RS: You're a prolific freelance writer, contributing to The Awl, Gawker and everywhere in between. What advice do you have for writers trying to find their way as a freelancer?
BOC: I feel like I am still trying to find my own way! And I don't really feel like categorizing anything as advice, because everyone's just figuring it out and we're all on the brink of falling apart at any given moment. Me especially. But! Hmm. Practically speaking, it's incredibly useful to have some kind of steady gig that raises the floor of your monthly income, rather than relying entirely on writing. Whether that's in media or outside of it, doesn't really matter. This is all kind of obvious stuff, maybe. But it's also not the kind of thing I was thinking about in high school or college when I thought to myself, "I want to be a writer." (Ugh.) In terms of writing and reporting, though—just follow your heart! Really! Write about what is interesting to you. Read the New York Times and the Associate Press wires and local blogs, learn about what's going on around you, and when you read something that makes you stop and think and want to learn more, well, maybe there's a story there. Probably there is!
You and Bijan Stephen are typically heralded as the two best-looking/best-dressed men in New York media. Do you guys ever talk about this when you hang out together?
We just try to stay humble.
What's your favorite holiday food item?
Pie. Pie is a food item for all seasons really—or at least it is in my family—but during the holidays it takes on a special significance, for me. Maybe it's because during the rest of the year, my mom or grandmother might decide to bake a pie, and they'll just bake the one pie, but during the holidays there will always be several pies of different flavors.