What the Roomba Teaches Us About Pushing Through Fear of Failure

A Roomba robotic vacuum goes about its programmed task, leaving its dock, collecting dirt and dust in a preset grid of space, and then returning to its dock. Like all robots, it does its job with no sense of success or failure outside of completing its mission.

What if we went about the work of disruption like that—impervious to outside perceptions, biases, or opinions and focused only on solving the problem, whether it’s cleaning crumbs under the couch or curing cancer?

How could we do it?

For a recent episode of my podcast The Combustion Chronicles, I spoke with Terry Jones, who founded Kayak and Travelocity. When I asked him how he solved problems that consumers didn’t even know existed, he said he did it by failing.


terry jones

Terry Jones, digital disruptor, author, and founder of Kayak and Travelocity.


Yes, failing. Terry considers his most important lessons to be his failures.

Can you imagine that? Investing millions of dollars in solving a problem, then not solving it, and losing your investment?

But Terry says he considers his multimillion-dollar losses to be like a graduate education. Here’s what he told me:


“My last startup didn’t work. It failed. And I look at that as a $15-million postgraduate course in what not to do. I’m still learning.”


He says he learned he needed to study more, to avoid zigging when he should have zagged. And chances are his next startup will be better as a result.

A lot of high-profile, successful people might be embarrassed about their equally high-profile failures. Not Terry. He learns, and then he keeps going. He understands the power of failing forward.

Which brings me back to robotic vacuums. Here’s how Virginia Heffernan described her Roomba’s attitude toward failure in a recent Wired article:


“To my Roomba, hitting a doorjamb and cleaning with dispatch are one and the same. There is no success or failure. She might be stuck in a rut under the sofa for ages, blind to a fairly simple escape, but she feels no embarrassment; when she’s executing a perfect beeline back to her base station to recharge, she betrays no smugness. There is no ‘clumsiness’ or ‘grace’ in her world.”


The Roomba is like a honey badger. It doesn’t give a sh*t. Literally. It doesn’t even care if it flings dog poop everywhere instead of cleaning, as long as it performs the task it was programmed to do. When it crashes headfirst into a wall, it simply pivots and keeps moving, learning from the collision, and adjusting its approach. It’s prepared to hit walls (or fall downstairs), and when it does it considers that part of the learning process.

What if we considered our walls part of the process for success? What if we stopped giving a sh*t about failure, and instead focused on our purpose, on the tasks we were designed to do? What would we need to break through the fear of failing?

1. Willingness to make mistakes

Jeremiah Uffort says, “If the fast lane to truth is paved with error, then anyone who’s interested in getting to the truth had better get on with making some good, productive errors rather than waffling around, terrified of putting a foot wrong.”

And that’s Terry’s philosophy as well.

In his book Disruption Off, he says, “You may be afraid to disrupt your organization because you’re afraid it will fail,” he writes. “The irony is, your organization will fail if you do not disrupt it.”

A willingness to make mistakes and to take bold risks without fear of failure is, ironically, essential to your success as a disruptor. Kids and younger adults have a greater tolerance for trying new things and accepting failure than the rest of us. They’re not jaded by past mistakes or failed attempts.

2. A culture that encourages failure

 A Roomba knows its purpose—to move back and forth within a predetermined space with its sweeping function on. This clear purpose explains why it cannot be swayed from its task, despite outside influences or what we perceive as unsuccessful attempts.

Likewise, disruptors need to design a culture that provides teams with a clear vision, a predetermined goal, and a mindset that failure is inevitable, even encouraged.

In his first book, Terry wrote, “The biggest problem at big companies is that either they don’t allow experiments or when something fails, they kill the person instead of killing the project. So you get a culture where no one will raise their head, no one is going to try anything new, because there are no rewards. There’s only punishment.”

He believes the biggest challenge for companies is the lack of willingness to change or try something new. So get busy creating a culture that embraces experimentation and acknowledges that we rarely get new ideas right the first time. The Wright Brothers didn’t fly on their first attempt; why should everyday employees be expected to?

3. An obsession with the problem, not the solution

Although a Roomba doesn’t know the meaning of failure, its manufacturer, iRobot, does. It’s original Roomba marketing strategy was a bust because they were marketing to clean freaks, people whose standard of cleanliness couldn’t be met with a robotic device. By leading with their technology, they failed to realize that their best customers would be the 80% of people who live by the “done is better than perfect standard.”

Likewise, Terry’s $15-million failure involved selling an AI solution to an audience that didn’t yet want it. Here’s how he describes it:

“This was an AI startup, and it started because I got a call from Ginni Rometty, the chairman of IBM, who I knew, and she asked me, ‘Could I come up and teach Watson, IBM Watson, about travel?’ … They invested in a startup, but you know, we were taking technology first and then looking for the problem. I think we solved some really interesting problems. We did some amazing stuff… But it wasn’t until the company failed that I managed to see a report from McKinsey… Travel just isn’t using AI. They should be. They’re the biggest part of e-commerce, but they’re not. So, even though I knew the industry well and I figured out what to do; it just wasn’t ready to take the risk of AI.”

What risks are you ready to take? And are you willing to keep bumping your head against the wall until you achieve success?