I pursued standup comedy for 10 years in New York City. It didn’t work out, in the sense that I am now writing this newsletter instead of being someone who a Boomer parent told you they saw on Netflix.
But it very much worked out as an education about people, group dynamics, and how the world works. There are many lessons from this quasi-career that I’d like to impart on my two daughters. Here are a few:
Relationships can be transactional. Don’t treat them that way
When I was trying to climb the ranks in the mid- to late-2010s, the NYC comedy ladder was a giant supply and demand problem. There were simply too many comics for the amount of stage time available. People like me (and people way worse than me) were theoretically competing for the same stages as Chris Rock and Amy Schumer.
I was once running a show in Greenwich Village when another comic cornered me on the street. This was someone who I had “barked”1 for in previous years, but never treated me particularly well. Sometimes when you’re the low man on the totem pole responsible for bringing in audience, the comic running the show treats you as a valued member of the team. Other times, the implied hierarchy is made abundantly clear and you are made to feel less than.
This comic pretended as if we were old friends, a likely sign that something was about to be extracted from me.
Sure enough, this comic was auditioning for JFL (a major showcase that used to really make careers), and not so much asked, but demanded that I provide stage time that very night, implying that they would ideally like to bump the next comic on the lineup. The show was already overbooked, we were running late, and I knew that giving this comic stage time would come at the expense of my own. I felt that there was nothing I owed this person given that this was the first time they had really treated me as an equal, and that the favor would never be reciprocated. I declined, and offered stage time in the future.
This comic wouldn’t take no for an answer and proceeded to make a scene. I relented, weighing the newfound consequences. This person had more power than I did in the standup world, and it was not worth making an enemy.
I think about this transaction fairly regularly. It embodied everything I hated about the interpersonal side of standup, but there was also an element that I respected. This comic was nakedly transactional, and knew what it took to succeed. Many standups acted as if they were your friend in the short- to medium-term while hoping to extract something from you—stage time, associative status, a specific opportunity—only to drop you and move onto the next target the second their goal was satisfied.
The fact that this behavior was commonplace was depressing, but also understandable given the cutthroat environment and the scarcity mindset incentives the standup scene encouraged.
The theologist Martin Buber distinguishes between two types of relationships; I-It and I-Thou. While I-It relationships are purely transactional (think customer service, grocery checkout), I-Thou relationships are fuller recognitions of humanity. Ones predicated on genuine connection and recognizing someone beyond what they have to offer you.
We generally interact with strangers and colleagues in an I-It fashion and reserve our I-Thou for close friends, family, and relationships. But it’s possible to treat mundane or strictly professional relationships as I-Thou. It’s something I am increasingly striving to do, and something I’d like to emphasize to my daughters.
Hard work is great but you also need a strategy
When you first start out in standup you have to do open mics, which is basically people in their early 20s voluntarily signing up for mild torture2. While open mics are undoubtedly terrible, they’re a very necessary weed-out mechanism. If you are able to handle the heavy and oftentimes angry silence of these rooms, shows with 5 audience members who actually want to be there feel like a privilege.
In the open mic scene there was a certain subculture that oriented itself entirely around volume, equating success with reaching Malcolm Gladwell’s 10,000 hours as quickly as possible. On most days in New York City you could hit your first open mic at 5 and keep going until midnight. In the height of my own time as an open micer I’d usually do 2-3 per night, occasionally 4. But if you game the sign up lists, inter-borough logistics, and don’t care at all about supporting fellow comics, you could easily hit 5-6 stages.
I remember some open micers bragging about getting on stage 40+ times per week. They’d map out routes and sign ups with an obsessiveness reminiscent of Elon Musk trying to destroy the career of a lifetime public servant. It was all very impressive in its own way.
Then two years later I’d look around and realize that they were no longer in comedy.
I gradually noticed that the comics who would work very hard but also had some sort of larger plan were the ones that typically made it to the next step.
If a particular open mic was a complete waste of time, they may ditch it the following week and instead spend that time writing or hanging around a club they wanted to break into. They clearly took a step back quite often to deliberately map out where they wanted to go, and how it made sense to get there. Figuring out how exactly you want to play the game while being equally immersed in whatever the game requires seems to be essential, no matter what line of work you’re in.
Your world is not be THE world
One of the first road shows I ever did was just outside Binghamton, New York. I was in my early 20s, and up to that point had strictly done shows in New York City, often to crowds that aligned with my worldview and life experience.
I don’t quite remember what terrible joke I opened my set with, but I’ll never forget the reaction. There’s a rejection-flavored silence that accompanies bombing, but this wasn’t that. It was more like intense confusion.
It was ~200 people of ages and backgrounds completely different than mine, not having any idea what to do with the 24 year-old kid in a flat-brimmed hat talking like he knew anything about…well, anything.
I could sense I had one more joke until their confusion turned to anger for wasting their hard earned money and time. I gathered myself, did my best joke at the time to save myself (about totinos pizza rolls), and barely survived the rest of the set.
For the vast majority of standup comics, building a career in comedy means performing to all sorts of different groups of people that you’d probably never interact with otherwise; with stress on the group part. You’ll do coffee shops in a chic part of the city where the NPR set nods instead of laughs, hostels with audiences who barely speak English, rooms with all sorts of different ethnic/racial/socio-economic makeups that may have completely different cultural dynamics than you’re accustomed to, rooms in rural areas where a joke about Uber Eats will hit with a resounding thud, rooms where everyone is over 65 and can barely hear, and everything in between.
Doing all sorts of rooms for many years, I slowly learned that my particular understanding of the world contained some things that were universal to the human experience, and other things that were completely foreign and borderline insulting to a decent chunk of the population.
As a standup, it is your job to get people of vastly different life experiences all on the same page. It’s an enormous task given the polarized realities of our day and age, but it keeps you plugged into the reality of which parts of your own life experience are, well, real.
A great standup comic can connect with literally any type of person on a deeply human level. Even if what they’re saying is not something that they would be naturally inclined to agree with. This is probably something that we could all work on.
Weekly News and Notes
While we’re on the subject of jokes, subscribers of this newsletter may be interested in the “Dad Says Jokes” for some great weekly Dad Jokes.
The Knicks are in the NBA finals. I am writing this before Game 1. I’m a Knicks fan but given parenting chaos and responsibilities, almost never have time to watch sports at all. I’m probably going to write something at some point about how watching sports changes when you’re dealing with newborn/early childhood chaos. If you’re interested in sharing your perspective on this or simply want to commiserate, reply to this email or use our contact form.
As always, like, subscribe, and share. Our growth happens because great subscribers like you are sharing these articles within their own personal close friendships and networks. If you enjoyed this, sending it to one friend who you think would like it makes a big difference. And if you haven’t already:
1 The act of standing on a street corner/outside a venue to get people into a show. Typically a way for newer comics to get stage time.
2 Note: I found the quality of open mics to vary wildly by city. In New York, they were terrible, as it was almost always comics performing to other comics. In cities with not as big a standup scene they were sometimes fantastic, because genuine audience members would show.)
The family trip your kids will still talk about at 30
Intrepid just launched eight new Premium Family trips across Borneo, Morocco, India, Costa Rica and more — small groups, experienced local guides, elevated stays, and immersive cultural experiences designed specifically for families. All the logistics sorted so you can actually enjoy it.