Lessons from a Life (Long Ago) in Stand-Up Comedy
For a dozen years, I worked in technology during the day and in comedy clubs at night.
My home club was a little joint in the East Village called the Comedy Cellar.
Best club in the world! Still.
Normally I wouldn’t write about it but a book is coming out this month about The Comedy Cellar’s history and I’m thrilled-- and a little nostalgic-- to be in it. (Note: don’t expect to read it for laughs. It’s actually about the challenges of cultivating creative expression during a period that the NY Times described as “The Long and Tortured History of Cancel Culture.”)
I learned a ton doing stand-up, most of which will never add value to corporate life.
But... some of it does… or might… so here are some lessons I learned that might be useful.
1. Don’t Look Up
My stint with show business culminated in the early 00’s when I worked nightly with absolute nobodies like Colin Quinn, Jim Norton, Kevin Hart, Bill Burr, Marc Maron, Jeff Ross, Dave Atell. Yes, I also worked with bigger names in the industry that you’d recognize but-- in retrospect-- never with better people than my nobodies.
Regardless of where we sit in the achievement hierarchy-- or the corporate hierarchy-- we tend to idolize our seniors-- the George Carlins and Robin Williams of the classes above and ahead.
That’s a mistake.
You’re missing the magic to your left and right.
2. Be Authentic
The development arc of the best stand-ups is actually about their path to being their genuine selves on stage. In the non-comedy world, we call that authenticity-- to discover and continuously refine your voice, purpose, mission.
So if anyone has ever told you to “be yourself” before you give a presentation, they’ve guided you right. They probably just left off the part about how it’s a life-long journey to get that right… because you’ll never stop growing… so you’re never actually going to be yourself.
Yep, Walt Whitman had good reason to be smug. You are, in fact, multitudes. And they’re all vulnerable and awkward and sweating inappropriately.
And that’s ok. Join the club. And bring that authentic you to the table at work.
3. Don’t Look Down
Everyone’s afraid that they’re performing without a net. But your worst possible outcome-- your horrific nightmare scenario-- will very quickly become your absolute favorite story to tell.
No one wants to hear about that day when everything went right. Just like no one wants to see your wedding photos.
I learned this because all the big named celebrities would drop by the Cellar for sets. So nobodies like me would regularly follow a Jerry Seinfeld or a Chris Rock. Which is terrifying. Because the house would literally shake with applause when they were introduced.
And you know what? We’d kill.
Not because we were funnier. We clearly were.
We’d kill because celebrities raise audience expectations and when they’re testing new material, it’s near impossible for them to live up to the perfectly funny Jerry you saw on TV.
The lesson here is: be fearless. When you’re holding on to the trapeze and you look down into the darkness, your imagination will signal that there’s no net down below.
You. Are. Not. On. A. Trapeze.
You’re on a jungle gym.
Let go.
Take a walk around the playground.
Come back when you’re ready.
And tell that story like your life depends on it. Everyone will love you for it.
4. Be Kind
There’s one you didn’t expect from a NY stand-up! Regardless of what type of business you’re in, a kind word goes a long way.
It always struck me how supportive comics were to one another. Insult comics especially. Jeff Ross. Lisa Lampanelli. The god of insults himself -- Don Rickles. Notoriously nice people.
Colin Quinn-- who pretends to be “NY hard” on stage-- is the warmest, most welcoming person you’ll ever meet. As a fellow comic, he’d pick your bad set over the audience’s correct assessment of how much you sucked… every time. I’m convinced that if he hadn’t landed in entertainment, he’d be a CEO of a Fortune 100 company. It’d be in Chapter 11 but he’d be the CEO.
My own personal story is super cheesy. A couple of years back, more than a decade after I’d left comedy, a colleague of mine was curious about my stand-up past so she googled me and forwarded an interview with a cast member of Jon Stewart’s Daily Show.
In the article, this cast member-- who went on to have his own show on HBO-- talked about his first time on stage. It was at an open mic night at a club in North Carolina called Charlie Goodnights.
He had always dreamed about doing comedy so he wrote 3 minutes worth of material-- which was perfect because that’s all open mic’ers got: 3 minutes.
So… the emcee introduces him and goes out to get a smoke.
The guy does all 3 minutes of material in about a minute. Devastating results. For the audience and for him. He walks off the stage after that minute… with the emcee mid-cigarette outside.
In the article, he said that he came off stage thinking he’ll never do comedy again.
Enter the headliner that night: a middle eastern dude out of NY. The headliner told him that he saw something special in that minute and that he shouldn’t give up.
And so he stuck with it.
That idiot was me.
He remembered me by name.
When I read the piece I actually cried… a “NY hard” cry.
A kind word goes a long way.
[Ok. Let’s never publish this piece.]
5. Enough with the “Don’t Look this way or that way” theme. Look! Look!
Be curious!
There is nothing more powerful than curiosity. There is no better source for humor or innovation or leadership. Even empathy plays second fiddle here.
Learn to listen. Learn to care.
Ask a million questions.
Be a child. That’s all observational humor is: a child’s perspective on adult life.
And Finally...
Do both our careers a favor and never ask me to tell a joke. In public, in private, ever.
I won’t.
Not because I’ll get a call from HR. I definitely will.
The real reason is because what you expect from me will never be as funny as you imagine it will be.
See -- even a nobody can learn from a Jerry and a Chris.