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On getting lucky and earning it retroactively with feature writer Chris Jones
And his new book The Eye Test about the value of human creativity in an age of analytics
Hello subscribers! Perhaps you’ve forgotten what this is due to my negligence. This is Foolish Careers, a (currently irregular) newsletter featuring storytellers, artists and creative entrepreneurs in Asia who are building careers and businesses their way.
This issue features writer Chris Jones. He is not based in Asia but when a book publicist reaches out to your fledgling newsletter offering an interview with a writer you’ve been reading for years, you say yes. Chris talks about getting lucky early in his career, earning it retroactively, and the transition to screenwriting.
We also talk about his new book The Eye Test, about valuing creative expertise — that combination of raw talent honed through years of study and effort — alongside the data and analytics so dominant in today’s decision-making.
The book features artists, craftsmen, scientists, athletes, and other pros at the top of their game, and is inspired by his son Charley, who has autism and has worked out how to read by memorizing the shape of words.
Highlights from our conversation are below, and you can listen to the full podcast episode here👇🏼
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Much as journalist Chris Jones would have preferred to play out his entire career as an award-winning magazine writer, the world he knew at Esquire no longer existed.
He had talked his way into the magazine as a young reporter. The story involves a saintly janitor, donuts, and the naïveté of youth:
Fourteen years of world-class storytelling, two National Magazine Awards, and a stream of how-did-I-get-into-this situations ensue.
Walking around Comic-Con with Justin Timberlake, disguised as Ernie (Justin) and Bert (Chris):
Interviewing George Clooney the morning after emergency gall bladder surgery:
Inviting strangers to join him on assignment for three days of drinking at the best bar in America:
Amid a regime change at the publication, the entire writing staff was fired. The same year, Chris also got divorced. So at 43, he had to figure out how to parlay his writer skills into viable work.
Luckily, the last feature story he filed for Esquire, Home, about astronauts who spent a year in space, was optioned by Hollywood for $30,000 a year. Chris got paid another $750,000 when the show got the green light, another stroke of luck in an industry known for scripts languishing, unmade. (The show is now the drama series Away, starring Hilary Swank, on Netflix.) And luckiest of all, Chris got a job in the writers’ room, which kicked off his screenwriting career.
So it isn’t an exaggeration to say that during that annus horribilis, Chris’ body of work saved him financially and emotionally. He says:
“There were delicious snacks. I liked everyone who worked in the room. I enjoyed how not lonely it was. I'd just been divorced and it was like medicine going to this hopeful place to work.”
Here are highlights from our conversation:
There must’ve been something in you that made you walk into the Esquire building.
Idiocy. I would never do that now.
Do you think people can replicate that now?
Hearst, the parent company, built this massive skyscraper in New York. Esquire's on the 21st floor. You would never get in. It was only because Esquire was in this little building that you could walk right in.
I still think you get jobs in creative fields by meeting the right people. And I think if you ask most successful creative people if there was a point in their life when someone just took a weird chance on you, they would almost all have a story about someone who just said, “I don't know why, but I'm going to give you a shot.”
Writers will talk about someone's luck and it would bother me because it diminishes the work you did. Now that I'm older, I recognize how lucky I got. I feel like I earned it retroactively.
Were you aware that you had to earn it retroactively?
Yeah. The thing about working at a place like Esquire, you're surrounded by really talented people. I was probably 28 [when I started], and Esquire had this very established core of great writers: Tom Juneau and Charlie Pierce and Tom Chiarella. Mike Sager. Scott Rabb. I loved reading them, but there's a weird intimidation that happens when your stories show up next to their stories. You realize you have to really pick up your game because you can be embarrassed by the comparison.
Do you remember the first story where you felt, ‘I'm earning this’?
Yes. and I felt that way because my editor told me that. I wrote the sports column for a while, and then I got to write my first not-sports feature. It was a story about three astronauts who were on the international space station when Columbia, the space shuttle, exploded.
It's also the same one that won you a National Magazine Award.
Yes. So that's how I knew I got there. In the magazine business that's like the equivalent of a Pulitzer. The next day I went into the office and [editor in chief] David Granger made me a writer-at-large. That meant you were a staff writer who could write about anything. It was like being knighted.
What do you like, and not like, about screenwriting?
Well, the money is great. It's a lot less lonely than magazine writing because you write as a group of people. You literally sit in a room together with bulletin boards and index cards. It looks like a serial killer lives in that room.
And it's just scene, scene, scene, scene, and you're moving them around. And eventually what you end up with is a season of television mapped out with index cards, and then you go and write an episode that's “yours.” And then other people will work on those shows, you'll work on other people's shows.
What I don't like about it is that a lot of writing happens that never becomes anything. And for someone who grew up in magazines, if we got assigned a story, we wrote the story and it showed up in a magazine, there was never work that happened for no reason.
Whereas, I've worked steadily as a screenwriter now for five years. I've had that one show come out. Nothing else I've written has come out. I'm getting paid, but it doesn't show. I have friends who are screenwriters, who've worked their whole careers and made good livings and never had a single thing come out. That, as a business model, seems very wasteful.
The book cover is a tribute to your son Charley.
Can you share a bit about Charley and how he reads?
Oh, It's my favorite part of the book. Charley is my oldest son. He's about to turn 16, which is crazy to me. Charley has autism. He can talk, he's very loving, he hugs, but he has some profound disabilities. He doesn't understand numbers. Charley will never understand that 1985 happened before 1994. And he has this amazing memory, but he doesn't have the motor skills to write.
One of the things that always confused me about Charley was he always read. He could read when he was two and everywhere he goes, he carries a giant bag of books. The idea of Charley not having something to read is his nightmare. So this bag of books goes everywhere he goes, and I couldn't understand how he read when he couldn't spell or write.
I learned to read with phonics, you sound out the syllables. Charley never did that, but he would ask what words were. And so we were constantly saying: That is car. That is dolphin.
And what we realized through his therapy is that he just memorized words. He memorized the shapes of words the way you remember faces. The shape of the word is somehow stamped in his mind because he has this incredible memory.
If I asked you to picture a friend of yours, you could. But you probably couldn't draw a perfect portrait. Charley recognizes that word as a friend, but can't replicate that outside of the reading experience. Charley is just as good at reading as someone who learned through phonics, it's just different.
I spent a lot of my life being a very black-and-white thinker about the right way to do things. Being Charley's dad has taught me that's not true, that the world is much more complicated than that. And those different perspectives and different techniques are really useful. They open doors that would otherwise be closed.
In the book, you talked about Penn & Teller and their magic trick Shadows as an example of what you call embodied analysis. Teller the magician told you:
Sometimes magic is somebody just spending more time on something than anyone else might reasonably expect.
Best quote I've ever gotten. We were sitting in his kitchen. I remember it was like I had found the fountain of youth or something.
What Teller was trying to say is: what we perceive to be raw talent — where we use the expression “overnight success” like someone got struck by lightning — actually someone has worked really hard at something for a really long time, more than you would ever imagine. And then you go, oh, that's magic. Meanwhile, the person who's doing it is: No, I spent six years perfecting this thing.
As a professional writer, what's your own embodied analysis?
You're asking me to be egotistical?
I can pretty quickly figure out where someone's coming from. Can I trust them or their motivations? One of the great gifts of being a journalist is you get to ask the questions and then you sit back and listen. And if you're a good listener, you learn a lot about people and how the world works. I think I'm a good listener. And now it's pretty quick. I can meet a stranger in a bar and I can pretty quickly figure out what's going on about them.
Are you still in touch with Joe from Missouri?
Yes, we emailed just yesterday.
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