🎶 Reflect by OVERWERK
The longer you live, the more you fail. Failure is the mark of a life well lived.Brandon Sanderson, Oathbringer*
A few weeks ago, a Good Work reader asked if I’d write about recovering from failure. At Holloway, we have a policy of keeping Good Work to four paragraphs and a set of links. But I felt like this subject was worth making an exception for. I was grateful to have been given the opportunity to think about this one.
In my twenties, I started two companies. One never grew past three people and a bank balance of $50K. For the other, we raised $17M, hired over 70 people, and had product-market fit. Both companies ultimately failed, and each failure taught me something different.
When we talk about failure, we’re usually talking about it like it’s an event. Post mortems have become de rigueur. “I’m sitting in my office, we just sold all the chairs, it’s over.” But the event of something ending is rarely the worst part of the affair. Failure is actually a process, the downward ridge into despair, a spiraling slide with neon reminders of how far you are from ever getting back on top of things.
At 22, I got fired when I told my boss I was flying from Ohio to California for an interview with Y Combinator. I’d been working on a side project with a couple of friends, and we were going to see if we could turn it into a real company. I can’t speak to why my co-founders (still two of my best friends) wanted to build a startup, but my reasons were all the wrong ones. Less than a year later, the whole operation turned out the way things do when a kid straps on wooden wings and jumps off a barn. Except that I was an adult, and this failure didn’t end with a broken arm but with me standing on a train platform wondering whether jumping would be better than whatever was coming next.
Looking back, I can’t help but be ashamed of what I see as the juvenile reaction of a kid from the suburbs experiencing something truly hard for the first time. But it’s exactly this kind of negative self-talk that leads us to spiral when we’re already tumbling. Whether I was justified in how I felt didn’t matter. I felt how I felt, and you can’t deal with those feelings if you’re ashamed of them.
Sometime around then, I met up with my friend Danielle Morrill. She noticed something was off, asked me if I was broke, and offered to cook me dinner. She poured some confidence in my cup, and I used to it call my parents. It turns out my Dad had socked away half of my allowance each year as a kid and put it in some stocks. “It’s your money,” he said. It was about two months of cash. I used it to stay out of Mom and Dad’s basement, email everyone I could, begin interviewing, and teach myself the easy half of front-end development. This part is important, because I didn’t lift myself out of failure all on my own. I had help, and I know not everyone does.
Two months later, I had a job offer to move to New York. I told Danielle. To my surprise, she told me she was going to take the cash remaining in her startup’s bank account and start something new. Would I join her? I told the other company no and yes to Danielle. Two months after that, we named the company Mattermark.
Able to pay rent, I was, in many ways, out of the woods. But whatever confidence I had at 22 when I moved to California was gone. Someone once said not to compare others’ outsides to your insides. I did a lot of this at that point in my life. And I projected a stable outside as often as I could, too. My Facebook feed was full of fundraising announcements and photos of our team having a good time. The reality was that I drank too much, smoked too much, and exercised only because it made me feel something.
After things go pear shaped, we struggle just to grasp what’s going on, it’s next to impossible to figure out how to get our footing. Up until 2015, I had flirted with writing a few times. When my first company failed, I wrote a series on what went wrong to process the lessons. I journaled here and there, but in 2015 I set out to start writing 750 words a day as often as I could. In 2014, I journaled seventeen times. In 2015, that number rose to sixty-eight, and in 2016 I hit seventy-five.
Writing became the place I could go to have an honest conversation. My audience—me—knew all my secrets. I didn’t have to hide anything or contextualize how I felt, but I could pull on some threads and patterns to figure out why I was so unhappy. Building Mattermark wasn’t center-stage for me. This was.
Meanwhile, Mattermark was on its way down. We’d started a business. Despite being in a market too small for our venture capital britches, we had product-market fit. We built a terrific team. We formed and deepened friendships. We raised a truckload of capital. But we were poor managers, reactionary to markets and conversations. We wavered in our decision making, and we ultimately tried to scale prematurely inside a market we didn’t fully understand.
It was a more spectacular failure than my first business, but this one didn’t hit me like the first one did. Partially because I left before we hit the bottom, not jumping ship out of fear but because I saw what this company was doing to me. In many ways, Danielle saved me. But as I clawed my way up from the bottom while the company grew, I regained my agency and ultimately I saw that, in order to get back to the top, I needed to build my own path, not someone else’s. So I left. We sold the company, the story was not favorable, and I often wonder if it was my fault for failing to stay to try and right the ship’s course.
In the weeks after my last day at Mattermark, even though the thing itself was a failure, I felt like I had finally crawled out of the crater I’d descended into from 22 to 27. But two years later, I was still struggling for confidence. Only now, in the last three months or so, do I feel like I’ve traveled far beyond my origin of failure, into new territory.
Recovering from failure took me seven years. And I’m sure there’s some shadow lurking around a corner that will make me laugh at that sentence in a few years. Maybe we’re always in recovery. If we want to stay vigilant, we should think of it that way.
What I learned from writing is that our body is profoundly good at setting off biological klaxons, screaming at us to head for the exits. The impulse to drink, smoke, turn our brains off, check out, or criticise others, and emotional reactions like short fuses, inability to sleep, grinding our teeth, all of these things are how our body tells us something is wrong.
I learned to listen to those messages—to hear them—by seeking help from a lot of different people, from friends and coaches, but most importantly through writing. I started to really reflect on what had happened to me in the past, on things I had done, and how they were still affecting me. In turn, I began to think about how things could be different and what could happen next.
In many ways, failure is the most incredible, beautiful thing. Had I not failed so early, who knows if I ever would have found my love of writing, written a book, or founded a company to give authors a better way to publish books online. My experience of failure helped me empathize with those who didn’t have anywhere near the head start I had. It showed me that depression isn’t a mood you get, it’s a disease you can catch. It taught me to feel my fear, listen to it, follow it, and face it. But most importantly, it taught me that I could survive it the next time it came around.
That’s Good Work for this week. Looking forward to what’s next.
Andy and the Holloway team