Confronting Failure as a Core Life Skill

The Scream by Edvard Munch

A spread of colorful dishes lies before me. Banh mi buns, marinated meats, vegetables to grill, aromatic herbs. Fresh coconuts galore. It’s the end of my first week in Vietnam and I find myself in Da Lat, a smaller city whose cool climate is an oasis amidst the humidity. My past few days have been filled with mountain biking in the hills and running alongside the lake. 

The present stands in striking contrast to my life a year ago. Twelve months prior, I was toiling away at my desk in San Francisco, on back-to-back Zoom meetings, shoveling DoorDash’ed salad into my mouth during a 5-minute lunch, and furiously shooting messages in Slack to resolve fires. 

A voice disturbs the peace. “So, what did you do for work in the US?” This question triggers difficult emotions and self-doubts.

“I ran a digital health company for four years. I exited this year, and now I’m traveling to blow off some steam.”

“Oh wow, so you sold your company? Congratulations, that’s incredible, you must be really happy.” 

The comment unsettles me. Yes, we were acquired, but it was not a good outcome. I’m flooded with memories of our last few months of operation. As we approached tapping into venture debt, I scrambled to find a buyer to salvage the value we had created and secure a home for our team. Incongruence isn’t good for the soul.

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How do you talk about your failures? The big ones like shutting down your company, going unemployed for months, or getting fired. In the months after I shut down my company, questions about Songbird felt like salt rubbed into a fresh wound. Talking about failure is particularly hard when you pour everything you have into something. The endeavor becomes your identity. It becomes you. 

I used to carefully craft my response as if it were part of a marketing campaign. I’d explain that we decided to exit, found a home for the business, and sold the company. I’d feign an upbeat confidence while grappling with internal turmoil. This narrative wasn’t false, but not the whole story. So sometimes I’d casually mention that it wasn’t a great outcome. I’d throw around words like “acquisition” and “exit” so it seemed the 4 years were worth it. But in the back of my head, I wondered if they were.

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Yesterday, I was at a dinner with some entrepreneurs I met through a friend. Over delicious vegetarian Vietnamese food, they posed the dreaded question. 

“What did you do for work in the US and why are you traveling?” 

I’m not sure why, but I didn’t go with my regular line. Maybe because I wasn’t likely to meet them again. Or perhaps it was one of those days when I felt a greater sense of distance from my rollercoaster four-year journey. 

“I just shut down the company I started four years ago. We had this huge vision, and we failed.

Let me know if you want the short or long story but… I ran a digital health startup. We were a tech-enabled therapy platform for children with autism. I recently decided to stop working on it, we sold part of the company, and I shut the rest down. It was a wild ride: we were sued, we raised millions of dollars, hired over 130 people, and I made tons of mistakes. Now I’m traveling and reflecting.”

My candor surprised them. It piqued their interest, and they leaned in. 

“I definitely want the long story.” “How did you land on the business idea in autism?” “Tell us the story of how you were sued, that sounds crazy!” “I’m also building an operationally intensive company - what were your biggest learnings?”

We ended up having a long and ranging conversation about my entrepreneurial journey. I shared our origin story, our focus on a pain point from our own families, and how we interviewed random people on Craigslist to understand it. I talked about how we toiled away in an apartment and borrowed money from our parents to start the company. 

I leaned into the failures of my journey: losing investors’ money, hiring and managing a large team only to lay some off later, and struggling with gross margin. The back-and-forth also drew out our successes: clinicians and employees raving about our culture, building a sizable business, and raising funding from great investors. 

Surprisingly, my new friends don’t focus on our failures. They are simply curious about the details of the adventure.

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How one communicates about failure expresses our relationship to it. Failure presents us with an opportunity, and when we shy away from confronting it, we do a disservice to ourselves. Talking about a failure like a success conveys one’s own insecurity because it inevitably sounds fake. 

Calling an asset sale an acquisition might work when meeting someone random, but friends and the people who matter see through LinkedIn embellishing. It’s analogous to male baldness - we cringe at the insecurity emanating from the guy hiding balding with a hat and respect those who embrace it by shaving their head. 

Embellishing failure also robs us of an opportunity to have genuine dialogue. With fellow entrepreneurs, overselling success makes them feel more insecure. No one wants to hear someone else brag about how the business is growing perfectly. We are curious about what’s actually happening and what isn’t going well so that we might learn something for ourselves. 

Even with potential business partners like future investors or employers, embellishing failure is misguided. LinkedIn paints everyone as an exited startup founder, angel investor, or other “insert grandiose title here.” In a world of abundant superficiality, candor about experiences and past learning becomes the scarce sought-after resource.

Most of all, a healthy approach to failure is important because failure is a byproduct of ambition.  Doing anything meaningful or interesting requires setting lofty goals, testing the boundaries, and doing things that haven’t been done before. 

Confronting, grappling with, and learning from failure is a skill. Let’s examine and practice it like one.