as a short-term intern at the Environmental Defense Fund, which is cool. Thank you to the EDF. But my dad at that same age was a Rhodes Scholar, traveling through the world on his way to being a tenured professor at age 27. My dad didn't get punched in the mouth professionally until much later in life when he realized, Wait, what's happening? Why are things so much harder? He used to say, "He whom the gods wish to destroy, they first make promising." I wonder what would have happened if you ran both things. What if I had won a Rhodes Scholarship and not understood that life is hard until much later? Or what if he had not won a Rhodes Scholarship, had understood that, and then struggled?

Jackson: (1:28:17) Right.

Nick: (1:28:22) Who knows? But I do think there is a real difference in that we were extraordinarily similar the day we both graduated from Stanford. Then one of the big differences is that the day after, I started tumbling down a hill and bloodying my lip, and he went to Oxford.

Jackson: (1:28:35) In the acknowledgments you say "this is a book about what you learned from him (Dad), but there is so much more that you learned from her (mom)."

Nick: (1:28:45) Yeah.

Jackson: (1:28:46) What have you learned from your mom?

Nick: (1:28:48) It is true about my personality. People who read the book carefully notice this. I wrote a book about my dad because his life is bonkers. People ask what your parents do for a living. My mom is an art historian in Boston, and my dad runs a male brothel in Bali. The narrative in the story is that my dad has this crazy cinematic life, but my mom is a different kind of movie character. She carries the weight of the world with infinite love. I mentioned in the book that she has twenty godchildren. All she has is just love for people. When I think of my mother, I think of her carrying the three of us children at the same time—my two sisters and me—with this intense intelligence, but also this patience and kindness. My dad looked at somebody and wondered, Can I sleep with this person? Is this person going to be professionally interesting to me? Is this a person who can advance these things? If my mother looks at a person, she asks, Is this person good or is this person bad? from an ethical, Christian sense. I learn a lot from that. I learn about patience, perseverance, and morality. I'm a pretty calm person, whereas my dad was a madman, spinning up and down out of control. My mom, maybe to a fault, bears the burdens of the world. She was married to my dad, who came out of the closet and sued her every year on her birthday. Somehow she shielded her children from that and raised us while he was literally living with psychotic people. My sisters and I sometimes say the odds that none of us is a serial killer after being raised by our father... It's remarkable what our mother did.

(1:31:00) Merging Machine-like Discipline and Wild Curiosity, The Boat that Never Touched Water, and Who We Might Still Become

Jackson: (1:31:00) There's a thread that has run across a bunch of the stuff we talked about. There are these two halves of you, at least by my reading. On one hand, you are remarkably focused. With the running, you're like a machine. You're super disciplined and you show up... I talked to Steve Finley.

Nick: (1:31:17) You did? That's great.

Jackson: (1:31:22) He said you didn't have an execution problem, you just didn't have a great strategy, and he gave you a better one. He said you're the perfect person to coach.

Nick: (1:31:42) (Laughs).

Jackson: (1:31:47) Yet you're also super curious. You're an amazing interviewer and an explorer. You even talked about not being able to stay in one place for that long. Those two things seem at odds with each other, and yet somehow you have harmonized them or compartmentalized the focus, consistency, and deliberateness. Does that resonate? Do they feel at odds? Is it something you're constantly thinking about?

Nick: (1:32:10) It is something I'm constantly thinking about. I try to figure out what things I want, how much time I can allocate, and how to be most efficient in that time. That allows you to do a bunch of things. You move from one thing to another, but ideally perform at a high level on all of them. This goes back to Finley. I did have a strategy, which was to try to train as little as possible while being a top runner. I just didn't have a sub-strategy of how to maximize my lactate threshold and my VO2 max workouts. I didn't have a belief that I could be faster than I was. Finley changed all that and got me onto a different trajectory. I could have run a 2:20 marathon in my 30s for sure, if I had been the kind of person who could singly focus, and if that was the thing I wanted to do. But it was never the thing I wanted to do, because I wanted to do a lot of things. It was never more important than my work or my family, and for long periods of time, it wasn't even more important than my guitar career. I never reached that. It was only when Finley helped me understand how to run a 2:20-something marathon in my 40s while balancing it with the rest of my life. Maybe if I had focused on one thing, or a particular part of my job, or if I just said I was going to be a writer, I could have been a much more successful writer or a better editor than I was. But I didn't. I bounced between things and got this mix, which has worked out well. I found a niche in the world that fits my skills. My niche is helping run this media company where there are a bunch of things that matter that make me better than average at the job. One is my knowledge of the tech industry, which I got because I was a tech reporter. Now the tech industry is like a hurricane blowing through my industry, so it's helpful that I've reported on it. I can also talk about it, which helps our advertising business. I've worked as a writer and an editor. I have the discipline from running. There's this whole mix of things that have come together. I have a little bit of the curiosity of my father and the patience of my mother. These skills make a mix that is valuable in this job right now. There are other things that I could do to be better at my job, but it's okay.

Jackson: (1:34:39) I think we're all searching for the you-shaped mix, or hole in the world.

Nick: (1:34:45) Totally.

Jackson: (1:34:46) I think the most vulnerable part of the book—obviously some of the stuff with your dad is really meaningful—is a part where you talk about a boat that never touched water. It's the little canoe that you run by.

Nick: (1:35:01) (Laughs). You're the first person to ask me about this. That detail matters so much to me, and no one has asked me about it, so thank you. I've done a hundred interviews about the book, and every time someone asks about a passage or a sentence that no one else has noticed, it makes me happy. Thank you for noticing that darn canoe.

Jackson: (1:35:16) There's a canoe that you suppose has probably never touched the water. It's in the context of finally reaching 2:29 and working with Steve. There's one line where you said "the faster Nick had always been in there." Then there are a few excerpts that I really liked. First, you say, "Every year I could run that speed was another year that I knew I was still alive." The speed pre-cancer. "This kept me going, but it also held me back. I had tried harder each year, but I only changed enough to keep everything the same. I hadn't been able to run a fast marathon in the past because I hadn't wanted to. Or more precisely, I hadn't really cared about going that fast because all I really wanted was something else. I thought about how long I had been satisfied to run 2:43 after 2:43 after 2:43. If I hadn't found Finley, I would never have figured that out." You refer to the boat that probably has never touched water, but might one day. Then you finally say, and this is the vulnerable part, "I wondered then, as I wonder now, what other versions of me exist that there may no longer be time to find."

Nick: (1:36:14) Right.

Jackson: (1:36:18) Do you have any theories? Do you have any lost dreams?

Nick: (1:36:22) First, let me explain the boat. I used to run every day, and I still do many days, across the Brooklyn Bridge. When you go across the Brooklyn Bridge, there's a big apartment building that you see as you start to descend. It's one of those buildings where maybe a couple thousand people live. Many of them have short decks where you can probably fit two chairs. One of them had a yellow canoe. For years, I didn't know whether anybody else running across the bridge noticed the yellow canoe sitting there, but I did every day. Every day I wondered why it was still there. If you lived in that building and you're listening to this podcast right now, please send me an email. It's a brown building to the left when you're running down the Brooklyn Bridge. The canoe is not still there, but it was seven-eighths of the way up. Someone had a yellow canoe or kayak out on the porch by the two chairs. Please get in touch with Nicholas Thompson. I was fascinated by it. Surely some days they must go out for the weekend, but I run on the weekends. I had a big insight into the book when I was running across the bridge, and I sat down on a bench where I could see the canoe. To your question, its the truth with anybody: what are the paths you could have taken? I've been exceptionally fortunate with certain paths. I got incredibly lucky with the woman I married.

Jackson: (1:37:55) You're deep in the compounding with a few of these certain paths in an amazing way.

Nick: (1:37:59) In an amazing way. I fell in love with a person who turns out to be a great match for me. I fell in love in college, which means that I didn't have to go through the heartbreak of breakups, the complexity of dating, and choosing a life partner. We turned out to be a great couple, and we are really happy with each other and have been since we were 21 years old. We are pretty lucky. Some things really worked out. My kids were born healthy and are good kids, which has made life much simpler. Things have just worked out and compounded, but there are, of course, questions. You wonder about this with running. You run 2:29 at 44. Obviously, you could run 2:29 at 43, 42, or 41. There's nothing... everything is worse objectively. How fast could you run? It doesn't really matter. Maybe I could have run a 2:22, or maybe I could have run 2:17. Who knows? It's not that important, but then you also wonder. That's interesting. If I had figured this thing out in my 40s, maybe I could have been a great reporter. Maybe I should have gone on a different career trajectory. Maybe this thing that I'm pretty good at, I should have gone down that path. What about this professional path that I missed? There were some moments professionally that would have opened up interesting doors and might have led to very interesting lives. You just don't know. Life can only be lived forwards and understood backwards. It's not like I wish I could go back and change something. It's not like I look back and wish I had gone through the red door instead of the green door when I was 25. I don't know what those things are, but I do wonder a lot. That experience of finding a version of myself and stumbling into that fact is interesting. Let me step back for a second. What is interesting about my running is not that I ran a 2:29 at 44. That's not that interesting. That's very fast for a 44-year-old, but who cares? What's interesting is that I ran a 2:29 at 44 having trained like a maniac and trained really hard through my 30s without getting close to that. The interesting thing is realizing that I had to get through a conception of myself that I could only be this fast because I could not be faster than I had been before I got cancer. That is an interesting revelation. A mid-40s guy trains hard and runs fast. So what? A mid-40s guy trains fast and goes a lot faster than he did in his 30s because he didn't understand the psychological effect of having gone through cancer at 29. Now that's an interesting insight. That was what propelled me to write the book, and it also led me to think about what other things are out there.

Jackson: (1:40:53) Yes. I'm not interested in what the alternative paths could have been. I'm interested in... Have you ever read this guy named John W. Gardner who worked in the government for a while? He gave this speech to McKinsey Co. called Personal Renewal.

Nick: (1:41:08) I feel like I have.

Jackson: (1:41:09) He opens by comparing people to barnacles. He says many of you are like barnacles. A barnacle attaches its head to a rock early in its life, and then it just stays there.

Nick: (1:41:18) That's great.

Jackson: (1:41:19) I think in general, most people succumb to inertia. They make a few choices, and then they get carried along. Obviously, you are an exceptional person in more ways than one. Yet, even so, you're 50, by the way. I don't think it's about alternative past paths. I'm more interested in looking ahead.

Nick: (1:41:40) The future. That's interesting. I'm going through this right now. My eldest son is choosing colleges. He's got two choices, and he loves them both. He's going to have to decide on basically no information. Lots of information, but he can't objectively choose...

Jackson: (1:42:07) No.

Nick: (1:42:08) You have no idea. You're making a choice for your future self. I chose to go to Stanford, and because of that, my life was shaped. My introduction to Silicon Valley probably comes from that. I adore the tech industry, cover AI, am fascinated by this, and have strong feelings about it. I was shaped by the libertarian, Linux, open-source, late 90s cyberpunks that influenced me in a deep way. My views about technology as a force that can bring about democracy wouldn't have developed if I had gone to a school on the East Coast. Then I met the woman I ended up marrying. All these things happened that profoundly shaped my life, and I had no idea. I chose Stanford because they had an elite cross-country team and an environmental science program. I kinda liked the lemon trees, and my dad said I should go there. My son has the same choice now. He's literally choosing between the same two schools I did, and he has no information about what he's going to do. We just don't know. It's a total draw, and he's going to make a choice that will massively affect his life. The interesting question is, what are those choices for me? There's not going to be a single binary choice like that. I have much more information about them, and I understand my future self better than he understands his future self. My paths are narrower. You go through life, and when you're 18, you can go out on this very wide spectrum. When you're 50, you go on a much narrower spectrum. You still have choices and doors, but the paths are much narrower. You go through life, and when you're 70, your choices are even...

Jackson: (1:43:42) I think they're less narrow than we think they are almost always, though.

Nick: (1:43:47) You think so? Maybe. There will be a huge choice of retiring or not retiring at some point, which won't be for a while. But like... who knows. Who knows. I don't know when the last time I had a big choice to make in my life was. I don't know what the next time will be, but there will be a next time and it won't be that far away.

(1:44:11) Gratitude, Stalin's Daughter, Scott Thompson's Verve, and Feeling Most Alive

Jackson: (1:44:11) What are you most glad you did?

Nick: (1:44:14) Marry Danielle Goldman and start having children. I wish we had started having children sooner so we could have more children. I feel like Thanksgiving with five children would have been better than Thanksgiving with three children. I just love children. I was sick at 30, so we didn't have kids until I was 32. We would have had to start before I was 30. So, I don't know.

Jackson: (1:44:40) One of my favorite things you wrote is this crazy piece on your friendship with Svetlana (Stalin).

Nick: (1:44:52) (Laughs).

Jackson: (1:44:55) We're almost out of time, but one of the thoughts I had is, what is he getting out of this? I concluded that he doesn't need to be getting anything out of this. She's just crazy and weird and lovely. Do you have any thoughts or advice on unlikely, strange, large age-gap friendships?

Nick: (1:45:07) I do think I got something out of her. When I was writing my book about the Cold War, I learned that George Kennan, one of the two characters, had a very close relationship with Svetlana Stalin. I found her living in an old folks home in Wisconsin. Her name then was Lana Peters. We started corresponding, and she spoke to me because I asked her about George Kennan, not about Joseph Stalin. She had been approached over the years and everybody wanted to know about her dad. She didn't want to talk about her dad, so we started talking about George Kennan. Then we started talking about her. She had this amazing life and just became my pen pal. We spent years corresponding. It was interesting and weird and peculiar getting another letter from Stalin's daughter, but it wasn't just that. I actually really liked her. What had drawn me to her was that when you write a book about someone like George Kennan and start to interview people, pretty soon you're on a merry-go-round. You're hearing the same stories because everybody is telling you the stories they read about in the books that everybody read, which were then reinforced in their memories and told in other interviews.

Jackson: (1:46:17) It's cached.

Nick: (1:46:18) It's cached, and fresh memories are very hard to get. It's very hard to crack people open because these are people in their set... and they're not lying to you. Literally the only thing they remember about George Kennan is the thing that was in Walter Isaacson's book, and they're going to tell you about that thing.

Jackson: (1:46:36) You need a special prompt to get something new.

Nick: (1:46:37) Right. Then I write to Svetlana, and it's just this torrent of... WHAT? He had an affair with who? He believed what? This happened when? I thought, wow. For whatever reason—because of her growing up, because she had been living in this old folks home in Wisconsin, and because she was incredibly perceptive with an incredibly high IQ, she was just interesting. She was interesting on George Kennan, but she was interesting on everything. I liked talking to her because it was different. It wasn't just different because she had grown up in the Kremlin and knew about Beria. I would have watched Jeopardy with her and talked with her about what happened on Jeopardy. She was smart, surprising, and weird. It was great.

Jackson: (1:47:30) Just two more things. Personally, and also to generalize, how do you hope to be more like, and how do you hope the world is more like Scott Thompson?

Nick: (1:47:46) Alright. Sometimes I think about this. No one should be just like Scott Thompson. You'll probably get arrested. As I say in the book, those traffic lights in his head were always green. He loved life. He wanted to talk to people, do things, and get more experience. And not just... he read books and wasn't just social all the time. He wanted life to be interesting. He hated boredom and couldn't slow down. He was always going out and doing something. If he had to get on a plane and fly somewhere, he was going to go do it. If there was a party across town, he was on his way, driving 90 miles an hour. It was always fun and interesting, and you were never bored. I have no memory of being at his house and being bored. It wasn't in a forced way; it was just this kinetic...

Jackson: (1:49:02) Life is so rich.

Nick: (1:49:03) Life is so rich and interesting. I loved that about him. This constant curiosity about him. He could talk to anybody, and people loved talking to him. My friends' memories of my dad are awesome, and I hope my kids' friends' memories of me are like that. He could talk to anybody. Part of his sex addiction, maybe, was that he would talk to a 17-year-old prostitute on the street, and he could talk to the prime minister. He'd bring the 17-year-old prostitute to dinner with the prime minister. Sometimes the prime minister wouldn't want to talk to the prostitute, but Dad was there to be the bridge. That I loved. The curiosity. He would go anywhere. He wasn't afraid of anything. I say in the book, this is a kid who grew up in Bacone, Oklahoma, and died near Lake Taal in the Philippines, and was everywhere in between. If you drilled a whole in the center of the earth would you end up right near Lake Taal? Not that far. He was a remarkably passionate guy who loved life.

Jackson: (1:50:17) One last thing. In a LinkedIn post at the end of the year, you shared a bunch of your favorite stuff.

Nick: (1:50:17) Yes.

Jackson: (1:50:17) You shared what I think were your favorite closing words of anything you read. It's from Will Humanity Survive Artificial Intelligence? by Graham Burnett in the New Yorker. I wanted to read a little bit of it. "But we'll need vigilance, and a fighting courage, too, as we again take up this unending experience of coming into ourselves as free beings responsible for world-making. Because it is, of course, possible to turn the crank that instrumentalizes people, to brutalize them, to squeeze their humanity into a sickly green trickle called money and leave only a ruinous residue. The new machines are already pretty good at that. The algorithms that drive these systems are the same algorithms that drive the attention economy, remember? They will only get better. What it is like to be us, in our full humanity—this isn't out there in the interwebs. It isn't stored in any archive, and the neural networks cannot be inward with what it feels like to be you, right now, looking at these words, looking away from these words to think about your life and our lives, turning from all this to your day and to what you will do in it, with others or alone. That can only be lived. This remains to us. The machines can only ever approach it secondhand. But secondhand is precisely what being here isn't. The work of being here—of living, sensing, choosing—still awaits us. And there is plenty of it."

Nick: (1:51:46) That ties in so well with what I just said about my dad, doesn't it?

Jackson: (1:51:50) What makes you feel most alive?

Nick: (1:51:52) Being with my children. I felt pretty alive leading track practice with my son on Monday. I felt pretty alive running those 800s with my other son. I felt pretty alive talking to my third son about his college choices. Being with kids and being outside... Yeah. I feel most alive when I'm disconnected from my phone and just living and I'm outside. I feel less alive when I'm inside. I've always felt this way. I slept on the roof of my dorm every night in college, and I try to be outside as much as I can. I have certain mantras I repeat in my head. If you can do something outside, do it outside. Being outside with people I love, doing something interesting, and being in motion. There you go.

Jackson: (1:52:38) Thank you.

Nick: (1:52:39) The conversation was great. That was fabulous.

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