Failing repeatedly

What we (don’t) say about failurePermalink

Before quarantine I went to an event in San Francisco that explored failure. Panelists spoke of the volumes they’d written on the topic, and we learned strategies to reflect on past failures and avoid future failures. The event was uplifting because it made failure into something instructive and avoidable. What a high! A few moments after it ended I realized that it was totally inconsistent with my experience, or at least it was an incomplete picture.

We had analyzed failures of the closed variety. A plane crash, a layoff, a demotion, even a literal face plant. These singular events are clear misses that noone wants to repeat. I understand that we want to study them and learn to recognize early warning signs in an effort to avoid repeating them. I’m going to call these singular, clear-cut events Type 1 failures.

I want to talk about Type 2 failures - the kind of everyday failures that we may not want to avoid. A recent viral video comes to mind in which a small girl is trying to scale a wall. She fails a hundred times, and her dad is patiently recording her as she sprints full speed at a wall and leaps and crashes. She gets a little better over time and ultimately, she scales the wall. It must have been months. She must have gone to bed so many nights covered in bruises, dreaming about that wall. I think about that video every time I crash along my startup journey. So, roughly one to three times a day. She and her dad created a physical representation of my inner world, and to them I am grateful.

Type 2 failures are subtle and harder to parse. When do you give up? When do you keep going? I don’t know the answer, but I think that you have to find ways to enjoy the crashes. Sometimes you’re on a slowly sinking ship, and sometimes you’re unknowingly improving. Some of us are never going to scale that wall. When do we cut our losses? And when we do, what happens next?

You might question whether Type 2 failures really exist. “She’s getting better every day, so she’s not failing,” you might say. Well, to you I reply, “She’s literally crashing into the ground. Of course she’s failing.” And she doesn’t stop. She just keeps doing it. She isn’t following the steps of my workshop, in which we recognize failure so as to not repeat it. She is intentionally repeating it with grit and blind hope that she can achieve what is currently impossible.

Sometimes the answer is just to keep failing, knowingly, again and again, and not let it get you down. Powering through seems particularly hard these days, as we have become obsessed with reflection. We want to meditate on what has happened. We want to grow and never repeat the mistake. And wow do we want to talk about it. We want to process it and process how we processed it. All this effort towards self-improvement can prevent us from finding the best option - just keep going. It’s not, “Don’t be afraid of failure, because from failure you can learn and grow,” but “Don’t be afraid of failure because failure is just… fine. As is. Just keep doing it. Stop trying to reflect every time you fail.”

It would have taken that girl so much longer to scale that wall if she had reevaluated all her 6 years of life after every time she fell off that wall.

Find out if you’re failingPermalink

In the early days of building my startup I felt like I was losing all the time, and sometimes that was a real drag. Could I stop? Quit losing every day? Could I get a safe job that challenged me and provided solid mentorship and dental coverage? Of course! Should I?

I needed a way to know when to let go. When I started, I set a somewhat arbitrary timeline of six months to build a prototype and secure some funding. I didn’t know what I didn’t know, and six months had seemed kind of long but not so long that I’d need to start eating ramen and saving change for BART.

My original startup idea, the one for which I left my full time job, was interesting but it just wasn’t good enough, in ways both obvious and subtle. I sought feedback, felt the failures, adjusted my plan, rinse, repeat. By the time I reached the 6 month mark I felt like I was at capacity for Type 2 fails. Feedback from continuous user interviews and my early pitches had highlighted some GTM challenges, and that was beyond the simple math trouble that comes when you’re trying to address underserved communities with novel hardware. Keeping prices down was in conflict with high costs to build the thing. User and investor input had brought up many more paths to serve these communities.

I sent up a few emergency flares. I reached out to the network I’ve spent the last six months cultivating. These are people I look up to, some I’ve known and worked with for years, and others I barely know. To my genuine surprise, every single one of them replied. Over two days, I shared coffee, a phone call, a lunch and happy hour drinks. In our conversations they were open and critical, discerning and sharp. They challenged me and my assumptions and my ideas, and I realized I could keep honing in on the best solution for the problem I had chosen.

The products I was exploring near the end bore little functional similarity to the products I started with. Everyday I lost a little ground, and every week or so I gained more somewhere else. I was learning by failing rather than learning to avoid it.

When to quit (or at least when I did)Permalink

In the end I decided to close my startup, not because I had been worn down by the incessant failures, but because of the path they revealed. In my case, I slowly learned that the barrier I was trying to address didn’t primarily need a technical solution, it needed societal and insurance solutions. I knew myself well enough to know that I wouldn’t remain passionate enough in those spaces to sustain the onslaught of Type 2 failures.

My lesson about quitting is this – when doing something hard, I need to be passionate about both the problem I’m trying so solve, and about the type of solutions that I will create. The best solution to a problem you care about might not be something that you want to build.

If you’re failing right nowPermalink

Type 2 failure feels bad, and relentless, and you sometimes don’t always know whether you are progressing or realizing Einstein’s definition of insanity. It is a kind of learning that not everyone has the stomach for, and it’s easy to avoid. (There are lots of other valid ways to learn!)

If you’re going through it and thinking about giving up, my suggestion is to take a long break to fully mentally reset. After that, try to determine whether you still feel passionate about both the problem and the path. If not, can you shift them so that you do?

Also, read Mindset by Carol Dweck.