Clive Thompson has the kind of career that most writers would envy. He’s written two books for major publishing houses. He has a monthly column at Wired magazine. And he writes regular features for The New York Times Magazine and other glossy magazines.
But that kind of success didn’t come to him overnight. In fact, Thompson spent years toiling away writing for small publications making very little money. I recently interviewed him to discuss how he made his big break, what it takes to write the perfect magazine pitch, and why book publishers are more likely to award contracts to established journalists.
To listen to the interview, subscribe to The Business of Content on your favorite podcast player, or you can play the YouTube video below. If you scroll down you’ll also find a transcript of the interview.
This transcript has been edited for clarity.
Simon Owens: Hey Clive, thanks for joining us.
Clive Thompson: Good to be here.
Before we get into this interview, I was just on Twitter and I saw your wife tweet that this is your first Fourth of July as an American?
That’s right, I became an American last fall. I had been living in the United States for the past 20 years as a green card holder. It was finally time to pledge allegiance. And I did. It was a great, moving ceremony. There were about 300 of us in a courtroom here in Brooklyn.
The Donald Trump presidency got you so excited about America that you just had to finally bite the bullet?
It certainly illustrated the value of voting.
I wrote this recent article about the state of freelance journalism, and how this romantic era of cushy magazine gigs is over. A lot of journalists who are entering the field today are cobbling together low-paying web jobs, even when writing for established magazines.
But you’re one of those holdovers from that older era of freelancing. Walk me through your writing work as it stands today. Is it mainly a mixture of magazine writing and book writing?
That’s exactly it. The way it works is, on the average year when I’m not immersed in writing a book, I write 12 columns a year for Wired magazine. I usually write one to two features for Wired magazine. I usually write anywhere from two to three features for The New York Times Magazine. And I’m sort of an irregular columnist on the history of technology for Smithsonian magazine, and I’ve done as many as five and as few as two of those a year. And then a bunch of other ones that are more occasional. I usually write one major feature a year for Mother Jones, and then some other things.
That’s if I’m not writing a book. If I’m writing a book, then I scale the magazine work back to just the Wired column and just the occasional Smithsonian column. But the big magazine features, I can’t do those at the same time I write a book, usually.
I’ve heard you’re the longest-running columnist for Wired in its history.
I don’t know for sure, but it sounds right. I started in 2007. It’s been like 12 years now. The only one who might have been on for as long is Nicholas Negroponte, because he started in the beginning. He may have come close to how long I’ve been doing it, but I think he was out after six or seven years.
Tell me about your entry into journalism. A lot of people start out with some lowly editorial job, and then they eventually get the confidence and contacts to make the jump over to the freelancing. What was your experience?
My experience was I literally knew I wanted to be a journalist in high school. I’m old, so this was in the 80s. I went to college at the University of Toronto, because I’m Canadian. I didn’t want to go to journalism school, because I didn’t think I’d get a broad enough education. So I thought I’d go and study a liberal arts degree, English and political science, and I’d learn how to do journalism by getting very heavily involved in campus journalism, which is what I did.
University of Toronto, which is where I went, huge school, 50,000 students. It had like a dozen newspapers, some that published once a week, some two times a week. So I wrote hundreds, maybe thousands of news articles. I was an assistant news editor, and then a full time news editor of the campus paper. And then I wrote for a wire service. I graduated and knew how to be a journalist.
At that point in time, my goal was to get a daily reporting job at a Toronto newspaper. I tried really hard. But in five years of college I couldn’t even get an internship.
And those were the plump days of journalism, too.
Sort of, though keep in mind that in the late 80s and early 90s — in Canada there was a massive recession, an advertising recession. There had been a hiring freeze, and most of the newspapers in Canada, by the time I graduated in 92, had not hired anyone new on the order of 10 years. It was all a bunch of boomers who were in their 30s.
In fact, at the Toronto Star, they used to have an internship program that hired 10 interns. They scaled it back to like two interns, and they were hiring people that they laid off the year before. Their interns were two 45-year-olds.
So I did a bunch of other things. I was a database administrator for an arts organization. I worked for the League of Canadian Poets for a year as an administrator. I was a street musician. I did anything to make the money come in.
And then I eventually decided maybe I’d try to get a journalism degree, because that could unlock some hidden job market. Went for one year or two. Really didn’t like it. Dropped out. And I thought, ‘OK, I’ll freelance, because that’s the only way to be a journalist when no one will hire you.’
I had a couple lucky breaks. One was that I’m Canadian, and school was really cheap. Very easy to freelance when you live in a country with no student debt, your healthcare part of the tax base, and reasonably cheap rent. Basically I was just broke for a long time.
My goal was to write big long articles. If I’m going to be a magazine journalist, I wanted to write big, thinky pieces. My big lucky break was that the internet was just coming into the mainstream in the mid 90s. I start freelancing in 94, and all the boomer editors were convinced that the internet was just this stupid thing that was going to go away, and they had no interest in learning about it. So I started freelancing for the business press in Canada. And they had a lot of money, glossy magazines with business money, and an appetite for internet articles that no one wanted to write. So that was my entrance into tech journalism, through a combination of business journalism and also small political magazines. I would write for This Magazine, which was sort of like The Nation of Canada, except a lot funnier. I wrote a bunch of pieces for them. And then I worked for one and a half years as their editor. And then I was a freelance editor and freelance writer for a startup tech magazine called Shift, in Canada, which was like a version of Wired, but more cultural and weird.
After all that, I had built a career as a freelancer in Canada. It took like six or seven years. I was not making a lot of money. I could make a living. I could pay my rent. I was not saving any money. And in the middle of that, in 1998, I moved to the United States, because my wife at the time was doing a graduate degree at Rutgers. We didn’t want to live long distance.
So through a stroke of luck I got a green card. Her father naturalized as a citizen and supported us as independents. And I came down to the U.S. But now I had to start all over again. I didn’t know anyone in U.S. magazine journalism at all. So I was just doing the same thing. I started writing for smaller, more marginal magazines, which didn’t have a large budget, but would let me write something ambitious, like 4,000 or 5,000 word pieces. I wrote a little bit for Fortune. I wrote for a bunch of custom publishing magazines. Walmart would have a magazine, and they needed to hire people for it. I wrote for MTV magazine. I wrote for a bunch of things like that.
What was the process back then? Today, when I start writing for places, they’ve read something I’ve written somewhere else, and they say, ‘hey, I liked your stuff, if you ever want to pitch me something, go ahead.’ I feel like that would be a little bit harder in the print days, unless you were writing for really big publications. Were you literally just cutting out clips? How was that pitch process?
You’re exactly right. It was hard for other people to have seen what I had done, particularly because it was in Canada. It might as well have been on the dark side of the moon, as far as American publishers were concerned. They never saw it. So I’d written like 7,000 word, ambitious articles that were off the grid.
It was about trying to find someone who knew someone who could supply you with an email at a magazine. And then trying to find an idea to pitch to them. I was pitching Wired and I was pitching The New York Times Magazine, but I wasn’t getting anywhere. And what I realized after a couple years of this was that my pitches weren’t very good. I was not putting enough work to do a lot of research to make the pitch rock solid, and also find genuinely great stories.
My pitches all had that kind of feel that I had learned a bunch online by googling a couple topics, but I hadn’t actually done any footwork. Editors at major magazines, when they’re assigning you a big piece, they’re devoting thousands of dollars and a big spot like seven months from now, in an issue that only has three or four of those types of features. It’s a huge risk for them. And they don’t want to take that risk if it’s a pitch for which someone just sat around googling stuff. They want something more rock solid.
But at the same time that’s hard for the freelancer. When you’re a staff writer, you have that time to really…
But here’s the thing, I sometimes go into journalism schools to scare the hell out of aspiring magazine journalists. I draw a chart on the wall and I say ‘OK, here’s a hundred percent of my hours. Right now, 20 years in. I’m well known and people will actually respond to my calls. Here’s what my year looks like.’ I say to them, ‘You guys are all writers who like moving your fingers on the keyboard writing sentences. How much of my year do I spend writing?’ I draw like a 5 percent sliver. That’s it. That’s how much time I spend writing sentences, editing them, crafting them. Making them amazing.
What’s the rest of the time? I draw a line down the bottom. That’s reporting. That’s 45 percent of my time. I’m being paid more to report than I am to write. Obviously I have to be a good writer, but when you’re doing magazine pieces, you’re gathering 100X stuff and putting 2X in the piece, which is very different from web writing, where you gather 100X and put 80X in the piece. Because with magazine pieces you’re trying to find not just an anecdote, but the best anecdote. Not just a quote, but the best quote.
But what the hell is the other 50 percent of my time? That’s looking for story ideas. Magazine editors aren’t really hiring you to write, because anyone can write. They’re not really hiring you to report, because anyone can report. They’re hiring you to find an incredibly amazing idea that they’ve never heard of before. That’s your job. That’s your main job. And if you don’t treat that as your main job, then you’re not going to find the amazing stories that they actually want to publish.
I’ll be in the middle of writing a magazine piece. It’s overdue. I’m way behind. I’m about to blow my reputation with this editor. But if I see something or hear something that might become an amazing story, I will spend a day making phone calls to report it out, only to discover that there’s nothing there. Most of that prospecting leads nowhere. But if you don’t spend actual time reporting stories, you’re just going to find the same stuff online that everyone else knows about. And your pitches won’t be as strong and the editors won’t be interested in them.
This is brutal. This is hard. No one is paying you for that research. But if you don’t do it, you’re not going to come up with the absolutely amazing stories. You’re going to have the same things based on the same stuff that everyone else is seeing online.
So tell me about how you then finally got your foot in the door with Wired and The New York Times Magazine.
I’ll tell you about how the New York Times Magazine story came about. I decided, okay, my pitches suck. I’m pitching the same stuff everyone else was pitching. So I’m not gonna pitch anything until I’ve done so much research that I could probably write a 3,000-word weekend newspaper piece about it. That’s going to be the research that goes into the pitch. And the other thing is like, people, when they pitch magazines, they’re so caught up in the news of the day, but magazines are thinking three months to seven months to a year to two years out. Like I routinely start work on stories that will appear seven months to two years from now.
And so you have to actually completely decouple yourself from the news cycle, which is incredibly hard to do with social media. I mean you have to sort of care about it, but not enough that it’s occupying what you think is important. Cause what’s actually going to be important for magazine is a story that — you can’t be reacting to something that’s happening. You have to be in introducing an entirely new subject matter, whereas, a lot of online writing is, hey, this happened, here’s our reaction to it. And you can’t do that with magazines. Like even with Wired right now, like something might be just going absolutely huge in the news cycle right now, but I can’t pitch a column on that cause it’s going to appear three to four months from now. And who knows whether anyone’s going to care about that.
So the first piece that I got into The New York Times happened this way. I was thinking, okay, what do I have expertise in or some knowledge about? Because, you know, I always tell people, if you want to find an article that the editor has never heard of, start with the stuff that you’re obsessed with on your own because that’s what you’re going to have knowledge of where the interesting, weird, cool stuff is that would never occur to them. Because editors spend their days sitting at a desk just thinking about what’s happening and what possible articles they could assign on that. And there is no way that looking at what’s happening in the well known news cycle that everyone’s looking at, there’s no way that you will be better at wargaming those five or six brains. Like you will not come up with an idea that they didn’t think about three weeks, two months, a year ago. So it’s better to start with the weird stuff that you care about and try and find something that is in there that is of national significance.
Back then — this is like 2001 — I was into tech stuff. I had written a bunch about AI and chatbots and I was noticing that like, okay, so instant messaging was becoming a big thing. People were really into it. It was becoming a new way to communicate and it was creating these interesting questions of how do you perform a version of yourself in text, and how do you know the person you’re talking to is who they say they are? This is the first time that mass American society was sort of grappling with this. And so I decided that it would be kind of fun to write about chatbots, which were starting to happen. And the question of how do you craft something that can sort of pass the Turing Test? Right? And even just to introduce intellectually the Turing Test to a mainstream audience would be kind of fun, because back then most people had simply never heard of it. But I needed a profile subject. I need someone that had written a really good chatbot. So I was looking around and there was a thing called the Loebner Prize, which was a competition for chatbots that had just started up five years earlier. And there was an award given out every year for the most lifelike chatbots. I mean, no one ever fooled the judges, but whichever one came closest, and I noticed the same person had won like three years in a row. It was this guy, Richard Wallace. And I thought, Huh, well, you know, that’s interesting. He’s got like, you know, what is really considered to be a really good chat bot. It was also an open source chatbot, which is pretty cool. He was letting anyone use the code base. So I started reading up on it and I went to his website and it had a — he was a very prestigious guy. He’d been a computer scientist at Carnegie Mellon University, and it mentioned that he was now living on medical disability, mental health disability in California. And I thought, well that’s kind of an interesting story. Maybe let’s find out what’s up with that.
So I called him up because I’m, you know, wanting to do actual reporting. I don’t want to just go with what’s online. And I said, hey, you know, I’m going to pitch a story. Can I talk to you about this? We have a long chat. He’s a fascinating guy. He’s a brilliant guy. It turns out the reason why he’s not working at those places anymore is because he was laid off because he is, as he told me at the time, bipolar and, like many computer scientists, did not like taking the medication because they feel like it dulls down their thinking.
And so the problem was he would get in conflicts with staff. And so he’s like I’ve burned a bunch of bridges. The people there really don’t like me. I’m not well liked in my industry. He would do medical marijuana in California, which is what you can do. And he found that actually made it a lot easier and it made him very productive. And he would just crank on this chatbot. This is now becoming a really interesting story. You know, here’s a guy who is like an incredibly talented computer scientist, amazing at sort of capturing the dynamics of convivial conversation, but who by his own admission just, you know, has burned a lot of bridges and doesn’t get along with people.
I think the joke that I realized as I was researching this is he’s created a form of artificial life that gets along with people better than he does. He gave me names of people he’d work with and I called them up and they’re like, yeah, he’s a genius. He’s had trouble finding a way to do his work, but he’s made this open source thing. I talked to people at AT&T who are using his open source chatbot to make smart homes. I talked to people who frankly didn’t like him very much because they’d gotten in conflicts with him.
So finally I had like a really solid pitch and it was latticed to some interesting ideas. And that was the first thing that got me into The New York Times Magazine. But you know, that was weeks of research to make a 600 word pitch that was really, really rock solid.
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Was that worth it though? From a remuneration standpoint? Like was it worth the work you put into that?
Yeah, absolutely. The one thing I want to finish the point, by the way, Richard Wallace himself no longer actually thinks he’s bipolar. He never got formally diagnosed. I wanted to put that on the record.
Yes, it’s, it’s worth it and it’s always worth it because it’s the only way to get the good stories. If you don’t do it, you won’t get the good stories and you will not get in those magazines. I mean I wish there were an easier way, but that’s just what it is. You’re going to have the same stuff that everyone else is talking about because they’re looking at the same things online.
What I’m saying is like that was kind of like a one off piece.
Yeah. But I do that today. I still do that today.
You made the transition from turning these one off pieces — you got your foot in the door, but then it seems like you turned those into regular gigs.
Right. You’re right. So I’m under contract now. Though the contracts are like, if I don’t publish it, they don’t pay me anything. It’s not a contract for like, you know, x amount of words a year, basically. You know, I could not publish and that would suck and they wouldn’t like it and I wouldn’t like it. But it wouldn’t violate a contract. The contract is just an agreement on rates. Same thing with Smithsonian. There’s no set amount, right. So I could just not work and I wouldn’t get paid, you know, and it wouldn’t violate the contracts. So I still have to find really great stories and pitch them now.
And I will say that, even with my Wired columns, sometimes we’ve been able to work them out just on the phone with me doing a bunch of research for a week, and I will literally spend a week researching ideas to come up with three ideas so I can write a column that probably takes me three days to actually execute. The amount of time I spend looking for the idea is considerably larger than the time it takes to execute the idea because I can’t go in there with a column that’s just an idea. I have to try and find a really, really, really good idea, you know I did that for years, but it turned out the phone pitching didn’t work out very well because if I didn’t actually write out the idea, it wasn’t really solid. So what I’ve gone back to now with my editor is I try and send her three full pitches that are about 500 words each. You could do the word count, and that’s 1,500 words of pitching to write a 600-word column.
How did you make that transition from landing the occasional New York Times Magazine piece to getting something more regular?
I would say at the point I’m at now, like 50 percent of the stuff is stuff they pitch me that they want me to do. But if I want to write something, it’s a passion project for me that I really want to do, I’ve got to convince them.
So how did that transition happen? Well it was hard. It was slow.I mean, even getting my foot in the door, it was like another five or six years before there was enough regular work coming in that I was kind of making like a decent middle-class living.
It was easier to do back then because, keep in mind, this is happening between 2003 and 2007, and there was a lot more money in magazines back then than there is now. It was easier. The long and short of it is there’s no magic. I was just pitching ideas and I was responding to ideas and just trying to kill it as best I could on every assignment, and based on my experience, the kind of people who can reliably turn around good copy in that that universe is pretty small. So an editor will latch onto you, and really kind of start to rely on you. So once you’re in the door, it’s a lot easier. What I tell young writers is that it’s like a hazing ritual because you’re so broke for so long — I mean, I was really broke until my mid thirties — and that takes a toll on you, right? I mean, it makes staff jobs where someone is, you know, paying your a regular check and your health insurance really seductive. I was definitely tempted at various points to try and apply for a job, and just get off that treadmill. But the truth is it’s fun to write magazine pieces and when I was able to do it it was really delightful. Like it was intellectually thrilling. It’s been enormously fun to be able to pull it off. But yeah, once you get past the hazing ritual and they realize you’re not going to go away and that you’re generally reliable, a switch really flicks.
Here’s the other thing about magazine writing. The number of people who get their 10,000 hours is pretty small because you get driven away. The pay is infrequent. A staff job comes along and you and you go for it. A lot of freelancing is being done by people who have a full time job and they’re kind of doing it in their spare time or they’re forced into freelancing because they got laid off and they’re trying to do it for six months, but they want to get a full time job. So the number of people who are nuts enough to actually just do it full time for a long time, it’s very small. I mean in my early years I was really only writing, you know, one or two feature length things a year. The rest of it was all sorts of weird patchwork ranging from database administration to being a street musician to make money. If someone hired me to work at a newspaper I would get my 10,000 hours in like four years, and I would know everything there is to know about quickly filing a couple pieces a day. When you’re writing magazine stuff and you want to write 5,000 word pieces for the first couple of years, you’re really only getting one or two of those pieces in print. And so you’re still sort of figuring out how to do it for a decade. I don’t think I hit my 10,000 hours until I was like 38 or something like that, you know? The editors sort of know this and they’re like, okay, well now we need the people who have their 10,000 hours and there’s like 19 of them on the entire continent of North America because it’s, it’s just unpleasant to be broke for that long, you know, or impossible.
Again, keep in mind the privilege I had, right? Canadian, no student debt, right? I can live a lot cheaper with a lot more precarious income for a lot longer time. Plus I did a bunch of magazine work up until I was 30 in Canada where I had my health insurance paid for. It’s a heck of a lot easier to freelance when you have no student debt and no health health insurance stuff. So I encourage a lot of people these days, if they want to magazine freelance, you know, by all means get a full time job, and aim to do like one really killer magazine piece a year for a couple of years until you’ve built that up and you can start having those relationships. Quality matters more than quantity in the years that you’re building your career.
Your anecdote about health care, that reminds me of my experience in 2008. I was a newspaper journalist and I got this opportunity to have PBS as an anchor client. That’s another thing that a lot of freelancers, when they make the jump, they find some anchor outlet to write for that wants to put them on a contract. So it was going to be enough to where I could try to use that as my anchor pay and then start cobbling together other freelance projects. But I called a health insurer, and was like, Hey, I wanted to inquire about getting healthcare. And the second they found out I had a chronic disease, they were like, we will not insure you for any amount of money. I could have offered to pay $100,000 a month. They wouldn’t have insured me.
Exactly. There are so many barriers to full time freelancing. Healthcare stuff. There’s pay. I didn’t have any family members that were relying on me for income in those early years. I’m a straight white dude from Canada, which, you know, it’s also easier to get to edge your way into these worlds. Right. So in one sense I think it’s a lot harder to make a living at full time freelancing today, but weirdly, it’s easier to write something long and ambitious and get it published because there’s a ton of online venues, particularly in my world of science and technology, there’s just all these like amazing online publications now that run stuff at 5,000 words. And I read it and I’m like, this stuff is amazing, you know? Um, it just doesn’t pay as well.
Yeah. I guess I would put an asterisk on that. If you want to do pure journalism, like if you want to just be a purist and do nothing but journalism, yes, it just doesn’t pay very well. But I found ways to make a living by taking my journalism skills and applying it to corporate marketing and different stuff like that. And then I’m able to work on my own journalism during my free time.I consider it like a loss leader.
Weirdly I think it would be easier now to get stuff published more quickly that is ambitious because when I was doing it, there wasn’t really any web journalism, right? It was going to be in a big magazine where the gatekeeping was pretty strict, even for people with my advantages. Now, if I was like a smart and ambitious young science or tech person, there’d be a lot of places that would even let me write some big long pieces, so it’s easier to get started, harder to make it a sustainable, longterm thing.
I’ve always been trying to diversify where my money comes from because you can never tell when something is going to dry up. This is one of the reasons why I pivoted to book writing. My first book, I got the contract when I was 40, but it was good because it started, you know, adding more places where money came from. And then once the books came out, I was invited to do some talks and some of them are paid, and I have some limits on where I can talk because having a contract with the New York Times Magazine means you can only be paid to talk from places that are nonpartisan. You know, like it’s gotta be like a university or a library or something. But nonetheless, that was some good money that came in like for like a year or two after the book came out.
So overall, I’ve been trying to constantly diversify the income and I’ve talked to younger journalists and ask them how they’re doing it. And it’s a combination of the freelance writing. There might be some corporate writing, like you’re talking about, some paid content writing. They might be working on a podcast and getting some sponsorship, or doing something like that. There are new ways to actually make money that didn’t exist when I was doing it. But it all requires a lot of hustle. I suppose that was true 20 years ago. Now, if you are the sort of person that wants to have an independent career in journalism, you have to sort of be the type of person that could also be comfortable running a donut store, right? Because you have to be just interested in marketing what you do and managing your business and thinking about your finances and all that stuff. There is a kind of an entrepreneurial aspect to it that can be unpleasant for people if they don’t like that.
You were an early blogger. You had this blog that was called Collision Detection. It seemed like it would kind of blow up every few months when you would start publishing a lot on it. What was kind of the calculus that went into it? Was it purely a hobby or was it like this calculated thing that would help with your career?
It was a blend of those two actually. I started in 2002, and I actually had a kind of a disastrous financial year in 2001 following the 9/11 attacks. There was just a huge plunge in advertising. There had already been kind of a recession coming on, but the dotcom collapse had stripped a lot of advertising out of publications. My income went down by two thirds between 2000 and 2001. It was pretty tight. So I decided to frantically try and escape the free market by getting a fellowship. I looked around and looked around and looked around. I actually wasn’t eligible to a lot of the American ones, but I finally found one and I got in the Knight Science Journalism Fellowship at MIT. And this is a lifesaver because it gave me nine months to just hang out and learn stuff. And that was great. But that’s when I started blogging because one of the things with the fellowship is they don’t want you writing professionally. They want you learning. So I wanted to keep myself fresh, and I thought, well, I’ll blog and that will keep me writing. And I discovered I love blogging. I loved the casual tone. I loved feeling what it was like writing with my own voice when I was not trying to satisfy the dictates of an inhouse style at a magazine. Also, there’s just a lot of weird stuff that I’m interested in that no one’s ever going to pay me to write about, but it was fun just to write a post about it.
So I did it originally without any sense of anything other than just I’m just sort of exercising my brain. But then people started reading it and commenting and I started becoming friends with the commenters. That was intellectually fascinating. It was useful for me, I think, for a good seven or eight years. It was a demonstration of the types of things that I was interested in, you know, and occasionally I would blog an interesting thing and it would get picked up on BoingBoing or some other large blog. It was useful as a signal of what my mind looked like at work.
I never put any ads on it. I never wanted to make any money off it. And then what happened is when I had kids beginning in the late aughts, I had child care responsibilities. And so the blog slowly deflated and then Twitter came along and I started using that as short form blogging. Twitter killed thousands of great blogs. I’ve periodically tried to start up blogging again, but it turns out that Twitter has continued to be a better place to do stuff. And I feel like I’ve struggled to figure out what blogging would look like for me now.
A lot of people talk about the death of blogging. It didn’t die. It actually got more popular than ever. It just became Twitter and Facebook basically.
Yes, absolutely. And Medium has created a whole different paradigm for blogging, right? It’s like you don’t have to sit around figuring out what kind of a structure for what your thing is going to be. You just have to kind of do something interesting every once in a while. And that’s pretty cool actually. I understand all the problems of you have to now participate in this Medium ecosystem and whatnot, but there are benefits that come with it too. Things that you lose and things you gain.
How did Collision Detection enhance your career? We have this concept of the personal brand now. Do you think that helped you in terms of rising above the noise to catch the attention among magazine editors?
I think it definitely helped. I heard from editors that they would read a post and then email me and go, oh my God, that was really interesting. The Wired editors, a lot of them were reading it and enjoying it. Once or twice Wired columns literally emerged from that. They would go like, you know, what you just wrote is fantastic. We would like you to make that into a column, you know? A lot of people in the world of technology were reading it and were digging it. So when I would call them up, I’d be like, I’m calling them from The New York Times, and they were like, ‘oh, that’s cool,’ but they were more interested when they discovered that I was the guy that wrote that blog actually.
It also gave me credit amongst a certain type of really hardcore nerd, because I was sometimes going really deep into some abstruse nerdy stuff. So there was a bunch of different benefits that came from it that I feel like I’ve actually lost, which is interesting, right? Now, people definitely respond to my professional writing, but that’s all. And Twitter. But I feel like I’ve lost the ability to demonstrate the stray contents of what I’m thinking about all the time. And I’ve been trying to think of how to get that back. I don’t know whether it’s like a newsletter, which is kind of where some longer form blogging energy went to, or a podcast. I feel like I’m kind of stuck and it’s one of those things where I should just experiment with something and see if it works.
Yeah. I’m someone who has both a newsletter and a podcast. So the podcast is great because especially if it’s something like this where it’s more Q&A, cause you don’t have to do that kind of deep level of research and the writing, which takes up so much time and it’s something that’s a nice addition to your writing in the sense that it allows your fan base to kind of just hang out with you and listen to you talk for a little while. I find it rewarding in some ways that are beneficial to the writing side of things.
The thing that always draws me to it is I spend a lot of time reading all the weird things where people are still putting out chunks of their mind in slightly longer form than Twitter, and I love it and I get so many ideas from it and I feel like, yeah, that’s an ecosystem. I’d like to try and figure out something fun to do again. We’ll see a year from now if I succeed. Once my kids got a little older and didn’t need quite so much childcare, I joined a band and now I’m rehearsing and performing and writing songs. And so that also sucks time that probably I would have been using for blogging in my thirties.
Tell me about your transition into book writing. Like I feel like that’s the natural progression of a magazine journalist; you’re really kind of transitioning to a book writer so that you’re going back and forth. There’s kind of the sweet spot you’re in now where you’re going back and forth between taking book leave and then spending a few years writing long form articles and then going back. Is that really where you were always heading?
Early on, I wanted to also write books. Like in my late twenties I was like, you know, I’m doing long magazine pieces in Canada, I actually had an idea that it would be intellectually fun to try and do something that was even bigger, like to try and immerse yourself in a subject in such a fun way in a long nonfiction bucket. And I craved doing that. I was also aware that it was probably good to nail that to my CV or my personal brand or whatever the heck you want to call it, that I’m someone who actually can do that because I was aware that editors had a certain respect for someone that can pull off a nonfiction book, right, just because they’re sort of aware of how much work goes into it when it’s a reported book, where you had to really do a lot of reporting.
I kind of wanted that for the intellectual challenge and for the street cred and also, if the book takes off, it’s financially good too. But I had trouble finding a book that I wanted to write. I found an agent in my early thirties, tried to pitch a couple book ideas. She didn’t like them at all. I got very discouraged. During my fellowship — again, I was probably 33 at that point in time — I actually got an idea for a good book. This is when Google was like a four year old company and I could see that it was radically reorienting the way that we think about information. And I pitched a book on that and my agent loved it. I had a new agent, and I was working on it and trying to get access. But in the middle of that, John Battelle, a founding editor for Wired, pitched a book on Google and got a contract and it just killed my thing dead cause you don’t want to be the also ran to a major person who’s way better known than I am writing a big book. So that killed it again and my book ambitions just — I struggled with figuring out what it is I wanted to write and it went underground for seven years.
It wasn’t until my late thirties that I kind of began conceiving what my first book became. And so yeah, I always wanted to do it and I thought that there’d be all sorts of values ranging from just emotional, psychological, intellectual satisfaction to the potential of it pushing my career forward. But man, I was stuck in the mud. I was very happy when I finally got it done. Although my God, they are hard to write. I mean, I’m actually sort of miserable writing books and my second book was even harder than the first one. I was worse at it. I liked the book. I like both books. I think I like the second book even more than the first, but the process of doing it, oh my God, it nearly killed me.
Yeah, I’ve read interviews with people who have written one book and were like, okay, I accomplished that. It really wasn’t worth the struggle. I mean, it was worth the struggle to get that first book out. But in terms of the reward, I like it where I’m more constantly creating creative work rather than waiting two years for this thing to finally enter the world.
I’ve got three and a half years each time for me actually. Yeah, it was a long haul. I mean, the truth is it still feels so satisfying to have done it. And the process of doing it, there are still some joys amongst all the hair pulling torment. So I actually still would like to write more books. But it is hard. The difficulty of pitching magazine pieces is decoupling yourself from the stuff that’s happening online so that you can think, okay, how do I think of an idea that someone wants to read three months, two years from now and ideally 10 years from now — something that has shelf life. That’s hard. There’s a similar type of jump up to book writing because now I’m having to think about something that is going to occupy many years of my life. When you write for a magazine or publication, you don’t have to worry about getting the audience to read your article there. It’s a magazine’s job to figure out how to get people to read that magazine. But you put a book out and your publisher definitely works hard to try and sell it, but a lot of it’s on the author. And so you have to think of an idea that has a market and it’s hard. I’m not great at it. I struggle with that a lot.
What goes into the calculus for the publisher accepting your pitch? Like I assume your past track record played a part in the decision. Is it just that they know you can produce quality work? Did they think you have this personal brand you can exploit or they can exploit in terms of selling books? I know that journalists seem to have an easier time selling these book proposals. What’s going through their mind with it?
That’s a good question that I can’t 100% speak to because I don’t know exactly what made them go for me, but my operating assumption is that it’s fairly evenly divided amongst a few things. One is the fact that I’ve done a body of work in long form journalism. So they figure that I can do something of greater length. And the second thing is that I have established an expertise in an area. Right. So because I spent, you know, almost 20 years reporting long form on the way technology and science impacts everyday life, they were probably a little more confident that I was going to bring some of those resources to bear.
But the third thing, and this one’s really important, is I worked incredibly hard on the book pitch. For the first book. I spent a year, probably way too long, but I spent a year researching and writing the book pitch. The second book, even with the editor saying, hey, come back for a second, we want another book, you still have to come up with a pitch that on its own is just exciting to them. Right? And that’s really hard to do. It’s a weird thing to do because you’re writing this document that has to be incredibly exciting and filled with actual research and thinking and with this vision that shows what the book is going to be, and yet no one’s gonna see this document except the editors.
So you have to toil incredibly hard on something that like seven people are ever going to see. So it’s hard to motivate yourself to do that, but that pitch is very, very important. I’ve heard from lots of agents that have said, you know, that the quality of the pitch, even from an established author, is a big, big deal. And it’s a huge deal if you’re a less established author. If you have just a remarkably amazing pitch that’s well-written and shows that you have already done research that demonstrates your access or your ability to pull this stuff together that really vaults things upwards. It’s this hard work of all the speculative work that goes into finding an idea and packaging it in a way that gets noticed.
Let me tell you a funny story that goes back to magazines, but this is an example of how the quality of a pitch and the quality of an idea is so key that it can take someone who has absolutely no contacts and get them right into a good situation.
About seven or eight years ago, I got an email out of the blue from this young guy who was writing for like some paper out in Kansas or something like that. And, you know, he’d been on staff for a couple of years and he wanted to make the jump to writing long magazine pieces. And he said to me, I want to pitch Wired. I have an idea. I like your work a lot. He’s very complimentary to me. And he asked, can you help me get in touch with Wired? And I said, look, here’s the deal. Send me the idea, because I can probably tell you if it’s something I think they might be interested in and it’s a good idea to always go with a strong hand.
So he sends me the idea. He’s based out in Kansas, and he’s doing his reporting and he’s discovered that there’s all these people doing meteorite hunting. It’s a flat area. And these meteorites the size of like a Hondai Alantra or a Toyota Corolla land and embed themselves like 15 feet in the ground and they’d been there for, you know, thousands or millions of years. And if you can find one, it’s worth a lot of money because there’s these hedge fund millionaires who want to have like a six foot long meteorite right in the lobby of their otherwise unoccupied Miami condo, right? So there were all these guys that were literally building by hand, massive metal detectors, like six, seven feet wide coils and they would drag them behind tractors all over these fields, and if they found something, they would split it with the farmer, right? It was all because someone had made a hit at one point a $5 million meteorite, right? Now there was this entire subculture around it. So this kid knew about this stuff, he’d already done ride alongs with them. So that’s already a great story, but there’s an amazing extra layer that he’s also uncovered, which is that scientists are freaking out because these meteorites are incredibly critical to understanding the origins of the universe. They should be in labs being studied, but they can’t outbid a bunch of hedge fund douchebags who want it to be in the lobby of their otherwise unoccupied Miami mansion. So like now you’ve got this amazing layer on top. He’s written this fantastic pitch. It’s got great details. It opens with a scene where he’s riding along in a tractor when a thing starts dinging, it’s all there and he’s like, do you think Wired’s going to want it? And I said, they’re going to say yes in like four minutes. Right. You have found an amazing story that’s completely perfect for Wired. You’ve documented what’s going on and sure enough, I think they probably accepted in like three minutes,. And so what I always tell people with magazine stuff and with books is that the best way to get them to say yes to an idea is to show them an idea to which they could not possibly say no.
How has your career fundamentally changed since publishing books? Obviously there’s the royalty aspect, so unlike magazine writing, there’s this thing where you get to play a bigger part in your success if it is successful. I’ve heard that books can launch speaking careers, especially if you can make it onto the New York Times Bestseller list. How was your career changed since publishing books?
I would say the main things that have changed is that it opened up the ability to do some of these speaking engagements that didn’t exist before. There’s something about having published a book that makes people much more interested in having you come and talk. I’d say that’s the single biggest change, because I was already writing for the magazines that I was writing for and I had been doing so for 15 years before I wrote my first book. I can’t say that it sort of opened up any doors magazine wise. I think it probably impressed my editors. I think they know how hard it is to write a book.
So I think it probably helps illustrate that I can work hard, basically. It didn’t really necessarily change the dimensions of my magazine writing. I definitely know younger writers I’ve talked to who did a book much earlier than I did, and if they were someone earlier in their career, they probably moved more quickly than I did because they actually had a book that convinced long form magazine editors to take a chance on them because this person wrote an amazing 80,000 word long nonfiction book with some great reporting in it. We would love to have them write a 6,000 word piece for us. That’s one of the reasons why I kind of wanted to write a book when I was younger, when I was like 30 and I had just arrived in the U.S., because I sort of perceived it as a way that it would actually be a useful calling card to these magazines, these big glossy magazines.
It’s just that again, I kinda sucked at coming up with good book ideas. Took me 10 years. It’s definitely opened up the ability to write more books, which is great. And it may also have some intangible effects that I’m unaware of in terms of cementing my reputation as a thinker in my particular field of understanding technology and its effect on everyday life. I mean, I think that’s definitely true. I mean, one of the things that starts happening is you publish books, and as you start becoming a character in journalism, people start calling you up and interviewing you because it’s like, hey, you know, you’ve written this book, we’re writing an article, can you be an expert? And it’s like you start getting these weird experiences of becoming one of the people that is responsible for generating knowledge. That’s kind of interesting, but I think it’s a little different for me. The effect that it had on my career because I came to book writing so much later.
Well, we’ve seen this explosion of streaming service, video streaming services, Netflix, Amazon now, and then all the linear TV cable channels, like Hollywood is super hungry for IP. I’ve seen reports that magazines are launching departments that are more aggressive about selling the IP for magazine articles and of course, the book industry has always been a healthy funnel for stories into Hollywood. How seriously involved are you in trying to sell your own IP to Hollywood?
So I have an agency, the William Morris Endeavor, WME, and they have fantastic agents whose job it is to try and find anything from movies to documentaries that might be interested in what I produce so I don’t have to do that work. I mean, my type of writing certainly in the two books I’ve done doesn’t have a lot of potential, I don’t think, for becoming a movie. I have not written a book where it’s like, here’s the story of a remarkable individual, you know, which is a type of stuff that Hollywood tends to go for.
You just did a piece in New York Times Magazine about the original women coders.
Yeah. And I’m definitely talking to some documentary people actually about specifically that. So like there is stuff that comes out of that, but yeah, it’s not like I wrote Argo. I’m not saying it wouldn’t happen to me, but it’s probably less likely to happen to me than to someone that writes a piece for Outside magazine that becomes a book about some disastrous attempt to get to the bottom of the Mariana Trench.
That’s more a Hollywood movie than the type of thing I’m doing. That could change. I mean, I’m actually kind of intrigued by the idea of making my next book project really a story of a person or an event. I kinda liked that idea. I have not done that type of challenge. I’ve definitely written profiles of people. I’ve told stories, but I tend to, because of just the way I’ve written stuff and what I’ve gotten good at doing and when I get asked to do, I tend to be asked to do these sort of big synthetic things where it’s like, hey, could you pull these nine threads together into one piece?
Yeah. It’s interesting to watch what Malcolm Gladwell is doing where he’s still publishing books and magazine articles, but now he’s kind of taking some of that intellectual energy and putting it into highly produced podcasts. Each episode is like a chapter from a book or something like that.
Yeah. I mean I think, I think that the challenge for me and for anyone that is interested in doing deep ideas journalism is figuring out what are the vessels that let you do that in an interesting way. Right. You know, the long magazine article — there are fewer of them now than it used to be. There’s not zero. Uh, there’s a lot of long buried smart stuff online, doesn’t pay well, but wow, you can get the idea out there and maybe that can be the thing that leads to a book, you know, or to a documentary.
There are podcasts, there are newsletters. In one sense there are doors that have closed for doing, you know, ambitious, long form journalism, but there are also doors that have opened. It’s hard for me to say in a weird way. I hear these stories from the magazine world in the early nineties, and it sounds bonkers, like the money was flowing in yet I was still sort of trying to bang my head against a door during those years. So I arrived at a good time. There was still a lot of money, but you could see the wind slackening in the sails even as I entered the industry. You hear these stories of almost bacchanalian excesses of spending in the late eighties and early nineties. I’m like, wow, that would’ve been interesting to be around.
At the same time too, it’s an exciting time to be a content creator. Like you think of the full time Youtuber, like you think about what it took to be a filmmaker pre-internet and now some guy living in some Midwestern state working from his basement can get a million subscribers on YouTube and make a career as a filmmaker. I mean obviously his version of film is something different than what you see in Hollywood.
There are a lot of amazing people that have YouTube followings and they have like, you know, half a million subscribers and I’m like, this is amazing. I mean, I know that YouTube has all sorts of, you know, crud on it and like flat out disinformation, but the sort of intellectual ferment, I think it’s exactly kind of probably what blogging was like for me with the potential for even more money, frankly. There’s always some new medium that is coming along that allows people that have ambition to tackle big and interesting ideas in a great way.
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