In the latest installment of our Community Profiles series, we spoke with long-time gun Kelly Caldwell. A former journalist, award-winning essayist, and current writing instructor and Associate Dean at Gotham Writers’ Workshop, Kelly was kind enough to speak with us about her work and her unconventional career trajectory.
Let’s do broad strokes first. How did you get started as a professional writer?
I always thought I was going to have a career in newspapers. Back in 1995, I landed a really exciting internship at New York Newsday. As it turns out, this was right when they were shutting the paper down.
Actually, it worked out for me. I came in as an intern, but suddenly I was the only reporter at the Features desk. All the veteran reporters took their buyouts, so I got an opportunity to do a lot more than I ever would have in a regular internship. Plus I got to see how an established publication was able to go about expanding its presence while really re-branding itself. I learned a lot there.
From there, I started freelancing. I found out pretty quickly that I was up against a lot of great reporters who were working in the same markets as I was. These were established reporters with Pulitzers on their desks. Looking back on it, it seems kind of silly that I ever thought I could compete with that, but I made it work somehow. I guess I was working with a pretty healthy dose of denial in those days.
So what does it take to make it work in a market like that?
I can’t really overstate the importance of learning how to be efficient in choosing and attracting projects. In the early days, I wasted too much time pitching stories that I wasn’t actually interested in writing. This is something that’s different for everyone, but it’s something every freelancer should — and in my experience, can — improve on. Figure out what you really want to be doing and figure out what you’re really good at. Hopefully, the two will intersect. If you don’t focus on building a niche for yourself, you’re going to end up pitching a lot of things you won’t get because you’re not really qualified. That’s a lot of wasted time. Likewise, if you don’t brand yourself correctly, you can also end up attracting projects that you don’t want.
Oh, and one more: cultivate relationships with editors. That’s the best way to get steady, reliable work that I can think of. I was lucky to have great editors at New York Newsday. When they left, they took me along with them.
So when did the jump into creative writing happen?
That’s an interesting story. A friend at People told me that I should be doing more on spec, so I started trying to do that. At the same time, my cousin pointed me to a feature in House Beautiful called “Thoughts of Home.” She thought I’d be great for it, but I wasn’t so sure. It was a personal essay feature and not at all my normal wheelhouse, but I decided to give it a shot. I actually called up the editor — which is completely unheard of now — and she said she’d read it. I wrote the piece on spec and sent it over, not really expecting much to come of it. But it got picked up, which was a huge surprise. Even more surprising was seeing it get picked up as a Notable Essay in Best American Essays 2001 and then in an anthology called If These Walls Could Talk: Thoughts of Home.
Sounds like you wrote an amazing essay. Why was its success so surprising?
Because it wasn’t reporting. It was about me. It was a personal essay and didn’t include any news. It was slower and more personal with a lot of description and reflection. I never really saw myself as having any aptitude for that. When I was in grad school at Columbia, a professor told me that I’d be great at creative writing. I didn’t believe him at the time.
And now you teach personal essay writing. You’re an Associate Dean, even.
I know! Funny how that works out. But it’s really not that different from working on a newspaper. No two days at Gotham are the same. Something always catches fire. For example, I’m in the process of finding judges for 700+ entries into a writing contest. I’m also at work on a memoir!