The Power of Failure Humor

Sometimes, when you’re entrenched in failure, you need to take your life less seriously in order to seriously put your life back together again.

Because if you seriously believe in the freeing power of FAILURE RULE #5: You Are Not Your Failures, then you will also freely learn to laugh at your failures.

If you know that You Are Not Your Failures, your spirit will be seriously lifted as you take your failures less seriously.

The best way to do this is to learn the art of Failure Humor.

Failure Humor is a cathartic, self-deprecating humor that makes light of life’s failures and leverages comedy to highlight insights, strength, and lessons extracted from failure.

Those who are able to cultivate a strong sense of Failure Humor are then able to ease the tension that exists when processing failures that are thrusted into their lives.

There are many social environments that naturally encourage the contagious spreading of failure humor. Hometown bars. Salons. Cigar lounges. Poker groups. Locker rooms. And barber shops.

I go to get my beard trimmed at Shaving Grace barber shop in the Philly suburb of Malvern every 3-4 weeks because when I do it myself, I fuck it up royally.

When I first starting going there I witnessed some great informal failure humor and ball-breaking between the barbers and their patrons. Pretense was non-existent. No one gave a shit about anyone’s resume. The ruling talk of the hour was governed by the most robust humor—original or plagiarized—that anyone could spontaneously muster. 

Much of this humor was deeply rooted in the freeing, irreverent, self-deprecating style of Failure Humor.

Now, the power of failure humor has strengthened me many times as I walked through failure and hard times.

When my financial planning practice was failing and I couldn’t pay the mortgage, I immersed myself in failure humor as a healthy defense mechanism to pull me through the difficulties of that time. 

I became obsessed with the comedy of Denis Leary. This was several years after the TV show Rescue Me on FX was released. Denis Leary’s character in that show, Tommy Gavin, resonated with me deeply. 

He was a post-9/11 alcoholic firefighter in New York City struggling with the reality of his family falling apart. I found myself binging on that show, going back and watching old episodes over and over. I internalized much of the sharp failure humor instincts that drove the show. I began subconsciously adopting them in my own life. This helped me tremendously as I navigated many similar relationship issues that the fictional character of Tommy Gavin struggled with in the show. 

I remember talking with my brother on the phone around this time. I was in a low place. Yet when we spoke, I had him laughing hysterically at my ironic self-deprecating, comedic positivity. 

I had listed off all the horrible circumstances in my life and finished my commentary by advising him my next career move was to figure out how to join the Somali pirates. I told him that if a nine-year-old in flip-flops could man an AK-47 and figure out how to properly rob and pillage, why couldn’t I? Hanging and banging on the high seas seemed like a growth industry to me. 

My brother couldn’t believe that I could joke and make fun of myself in such stressful times.

There are many benefits to learning the art of Failure Humor. 

One of the benefits is that by developing an instinct for failure humor, you often force yourself to take an overdue high resolution look at your current way of Being, so you can evolve into a better you.

Comedian Bill Burr knows this. He’s constantly funneling his own battles with his childhood-driven temper and anger into comedic stand-up masterpieces. His bits not only give him an outlet to make fun of himself, but the process of him converting his issues into humor actually forces him to look at himself and his issues honestly. 

In an interview on the Joe Rogan podcast, Bill described how he goes to therapy in order to actively work on unraveling the root causes of his reactionary temper outbursts. His art of performing Failure Humor helps him grapple with his issues, it seems to me, with a similar effectiveness as going to therapy. 

Louie C.K. has also been well known to display mastery in the art of Failure Humor. His entire persona is centered on his genuine struggle with trying to reconcile his imperfections, idiosyncrasies, and flaws with a world that holds no easy, natural place for him as an authentic, eccentric creative. His self-awareness of this disposition has ignited volumes of insightful, self-observational humor that the world has come to love, and still has shown to love—even post-controversy. 

Louie’s Failure Humor sensibility was captured well when he said:

 “Here’s how my brain works: it’s stupidity, followed by self-hatred, and then further analysis.”

It’s his acknowledgement of his need for further analysis here that brings the value full circle in his Failure Humor. 

Effective Failure Humor should always result in productive further self-analysis. Because as FAILURE RULE #1: Failure Purifies is true, it is also true that Failure Humor purifies.

There is no one who has perfected the use of failure humor more than the late, great comedian and actor, Rodney Dangerfield. 

Long before he joked about being in such bad physical shape that his body ought to be donated to science fiction, Rodney Dangerfield was clinically depressed, divorced, and suffering from meaning deficit as a fledgling aluminum siding salesman.

Rodney was bullied when he was younger for being Jewish. He was the constant butt of cruel anti-Semitic jokes. Most of the kids picking on him came from affluent families—a fact that explains a lot about Rodney’s failure humor that often focused on contrasting working-class folks with the wealthy upper class. Rodney never had the luck of being born with affluenza.

To cope with the pain of being tormented by his bully classmates for being Jewish, Rodney began writing jokes. 

Rodney figured out early on that sometimes the best way to traverse through the pain of being bullied is to use the power of failure humor. 

By age seventeen, Rodney was performing on amateur nights at various clubs. 

By nineteen, he was performing comedy full time.

But real life snuck up behind Rodney and slowly muzzled his internal spirit voice. He met singer Joyce Indig, fell in love, and settled down in the garden state to start a family. His full-time comedy pursuit was relegated to the rearview as putting food on the table emerged largely in the windshield forward view. This is when he began selling aluminum siding to make a living. 

While Rodney’s new life suppressed his internal spirit voice, it didn’t kill it. His Thing Two dream of being a full-time comedian didn’t go away. The internal spirit voice kept nudging him. His internal spirit voice broke through the fog created by the depression he suffered and the marriage issues he came to struggle with.

For a decade or more, he scribbled jokes down between appointments selling aluminum siding and paint. He did this diligently while continually processing the deterioration of his marriage and dealing with his clinical depression. Yet neither the depression, the failing marriage, nor the unfulfilling job managed to fully kill the Divinity of Purpose that bubbled up inside of Rodney and called him into a life of comedy. Rodney acted on his belief in FAILURE RULE #5: You Are Not Your Failures by resurrecting his pursuit of his Thing Two dream.

As Rodney grappled with the failures of his life, his internal spirit voice was urging him to embrace comedy. That voice continued to get louder and louder. Rodney eventually listened to it and began doing stand-up at night while still selling aluminum siding by day—invoking FAILURE RULE #4: Build Your Thing One and Thing Two Dependency.

Rodney’s comedy act was fully marked by his distinct brand of failure humor. His jokes were replete with comedic takes on bad marriages, references to absentee parenting, and stereotypes of the downtrodden working man.

In the classic film Easy Money, Rodney contrasts the lifestyle of a working-class slob with an upper-class snob. In one scene, the slob, Monty (played by Rodney) is being chewed out by the snob— his rich, judgmental mother-in-law. 

She tells him:

“You pollute the air with your smoking. You reek of liquor and God knows what else. You’re an ecological menace!” 

Monty’s response?

 “Yeah? Well, you were the inspiration for twin beds!” 

Rodney spent his life wrestling with the impressions of others. He used his gift of failure humor to rise above the anti-Semitic bullying he endured as a kid. He converted the failures and rejections that persisted in his life into brilliant comedy that has blessed and inspired multiple generations of fans. 

If you’re grappling with the messiness of failures—whether it’s being bullied, going through a divorce, or being stuck in a meaningless job—remember Rodney.

Take FAILURE RULE #5: You Are Not Your Failures seriously as you take your failures less seriously. Remember the power of Failure Humor. Find a way to use it to ease the tension of your life as you work to reshape your life. 

You may feel like you get no respect now, but like Rodney, that doesn’t have to stay that way forever.