Newsletter 100: The Old Life as a Loser Columns

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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 March 2018, about the long-dead “Life As A Loser” series I wrote more than a decade ago. That series ran 200 editions — here’s the last one — and since we just hit the 200th edition of this newsletter, it seemed like a good time to revisit it.

The final installment of my old “Life As A Loser” column, which ran (roughly) on a weekly basis for about five years back before most reasonable people were even wasting their their time with the Internet, pubbed on March 29, 2004. That’s right: I quit the Life As A Loser series exactly 14 years ago last Thursday. If you knew me at the time that I wrote that column, you, like me, have never felt so old.

The Life As A Loser column came out of the earliest days of online publishing, back when people were just figuring out how to use it, on platforms like Diaryland and Blogspot and even Friendster. (I used to write a different paragraph bio every week on Friendster just to make dumb jokes.) The whole idea of the Web, this amazing new place, is that you could write as long as you wanted to, about whatever you wanted. And that was it! You weren’t trying to get a million people to read what you wrote; in fact, you had no idea how many people were reading it, or even if anyone was reading it. You had no way to tell people about it other than personally emailing the link to them, but that was hardly the point anyway. The point was that, out of nowhere, this place existed where you could write, or say, or be whatever you wanted.

As someone who had known he wanted to write since he was in grade school, I found this incredibly exciting. No longer did I have to wait and beg a big publication to print something: I could just do it myself! My friend Andy Wang had started a site called Ironminds, and I was so fascinated by it and by him that I ended up helping him with the site and writing a movie column for him. But I wanted more. So I had this story about Ben Stein and fiancees and me being humiliated on national television that no one but my closest friends knew, and I decided that maybe it would be healthy for me to write about it.

So I did. Ignore the dateline in that link: It was written in spring 1999, just about a year-and-a-half after The Incident happened, when I was still coming to terms with it. Like any lovesick juvenile, I was convinced it was the worst thing that ever happened to anyone in recorded history. But I found that after I wrote it … I really did feel better. It did help to get it out. It felt right: It felt comfortable. It wasn’t that I had it off my chest. It was that I had written it. It felt like the first step in finding my voice. Andy asked I wanted to write more, and I agreed. We called it “Life As A Loser.” It just sounded catchy.

Thus, I started writing these stories once a week. Suffice it to say: It was definitely the first step in finding that voice, but there were many, many steps to go. Not all stories were as compelling as the Ben Stein story, and I hadn’t quite figured out how to make a story at least resemble something interesting even when nothing interesting is happening. And in the midst of the series — which ended up transferring from Ironminds to several other sites (and even some alt-weeklies back in the day) ultimately to The Black Table, the site I founded with Eric Gillin, A.J. Daulerio and Aileen Gallagher — I ended up getting laid off from my job and eventually not having much of a career at all. I was answering phones at doctor’s offices, I was folding envelopes for temp companies, I was working briefly as a receptionist at Telemundo. (It turns out you need to speak Spanish to be any good at that job.) I was just taking any job I could to pay my rent and keep me in New York, and let me keep writing. There were years out of my life where, honestly, that column, and the fact that I got it published, was the only thing I cared about or had going for me at all.

The column never had much of a following, but that didn’t matter so much to me. I just needed something that was mine, something that gave me discipline to sit down and write every week, even if no one was reading, even if no one cared. I had noticed, in my first few years in New York, that a lot of people you ran into at parties called themselves “writers” but never seemed to be physically writing anything. I never felt comfortable calling myself a writer — I just started doing it in these last couple of years — but I knew if I was gonna be one, I at least had to freaking write. So I had “Life As A Loser.” It was all I had.

I was far too loose about my discussing my personal life in the column back then. Because it was so important to me, I considered the whole world my material, including my personal relationships; I was reckless and dumb about that sometimes, and I regret it, particularly because I was doing it for no reason: It’s not like I had this massive audience to satisfy. I think I was just trying to prove to myself that I was serious about writing, that I would sacrifice anything for it, that I was always focused specifically on that destination. That’s also how people rationalize being an asshole.

But I kept writing it, because I felt it kept me in the game, it gave me something to hold onto. Life As A Loser eventually did become a linchpin of The Black Table, a way to make sure we had something on Monday mornings, and considering doing The Black Table with Eric, A.J. and Aileen was the most purely enjoyable professional experience of my career (and certainly the most important), I suppose that justified the existence of the column right there.

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That picture is from the “Life As A Loser” book party back in 2003. There was a book. You can (sort of) still buy it here. The story of that book, and its publication, and its publisher, and that whole experience, is far too mammoth and insane to get into here. Remind me to write a separate newsletter about that someday.

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By mid-2004, I knew it was getting time to stop writing the column. I was in my late-20s, a little too old to be so confessional and masturbatory, and besides: The Black Table was starting to get an audience and I was trying to grow up and write about things other than myself. In January of 2004, I announced that I had only 10 left: I would stop at №200. I was tired of living in public, or worrying that I would subconsciously sabotage my life just so I’d have good material for the column. I just wanted to be a normal person again.

Of course, one year after the column ended, Deadspin happened, and well, that was it for normal.

Needless to say, most of these columns are unreadable today. For my 40th birthday, my wife, brilliantly, had every person in attendance read a paragraph from the Life As A Loser canon aloud at the table. It was excruciating and hilarious in precisely the right way. (Not only was a shittier writer back then, I was also apparently a total moron.) There’s some good stuff in there, I suppose, and I do think the last one was the correct ending, at the correct time. But all told: I’d prefer you think of the person who wrote those as different than the person who is writing this. I sure do.

But Life As A Loser still lives on in little ways, and I suppose that’s most clear with this newsletter. This newsletter is the first time I ever tried writing anything personal after ending Loser, and I think it has been beneficial, not just because I like doing this newsletter but because it is now informing my professional work as well, as evidenced by the big New York cover story last month, a piece I’d have never felt comfortable writing a couple of years ago. And if you really pinned me down about it: I suppose I’d have to admit I did kind of miss it a little. I’m older now, and less concerned with my own anxieties and fears anymore: I have a family, three people live in my house who are more important to me than anything I could have imagined back in 2004, let alone 1999. But it’s still good sometimes to step back, take a deep breath and try to type it all out like in the old days: To try to make sense of it all the only way I know how: By writing my way through it. Life As A Loser was invaluable to me becoming the writer and the person I am now. I owe a debt to it. But please, I beg of you: Never read it.

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