Flipboard’s head of partnerships and editorial Josh Quittner on figuring out what you’re good at, taking risks and “genre leaping.“
Born the oldest of four boys, Josh Quittner was first in line to take over his father’s fireplace parts business. From the beginning, he knew that being a factory boss was something he’d hate and just “suck at.” But Josh went to work for his ‘old man’ anyway in a job that required him to be something he wasn’t – another thing he would never do well. Lucky for him but unlucky for his father, the business soon went under, freeing Josh Quittner to become one of the most successful failures you’ll ever meet. Josh proves that the things we are good at are the things that we are inclined to do anyway in life and career. What we struggle with in one area of life or environment can be the very thing that enables us to thrive in another.
When he was living on his cousin’s couch in Albuquerque, NM working as a delivery driver turned paralegal, he reached a point where he felt, “I was born to greater things than this.” Josh had no idea what this “greater thing” was. He started trying different things – some successful, and many that were not. But even in random jobs that would otherwise seem to have gotten him nowhere, Josh learned and got something from each experience to help get to his next step.
This carnival worker-day laborer/delivery driver/paralegal/co-comedy-writer/newspaper part-time weekend crime reporter/newspaper crime reporter/freelance journalist/national magazine journalist and editor/and now editorial director and head of partnerships at tech start-up Flipboard has “put his antenna up” throughout life, taking a series of calculated risks.
Who was the first person to believe in you or to validate that you were good at something?
I was the classic underachiever, scored high on IQ tests, but even as a kid, I knew I was not performing to my ability. My report cards said that I was mediocre but (after yelling at me in his library to try and do better), my father would always tell me that I was really smart. He threw books at me, and I found literature was my way to explore my thoughts, questions and ideas.
When and how did you know that writing was your thing?
[After my father’s business failed], I was free to go anywhere in the world I wanted, and I went to Albuquerque, NM. I took a series of jobs that offered me great anonymity, places where I could forge my own identity and not be ‘the boss’ son.’ While working as a delivery driver for a law firm, the firm discovered I had a pretty good education and that they could make more from me as a paralegal than delivery driver. They threw this book of criminal code to study, and I passed the exam and became a paralegal.
Around the same time I responded to an ad of someone who was looking for a comedy writing partner. He was the part-time weekend night crime reporter for the Albuquerque Journal, and I remember thinking, ‘Wow, how I do I get a job like that?’ There were then several points in my career where others ‘took a shine to me’ and points where ‘the rest was up to me’ but it all contributed to my first assignment as a reporter. My story appeared on the front page of the Albuquerque Journal. It was one of those moments in life when you say, yeah, this is what I want to do forever, that I’ll even pay you to let me keep doing this.
Also, the chaotic nature of newspaper journalism played to who I was – the guy who didn’t open the book until the night before the exam, someone capable of memorizing lots of information but then forgetting it instantly. As someone who was always attracted to the things you’re not supposed to do – I was drawn to this environment where people who don’t play by the rules could thrive.
After some time working at the newspaper, an editor at the Albuquerque Journal offered me a “no promises” job, even saying he said he didn’t want to get my hopes up. But it didn’t matter because I knew this [writing] was it. I remember thinking, just give me a shot, just give me a shot. Because I knew that once someone did, I wasn’t going to fail.
How do you know when it’s time to make a new move or travel a new path?
You need to ‘put your antenna up’ – that is, be receptive and start looking for new opportunities to get you to where you want to be. We don’t put our antennas up when things are good because there is no reason to.
But the moment things aren’t going well you have to start looking and asking yourself what would I like to do now? And, what would I be good at now? Putting your antenna up means you’re looking, but also realizing that things will most likely not come in a familiar or expected form.
What attracted me most about the job at TIME was that nobody had had the job before me. Unlike, taking over someone’s job at a newspaper where everything is inherited. I was attracted to doing something that was not only new to me but new to everyone.
How do you know when to it’s time to take a risk?
You just have to try. I have taken risks over and over again … when I was asked me to write about this emerging computer thing called the “Information Superhighway” (aka the Internet) … when I was approached to write for this start up tech magazine called WIRED… when Steve Levy (who wrote one of the greatest books on computers and technology) asked me to share my notes from a story I had done on hackers in New York City.
So when Walter Isaacson at TIME who was running basically TIME’s foray into online publishing with PATHFINDER called after seeing my WIRED cover story, saying, ‘you don’t know me but I want to meet you.’ I pulled my ponytail back, bought a suit and went to New York. Two weeks later I was offered a job being the first person to write exclusively about the Internet at TIME magazine. Your ability to successfully find ‘what you want to be when you grow up’ depends on your capacity for taking risks.
What’s the worst advice that you were ever given, and what did you do with it?
Lucky for me I have a bad memory, so I really don’t have mental 'space’ for a lot, especially negative memories… One of my teachers, this WWII Vet, gruff mans-man, who walked with a cane, yelled at me for 'asking stupid questions.’ It made me cry. He taught history, one of the few subjects in school I actually liked. Later, he pulled me out into the hall and apologized but said I had to 'stop asking so many stupid questions.’ Well, I’ve made a damn good living asking stupid questions about people and life.
What’s a job you’ve had or a venture that did not work out as you had planned? How do you mentally “shake it off” and move forward from the experience?
I’m one of the most successful failures you’ll ever meet. Some people only take on things that they know they’ll succeed in. I am not one of those people. I’ve worked on a magazine that went under. I couldn’t save Business 2.0 – a business I ran and eventually made profitable despite it losing lots of money and having 25 percent subscribers who were unemployed after 9/11. I’ve had to take a 40 percent pay cut while my enemies licked their chops, which was humiliating.
One day after playing way too many hours of online poker, feeling unhappy and depressed, I suddenly had this idea. I wanted to not just cover the demise of our industry in the clinical detached that we had been covering it, but in hopes of trying to find the answer, to find the 'cure.’ I pitched TIME on the idea and that’s what they let me write about.
However, since my antenna was up, soon after I was also contacted by Mike McCue who [with Evan Doll] had just started Flipboard. I made the decision to leave TIME with two years left on my contract, and move back to California. Working for a start-up was something I had always wanted to do. But I made the move (in part) because I knew that I would have been put out a job in a few years and then maybe have to do something I didn’t believe in. Sometimes life and risks has a lot to do with timing.
What is one unconventional or quiet lesson you learned from someone?
I interviewed Jeff Bezos [CEO, Amazon] for TIME Magazine’s 1999 Man of the Year, which basically means I lived with him for three weeks. I got to know this smart, humble math guy from Princeton who shared his 'regret minimalization’ framework with me. It basically was a fancy way of saying to himself, ‘at 90 years old was he going to look back at the roads not taken and regret not creating this online bookstore in 1993, or will I regret staying where I am and continue to make a good career doing it?’
His framework shows that even in your failure you may still be happier than in never having had tried it at all. Think about it. You can almost chart it out, right? If you do something that you like, there is a small chance you may end up regretting [if it doesn’t work out]. But if you do something you hate, you’re definitely going to regret it [when things don’t go as expected].
About Josh Quittner: Josh Quittner is the head of partnerships and editorial at Flipboard where he is helping Flipboard grow their publishing partnerships, with brands like Oprah’s magazine and National Geographic. He has co-authored five books with his wife, journalist Michelle Slatalla, including Masters of Deception: The Gang That Ruled Cyberspace (Harper-Collins, 1995). Josh has found ways to use who he is and what he does well really, really well – using metaphors in his writing, creative intuition and smart humor – to help others “leap genres” and how to see and think of something in an entirely different way. To date, the result is a pretty fulfilled and happy guy who has manifested his destiny (or at least part of it) and perhaps some his “purpose” by being willing to see “something else” where others would only see “failure.” Josh Quittner is a graduate of Grinnell College and the Columbia University Graduate School of Journalism.