A former intern of mine, Crissy Milazzo, asked to do an informational interview for her journalism class—which I’m posting here because I have very high self-esteem.

1) If I remember correctly, you said you really felt like you launched your career when you became an editor at Time Out Chicago. When did you begin freelance writing? 

Pretty much right around then. The job was to be the Comedy Editor, which was part time, and so I had to fill the other 20 hours of the week—WHO ARE WE KIDDING WE ALL WORK 10000 HOURS A WEEK—with other assignments to make ends meet. I could have gone the get-another-part-time-job route, but the other editors at TOC were really kind, and started asking me to fill in and write stories for them. And because of the rules of TOC, that counted as freelance. It was really easy to just walk across the hall and pitch a story, so it felt like grad school for freelancing, giving me some cajones to approach other editors at other Chicago publications, then national, then now, as of this morning, international.

2) What do you find to be the most challenging aspects about working on your own versus working in a team?

The constant self-doubt. I kid! But not really. When I’m the only one making decisions about work, I’m my own boss, intern, colleague, editor, researcher, transcriber…lover? Collaboration is such a natural part of the creative process that it only reveals its necessity when it’s suddenly gone. I go out of my way to be in touch with fellow freelance journos and meet editors IRL (shorthand for “in real life” just in case you have never heard of the Internet) to mitigate most of that anxiety, and reassure myself that I mostly know what I’m doing. Or give a human face to the byline. One that needs money. How can you say no to this face? [Please insert a flattering photo of me to garner sympathy…my assistant (me) can provide.]

3) How did you originally approach publications with your pitches and how has that evolved for you over time?

Well since I started at TOC itself, my pitches took the form of cornering an editor in the break room and saying, “You, me, article, yes?” I’ve learned since then that in the absence of a shorthand, you have to be very clear and concise about what the story is, why it’s a good one, and why I’m uniquely qualified to write it. No matter how well I know a person, all pitches have evolved to take that form; whether it’s laden with inside jokes or not is just a benefit of my friendship.

4) What is the difference between freelancing and permalancing? 

I’m not sure there’s too much of a difference other than a vernacular one, but I tend to think of it as: A freelancer bounces from assignment to assignment, whereas a permalancer is tied to a specific job or publication, but not as a staffer. A sly way for employers to avoid paying benefits and increasing my taxable revenue, at the expense of providing me a bit of security as to when my next paycheck is coming.

5) You have a versatile writing portfolio: TV reviews, satirical FOD posts, interviews, A.V. Club lists and a whole lot of critical journalism, to name a few. Did you always want to write in a variety of mediums? 

I’ll try anything once, but I have found over time that it helps to be very upfront and specific about what you want to do. There’s this knee-jerk fear that if you say, “I cover comedy, video games and television,” then people will be like, “THIS GUY KNOWS NOTHING ABOUT MOVIES NEVERMIND.” That’s just not true—good writing/writers win out every time. Saying, “I cover whatever” isn’t an invitation, it’s a blanket turnoff. That said, I’ve honed in on the fact that the comedy world is both the most welcoming one to me and the most curiosity-inducing. So I think critically about it, but can also provide an insider’s perspective through humor. Also, you might notice most of my TV reviews are about sitcoms or sketch shows. Comedy is everywhere. Look behind you! It’s comedy! RUN!!!

6) How has your blog helped you? Do you try to keep up with a “personal brand,” or do you think of it differently?

Over the last few years, I’ve learned that the specific media outlet no longer matters as much as having an individual platform, as far as getting my name out there. I’ll give you a vague example: I know an editor at a prestigious national monthly magazine, and she told me she hired some Twitter celeb to write a piece, and they went through nine—nine!—rounds of edits. Why did she hire this person, I asked smartly. “Well, you know, she’ll tweet it out when it’s done,” she replied, also smartly. Personal recognition is what snags people jobs nowadays, not necessarily a track record of repute. My personal blog is a way to ensure my “voice,” so to speak in the most pretentious way possible, has a home regardless of what editors decide to publish, and a sort of personally spearheaded grassroots marketing campaign for myself, in a way that I hope feels organic. Plus, it forces me to write things. If an editor says no, that’s no longer an excuse to fire up my PS3 (though pretty much every other thing is).

7) You wrote about the kerfuffle around UCB pay rates and encouraged both sides to strive for transparency and understanding. Do you think that sentiment applies to the world of writing?

Yes, absolutely. Really, it should apply to any form of art, of which journalism is one. I’ve noticed a disturbing trend recently in which every single media outlet I write for, when asked about their pay rates, replies the same way: “Oh, I’m almost embarrassed to tell you this because it’s so much lower than everyone else, but we can only pay [insert not very high number].” The thing is, they are all the same. So either there’s an obliviousness permeating the industry, or people are falsely modest about their lack of cash. I think the mistake a lot of people make is relying on the old school way of doing business, in that there was a separation between the money and the “performer”, of all stripes. Today, even the lowliest writer knows the economics of writing, because they have to in order to keep up. It should go the other way, too, with the business people trusting that we as artists understand the drill and don’t want smoke blown up our ass about how something might give us exposure to then start making more money. Because the money’s just not there. Be upfront. I’ll respect the hell out of that.

8) When did you start performing comedy?

In high school, I took a theater class on a whim and loved it, but the thing that really stuck out to me were the improv games—a way to kill time or as a reward for getting through a tough assignment. I loved the permission to be goofy, and I later continued the trend into my college improv group, where we did things like “Progressively Nude Theater,” a fake play where the characters enter with less clothing each time until a nude guy comes in with a box in front of his junk. I moved back home to Chicago after college and stayed a part of the improv scene for a few years, giving it up when I joined TOC because I felt it was a conflict of interest. But I’ve always enjoyed performing. Like my blog, it’s a way to have a voice, and hone that voice—and there’s nothing quite like having people gravitate to YOU, instead of “you.” Know what I mean? So I do reading series’ and my own karaoke-inspired comedy show The Jukebox. All the weirdo stuff that makes me push myself as a writer and performer simultaneously.

9) How do your experiences as a performer inform your writing?

Well, not to crib from the genius who answered question eight, but I see them as almost one and the same. People gravitate to honesty, whether it’s on the stage or on the page (YOU JUST ENTERED THE RHYMEZONE SON). Irony and sarcasm can only get you so far, and both writing and performing bring me closer to beautifully articulating the unarticulateable—that kernel of honesty.

10) Financials seem to be difficult for anyone working in a creative field. How do you come to agree on a going rate for your work? 

HAHAHAHAHAHAHAHAHAAHAHAHAAHAHAHAAHAAHAHAAHAAHAHAAHAAHAHAHAAH.

In all seriousness, people tell me their rates and I can say yes or no. There’s little negotiation. I’ve gotten to the point where I’m comfortable letting things go if they don’t pay well, but still, I have very little control.

Oh, another thing is hAHAHAHAHAAHAHAAHAHAAHAHAAHAHA.

11) You’ve spoken openly with Marc Maron and Danny Masterson about your criticisms of their work, or for Maron specifically, the field he’s working in. People were surprised you did that. Would 22-year-old you be surprised you did that?

Yes. Specifically, 22-year-old me would be surprised at how not starstruck I am by anyone anymore, which is a blessing and a curse. On the one hand, hooray, I am now secure enough in my opinions that I feel confident in expressing them to whoever, be them Mel Brooks or Mel Books (a made-up person who is probably a locksmith—bet you thought I was gonna say librarian, that’s called the ol’ jokesterino). I’ve found that no matter who they are, they value my openness because it speaks to my genuine interest in their work. I wouldn’t be as comfortable if I wasn’t well-versed in it and excited about the opportunity to do a job that speaks to my love of pop culture and comedy in particular. On the other hand, not being starstruck sucks some of the magic out of, say, speaking to Stephen Colbert or Stephen Coalminer (who is probably a coal miner). But it’s a trade-off. I think about work all the time because I love it, and thus when something is truly surprising, it sticks out as being all the more special.

12) I have this profound irrational fear of writing unoriginal things that tends to end up sounding like “you probably shouldn’t write at all. Go back to bed.” What about writing has scared you in the past and how did you deal with it?

Mostly exactly that. “Who cares?” is essentially the question that runs through my mind 24/7. I’m trying very hard to have an answer to that question, which is, “I care,” and to let that be enough. It’s an ongoing struggle, one I feel myself getting closer to winning every day. But it’s not easy. I guess that’s the devil’s bargain we make as a writer: We talk to others as a roundabout way of talking to ourselves.

13) What characteristics does a person in your field need to have?

The tenacity to keep going even after being told “no” about a hundred thousand times. The ability to occasionally leave your ego at the door, but also be willing to stand up for your words when you have to—striking that balance. A comfortable desk chair.

14) Do you have any advice on how people interested in this career should prepare?

Read a shit-ton of stuff from places you like. Think to yourself, “Why do I like this article so much?” Reverse-engineer the process of how they might have come to their conclusions, and notice how strong their words are. Write with that same reckless abandon. All the time.

15)  What kinds of tasks do you do on a typical day or in a typical week?

Check my email, brainstorm some pitches, check my email, do research for an interview, check my email, do some writing, fail at writing, watch some TV, try to write again, procrastinate with some Twittering, check my email, read Deadline.com to see what’s happening in the world of pop culture, forget it because I’m playing a Facebook game called Marvel: Alliances, check my email, question my life choices, check my email. At this point five minutes have passed, so I repeat until the heat death of the universe.