Stand-Up Comedians Make Me Better at Writing (and Living): On Failing Well and Laughing a Lot  – Christ and Pop Culture

I want to talk about comedy, but first, I need to talk about boxing. One of the greatest fighters of all time described his process in the ring like this: 

You have to be a relentless, ruthless person. You can slap me night after night after night. I’m going to keep coming back. And when I get you in the corner, I’m going to destroy you. There’s a kill instinct that a good fighter has. You know you have the opponent in trouble. They’re really getting into this, and now you’re going to pour it on… It’s totally war.

Stand-up comedy, like boxing, is a brutal endeavor. You are up there, alone, with a feedback loop nearly as instantaneous as getting punched in the jaw. If you get the laugh, you score a punch. If you hear crickets, you better pull yourself up from the mat quick, or it’ll be TKO.

Sound too dramatic? Well, that quote about boxing wasn’t about boxing. It was Jerry Seinfeld talking about his craft. The only words I changed were fighter and opponent. He actually said “comedian” and “audience.” Now, unlike Mike Tyson or Muhammad Ali, when a comedian “kills” on stage, it’s great news for everyone involved, even the “opponent.”

Comedians consistently use this kind of intense vocabulary to describe what they do. When they do well, they kill. When they fail, they bomb. Why are the stakes seemingly so high? Because in stand-up comedy, more than most other art forms, your work is critiqued live, and loud.

Many (most?) Christians have a weak theology of failure and regret. Our modern expression of the faith has been so utterly saturated by a Romans 8:28 mentality that we think it is unchristian to have regrets. Hogwash. Some of the best creators among us are the ones who fail the most. They’re called stand-up comedians. 

As I’ve dipped my toe in the water of this whole writing thing, I’ve gone through a journey of self-doubt. The stages I walked through mirror much of life’s realities. And they both can be improved by observing the comic’s craft. Looking more closely at the art form of comedy, I realized that there is even more to learn than just how to fail well.

Here’s how my writing and my life have improved by watching comedy.

You Have to Start (and Fail) Somewhere

Stand-up comedians are some of the grittiest people on earth. A common mantra among them is that “it takes ten years to make a comedian.” Only the toughest survive. Usually, that also means they’re the funniest. But they didn’t start like that. 

Here are a few real-world examples from some household names:

• Eddie Murphy skipped school and took the train to Jersey for gigs at 1:00 in the morning
• Robin Williams worked as a bartender of a comedy club until he could work his way up to the stage
• Though Sarah Silverman hit it big with SNL at the age of twenty-two, she’d been telling jokes on stage since she was fifteen. And it was getting fired from SNL that she credits for her ultimate success.
• Jerry Seinfeld went eleven years between landing his first gig and launching an hour-long special
• Jim Gaffigan had to take Improv classes to get over a fear of public speaking

The list goes on.

One of my favorite interviewers of comedians is Jesse David Fox on Good One: A Podcast About Jokes. In every episode, he asks “What is your best story of when you bombed on stage?” Comedians always have an answer. 

Comedians show us what it is like to inundate your career with radical candor. The best are the ones who adapt in response. The same is true of writing.

I’ve been publishing one essay a month (ish) for about two years now, and I’m not that great. But I’ve learned so much. And I know that my last four articles are far better than my first four. If I continue to write one essay a month every year for the next five years, I will have written eighty-four articles. I will have bombed. A lot. But comedy tells me that that’s a good thing. And it’s probably a good thing for the rest of life, too. 

When I was nineteen, I hated college. I never really thought I’d like it, and unfortunately, I was right. I found some friends, I made some memories, and I struggled profoundly with mental health. So, I had the grand idea of hopping on a plane and flying to England for a year-long ministry internship. 

Unfortunately, emotional baggage flies for free. I arrived and the mental health stuff was, predictably, far worse. A year-long internship turned into a month-long internship as I came home ashamed, licking my wounds. 

But I am better as a result. Here’s the thing: I do regret having gone to England. And I appreciate how it formed me. I don’t have to deny that it was a mistake to also celebrate God’s redemption of it. That season of rebuilding taught me to lean into the Lord and trust in good friends. It also taught me how to filter criticism, much like comedians do.

Hecklers Should (Mostly) Be Welcome

James Acaster is my favorite comedian right now. Acaster almost quit comedy because he hated his audiences so much. They wouldn’t laugh at the right moments. They would disrupt his set with commotion, distraction, and heckling. When they heckled, Acaster felt obligated to respond. 

But, despite his quick wit, he absolutely hated working with his audiences. After a good amount of therapy and some introspection, he realized that there were only certain things within his control. He developed a new set, and went on his “Hecklers Welcome” tour. The point of this tour was that people could heckle whenever and however they want.

The taping of it (available on HBO) features him in a boxing ring-like stage, surrounded by his audience. Just a man and his greatest enemy, coming to terms with each other’s existence. The set is a work of very weird and fun art. And at the end, Acaster reveals such an important truth for comedy, writing, life, you name it:

The audiences acted exactly the same as they always did. It didn’t matter if he gave them permission to heckle or not. Some people would always disrupt. Most wouldn’t. Acaster had no control over that. All he could control was his response to it.

When I returned from England, tail between my legs, I heard the most painful critique of my writing that I’ve ever received. As I began my stint abroad, it was the first time I’d ever blogged (in order to keep people attuned to how awesome my life was. It worked out great). When I returned, I wrote an honest piece about how I felt, why I returned, and what was next. 

A pastoral figure in my life read my blog and then said to my friend a statement I’ll never forget: 

“Many words cover a multitude of sins.”

I didn’t write anything else for nearly ten years. 

But, thanks to an understanding of the creative process and my own psyche, I came to realize that perhaps this pastor didn’t have it quite right. Maybe what could actually be said is that many witty lines cover a multitude of ignorance. Or at least, that just because you say something in a clever way, it doesn’t mean you’re right. 

So in 2024, I started a Substack. It was read by nine people (Shoutout to my wife for clicking on it nine times, I assume). 

Praise God for that failure in 2015. It made me more resilient, and helped me see that I don’t need to fear criticism, because I’ll get it regardless. 

Now, my little rant about a criticism that I had to learn to reject does not negate another important truth:

The Audience Is (Almost) Always Right

You can tell a lot about a comedian by observing how they view their audience. For someone like John Mulaney, the audience dictates what is funny. If he hears a pin drop after a joke, he knows he’s got to scrap it or at least give the joke a major face-lift. 

With my writing, it can be easy to blame the lack of feedback on the algorithm, lazy readers, or uninterested subscribers. “If they’d only just click on it, it would change their world!” Or maybe “Well, it didn’t change their world because they’re so addicted to short-form content, a twenty-minute read was too much for them. But I’m not changing.” 

Friends, that is a rough way to write. And an even rougher way to live. I need to have the guts to admit that my writing might not be getting noticed because I’m not that good… yet. So what? I keep writing. And in life, I listen to those around me. I take in feedback, and of course I filter it. But I listen. Then I look in the mirror and take it to the Lord. Maybe they’re right. Maybe there are some healthy ways I could adjust. 

Even when we do have an audience in mind, we don’t really seek to “please” others. But we do set out to make the best thing we can. To do that, we must never stop improving.

The Comedian Never (Really) Stops Refining

When I hit publish, it’s like I’m standing outside a comedy club handing out flyers. While you’re there, I will hear in the audience what you find funny (or good, or thoughtful, or…), what I should refine, and what I need to let die entirely. 

Comedians are some of our greatest communicators because they are some of our best listeners. Every week, comedians wait their turn at the local comedy club in order to try out material. When they fail, there is purpose behind it. They are always seeking to refine their work. If a joke doesn’t work, it could be because it’s not funny or relatable. But it could also be that it didn’t make sense, or felt clunky, or fell flat because of its context.

Even though I only publish once a month and this “craft,” if I get to call it that yet, is just one part of my life, I keep a note on my phone with new ideas. I have learned that when I think of an edit, I have about five minutes until it leaves my brain entirely. 

My writing benefits from a continual audit of how I’m doing. But my soul’s formation works similarly. I need consistent check-ins to identify areas of growth and areas of need in my own spiritual journey. This need not feel legalistic. I just want to walk with Jesus and sometimes that means evaluating and changing my habits. In fact, most of the time it means that. Because if it takes ten years to make a comedian, it takes a lifetime to make a Christian. But also, for the Christian, we have this thing called grace. For “God has perfected forever those who are being made holy.”

When I refine my writing or spiritual practice over a long duration, I interestingly improve in other areas of life.

I say all this to say, let’s be more like comedians, in writing and in life.

Be a failure.

Rest easy no matter what the hecklers shout.

Listen to the audience when they’re not shouting.

Refine your craft in your work and your formation.

And please, don’t take life too seriously.

You’ve been a wonderful crowd, thanks so much for coming. Have a good night.