What I Learned From “Failing” At Comedy

When your dreams don't come true, there are unexpected benefits

I was talking to my dad after I published my “Do I Miss Stand Up?” essay a couple weeks ago, and he brought up a really good point.  It was a point I already understood on a basic level, but sometimes you need a parent (even when you’re almost 40 years old) to help bring something into sharper focus.  

He thought that I was looking at my comedy career from the wrong perspective.  Sure, I didn’t make it to the level that I wanted, but I got a lot further and stayed with it far longer than most people would.  Because of that, I had great experiences and learned a lot that I can apply to my life now.  It’s not about what I didn’t do or achieve, it’s about how I take what I learned and use it going forward.

He’s right.  I do know that comedy has provided me with a lot of great benefits, but I don’t focus on them the way I should, especially in this Substack.  I don’t talk enough about all of the fantastic experiences I had.  At my home club in Washington DC, I got to open for comics like John Mulaney, Nate Bargatze and Amy Schumer in the early 2010s, way before they became household names.  I’ve written about the terrible New York bar shows I used to do all the time, but I never mention the nights where someone like Bill Burr or Louis CK would show up to work on new jokes, jokes I’d eventually see them do in their SNL monologues.  I never talk about the time I got to headline Caroline’s On Broadway for a night, just a couple years before it closed.  I never talk about the small shows I did that went so well, I walked out feeling like I was floating on air.

And I definitely don’t talk enough about all of the intangible personal benefits that came from comedy.  I’ve briefly touched on them in previous posts, but I don’t think I’ve quite conveyed how central they’ve become to my life and how they continue to benefit me to this day.  So, in the spirit of having a positive perspective, let’s pretend this Substack is 2010s-era Buzzfeed and create a good old fashioned listicle.   Without further ado, here are:

7 Unexpected Benefits That Came From “Failing” At Comedy

1. An Insane Work Capacity

You know how some athletes train by sprinting with those tiny little parachutes attached to them, so that when they eventually get in the game they can run faster?  That’s what my life is like now that I’m no longer doing stand-up.  

Comedy used to demand so much of my time and energy, and I had to manage a regular day job on top of it.  Now, without comedy, my day-to-day workload feels ridiculously simple.  I’ll get some big assignment or have to deal with some fire drill at work, something I see other coworkers stressing over, and I’m practically unfazed.  “Wait,” I think, “I have to do this work, but I don’t have to take the L train to Brooklyn afterwards to do a shitty open mic?  What’s the problem?”  Because of the daily workload I became accustomed to through stand-up, I can have a brutal day at the office and still feel like I’m able to take on more when I get out.  I think this will really start to pay dividends once my wife and I have children.

2. Extreme Tolerance For Failure

Mike Birbiglia once made a great point about the personal egoic risk that comedians take every time they get on stage.  When an actor or a musician fails, they can rationalize it as “The audience didn’t like the movie” or “The audience didn’t like the song.”  When a comedian fails, they can only think, “Oh, I guess the audience didn’t like me.”  

I have no problem with public speaking or giving presentations at work, simply because of what I’ve been through with stand-up.  What’s the worst that could happen?  I’ve had experiences on stage that would make the most seasoned executives crumble and drop into the fetal position.  I can handle a few PowerPoint slides.  They don’t even need to have punchlines.

Say I go to a party with friends, or a networking event for work, and I have an awkward interaction with someone.  So?  Who cares?  When you’ve had 200 people stare at you in complete silence when you’re supposed to be making them laugh, something going wrong with one person does not bother you.

This tolerance for failure also makes me more likely to take risks.  I find myself more willing to speak up at work, volunteering for assignments and sharing ideas that I have.  When you do this in an office environment, it projects an image of being invested in the job, which brightens your career (read: financial) prospects.  But eliminating that fear of speaking up is half the battle.  The thick skin I developed through comedy has allowed me to do that.

3. The Ability To Form Good Habits

There are certain things that you simply must do if you want to be a successful comedian.  You must write all the time.  You must get out of the house and get on stage on a daily basis.  You must watch tapes of yourself and provide honest critiques of your own performance.  None of this comes naturally.  These are all actions you have to force yourself to take.  Through comedy, I learned how to make myself complete tasks I didn’t necessarily want to do at the time, all because they were in service of a larger goal.

This paid dividends in my life outside of comedy even before I quit performing stand-up.  It’s helped me stay in relatively good shape as I’ve approached middle age.  I eat right and exercise regularly, all because comedy taught me how to build good habits.  I used to read obsessively as a kid, but moved away from it as I got older.  I’m now a regular reader again.  This started as a way to broaden my perspective and sharpen my stand-up, but now it’s something I do just for fun.  Comedy has shown me that good habits can compound over time and spill over into other areas of your life. 

I don’t think I’d be as locked in with these habits if I hadn’t had a practice run with stand-up first.  In fact, beyond building good habits, stand-up has provided me with an overall sense of…

4. Discipline  

Ultimately, discipline is the denial of an immediate pleasure in service of a future one.  It would feel good to stay in bed now, but you’ll feel even better later if you wake up and go work out instead.  It would feel good to lay on the couch instead of cleaning up your apartment now, but you’ll regret it in a couple days when the mess is twice as large and takes longer to clean up.  It would feel good to put off that assignment at work now, but you’ll be stressed out in a couple days when it’s due and you haven’t even started yet.

By building good habits, I deal with a lot of small annoyances in the short term to avoid larger problems down the line.  Sometimes I think the key to success in adult life is just making yourself do all the dumb little tasks that you don’t want to do and trying to have a positive attitude while doing them.  I feel like I have that skill, and that’s a direct benefit of the discipline I cultivated through stand-up.

5. Attention To Detail

When it comes to comedy, every word (every syllable even) matters in a joke.  There’s no detail that you can brush off, because it might be the one piece that makes the whole thing take off or crumble spectacularly.  Because of comedy, I have an incredibly high level of attention to detail (My wife calls it OCD, but whatever it is, it gets the dishes done after dinner).  I keep things neat and organized around the house and at my desk at work.  I try to be precise in my language, both written and verbal.  I try not to let the little things slide, because I know they’ll matter eventually.  When I watched Carmy set that table during the Season 3 premiere of The Bear, all I could think was “I get it.”  

6. Humility

Do you have any pretensions about your personal levels of intelligence, humor, or likability?  Well, stand-up will beat that right out of you.  When a comedian gets on stage for the first time, they do so because they think people will enjoy hearing what they have to say.  More often than not, they are totally wrong.  But by being knocked down and having your self-image shattered, you’re able to do two things.  One, you can build yourself back up into someone better and more honest.  Two, you start to carry a healthy sense of skepticism about your own opinion of yourself.  Struggling in stand-up has forced me to stop and ask, “Is what I think actually true, or is there something I’m missing here?”  In other words, you’re more likely to admit that you’re wrong.  You’re more likely to admit this to others, and perhaps most importantly, you’re more likely to admit this to yourself.

7. Self-Awareness

When I got on stage for the final time last December, I told a bunch of jokes I had never told before.  I talked about the ways stand-up has impacted my life, both positively and negatively.  The joke that got the biggest laugh was “Trying to be a better comedian has accidentally made me a better husband.  Because whatever an audience doesn’t like about you, your wife really doesn’t like about you.”

Stand-up forced me to reckon with my personal faults, although kind of by accident.  Like Ralph Macchio doing chores for Mr. Miyagi in The Karate Kid, I was learning something valuable without realizing I was learning it.  

Cultivating the skills I needed as a comedian (Being observant, asking questions, probing and going deeper to find something resembling honesty) had the unintended side effect of making me a better overall person.  I was trying to use these skills to write jokes about how annoyed I got when people said “Happy Friday” at work, or whatever other nonsense I thought was funny, and instead it bounced back on me and caused me to confront my own shortcomings.  I saw where I was lacking, which led to me making efforts to improve myself.

Because of comedy, I’ve become more patient, more considerate, less arrogant, a clearer communicator, more disciplined, more open to experiences, more social, less closed off, and just an overall better and more useful person.  By no means do I have myself or things completely figured out, but I’m much farther along than I would be if I had never pursued comedy.

You might notice that I put the word “Failing” in quotes when I titled this essay. I did that to highlight my attempt to follow my dad’s advice and shift my perspective on my stand-up career.  Sure, I never got to perform on The Tonight Show or at The Comedy Cellar, but that doesn’t mean the venture was a failure.  I earned skills and acquired lessons that will become invaluable for me moving forward.  I won’t know the true impact of these skills and lessons until many years from now, when the perspective granted by time makes things more clear.  Who knows, maybe one day, if I’m lucky, I’ll look back on my “failed” comedy career and think it was the best thing that ever happened to me.