Richard Morgan recently found a new measure of fame writing about writing, with his funny/terrifying piece “Seven Years as a Freelance Writer, or, How to Make Vitamin Soup.” Though Morgan’s work has appeared in some of the best-known outlets in print journalism – from New York magazine to Wired and The New York Times – his essay details the chronic humiliations of scrambling to make ends meet. We caught up with him by phone this week, as he prepared to leave freelancing for a post at The Commercial Appeal in Memphis. In these excerpts from our chat, he dishes on the unexpected blessings of kill fees, explains how to distill a story down to two sentences and recounts an unsettling encounter with a pineapple.

I recently heard “The Liars’ Club” author Mary Karr talking about how memoir shouldn’t be about payback. When you were writing “Seven Years,” were you thinking about payback, or was it something else?

There was a story that The Awl had done about a week before written by a woman who had been in New York for five years. It was a story about “What I’ve learned in five years of being in New York,” or something like that. I know Choire Sicha, the editor of The Awl; we’re friends. And I said, “Hey, I’m leaving.”

People always ask me about freelancing. I do this stuff where I go to Columbia and I give talks, and people ask me for help with editors and help with pitches. And so I said, “Why don’t I just write about my experience in the last seven years?” And he actually said that normally he would not be up for that, but he knew that a lot of my anecdotes were really crazy, and so he said yes.

It’s the kind of thing that I wrote in my head mostly, and then I just sort of poured it out the way I would a late night email to a boyfriend, or a letter from summer camp. So it wasn’t really payback.

I’m not suggesting your piece is payback, but Karr was saying that a lot of people write first-person pieces imagining that they’re going to pay back people who treated them badly. Her point was that the best first-person pieces really don’t do that.

I definitely was aware as a journalist that people would comb through it and try to decipher it. People do that for everything, with Stephen Glass’ memoirs, or Michael Finkel, or “The Devil Wears Prada,” or Toby Young. Those are a lot more payback and a lot more like, “I got inside, and here’s what it’s like.”

One of the things that I did want to do – which is not really payback – I wanted to relate the normalcy of these situations. There are so many people who would give their kidney to have a story in The New York Times, or a story in GQ. Once you’re inside it, and you see how the sausage is made, it’s not so fascinating. And also it’s not like you get made; it’s not like you’re a made man.

One of the most telling moments in New York was that a friend was a Harper’s intern, which was this already-storied position to be in – so many great people have gone through that role. He related that he had to deal with writers who would be calling and asking desperately about their paychecks. The takeaway wasn’t that Harper’s is financially in trouble or anything like that. The takeaway for us was that you could be someone who gets to do 8,000 words at Harper’s, and you’re still fretting about money, that it’s still this juggling act, this vaudevillian situation of catch as catch can.

I didn’t want to do payback in terms of spite against specific editors, but I did want to relate specific experiences in quoting. As much as I could, I tried to quote, “Here’s what an editor said to me.” Facts, so that it didn’t seem like me being moody and bitter.

You didn’t name names, which I thought was interesting.

I quoted things, but I didn’t name names. There’s really no point in naming which Times editor told me not to bother coming to him anymore. But obviously people at New York magazine knew the editor who sent me that condescending email. Other people pieced it together, and people obviously know who Steve is, although I didn’t put his full name. He doesn’t need that showing up in Google.

People like to do sleuthing in comments with things like this. And so I was surprised, in a good way, by the comments, because I would really not want feuding to happen. I just wanted to relate the experiences in an honest way, and the way to do that is to quote people in actual instances. Like the stuff with the Fortune editor – it’s not important who that person is. It’s more about the experience, and that things can be sloppy. I think a lot of those examples show me as sloppy.

The email I wrote to Adam Moss is insane. I think I wrote it on a Monday, and he took until Thursday to reply, and I basically thought for those four days that I would be banned forever from writing for New York. When I wrote the piece for The Awl, I told Choire, “We should run the whole email,” because I’m not really a fan of excerpting things. He said, “Yes, but it makes you look crazy.”

That’s actually the part of your piece that we’ve quoted in our commentary.

The thing to Adam – I bounced it off of one person, a friend who does communications for another newspaper in town – and she was like, “This is really intense.” At the end of the actual meeting with Adam, I told him, “Thanks for replying to my email even though I was kind of a crazy person.” And he said, “Yeah, it was really intense.”

And I said, “Yeah, you know, but it all worked out.” And instead of saying anything friendly, he said, “Yeah, it was much more intense than normal.” But he was very chatty later.

I wouldn’t say the piece was spiteful. If you click to the other first-person piece that I did – 3,000 words about being in unrequited love with a straight guy – that’s not a relationship vendetta or anything, the kind of spiteful or passive-aggressive thing you might see in those “Modern Love” columns in the Times. It’s more like, “Here’s an experience that people don’t talk about.” So if I talk about it, hopefully people will feel less lonely. I’m an immigrant. I’m a gay man. I’m a Southerner. I went to public schools, which in New York is really a thing. I didn’t go to Yale or Princeton or Harvard.

There’s a sense that people don’t talk about that, and so if you do talk about it, other people feel less lonely. And that’s one thing that I heard so much in emails with people getting back to me: “You really made me feel like I’m not alone, and that there’s a shot for me, that it’s possible.”

You can’t think if you get one book on the New York Times bestseller list, or you get one TV show pilot greenlit, or one feature in Rolling Stone, that you’re going to be set. It’s this constant hustle, and I think people don’t talk about that. I guess it was payback or spite against the mythos or fantasy world of the “made career.”

Did you see in the comments on your piece that someone thought your essay was a hoax because there’s no Richard Morgan at The Commercial Appeal?

That’s because I don’t start until the 16th, which is actually awkward, because that’s the day that Elvis died, and it’s a big day of mourning in Memphis. But that person actually emailed me and said, “Please tell me that you’re real, because I wouldn’t want this to be another viral marketing hoax.” One of the people in comments was Toby Young, and he said something like, “You should have been more spiteful. You played nice, and I got a movie.” But I found the comments more often said things like, “That is the scariest and sweetest thing that I’ve ever read,” “That was so nerve-wracking and romantic,” or “It filled me with hope and dread.” I didn’t know if they were compliments or not.

I think the piece said, “Here’s what happened. Here’s a dissection of my seven years. Judge for yourself if this was a success or not.” On paper, when people introduce me at panels, my resume looks really good. But in the middle, in the gaps between, it’s vitamin soup. That’s Choire’s phrase, by the way.

With the piece itself, did you just suggest it, and Choire said, “Go for it”?

He just greenlit it, and then I just sort of filed it, and then he cleaned it up a little. It was edited, but lightly edited. He changed transitions here and broke up a gigantic paragraph there. It was pretty direct and clean.

I remember being very scared, because he sent me back a one-word email that was all caps. And the only other time I ever had that was when I quit Gawker, there was this thing where I sent them my IM transcripts with Nick Denton. And when I did, the reporter sent me back one word that was all caps: FASCINATING. I became extremely scared.

But when Choire wrote back, it was PERFECTION. I got really nervous. I didn’t know if that was sarcastic or not. I started looking at it again and wondering if I should take this part out, if I should make it less moody, less emotional, less jokey. In the end, you just sort of have to make peace with the facts of it.

When you asked (in an email) about using humor and the first person, there are parts of it that are really didactic, just very cold pieces of a factual essay. But if you wrap it in humor, that’s the best use of humor. Humor is such a great medium for disturbing or upsetting information, which is why there are so many racist jokes and sexist jokes and political jokes. But when you read it, you can tell that it’s just me.

So you didn’t create a persona? You wrote it as yourself?

I think that’s really important. I did struggle with voice for a while. When you write for ESPN, it has to be quick and jabby and fratty and funny. And when I wrote for the Times, I always felt like I had to tell myself, “Write as if you were wearing a monocle.” When you freelance for a bunch of publications, there’s schizophrenia in terms of the different voices and different audiences. I sort of got tossed adrift in the beginning, and then I established my own voice.

If I can make a piece in Scientific American resonate with the same voice that a piece in ESPN does, I feel like that’s an accomplishment. And if that’s me, then I feel more comfortable. It’s actually one of those things where when you find your voice, you get more comfortable with your voice, and you do it more, and it gets stronger. If you read that other piece, the personal essay, the relationship essay, you can tell it’s the same kind of me, even though it’s a me that has retreated much more into research and academic stuff with the citations.

The other pieces I’ve seen from you are similarly off-kilter: a nerd who becomes a star for a day, Barbie goes vampire and such. It does feel like that’s part of your voice.

Yeah, I definitely sympathize with the underdog, with Fesh in his story. That was very frustrating. That was originally planned as a “Talk of the Town” piece, and they were sort of like, “This doesn’t feel right,” and that was it. There are a lot of editors who say, “Oh, this is good, but it’s not right for us.” And I think, “If it’s good, why don’t you run it?” I still get frustrated with that kind of thing.

You use humor, and you write a lot about comedy performers. Do you have any background in comedy?

No, but I love comedians. I moved a lot when I was a kid, so I had to be funny. Unless you’re the star of the football team, the only way to make friends quickly is to be funny. And comedians are amazing in terms of their storytelling. I’m hypnotized by improvised comedy. A comic touch is important – that’s how people remember things.

So you were never a comedian, but were you really a ranch hand in Colorado, an evangelist in China, a hitchhiker in Costa Rica and a track & field statistician in North Carolina?

Yeah, I tried out for the track team, but I collapsed with a quadruple heartbeat, and that’s when I learned I had a congenital heart defect. So I became a statistician, so that is the only way I could be around all the male runners. But I broke the gender barrier, if that matters.

And then I was in the Young Life Ministries, and I was in Campus Crusade for Christ. When I came out, I came out in my college paper – I had an opinion column, and I came out while I was the head of Campus Crusade for Christ, which was the largest organization on that campus, at North Carolina State University. It was 1300 students meeting every week, or maybe 1200. And we did an evangelism summer program in China. I was a ranch hand in Colorado at a place called Frontier Ranch in Buena Vista, Colorado. And Costa Rica? I got abandoned in Quepos, which is this Pacific Coast town, and I had to hitchhike my way back to San Jose, which is a three-hour drive over rope bridges. That was really rough, but I managed to do it.

But that bio – I keep meaning to fix that bio, because one time I interviewed a guy, an archaeologist, and he slam-dunked a giant pineapple onto the table when I first started the interview, and he waved it in front of me. My bio says, “Pineapples are his weakness.”

I assumed that meant you loved them.

Yeah, I would probably eat anything with pineapple on it. But he sort of waved it around as if it were kryptonite and made a joke about it. It was weird and awkward and made me think I shouldn’t put that much information about myself out there.

A lot of working journalists who work full time for news organizations imagine that if they lose their jobs at newspapers or magazines, they’ll try to make it as freelancers. You’re moving the opposite way, going from freelancing to a newspaper gig. What would you say to them?

There are so many different considerations. You’re OK to be a freelancer if you have a spouse who has a job where you can get health insurance or you can lean on their salary. I don’t have that. But also the thing that’s difficult with freelancing is that if you sold a story today to GQ – a 5,000-word story at $2 a word – you’d get $10,000 three months from now, after it runs. It would be two weeks after publication – at least that’s how Condé Nast works. So you can have success right now, but there’s this perpetual motion machine where the money I’m earning now from freelancing is not related at all to the work I’m doing now. It’s related to the work I did three months ago or two months ago. The work I’m doing now will allow me to have a life three months from now.

When you first start that, you’re existing off the freelancing you did three months ago, which was nothing. So there’s this initial drought period. And then maybe you luck out, but it really takes a while to get a lot of work going. There’s a part of The Awl piece where I describe it as “choosy begging.” People emphasize the choosy part when they fantasize about being a freelancer, and not the begging part. But there’s so much freelancing you have to do that’s just 300-word stories.

Nobody wants to point to some 200-word infographic in the front of the book of some random magazine and say, “That’s what my career is.” But that’s what you have to do – you have to have a bunch of those to float your passions.

I really don’t want to say anything bad about any of my J-school professors, because they were all amazing, and I would not be the person I am today without them. But J-school has a problem where it only teaches how to do an 800-word AP story or a 5,000-word New Yorker story. I don’t know what they teach for broadcast, because I didn’t do any of that.

J-school doesn’t prepare you for 300-word front-of-the-book items. It shouldn’t – because like any education, J-school should be aspirational – but it’s really easy to write an 800-word AP story if you’re being told that a story has a lede and a kicker, and a beginning and a middle and an end. But it’s really hard to do all that and distill it into a haiku version for those front-of-the-book pieces that magazines require. One professor told me something that helped me a lot: “Stories are not beginning, middle and end. Stories are change over time. All you have to do is have the end of it, and the beginning of it, and then what happened in the middle.” Which is basically the same, but having it distilled as “change over time” makes it so that you can do it in two sentences. You can do it in sort of a Harper’s Index way, with just one sentence and another sentence, and that’s a story.

That was another one of those stress-relief moments for me. It really let me feel comfortable approaching things like tone, rather than dealing with structure. Structure is the most frustrating thing to deal with, but once you get over that, you can focus on tone and doing that subliminal aspect of journalism as a certain kind of evangelism.

And even when you can pull that off, editors will still sometimes kill the story.

You have to know that freelancing can be like an abusive relationship. You sort of get slapped in the face, and you say, “OK, great. I’ll try that again later. That’ll be great.” It’s extremely frustrating.

But you just stick with it. There are so many stories where I’ve made more money off of kill fees than from publication, because a story just got shoved from magazine to magazine or from department to department.

You have to be very hopeful. You can tell in that Awl piece that I’m basically hopelessly romantic and optimistic. You have to be someone who believes in what you do and believes that being a writer is who you are. I couldn’t be an ad guy. I could use my writing skills and my communications skills in PR or speechwriting, or advertising, or in book publishing, but I just know that I’m a writer. You have to know that.

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