Why I Never Made It In Comedy

A working theory

Last year, when I first started this Substack, I wrote an introductory post on why I decided to quit pursuing a career in stand-up comedy after fifteen years. It included the following sentence:

I never came anywhere close to my ultimate goal of making a living in comedy (An explanation as to why this happened is something that deserves its own post. A discussion for another day I suppose).

I fully intended to write this post at the time, but I never got around to it (or maybe I was avoiding it). I always found another topic I was more interested in exploring. But then, a couple months ago, a reader posted that original piece to the r/Standup subreddit, and it generated a small flurry of comments. One user asked the below question:

I'm curious to hear why you think it didn't happen after 15 years. You talk about your peers making it to late night and headlining big clubs, but why weren't you moving up with them? Why weren't you opening for them? Was your material different from what was getting popular? Were you not clicking with other comics who were making it?

After reading that, I realized I had never fully explained why I didn’t make it in comedy. Well, I believe the moment has come. It’s time for me to tell you all why I never made it. Ready? Here it is.

I wasn’t funny enough.

That’s it. That’s the answer.

Well, it’s the short answer at least. You could stop reading this essay right now and be fully informed as to why I’m working in an office every weekday instead of headlining comedy clubs every weekend. The long answer, however, is a little more complicated.

The long answer is that I neglected the most important part of finding success in any business or creative scene: relationship building. “It’s all about who you know” is a well-worn cliche, but I’ve learned the hard way that cliches are cliche for a reason. They get repeated so often because they’re uniquely true and useful. The problem is that we mistake their repetition for a lack of vitality and insight and choose to ignore them, often at our own peril.

When I moved to New York in 2012, I was temperamentally averse to networking, both in real life and online. The whole thing just seemed so gross and transactional to me. I saw comics glad-handing each other at shows and complimenting/tagging each other’s jokes on Facebook and Twitter, and I was immediately put off. There used to be a very mean-spirited (but incredibly accurate) Tumblr account called Comedians Complimenting Comedians that perfectly sums up the sort of thing I’m talking about. And no, I was not behind it.

The problem wasn’t with the other comedians though, the problem was with me. In my narrow little worldview, I thought stand-up was supposed to solely be about art and merit, and that trying to network your way into a career was incredibly disingenuous. That all sounds nice and high-minded, but I don’t think my motivations were entirely pure.

Yes, I do believe that stand-up should be about who’s the funniest and most original, but that belief wasn’t the only thing holding me back. I think my aversion to networking was also based in fear. I was worried that if I tried to engage in these transactional relationships to get ahead, nobody would want to transact with me and I would have failed twice. I would have gone against my values and gotten nothing out of it. It’s like that Dostoevsky line “Your worst sin is that you've destroyed and betrayed yourself for nothing.” So, motivated by a mixture of principles and fear, I stayed away from networking and tried to make it on funny alone.

I was relatively funny, but not funny enough to do THAT. So I sat and watched other comedians who were less funny than me get opportunities and perform on shows that they didn’t quite deserve, simply because of who they were friends with. This filled me with a tremendous amount of rage. I remember sitting in the back of many rooms, watching someone bomb their face off, and thinking to myself “They don’t deserve this. That person took MY spot.” While my sense of entitlement was not accurate, my assessment of the comedian usually was. They didn’t deserve that spot and the audience reaction proved that.

But then something interesting happened. Because a comedian (who might have been less funny than me at the time) built relationships and ingratiated themselves in the scene, they got more opportunities for quality stage time and eventually became funnier than me. Years later, I’d watch that same comic generate rolling waves of laughter with their jokes, and it would be painfully obvious that I had been surpassed.

Because I didn’t have any close relationships with other comedians, I was trying to improve by doing open mics, bar shows, late night comedy club spots, and whatever other scraps of stage time I could hustle up for myself. Every rep on stage is important, but not all reps are created equal. You can’t always get a good read on material doing the spots I was doing, and that negatively impacted my artistic growth. These other comics were performing in front of real audiences on a regular basis, and it was like they hit one of those accelerator ramps in Mario Kart. I, meanwhile, had run off the track and was spinning around in circles.

I also had a hard time relating to other comedians, mostly because our lifestyles were so different. I held down a regular office job, and most of them worked temp jobs or walked dogs for a (very meager) living. I know myself, and there’s no way I could have lived like that. I needed the stability of a regular paycheck and health insurance if I was going to make a real go at comedy. But this set me at odds with my peers. I couldn’t stay out at a bar in Bushwick until 2am on a Tuesday, even if I wanted to, because I had to wake up early for work the next day.

My job impacted my ability to relate in other ways as well. For my first three years in New York, I worked for a company that required me to wear business casual clothes every day. Since I didn’t have time to go home and change between work and open mics, I would show up to these bars and comedy clubs dressed like an extra from Office Space while everyone else was wearing jeans and comic book t-shirts. I can’t pretend that didn’t impact the way I was perceived, and the way I perceived others as well. “I’m not like these people,” I thought, and I’m sure they felt the same way about me.

With the benefit of hindsight and the personal growth that comes with maturity, I now know what I should have done differently. I should have gotten over myself. Networking was not, and is not, the painful scourge I made it out to be. It’s a necessary part of building a career. I was just too young and inexperienced to realize it at the time, and I didn’t want to listen to anyone who told me otherwise, no matter who they were.

The week before I moved to New York, I opened for Neal Brennan at my hometown club in Washington, DC. I asked him what advice he had, and he said “Worry about winning over your peers before winning over the audience.” I nodded along but ultimately chose to ignore him because it wasn’t what I wanted to hear. Looking back on it now, I feel like Matthew McConaughey stuck in the bookshelf in Interstellar, screaming at my younger self to pay attention.

There’s a way you can network authentically, without it being phony or hollow. You can show up someplace, be friendly, introduce yourself, and talk to people without any expectation of reciprocity. Just being around, making yourself known, and getting to know others can often be enough. When the time comes and there’s an opportunity someone can assist you with, you’ll have a genuine relationship in place that makes asking for help less awkward. But you have to lead with authenticity and genuine interest in the other person. If you’re always operating with the ulterior motive of extracting professional gain from a personal relationship, people will eventually sniff that out. It’s also a very cold and unsatisfying way to move through the world. It pays no dividends either way.

The whole thing was way easier than I was making it out to be. I should have just gone places without any expectations, talked to people and been myself. Most importantly, I should have been confident that “myself” was enough. I didn’t have to put on an act or engage in some kind of Machiavellian scheme to try and get on The Tonight Show. I just had to be the guy I naturally was and accept whatever outcome that generated. Maybe then I would have built genuine relationships with my peers, bridged the differences in our lifestyles, gotten a lot funnier, and enjoyed myself much more in the process.

I also should have brought jeans and a t-shirt to change into after I left work. Nobody wants to laugh at a guy wearing pressed khakis on stage. If Neal Brennan had told me that, I probably would have listened.