How to write about failures

People like a winning image. 

I believe this, and I see examples of it every day. I feel it too. I don’t like pity parties, sadness, or discouragement; I’m drawn to hope, encouragement, and excitement.

I used to think that this meant people wouldn’t want to read about anything except the W’s. 

By extension, that means if you’ve experienced a setback, don’t write about it. Experiences that contain even a whiff of embarrassment, loss, or failure, are all meant to be stuffed away, kept in obscurity, and to be disguised as if they didn’t happen. 

The caveat to this is you can reveal a failure after it happened, but only after you’ve won or consider yourself a success. Or so I thought.

This observation became clear to me as I skimmed Sahil Lavingia’s, “Reflecting on My Failure to Build a Billion-Dollar Company,” which was a really great essay (that got him a traditional book deal!), ending on a positive note that he’d redefined success, and that Gumroad had transitioned from a VC-backed hypergrowth company to a sustainable business. This is a belief that Gumroad Lavingia and I shared:

It’s deeper than that.

I recently picked up The Moth’s How to Tell a Story, and in the introduction, Chenjerai Kumanyika shares to a similar belief:

“Up until this point in my life, I had presented myself, and been taken seriously, as a scholar, organizer, journalist, and hip-hop artist. Stories about the confusing, awkward, and downright embarrassing parts of my life, and the lessons that might be learned from them, had been pushed to the margins of my mind. They would spill out, poorly developed, at family dinners or on dates, or in the classroom.”

Kumanyika also recalls director Jay Allison saying:

“Well, Chenjerai, Moth stories can be deeply inspirational, but they’re very different from the exclusively heroic or positive tales that some other places invite you to tell. I don’t know where you’ll end, but as a place to start, remember that everyone is entertained by, and relates to, a train wreck. Stories about failure and learning can be powerful.”

As Kumanyika developed his story, one in which he bumped into Laurence Fishburne twice. The first time, he was working as an emerging artist as part of the music group, Spooks. The second time, he was working as a security guard and was mortified Fishburne might recognize him and see him as a failure. He writes:

“When I first shared my story, I thought that having been famous—and then not—was the point of the story, and that meeting Fishburne twice was the punchline. I thought the ending of the story was me in my humiliated state. None of those initial instincts was correct.”

After working with artistic director Catherine Burns, Kumanyika realized:

“As I got closer to the show, I remembered a turning point in my story. I was applying for a new temp job, feeling defeated, wearing the same JCPenney suit, when I heard a Spooks song playing and I saw people in the temp office enjoying it. This reminded me that the power of my music wasn’t contingent on my own fame or hanging with celebrities. It was about the joy of dreaming up and shaping my art. The office workers were enjoying what I had made, and they reminded me of the power and joy I had felt creating it. 

In the final scene of my story, I talked about sharing a lesson with my students: Follow your passions, but be prepared to brace for impact. And after going to sleep thinking hard about the core message of my story, I woke up with the line ‘Sometimes you have to figure out who you’re not before you can become who you are.’”

(You can listen to Kumanyika’s story here.)

Kumanyika’s writing set off a lightbulb in my head too. The story itself matters, of course. But… 

You get to decide where it starts and where it ends.

I believe that was what I missed from my initial reading of Lavingia’s piece; he writes, “I consider myself ‘successful’ now. Not exactly in the way I intended, though I think what I’m doing now counts.” 

Lavingia’s not deluding himself—there’s evidence of success—and he’s also accepted that he failed at what he set out to do to begin with. 

Kumanyika had to reckon with a similar challenge; recognizing that he didn’t succeed the way he thought he would, but it didn’t matter because—as he listened to his colleagues enjoying his music—that wasn’t the point

From this light, we realize not everyone will see our faults or mistakes as dealbreakers; how we learn to accept them, to move forward in spite of—or with—them, and even to grow to appreciate them, is where we can share value with people. 

There are some great prompts in How to Tell a Story, here are three:

  • What is this story ultimately about for you? 
  • Why is this story important for you to tell? 
  • How would you describe yourself at the beginning of the story, and who had you become by the end?

And on where to begin:

Think back to those moments when you encountered something a little out of the ordinary: 

Getting off at the wrong stop or exit. 

A phone number found in a pocket. 

The eyes meeting across the room. 

The last—I swear, the last—shot of tequila. 

A kiss. 

A lie. 

A promise. 

A betrayal. 

A windfall. 

A comeback. 

Your ex at the door. 

The final straw.

Walker & Company founder Tristan Walker says, “The best advice I received came from Tyler Perry. He told me that the trials you go through as an entrepreneur and the blessings you receive are the exact same things. Those trials are lessons you can learn from, and those learnings are blessings.” 

Acknowledging and accepting your potential embarrassment is the first step to working around it. I love this speech by Eddie Huang from a decade ago, when he says:

Don’t be afraid to offend people… One of the things I find very interesting about people starting businesses—they’re embarrassed to get money. They’re embarrassed to be chasing their dreams, and get money, and be successful. They’re always apologizing. Every pitch meeting I’m in, every brand I meet, people always like, “It’s not about money, it’s not about money.” It is about money, [you] should not be embarrassed to be about money. I’m about money. I’m also about a healthy disrespect…

I want to end on Huang’s note about a healthy disrespect, because that’s also what it takes to develop a story worth telling. It’s about a healthy disrespect for convention, for what you know other people think you should think or feel—and accepting, owning, and being proud of how you survived your journey and moved beyond your failures. 

It goes without saying, all of this should happen at its own pace; the stories emerge through work on yourself, through reflecting, through developing hard learned lessons, and flow out through the writing—not the other way around. 

Focus on what makes the experience matter, and not on the experience itself.

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