I am obsessed with failure.
Most of the time, it’s all I can focus on. The obvious failures hurt: the projects we lost, the clients who left, the money we left on the table, some of the friends I used to have who I don’t talk to anymore, and the million little decisions I’d make differently if I could do them again. But I can find failure in the successes too. There are shots in the Björk video I produced 18 years ago that I hate. Creative Control, a feature I produced 10 years ago, has one scene that still makes me cringe. Give me almost any success from the last 20 years and I can probably tell you what was wrong with it.
Instead of seeing the finished thing, I see the version that could have been. The shot we should have gotten, the idea we should have pushed harder, the decision I would make differently now. Success has a way of fading into the past pretty quickly. The mistakes stick around because my brain keeps trying to fix them.
As a leader and a boss, I’ve had to learn not to let that instinct turn me into someone who’s constantly pointing out what’s wrong. I’m better at it than I used to be, but deep down I still find it hard to ever be completely satisfied. That doesn’t mean I’m not grateful. I know how incredibly lucky I am to do what I do. Running a creative company for more than 20 years is a success in and of itself. It’s also an enormous privilege.
But I also think all of this obsessing over what went wrong has probably been useful. Failure is a form of learning. Educators call it “productive struggle.” The business world has its own, slightly more obnoxious term for it: “fail fast.” The basic premise is pretty simple: try something, figure out whether it works as quickly as possible, learn from it, and move on before you’ve spent too much time or money going in the wrong direction.
When I was still in film school, I worked on everything I could. It took me outside my friend group and my comfort zone and put me in situations I probably never would have found myself in otherwise. Mostly, I just wanted to start getting paid, so I took whatever I could find on Craigslist that would give me $100 (along with plenty of other things that paid me nothing at all). Eventually I met Zach Mortensen on Craigslist, and the two of us started working together.
At the time, I thought the goal was to make movies. I wanted to be a filmmaker because filmmaking felt noble and good. But after working on a half-dozen feature films, I got restless. I just wasn’t failing fast enough. I could usually tell within the first week of production that a movie was doomed, but it didn’t matter. I was still going to spend the next two months sweating, suffering and getting very little sleep making the thing.
I also started realizing that there was a difference between doing a good job on someone else’s project and making something I actually cared about. On those feature films, I could work my ass off, do everything I was supposed to do, and still end up with a movie I didn’t particularly like. I didn’t have much say in the creative decisions, but I was spending months of my life executing them.
In between those features, I would make music videos with friends, or random people I met online, and that’s where I found my groove. I had more ownership over what we were making, which meant I could take more chances and make my own mistakes. A few weeks later, I’d have a finished video, a new skill, and a much better idea of what I’d do differently next time. Of course, I would watch the finished video and mostly notice the things I wished we had done better.
Music videos led to commercials, and eventually we built a company around trying things we hadn’t done before. That was always the part that interested me. Why would I want to do the same thing over and over again? Why would I want to work with a director who only made car commercials, or only made comedy spots? I was much more interested in finding people who were willing to take some risk together and figure it out as we went.
As we got deeper into the commercial world, we started bumping into the wall of conservative corporate America. So much of advertising is designed to mitigate risk, which makes sense. If you’re pouring hundreds of thousands, or millions, of dollars into something, you probably don’t want the people making it to say, “We’ve never done this before, but trust us.”
So we started pushing the edges of what people expected from us. The client didn’t ask us to write the script, but we wrote one anyway. We made deliverables we didn’t owe and were early to embrace that new piece of technology or social platform everyone just started using. At some point we started using strategy to sell our ideas even though none of us had ever actually worked with a strategist.
We did this for a good 10 years. We got in way over our heads plenty of times, but that was the beauty of it. A few weeks later, the project would be over, we’d know a little more than we did before, and then we’d go try something else. Eventually all of those little experiments became the business model.
Some of the experiments went better than others.
We once went completely overboard pitching a huge tech brand. We made a video on spec, worked our asses off, and got a round of applause at the end of the presentation. Then the CMO walked in and killed it.
A line producer accidentally cc’d a client on an email talking shit about them. Three separate million-dollar productions got canceled, and we had to sue one client to get paid. An actor posted pictures from set and got a video canceled. Two employees disappeared, one with a bunch of cash, the other with his computer. We got sued after a PA allegedly hit someone with a cube truck. Someone broke into our office.
There’s more. A lot more.
And weirdly, I wouldn’t trade most of it. Some of those experiences were miserable, expensive, or embarrassing, and plenty of them weren’t even our fault. But they changed how we worked, who we trusted, and what we did the next time something went wrong.
It’s probably also why I’m a little suspicious of expertise that comes from doing the same thing over and over again. Repetition can make you incredibly good at something. But it can also make you incredibly good at avoiding situations where you might be bad at something, and I’m not sure that’s always a good thing. I still like being a beginner. I like trying something I don’t totally know how to do yet.
The funny thing is that after spending most of my career trying to convince clients that it was okay to let us try something we hadn’t done before, that’s increasingly the actual need. Social alone has made it almost impossible to know exactly what’s going to work before you make it. You make a bunch of things, some work, some don’t, something weird takes off that nobody expected, and then six months later the thing that worked doesn’t work anymore.
That requires getting a little more comfortable with things not working, which is a hard thing to ask of people who are spending a lot of money and have bosses of their own. You can’t spend six months trying to engineer the risk out of every idea, but you also can’t just throw a bunch of shit at the wall and call it experimentation.
This is probably the part I understand better now than I did 20 years ago. Taking risks and being reckless aren’t the same thing. If you’re going to experiment, you need something solid underneath you. You need to know who you are and what you’re trying to say. You need some systems and some structure so you’re not starting over every single time. The goal isn’t to make failure impossible. It’s to make sure one bad idea doesn’t burn the whole thing down.
Twenty years of failing hasn’t taught me how to eliminate risk. If anything, I’m less interested in eliminating it than I’ve ever been. What I’ve gotten better at is creating the conditions where we can take risks without betting everything on every single one. Experience makes the landing a little softer. It helps you recognize the difference between a worthwhile experiment and a stupid gamble, and when something doesn’t work, figure out why so the next thing can be better.
I still have plenty more things to screw up. But they’ll be new, exciting things. I can’t wait.
