What I learned from working on Conan’s Season 2 and my own fears

Actor John Lithgow playfully tossed me a show, boxer Larry Holmes jokingly (I think) threatened to knock me out, and actress Jennifer Tilly might have flirted with me on the phone until she realized I was just an intern and not a segment producer . Memories like this and a sign with my name on the locker room were what I picked up while studying the second season of Late Night with Conan O’Brien. And looking back, I should never have left the show.

Conan retired from late-night TV this week after an astonishing 28-year run, an incredible milestone in every way but especially impressive considering where he started: a talented writer but minimal screen experience. When I started, Late Night aired at 12:30 p.m. and was still in quarterly renewal cycles, which means NBC hadn’t even decided to give Conan (and his team) the stability of an annual commitment. Despite his rawness, two things were clear: (a) Conan is incredibly smart, and (b) they put together a team of new voices willing to take risks and commit to the show’s mission. Sounds like a startup doesn’t it?

So what did I do as part of this group? First and foremost, you research upcoming prominent guests and formulate potentially interesting interview questions. If they were on the show before I’d re-watched previous appearances to jot down stories they’d already told and / or callbacks / run gags that might be revisited. And every now and then I would fact check monologue jokes or run around NYC to get props for celebrities (the vintage denim jacket photoshoot they came out before fame, the only Japanese release of a terrible movie the they wanted to try buried) – You must remember that this was 1994-95 and the consumer internet was still largely in its origins.

My time on Conan meant spending much of my senior year at Vassar off campus in NYC, breaking down with family and friends, or catching early morning and late evening trains to / from Poughkeepsie. My thesis on America’s first national women’s magazine filled the other available hours, especially since the primary research could only be done in the special collection room of our beautiful library. And thanks to a supportive professor, I was able to incorporate the talk show experience into another independent study project on the importance of celebrities in American political history (Davy Crockett, Daniel Boone, Ronald Reagan) that gave me all the credits I needed to graduate needed with the rest of my class.

Several people from my internship cohort got on the show after graduation, but I wasn’t one of them. Late Night was picking up speed and the signs that it might be special spread beyond our small offices in Rockefeller Center. Why didn’t I look to stay? Ego mostly. I thought I was “smarter” than the other newcomers and decided to work in management consulting. But when I reconsider this internal narrative, it was probably also because I was afraid to be 100% myself. If I tried counseling and didn’t make it, I could always tell myself that it was because the job was just a costume I put on, something I did because it paid well and the respect of my colleagues and my family had. Choosing something less important was an excuse and protected my most vulnerable questions: Was I creative? Was i interesting? was i popular?

I left management consulting after the analyst program ended. With more confidence and self-esteem towards a next set of career choices that corrected the identity gap and embraced the idea that there would be no more separation between Hunter the Person and Hunter the Professional. 12 years at the intersection of creativity and consumer tech, followed by starting a venture company with a friend and former colleague to support founders who were on their own missions.

And now in 2021, although I overflow with joy and satisfaction with what I have achieved and what I still have to do, there is still one truth: If I had had more courage, I would have never left Studio 6B in 1995 been there for 26 years (and a few changes of location). Or eventually left the show with my boss, who later became an early producer on Rosie O’Donnells and then on Ellen’s shows (remember, I mentioned that the early Conan team were * very * talented themselves). Or be somewhere else in the mix of media, technology and entertainment.

Is there a lesson? Basically, if you have the chance to join a 6’4 ″ flame haired prodigy on an innovative new project, please take it. Whether it’s a TV show, startup, marriage, or anything else that feels * so right * to you. Even if you are a little scared. Actually, ESPECIALLY if you’re a little scared.


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