15 Years Since Day 1 At 30 Rock

On Monday, May 20, 2002— exactly 15 years ago— I took the Long Island Railroad into Manhattan to my first day of my summer internship at Late Night with Conan O’Brien. My Junior year had just ended at CW Post College, I was 21 years old, and I was running late. Not a great start, but that's probably the smallest thing I'd go back and do differently.

I like to keep track of time and I love math. There was a time in my 20’s when I thought about going back to college to become a math teacher. I love numbers and systems and patterns and lists. I get excited about buying a new calendar the way my wife does about buying anything she can wear. In fact, the reason I know that first day at Conan was Monday, May 20th is that I still have my 2002 date book that says so. (It was a Gary Larson “Far Side” themed calendar, by the way.) 

15 years ago. Fifteen

How did this happen? How did I get here?

Let’s crunch some numbers: When I started that internship in 2002, Conan had been on the air for almost 10 years. Conan himself was 39. I’m now 36. This coming fall, I’ll have been performing entry-level standup comedy almost daily for three and a half years. It takes ten years to get good according to the experts…

When I run these values through my Regret Algorithm I always get the same instantaneous, demoralizing result: There’s no way you can make it in this business. You missed your shot. You’re too far behind now. 

How did I get here??

I majored in TV production and Conan was my second internship. The first was at VH1 in the summer of 2000 at 1515 Broadway in Times Square. A few times a week I’d walk past a restaurant called Hamburger Harry’s (now it’s a Planet Hollywood or Buca Di Beppo’s or some other enormous chain restaurant) and I’d see a sign in the window that said “Gladys’ Comedy Room - Open Mic Every Monday” or something like that. I had a secret desire to be a standup comedian since I was a kid and that sign felt like an invitation. Long story short, I “performed” (bombed) on that open mic twice or so, did the same a couple more times at campus open mics that following semester, and then, as a fragile, perfectionist 19 year old who couldn’t process failure, didn’t attempt standup again until I was in my thirties.

When the Conan summer job came along I’d already reinvented myself. I was in a band now. A silly band. I figured since I couldn’t be funny alone onstage, I’d do it with songs and backup from other people. We had lyrics about partying, girls, and Chinese food. I was one of the rappers of the group and I also shouted punk lyrics and played some sloppy guitar. I liked to think I had funny in-between song banter. I bought a velour suit by Enycé that I wore on stage. I was a cartoon character who convinced himself that he was a musician to avoid the pain of being a new comic.

Three days a week I’d go into my internship at Conan. According to my Far Side calendar, I called out sick a few times. I left early a couple other times. Clearly it wasn’t my highest priority. How could it be? I was in a band. I had a new girlfriend. My drinking was ramping up. The 30 Rock experience was cool and all, and of course I did the tasks I was assigned, but I didn't do much more than the bare minimum. I had rehearsals to be at and gigs to promote.

What. A. Punkass.

What an ungrateful, arrogant little prick.

What a crappy attitude.

If it were possible to flip the pages of the last fifteen years' worth of date books backward and travel through time, I’d have quite a few things to tell 21 year old me, but for now I’ll keep it to one message:

Be honest with yourself! Get real about what you want in this life. Admit the truth and just say you want to be a standup comedian. Tell someone. Say it in the mirror. Write it on a post-it note and keep it in your wallet. Whatever you do, don’t give up right away because it’s too hard. Don’t suppress your main aspiration by convincing yourself that getting onstage as an idiot rapper is close enough to what you really want. Bottom line: Don’t lie to yourself. Don’t live in denial. Denial is powerful and easy and comfortable. And a total waste of time. Before you know it, 15 years will go by and you’ll think “How did I get here?”

Try open mics again. Get comfortable knowing that you’ll suck at it for a long time. Power through the failure. Don’t overthink it. Do it 50 times before you decide whether you’re a comic or a musician. Hell, be in a band AND do comedy! Trust that there is creative abundance and you don’t have to choose one or the other. You will be a pretty crappy musician, so why not be a crappy comic at the same time? Perfect is the enemy of good. And you gotta be bad before you can get good. Plus, if you stay in the band, you’ll grow huge balls on stage. You’ll learn about crowd dynamics and how to be silly and have fun on a mic. You’ll get good at promotion and communications and many of the business aspects to being a performance artist. You’ll make friends for life. Plus you’ll know your way around audio and lighting equipment of all types. Yeah, that’s the answer: Stay in the band, be silly, get weird, but also keep doing standup. Allow yourself to bomb. 

Same with when you graduate: Yes, you will need to get a “real” job. But just because you get a job working behind the camera, doesn’t mean you need to hide your desire to be in front of it. You can do both. You can continue doing open mics while keeping a day job. Oh, and one more thing: This will all be much easier if you don’t drink so much. But that’s another speech for another time.

I wish I knew the opportunity I had back then as an intern at Conan. I wish I would've properly honored the chance I was given by my good friend who got me the position in the first place. I wish I recognized that many of the people who worked on the show all probably started at open mics. When I was there, the writing staff consisted of comedy legends like Robert Smigel, Mike Sweeney, and Brian Stack. Also Jon Glaser, Kevin Dorff, Andy Blitz, Allison Silverman, and Andy Secunda— accomplished comedians who have the kind of careers I hope to have some day. Maybe if I would’ve put my best foot forward and took it a little more seriously, I could’ve learned something from them. All I would’ve needed to hear is someone to say “yeah, no one is good at standup at first.” On an anniversary like this, it’s really hard to not look back that far and see it as an opportunity squandered and the beginning of a lot of lost time. 

Luckily, I’ve got lots of tools these days. I know it’s a waste of energy to wonder what my life would be like now if I stuck with standup from the start. There are lots of great clichés I use regularly to remind myself of that. “Everything is as it should be or else it would be different” or “Abandon all hope for a better past,” for example. 

In order to keep my sanity and to not fall too far into the pit of regret, I keep it simple. The last 15 years weren’t a waste. They were research. In order to create comedy, we need material. I may not have been honing my standup in my twenties, but I definitely cooked up some stuff to talk about.

Hopefully, one day, I’ll get to perform standup on Conan and it goes well. My last joke gets a big laugh and the band kicks in. Conan says my name one more time, goodnight to the audience, and after the cameras cut away to credits, I get yanked off my mark by stage manager Steve Hollander. Maybe on my way backstage I’ll get a quick moment alone to wonder, “How did this happen? How did I get here?”