End of an Error: As Conan O’Brien Wraps Up 28 Years of Late Night, I Was an Idiot to Leave the Show

What I Learned From Working On Conan’s Season #2 and My Own Fears

Actor John Lithgow playfully tossed a show at me, boxer Larry Holmes jokingly (I think) threatened to knock me out and actress Jennifer Tilly might have flirted with me over the phone until she realized I was just an intern and not a Segment Producer. Memories like those, plus a dressing room sign with my name on it, were what I took away from interning on Season Two of Late Night with Conan O’Brien while in college. And looking back, I never should have left the show.

Conan bid farewell to late night TV this week after an amazing 28 year run, an incredible milestone by anyone’s measure, but especially impressive given where he started: a talented writer but minimal on-screen experience. When I joined, Late Night aired at 12:30am and was still on quarterly renewal cycles, meaning that NBC hadn’t yet even decided to give Conan (and his team) the stability of an annual commitment. Despite his rawness two things were clear: (a) Conan is wicked smart and (b) they assembled a team of new voices who were willing to take risks and commit to the mission of the show. Sounds like a startup, no?

So what was I doing as part of this group? Primarily researching upcoming celebrity guests and drafting potentially interesting interview questions. If they’d been on the show before I rewatched the previous appearances to note stories they’d already told and/or callbacks/running gags that could be revisited. And every once in a while I fact-checked monologue jokes or ran across NYC to pick up celebrity-related props (the vintage denim jacket photoshoot they appeared in pre-stardom, the Japan-only release of a terrible movie they’d try to bury) — you have to remember this was 1994–95 and the consumer internet was still largely in its formative stages.

My time on Conan meant that I spent much of my senior year at Vassar off-campus in NYC, crashing with family and friends, or taking early morning and late night trains to/from Poughkeepsie. My senior 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 collections room of our gorgeous library. And thanks to a supportive professor, I was able to spin the talkshow experience into another independent study project on the importance of celebrity in American political history (Davy Crockett, Daniel Boone, Ronald Reagan), which gave me all the credits I needed to graduate with the rest of my class.

Several folks from my intern cohort joined the show after graduation but I was not one of them. Late Night had begun to pick up some momentum and the signs it could be something special started to spill beyond our small Rockefeller Center offices. Why didn’t I look to stay? Ego mostly. I thought I was ‘smarter’ than the other new hires and decided to take a job in management consulting. But if I revisit that internal narrative it was probably also that I was afraid to be 100% myself. If I tried consulting and didn’t achieve 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 had the respect of my peers and family. Picking something less important to me provided an excuse and protected my most vulnerable questions: was I creative? was I interesting? was I liked?

I left management consulting after the analyst program ended. With more confidence and self-awareness steered towards a next set of career choices which corrected the identity gap, embracing the idea there’d no longer be a separation between Hunter the Person and Hunter the Professional. 12 years at the intersection of creativity and consumer tech, followed by starting an venture firm with a friend and former colleague to back founders who were on their own missions.

And now in 2021 despite overflowing with joy and satisfaction on what’s been done and what I still have left to do, there still sits one truth: that if I’d had more guts, I never would have left Studio 6B in 1995. Maybe I would have been there through 26 more years (and a few location changes). Or eventually left the show with my boss, who went on to become an early producer on Rosie O’Donnell’s, and then and Ellen’s, shows (remember, I mentioned the early Conan team was *very* talented in their own right). 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 wonderkid on a cutting edge new project, please take it. Whether it’s a tv show, a startup, a marriage or anything else that feels *so right* for you. Even if you’re a little scared. Actually ESPECIALLY if you’re a little scared.