Now What? How Answering This Question Lead Us to Changing Everything

by Ceda Xiong and David Wolinsky

This is a new series following two Chicago writer-producers as they try to make it in Los Angeles.

None of this was supposed to happen.

She was supposed to go off to business school, and I was supposed to keep scraping at entertainment journalism and academia’s collective glass ceiling. But in 2012, we met one another in a writing class at The Second City in Chicago taught by Caitlin Kunkel, a woman who inspired us to start obsessing over story structure.

Ceda was there finishing up the writing program, while I was there with residual energy I built up from another class taught by the head of the writing program, Andy Eninger. I took his class just to get in the same room with him, and hopefully to prompt this realization: “Gee, I owe David some emails back about getting in the door to start teaching here.” I wasn’t planning on having Caitlin sub for Andy one day, intriguing me to sign up for another story-structure class. But it got Ceda and I in the same room. And, shortly thereafter, it got me hired.

It took months for us to actually reach out to one another and start collaborating.

Ceda and I could not be more different — and not just because she’s a woman and I’m a man and, no, we’re not dating. But we wanted to share how two wildly contrasting individuals came to the same conclusion. In the Chicago comedy world, people tend to disappear in a few different ways: You’re either knighted for the stage and you’re on TV five years later, you journey off to L.A. to “make it” as we are attempting, or you simply burn out. The second example is the most common, and for those select few who boomerang back, they tend not to talk about Los Angeles at all.

If they do, it’s only in weary tones, with stories about how the city is isolating or “doesn’t get” what they were trying to do. It’s all in before/after terms. But life changes aren’t like lap-band surgeries. They’re an ongoing process, and even the decision to pull the trigger is itself a major undertaking. The journey can’t begin without a beginning, and it’s seldom talked about in honest, practical terms that can help others. That’s what we want to do here. We wanted to share what it’s like to try as we’re gearing up to box up our lives, put our poor cats in crates, and drive across the country.

I’m Not Ready

Ceda: I’d been living in Chicago since 2001. I came as a college transplant from Knoxville. And I liked Chicago. A lot. I still do. And like anyone else who lives somewhere for a long time, I had my routines. I biked everywhere. I had improv classes. I had a food blog, which quickly just became me eating and not writing about food. I had my favorite hot dog (Hot Doug’s duck sausage with foie gras), a rotation of sandwich shops I made a point of re-ranking every year (2013 was the year of the Pastoral le canard, 2012 was Cemitas Puebla’s Milanesa cemita, 2011 was the Ba Le Chinese pork banh mi), and the many Pinterest home-improvement projects I made my boyfriend Jorge build (like the Readymade pipe shelves). Jorge and I also started a family together: Over the years we were blessed with two obese cats.

Career-wise, I had a job that always kept me comfortable and debt-free: I’m a software consultant at a large corporation. But I knew it wasn’t something I could do for the next 20 years without a salaryman’s death. But I also thought I was doing what I was supposed to be doing because that was what everyone around me was doing: business school applications, GMAT classes, and trying to get recommendations. I needed to get about 70 points higher on my first GMAT score, but I couldn’t get myself to sign up for a second round for some reason that is obvious now. Well, that, and I just finished paying off my student loans last year. So the idea of going into another $200,000 in debt seemed foolish.

David: I actually didn’t realize you were that close to going to business school when we met. You never really talked about it. I thought you were just considering it idly. For me, there was far less stuff keeping me in Chicago. I was born there and left Chicago for college — unlike literally everyone else in my extended family who went to Champaign-Urbana. Before my last semester at Middle Tennessee State University, I had an internship at Rolling Stone in New York, and also took an improv class at the Upright Citizen’s Brigade. They were unintentional life-informing decisions that set the course for what I would do, honestly, to this day.

For a long while after college, I had fantastic momentum. Less than a year after getting my degree, I was the Chicago city editor for The Onion’s entertainment section, The A.V. Club. I was there for five years before being let go like 90 percent of print media. From there I decided to pursue the fast-paced world of collecting unemployment and hustling freelance writing work as doggedly as I could. It was great, for a while: I wrote for Wired, was an editorial consultant for Adult Swim, and then was finally teaching at Second City. I was doing that, plus teaching at DePaul University, and also freelancing for lots of other places, but what I was really doing was still operating in post-layoff, survive-at-all-costs mode. When you’re a freelancer, you keep doing what you’re doing so you can keep doing what you’re doing. It’s a treadmill, and even though my treadmill had many impressive brands on them, I was feeling professionally flabby. And if I’m being honest, I think I felt sort of guilty about not getting the charge out of those brands that everyone around me did as observers. I was hanging in so long as a freelancer because I felt like something would take off in a bigger way somewhere, somehow, but after nearly half a decade my patience wore thin and my restlessness soared. In short, I had the worst life of anyone ever.

I mean, leaving for Los Angeles was never an issue for me from this perspective. But I wasn’t sure how I would land with a job or what it would be. That was my sticking point for the longest time in this whole process. What we should explore here is how we each went from simmering dissatisfaction to imminent action. If you were plugging along, why uproot yourself? And why uproot yourself with me, a dude you met in a Second City class?

Ceda: I mean, when we first met, you were one of the only working writers I knew. For me, someone who was also trying to start a writing career on the side after college, freelancing always sounded much more glamorous even though my limited experience with it was so unrewarding I had kind of given up on it. I had reached my limit of pathetic pitches to McSweeney’s (“Things McDonalds has Not Yet McNamed”) or Nerve (“Urban Sex Parkour: Why it Matters”), and I was also sick of writing restaurant reviews for Not For Tourists. I knew I still wanted to write somehow, so I decided to go through the sketch-writing program at Second City in 2011 to flex a new muscle. By the time I ended up in Caitlin’s Story for TV and Film class, I’d spent a year and a half honing a completely new skill and way of expressing myself. With my egghead education at University of Chicago, I had learned more criticism and deconstruction. Symbolism, taking apart what an author means through close reading, long pedantic arguments over what the cistern means in Bartleby the Scrivener — all that was certainly educational, but what I needed to be a better writer was the ability to create worlds and characters. Second City taught me that.

All that added up to me becoming so enamored with writing again and approaching it with a totally different mindset that my career suddenly became my day job. That’s when we started working together. I had worked with other writing partners in the past, but nobody had as much dedication to a project as I did until you. Our rabid attention to detail were what scared everyone else off from working with us in the past, but also started this game of chicken to see how seriously we could take our work.

What’s funny is I was the one who pushed for this move to begin with. At the end of April, my shady landlord sold my and Jorge’s building out from under our oblivious noses and demanded we leave our home of six years in 30 days. We were a year into writing our web series, Bike Gang, and on the verge of producing. We had our actors. We had our crew. We had our locations. Along the way, I had heard of this magical places called Los Angeles where people get paid to write and the streets are paved with blowjobs‽

At your encouragement, I had flipped my network upside down to look for any industry connections. I was on the phone every day, asking for informational interviews and feeling out L.A., talking to people about how they broke in and where they saw any possible connections with what I do now that could be applicable out there. I didn’t know where this new habit was taking me, but very suddenly it took me to LA in person for the very first time. I impulsively booked a round-trip ticket when a writer on the ABC Family series Switched at Birth suggested we get together for coffee in Beverly Hills the next week. This was the beginning of September. That week taught me two things: that having face-to-face time is far more valuable and memorable than being a well-intentioned voice on the phone; and that I wanted to move out here as soon as possible.

What Will I Do For Money?

David: I come out to L.A. every June for E3, the big video-game industry convention. Inspired by that Jim McKairnes book you recommended to me earlier in the year, 103 Ways to Get Into TV (By 102 Who Did, Plus Me), I decided to stick around in Los Angeles for an extra week after the show and see who I could arrange meetings with from my entertainment-journalism Rolodex. I crashed in West Hollywood with my buddy Eric, and had packed my week full of lunches, dinners, and drinks with producers, writers, and actors. Everyone was incredibly encouraging about Los Angeles and my ability to make the transition into the industry, and I realized the past decade I spent as a writer-editor and managing people is essentially the same as producing. I had just never thought of it that way, but industry people connected those dots for me in meeting after meeting. It planted a seed in my mind — but the thing about L.A., as you hear over and over again, is you have to be there “in the room” to get jobs.

Nevertheless, after I came back to Chicago, my resilient networking resulted in landing four job interviews in September. One was to be a writers’ assistant for an Adult Swim show; I had three consecutive interviews with Funny or Die to be a web producer. One particularly devastating night in early October, I heard back from both places: I didn’t get either job. Before then, I knew I wanted to move to Los Angeles, but was hung up on trying to land with a job. I didn’t think it could happen for me any other way.

Ceda: And I remember being sympathetic, but also telling you that now you were the only thing holding you back from Los Angeles now. But I was also being kinda less empathetic because I knew I could move with my job since I work from home.

David: Right. But I needed that. And I think I was trying to duplicate your model of approaching the move by going there with work. Then again, another pressure I had on me that you didn’t is a mortgage payment due every month. Disappearing to Hollywood to reinvent yourself is a great romantic fantasy, but less so when you have to foreclose on your apartment in Chicago and live on the beach in Los Angeles with your cat because you wanted to be more personally fulfilled.

But, cheesy as it sounds, not getting either of those jobs wound up being two of the best things that ever happened to me because it forced me to call in all bets with everywhere I worked that needed me physically in Chicago. It forced me to be a more active participant in my own future. It also bizarrely prompted one of my newer, less-defined professional relationships to invest in my services as a consultant to support my move. The revelatory thing I found about telling people exactly what you need from them is you discover who’s stringing you along and who’s in your corner. But I think what we’re both talking about is we each needed a higher calling.

Ceda: Parallel to that, we had been shopping our show around to different possible sponsors and also going through our own crash course in filmmaking by constantly reaching out and interviewing producers, actors, and writers in Chicago. We had all this great information but also didn’t realize we were actually doing market research. You texted me on assignment from that Motorcycle Expo in Alabama, “I think I found a way for what we do to be part of something bigger.” At our level of content creators, aspiring writers tend to underestimate production logistics they should really embrace, and people getting paid as crew are desperate to find narrative-based shoots to work on. You hit on this idea of trying to connect people at that level regardless of where we would be physically. And that’s how we started Now What?, our reason for being in Los Angeles and our way to help comedy scenes everywhere.

David: Right. And obviously we don’t want to use this post on The Billfold to shill for our new company, but it made our moving to Los Angeles not just whimsical, but a logical next step. It also makes it all the more audacious, which we’re very aware of. Now What? is us building a bridge to Los Angeles and a selectively crowdsourced channel for ourselves and aspiring writers/actors/video-makers from wherever in the world. We want to collaborate with other people whose work we like and help them the way we’ve helped each other. And we also just want to get everyone’s work seen. By pooling everyone’s stuff together, we’re tapping into their communities, their networks, and hopefully helping their careers. If we can help be guides to the city, the industry, and how it works as we become more acclimated to it, then that’s something valuable we’re giving back. That’s a higher calling.

Us being Midwesterners, though, it doesn’t seem fair to charge people until we have tons of stuff to show for it. So, basically, we want to move to Los Angeles and start a company and not worry about whether it generates any revenue. So the answer to how we will make money is — we won’t. Not from this. Not at the beginning. But I got this consulting gig out of this whole rigamarole, and that’s enough to keep me afloat and pushing on this, plus I’ll be building some online classes for Second City. That’s enough for me. Plus we’re getting $50 to write this series, so I think we’ll be set for life!

What If I Don’t Succeed?

Ceda: You can’t predict the obstacles that life will present you with. I was so cocky about this move because I had a job I could still perform from Los Angeles, I had convinced Jorge of moving with me to the land of sunshine right before the winter of Chicago, and I knew the opportunities I wanted were in Los Angeles. One by one, I crushed each new problem. Need a place? I found an apartment in East Hollywood. You couldn’t find a roommate, so we decided to live together. We had a ton of shit, so I found an awesome moving service.

But four days before we were supposed to drive across the country, Jorge got in a car accident — in the car I just bought three weeks earlier. He’s fine, thankfully, but the car looked like it had been shredded by a giant can opener. Suddenly, the move tripled in cost. That left us with three business days before our move date, which was one day after Thanksgiving. I had already rented out my apartment and we had shipped all our stuff to Los Angeles, but it started to look like it and we would soon be homeless unless we could figure something out fast. It seemed impossible. But once I calmed down, I realized I had people who would help me. And they did. We found a rental. The insurance company worked with me to figure a way to get my car fixed and out to Los Angeles. We were able to have our fried turkey dinners with lots of whiskey.

Obviously, our careers not working out quite the way we’d like them to in a new city isn’t quite the same as being in a car accident. But it reminded me of our tenacity and ability to adapt. Even if Ron Howard will never meet with us or we don’t sell a movie or never make a single cent from this new business, we’ll find ways to figure it out.

David: I guess I’m pooching what would be a touching way to end this with my lower-stakes thoughts on everything, but I don’t think of Los Angeles as being that binary. The last six months I’ve been reassessing my career and trying to re-contextualize myself mentally as a professional, trying to make sense of who I am and where I’m going and what I’m headed towards. I honestly love not knowing where this is taking us, but I trust that when we get there, it will seem wholeheartedly inevitable.

Ceda Xiong and David Wolinsky are newly Los Angeles-based writers and producers and the co-founders of Now What?, an online channel that helps people create funny stuff for the Internet. They are podcasting about L.A,, their careers, and writing on a show called Writers Write, Right? with another writing pair still living in Chicago.

David created Second City Chicago’s Humor Writing for the Internet program, helped The Onion take its local sections online as the Chicago city editor, and is a video producer for E3. Ceda has freelanced for publications such as Venus, McSweeney’s, and Nerve. They live with her boyfriend and their three cats.

Photo: Ron Reiring