The Up Side of Down: Why Failing Well Is the Key to Success - Hardcover

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1 Failure is Fundamental

How a Brain Scientist and a Psychologist

Helped Me Stop Procrastinating

Around the turn of the millennium, Peter Skillman embarked on an interesting exercise in design philosophy. Skillman, who is now an executive at Nokia, was the head of “user experience” for Palm, the company that essentially invented the handheld computer. For five years, he ran various groups of people through a design exercise he created, which would come to be called the Spaghetti Problem. He assembled a variety of different groups, from American students to 150 Taiwanese telecom engineers, and split them into smaller units of three or four, at which point they were given twenty pieces of spaghetti, a meter of tape, a marshmallow, and a piece of string. They had eighteen minutes to create the tallest freestanding structure that would support a marshmallow.

This sort of team-building exercise is not new; I did a version of it involving straws and an egg with eight fellow students during my business school orientation weekend. What was new was Skill- man’s perspective: instead of looking at it like a management guru, Skillman thought about it like a designer. In 2007, he shared what he had learned with the Gel conference, a sort of smaller version of TED.1

Unsurprisingly, the engineers did very well. The business school students finished dead last, which is probably also unsurprising to anyone who has spent a weekend doing team- building exercises with future MBAs. According to Skillman, they spent too much time arguing about who was going to be the CEO of Spaghetti, Inc. Lawyers did almost as badly.

And who did the very best? Skillman unveiled their pictures, and a wave of laughter swept through the audience. Up on the screen was a series of snapshots of kindergarten students, mugging for the camera in front of . . . well, about what you’d expect if your kindergartner made you something out of spaghetti and tape.

How did the kindergartners beat the engineers? By the simple process of experimentation and iteration. They didn’t let themselves get hemmed in by assumptions about what the rules were—they were the only group of people who asked for more spaghetti. And because they had more spaghetti, they didn’t have to waste time sit- ting around talking about how the tower should look, or who should get to write the vision statement. They just dove in and started creating, discarding anything that didn’t work. Since, as Skillman points out, “very few people understand the structural properties of spaghetti,” this was the fastest route to success.

The structures built by the engineers rose above the workspace with the elegant logic of a suspension bridge. The wild, asymmetrical kindergarten creations lurched drunkenly like modern art installations on a debauched spree. Yet they all supported a marshmallow, at a height that was on average a full inch taller than what the engineers had achieved. The engineers had years of schooling and work experience to teach them how to build sound structures. But the kindergartners had something even more powerful: they were not afraid of failure. By trying and failing, they learned what didn’t work—which, it turned out, was all the knowledge they needed to figure out what did.

“Multiple iterations,” Skillman told the audience, “almost always beats single-minded focus around a single idea.” The people who were planning weren’t learning. The people who were trying and failing were.

“If you have a short amount of time, it’s more important that you fail,” he said minutes later. “You fail early to succeed soon.”

I was sitting in the audience the day he gave that talk. Five years

later, interviewing people for this book, I have heard this thesis echoed over and over again by entrepreneurs. For most of the rest of us, Skillman’s story goes against every instinct we have about how the world is supposed to work. It should not be possible to blunder your way to the top. Success is supposed to be the product of hard- won skill and prudent planning, not breaking spaghetti with abandon. The problem is, most of our instincts about failure are wrong.

Jim Manzi, the founder of Applied Predictive Technologies, tells a typical story.2 His company, which you’ll hear about in a later chapter, was struggling with its business model. They were designing custom software products that they then installed at the client’s location using thousands of dollars worth of equipment, and struggling to get enough sales. Then one day, their biggest client happened to notice the on-site team using a Web interface to do some testing. “Can’t we just do it this way, on the Web?” the client asked.

Manzi said no. Then he said it again. And again. The client kept asking. Eventually, with money getting very tight, Manzi gave in. He had discovered the software-as-service model of delivering applications to a client, where you own the servers, and they pay you monthly rent to access your product. Then novel, it now dominates most application development.

“It was a combination of luck, having our backs to the wall, running out of money, and listening to what the market was telling us,” says Manzi. “In my experience, most entrepreneurs, they’ll have a similar story. ‘The company almost died, and then we figured out in crisis what we really did for a living.’”

“When we’re sitting in our offices perfecting a product,” says Jeff Stibel, the CEO of Dun & Bradstreet Credibility Corp, “we’re making the product better for us. The problem is, we’re not the customer.”3

Failure, says Stibel, is “the only way a business grows,” because it’s “the only way you really learn.” When he says that, he’s not just

staking out a philosophical position. Before he was a serial entrepreneur, Stibel was a graduate student in cognitive science at Brown University, where he talked his way into the program by passionately arguing to his adviser that “the Internet is a brain.”

Stibel is the distilled essence of a successful entrepreneur: lean and compact, with an intense dark gaze, and the hypomanic charm you find in so many business founders. He fires off ideas like “the Internet is a brain” at a steady rate of about one per minute, usually some mixture of philosophy, management theory, technofuturism, and his beloved cognitive science. Like Skillman, he is voluble on the role that failure plays in learning. Only, he thinks that failure isn’t just a way to learn faster: it’s the only way to learn at all.

“The brain is a failure machine,” he told me. “When you’re born, you have about all the neurons you’ll ever have. When you’re four, you have pretty much all the connections between those neurons you’ll ever have. Then the brain starts pruning. The brain starts shrinking.

“When the brain is shrinking,” Stibel says, “you’re actually learning by failure.”

Think about the last time you tried to learn a new skill—using a spreadsheet, hitting a badminton shuttlecock, baking a cake. When you watched someone else do it, or read the instructions, it probably seemed pretty straightforward. Then you tried it, and nothing came out right. You lost a column and couldn’t get it back. The shuttle- cock flew off in entirely unexpected directions, or landed, unmo- lested, on the ground near your feet. The cake was half an inch of soggy crumbs.

Maybe you gave up right then. But if you tried again, you probably had a few more...