Disappointed in myself for asking the editor of McSweeney’s for a selfie. But obviously not disappointed enough to not do it.

A Conversation with Chris Monks, Managing Editor of McSweeney’s Internet Tendency >>> Part 1: Sweatpants and Ambition

In the past year or so I’ve had three great meetings related to writing. One was at Chateau Marmont. Two have been at Panera. The main differences: 1) No one at Panera comments on how weird it is that you’re eating bread, 2) No one is waiting in line to see the valet pull up with your shitty rental car at Panera, and 3) You could be sharing bagels with twenty New York Times best-selling authors and your fellow Panera diners would just assume that all y’alls are the neighborhood book club. Thank you, Panera, for just being you.

And although the Panera lunch crowd probably assumed I was trying to sell Chris Monks insurance, our two-hour-long conversation left me with tons to think about and laugh over. If you’re a writer-in-general, a humor writer specifically, a writer who thinks other writers don’t get rejected, someone who works from home, a parent, a middle-aged person of some sort, a person in search of a (good) habit, a person who questions their ambition, and/or a person who understands sweatpants, well guess what, this first part of my three-part interview is for you.

Kimberly Harrington: Can you talk a little bit about your history with the site? Were you writing for McSweeney’s Internet Tendency before becoming editor?

Chris Monks: Yeah, I was contributing to the site in the early 2000s. My first piece got on in 2003 and that was a huge thing. I was a third grade teacher and then I had kids and became a stay-at-home Dad. In what free time I had, I wrote a lot. I wrote short silly pieces about parenting and being a stay-at-home Dad. I had a blog that was a semi-fictional blog of a bored stay-at-home Dad. And I wrote other things that weren’t related to parenting at all.

At the time there was an explosion of humor sites. McSweeney’s was the big one but there was Haypenny, Uber, Hobart, and a bunch of little presses. So I started submitting and getting acceptances. My goal was to get on McSweeney’s one day. Eventually I did and once you get on it’s a little bit easier to get on again. I don’t know if you’ve found that?

KH: A bit, yeah.

CM: Then around 2007, John Warner — who was the editor at the time — wanted to take some time off and he asked if I was interested in taking over. I interviewed, it went well with him, I talked to Dave [Eggers], it went well with him and then I got it. Initially it was just on an interim basis, the idea being that it would probably turn into a permanent thing and sure enough it did. John just didn’t have the time to go back to it.

KH: That’s CRAZY.

CM: I know.

KH: Did he have a pool of people he was interviewing?

CM: There was one other person, another contributor, Jason Roeder who’s really funny. He had a lot of stuff on the site. I think what ultimately won me the job was the fact that I was already working from home and I had a lot of free time [laughs]. Jason has since gone on to write for The Onion, so he’s fine.

KH: He’s recovered?

CM: [laughs] Yeah, he has. So that was 2007 and I’ve been doing it ever since. Surprisingly. I didn’t think I’d be doing it as long as I have. At the time I was almost 40, I couldn’t conceive of an editor of McSweeney’s pushing 50.

KH: And yet …

CM: [laughs] Here I am!

KH: Do you remember how many pieces you had rejected before you got on the site?

CM: A lot. Tons. Before John got there, the editors weren’t nearly as good about replying quickly, it was frustrating. I actually got one piece accepted and three months went by. I checked in and they were, “Oh yeah we’ll still run it” but it never ran. I stopped submitting to McSweeney’s altogether and started submitting to those other sites I mentioned. When John took over he totally changed the way the editing process was done. He was really good about getting back to people, within a week usually.

KH: That part amazes me.

CM: It’s hard to do because we get about 200 submissions a week.

KH: Of that number, how many are accepted?

CM: It depends. In a good week maybe five but usually it’s more like two or three.

KH: Are some of them so off—or they’re the wrong format—that you can cut through them quickly?

CM: Yeah, I can read the first paragraph and know. Maybe a sixth or seventh of those submissions are people who start throwing something out there, know very little about McSweeney’s or what it means, don’t even bother to read the guidelines. They’re just so desperate to get published that it’s like, “Oh, here’s something I wrote in college. Oh wow, I’ll give it a shot.”

KH: Are you still writing?

CM: I don’t really write short humor anymore. Occasionally someone will reach out and ask me to write a piece, like The Washington Post did about a year ago. And I just finished a first draft of my next book, it’s a memoir about parenting, gracelessly becoming middle aged, and my son’s last season of little league baseball.

It’s funny though because when I first got the job I thought, “This is gonna be great, I’m going to be inspired by all the great stuff I’m reading and I’ll be a machine, I’ll be a comedy writing machine.” For some reason that just never really happened.

I wrote a book right when I got the job, The Ultimate Game Guide to Your Life, then I found it really hard to write my own stuff for a long time after that. I don’t know if it’s because I’m doing so much reading that I just need a break. That’s probably part of it. That takes up a lot of my time. And I still consider myself a family man, I’m the go-to person at home, my wife is the breadwinner, so I’m hanging out with my kids after school.

And I don’t know if you’ve found this, but when you’re working from home, motivation is just really hard. It’s hard to make yourself do stuff, especially after you’ve been reading submissions for three hours.

The other thing is I’m an incessant self-editor, so as I write I’m just constantly editing. That’s exhausting. Especially considering I’m editing other people’s work. But before I got this job, I had my blog. And I forced myself to write a new entry every day. It wasn’t great all the time but it built a routine. Every day for two hours, during my kids’ nap time, I’d write. It’s true what they say, you need to write every day. So I try to do that. But it’s hard.

It’s funny though, as I’ve gotten older, I’ve become much more introverted and less concerned about my career. And I was never very ambitious in the first place [laughs] so it’s all sort of catching up with me. When I got the McSweeney’s job I was like, “Oh, I’ll be going to literary readings, I’ll be on panels …”

KH: “I’ll be traveling all the time …”

CM: Yeah, “I’ll be traveling all the time” and that stuff has happened but thank God not as much as I thought, because I dread it and get so anxious. I just want to be home in my pajamas reading submissions.

KH: The same thing has happened to me. I watch my friends move up their career ladders and I’m like, I don’t know, man. I barely interact with human beings. On one hand I make a good living but on the other I’ve lost all the skills I built up over my entire career because I’m working from home now [laughs].

CM: I’m totally the same way, when I was like 25 I wanted to be David Letterman. So I’d consider myself on stage, all the time. And now it’s like, I just want to hang out with my wife and kids and watch TV [laughs]. A former contributor to the site is now the executive producer of a late-night show. He told me that if I was ever interested in writing for the show, he’d let me know the next time submissions were open. I was like, “Oh wow, that’s awesome. Well, ten years ago it would’ve been awesome.” [laughs] But now there’s no way I could move to New York City. So it’s a bummer. There’s this great opportunity that’s dropped at my feet and all I’m thinking is, well, I’d miss my kid’s baseball game [laughs], I’ll miss back to school nights, and I’ll miss watching Survivor. It’s funny how you view your life and where you want it to be. It shifts.

KH: I also think if you’re home early on you see it through a different lens. My kids were little when I was laid off so I’ve basically had a stay-at-home parent’s schedule even though I’ve been working this whole time. In the last seven years I’ve had job offers where I felt like, I know I should want that. I basically would’ve murdered someone for that opportunity in my twenties [laughs]. But I’m just not there anymore, that’s a former me who had that kind of ambition.

KH: I need to know, do you understand every single piece you accept?

CM: For the most part. Because I’m home all the time I’m very pop culture savvy [laughs], I’m on the Internet all the time or watching TV. One of the things John said when I got the job was, “The ideal writer and the ideal editor of McSweeney’s is someone who’s familiar with Shakespeare and also watches Jersey Shore.” I mean that’s dated now but the thought behind it is the same.

KH: What’s a typical day like for you?

CM: I wake up, I skim through submissions that might’ve come in overnight. I’m either editing stuff I’ve already accepted or I’m looking through the Maybe folder. Usually when something comes in I’ll skim through it, I’ll let it sit, if I know it has potential I’ll immediately throw it in the Maybe folder.

I’ll look back through the stuff that came in the previous five or six days and see what needs to be sent out in terms of rejections. I look at pieces that I put in the Maybes and see if I still like them as much. I do that until 10-ish and then I try to write my own stuff for a couple of hours before lunch. After lunch I get back to work, usually editing pieces that are going up in the following week or two on the site.

I’m always reading submissions. If I don’t keep on top of them it would get crazy. Odds are if you submit something, I will have looked at it one or two days after it’s come in. Sometimes I’ll make up my mind already and write a draft of a rejection and then let it sit. And then look at it one more time, five or six days later, and see if it’s true and then I’ll just send it.

Then at night I do it again. It’s great that I’m working from home and can make my own hours, but it’s also constant. I’m almost obsessed. I mean after I get home from this interview the first thing I’m gonna do is look at the submissions inbox and start filing them.

KH: It’s funny, I was going back through the rejection e-mails I still have from you and remembered how I was trying to read between the lines of a one or two sentence response. The initial ones, the pieces that were pretty bad, the vibe of your response was, “No, we’re good” and then in later ones any positive mention of anything was like, “YES! STILL REJECTED BUT BETTER!”

CM: It’s hard because we get so many submissions that I can’t treat rejections as a writers’ workshop. But I pride myself in being very polite in my replies, primarily because I hate conflict [laughs]. I would say 90% of the people who bother to reply to a rejection, it’s always, “Thank you very much” and that’s all you should really say. Either don’t reply or just be very polite. But maybe three or four times people will really go off.

KH: Wow.

CM: Yeah. I think part of the problem is that some people have the wrong idea of who I am. They think I’m some twenty-something San Francisco hipster and I’m not that.

KH: Oh for sure. In my head, the McSweeney’s submissions situation was a cross between the SNL writers’ room and The Onion where it’s all dudes, all in their twenties, and here I am, this middle-aged Mom in Vermont who works in advertising. I remember feeling almost nauseous, like I won’t be there to witness it, but I know whatever I submit is going to get ripped to shreds.

But then I came across this John Warner interview. It was heartening to read it and realize, hey, I’m like these guys. It’s not so different from how I’m living my life. I think a lot of people have that same wrong impression that I had early on.

CM: Oh yeah. People think we’re like The Onion and it’s a huge staff of writers. Most people don’t get that there’s only one person running the show, all of our submissions are unsolicited, and most of my work is done at my dining room table while my kids are eating breakfast.


Part 2 of this interview is here.

Part 3 is here.

Chris Monks is the Managing Editor of McSweeney’s Internet Tendency and the author of The Ultimate Game Guide to Your Life. If you meet him at Panera he might buy you an orange juice. No promises. Follow him on Twitter.

Kimberly Harrington is a Writer and Creative Director, contributor to McSweeney’s Internet Tendency and Co-Founder and Editor of RAZED. Follow her / me on Twitter.