I’ve never been afraid of failure. I always think of the potential for failure as pure “dare”—and can’t resist staring it straight in the face to see if I can beat it. I always thought this was a noteworthy trait of mine, a good trait. Hell, I even gave speeches about the benefits of not being afraid of failing: learning, experience, trying out innovative ideas, pushing your boundaries, surprising yourself.
The trick, I say in those speeches, is to pick good failures, failures that give you more than you lose, whether insights or learning or experiences or, heck, even just great friends or one helluva a good story. You weigh the pros of what you might achieve and accomplish against what the worst-case scenario might be and say: Can I live with the worst, if it comes to that?
I had always taken risks in publishing, tried to do things people said “couldn’t be done,” made things from scratch without enough money or enough time or enough team or all three. I did these things, often with thrilling, rewarding, award-winning results — the best part of which was always the joy of creating something original (and maybe even amazing) with a great team.
And yes, sometimes the magazine we launched folded. And yes, sometimes we ran out of money before we had taken flight. But the failure always felt good because the shared effort was bigger than the loss somehow.
But good was not at all what I was feeling early one morning in San Francisco during the 2000 dot.com gold rush. I was sitting in my car, parked on a hill on a beaten-down downtown street early one morning, sobbing — can’t-catch-my-breath, nose-running sobbing — to a friend and coworker in my company’s other office in New York City.
“How did this happen?” I wailed. “How did we get here?”
I had finally seen that I was on the Titanic and that a whole bunch of really great people I pulled from other jobs — more secure jobs, perfectly great jobs — are going to go down with me. We have already been working without pay for a week. We are not expecting to get paid next week or the week after, either.I thought I knew how to do impossible things. I feel the bitter aftertaste of hubris in the back of my throat.
The person we are working for is someone of decidedly elastic ethics, meaning anything that will keep our company alive is fair game. I watched late one night as she stood behind our CFO and made him respin the numbers in front of him on the computer screen, recalculating them till a single tear slipped out of each of his eyes as he tried to make the spreadsheet say something different than what it had originally reported, for her to take to the board and show to potential investors.
I’ve written memo after memo explaining how to drop financial weight, cut staff, reduce overhead, shrink down our mission and focus on only the highest functional parts of the website and the magazine. But these ideas are all being rejected because of the slight possibility of revenue attached each one. We are being asked to do impossible things.
I thought I knew how to do impossible things. I feel the bitter aftertaste of hubris in the back of my throat.
I didn’t realize until that moment sobbing in my car, alone in a city that isn’t my own even though I live here, that I have never lied to my team, no matter how dire things got in the other launches I’ve worked on. I’ve told only what needed to be told; I’ve protected and revealed in equal measure. But now I’m being asked to lie. Actually, not even being asked. I just suddenly find myself on the other side of a line I never, ever imagined I would cross.
I lie to my team, to our business partners. To support a not-quite-true story about our finances and our fundraising in order to get that company to loan us some money so we can print the issue we have stopped working on while we aren’t getting paid. They make the loan. The amazing team I work with buckles down, and we basically produce an entire magazine in four days. It’s insane. It’s not possible that we did that, but, somehow, we did.
I still know how to lead a team. Maybe. But I failed to have the necessary imagination to foresee these kinds of quandaries.
I want to quit. Quit as an act of refusal to support intentions and actions that I feel morally opposed to. But if I quit, I know for sure the company will fold. We’re creating all the content we make for pennies, using every trick I know to hold down costs and still create something refined, original, beautiful. It’s not that I’m so smart – I’m just the only one with any kind of experience crunching down budgets to make a very expensive-looking magazine very cheaply. It’s not rocket science, but it’s also not obvious. It’s a learned skill. One I learned from having failed at things before. Failing to be on budget, and then cleaning up the consequences.
What’s failing now is my faith that I am doing the right thing, and my conscience is suffering. And I feel the weight of every mistake I’ve made while I was here sitting on my chest like a thousand-pound gorilla. I can only cry to my friend that I have no idea what to do.
I never don’t know what to do. The gift of being an experienced leader is that when you don’t know what to do, you still know how to decide what to do.
I keep going. We keep going. The stock market has crashed. The issue has printed. It’s gorgeous, a real triumph. I keep writing memos. I kick up some dust.
Then comes the day that my boss decides not to fire me and I decided not to quit; the only thing we can agree on is separating with as little trauma created for the team as possible. She explains to me how I just don’t have a vision that aligns with hers; I explain to her that what she wants to do is literally impossible. We don’t shake hands.
I’m crushed. I’m relieved. I’m traumatized. I have failed. I have failed my team. I have failed myself.
I have failed to do something that always seemed so utterly simple to me: stay on the right side of things. Never find myself in a moral morass. Don’t lie. Don’t cheat. Don’t steal.
So, yeah. I failed. Bigger than I ever could have imagined. Yes, I made great friends. Yes, we made a beautiful new-media company that broke new ground; yes, we made a gorgeous magazine that won awards and sold well at newsstand.
But the failure math just didn’t work out this time. For me, the failure equation was forever changed.
I still take risks, and I take them as often as I ever did. I just know how much more there is to lose now: Turns out, you can lose yourself.