Newsletter 142: Celebrating 15 Years of Not Working in an Office

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I’ve decided to start putting some of the best newsletter essays here on Medium, so more people can read them. You’re still better off just subscribing. This one is from January 2019, about working out of home. Next month, it will have been 15 years since I worked in an office environment. I’ll confess, I do not miss it.

Do you realize the last time I worked in an office was 2005? My last job where I had to commute to an office every day was Registered Rep. magazine, in a tiny little cubicle enclave on 14th Street and Eighth Avenue in Manhattan. I hopped on the C train at 72nd Street, giving me enough time to skim the entire New York Daily News by the time I arrived downtown. I had to be in by 10 a.m., but I always got there by 9 so I’d have time to answer emails — I didn’t have a computer or Web access in my apartment, a time that is increasingly feeling like the Golden Age — and edit all The Black Table stories for the next day. I was terrible at the job. I had no interest in financial reporting and in fact couldn’t balance a checkbook myself. But it was an office and it had internet and it was a job and it paid my bills while I figured out what the hell I was going to do with my life. As you can see, the stakes of my life in 2005 were not terribly high.

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I quit the job that March after about 18 months — 18 months sure feels a lot longer at 30 than it does at 43 — because I knew it was only a matter of time until my boss figured out I had no idea what I was doing and had no business working there at all. I was also starting to feel incredibly restless with my career and my life; it felt like a time to blow things up. I told myself at the time that I would “freelance,” but now it’s obvious that idea was cartoonishly short-sighted: I had no contacts, no prospects and no particular area of expertise. I had no plan at all. I would end up being saved by pure dumb luck, when Lockhart Steele at Gawker, who had read my work at The Black Table, asked me if I’d be willing to work on a gambling blog for them. I told him I didn’t much care for gambling, but I had an idea for a sports site …

And ever since I was hired to do Deadspin, I have worked from home. (I eventually did get a computer and web connection and am thus now as ensnared as the rest of you.) When I left Deadspin for New York in 2008, I had a desk, and I went to the office every day for a couple of weeks, but then I stopped, realizing quickly that all the commute was doing was robbing me of two hours of time I could have been writing. I finally lost that desk a couple of years ago; they kept it for me even though I’d been in Georgia for a couple of years, which I found touching.

People often ask me if it’s difficult to work out of home — 14 years in March! — saying things like, “Oh, I’d have a hard time not just taking a nap or zoning out watching television if I were home all day.” I tend to have the opposite problem. When you are working at home, you are always at the office; if I’m not careful, I’ll just work 16 hours a day. There’s always something to do, after all.

I find myself occasionally envious of the camaraderie that develops when people work long hours in close quarters in an office — every time I go into the NY Mag office now, or the Sports Illustrated office, or the office, I find myself spending the first hour getting caught up on all the in-jokes — but I do believe it can sometimes lead to a groupthink, bunker mentality that can get in the way of creativity and productivity. It can seem like the actual “job” part of the job gets in the way of, even overwhelms, the “work” part of the job. Even when I was in an office, I was always more comfortable putting my headphones on and plowing through all I had to do in solitude. I suppose I was perpetually working from home in spirit.

The one part of office dynamics I always struggled with was the idea of a boss. I write for many places, and do many jobs, and at each of those places there is ostensibly a boss, someone who could fire me at anytime if they wanted to. So in that aspect, yes, I suppose I have a boss, several bosses. But I think of my editors more as my bosses: My job is to write good pieces for them and to make their lives easier. If I do that, I can become the Set It And Forget It writer: You can count on me to turn in everything on time, and make it clean and readable, and hopefully inform and/or entertain, and if I do that every day, you’ll let me keep doing it without either one of us getting in each other’s way. That’s the goal. We’re less boss-employee than partners working toward the same goal.

But when I was in an office, even if this were the intention, it never turned out like that. There were always some sort of weird power dynamics in play; the bosses and managers were always separate, causing people to tense up, just a little, any time they walked by. Even though they were just normal regular dumbass human beings stumbling around like the rest of us, that they had a different title, or made a little bit more money, or had to sit in more meetings, turned them into a different person … and totally changed our perception of them. It was like every day was a reminder that they had been in this job longer than you and thus had more on the line than you did — — and thus every day was as much about navigating their constantly shifting moods and priorities as it was about actually getting work done. (It is also possible that I felt this way because I disliked my job.). I had a hard time getting the rhythm of the boss-employee relationship down. I always felt like they were sort of sad and bad at their jobs, and also that I was a terrible person because I was constantly letting them down, and that if I were better they wouldn’t be so upset all the time. I never quite figured it out.

The only way to understand my bosses as human beings, I found, was to leave the job entirely. Once you no longer work in the same confined space together, you remember, oh yeah, that’s just another person over there, with their own hopes and fears and dreams like the rest of us. Once the artificial construct of a corporate environment was stripped away, we could all interact like regular people again. I grew to ultimately really like my boss at Registered Rep. and completely understand the frustration of his job, and with me. I had a beer a few years ago with my first boss ever, Don, who hired me to sweep the floor and load the projector at the old Time Theater in Mattoon. He was a nice fella. The only thing I remembered about him is that he used to drive home when he needed to poop rather than use the theater bathroom, which was peculiar because he was the one who was in charge of making sure the bathroom was clean. Never trust a cook who won’t eat his own food, one supposes.

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The best boss I’ve ever had just announced he’s quitting his job of 15 years: Adam Moss, the editor-in-chief of New York, is leaving at the end of March. Adam is the guy who brought me into New York, who encouraged me to try different things, who pushed me to get out of my comfort zone, who never heard a story idea that he couldn’t think over for 15 minutes and make 1,000 times better. He was the best boss because he made you feel smart and important just because he wanted you to work for him. He was the type of editor who, when he complimented you, made you feel like you could fly.

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That email turns a decade old next month, and I’ll remember it for the next 50 years.

When I went into Adam’s office to tell him I was moving to Georgia in 2013, I thanked him for all the opportunities he gave me, and had a whole speech I wanted to go into about how much of an honor it was to be on his staff, when he stopped me: “Yeah, that’s great, enjoy Georgia. You’re still gonna write for us all the time, though, right?” It was one of the proudest moments of my career. Six years later, I’m still on staff.

Adam said in his final note to staff that, “My job has been to point the way, surround myself with people I trust, and hope for the best … I actually think my real talent is that I hire well and because I have always hired for some combination of wild talent, personal decency and a refusal to take things too seriously (and because I hope those traits have been contagious down the line), I find myself surrounded by a team of people I adore.” That seems like what a boss is supposed to be. Someone who trusts their staff and gets out of their way.

Of course, I also loved working for him because we saw each other roughly once every two years. That also probably helped.

God forbid, by the way, if I ever have to take a job when I have to go into the office again. It has been 14 years. I will have absolutely no idea how to comport myself. If this ever happens, I only ask you this: Please never show my boss this newsletter.

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Written by

Writer, New York, NYT, MLB, WaPo, others. Founder, Deadspin. Author of four books, with fifth, “How Lucky,” coming May 2021.

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