[Editor’s note: The following is the first in a three-part series of posts adapted from Warren Berger’s new book, A More Beautiful Question (Bloomsbury), for which he spoke with top designers, tech innovators, entrepreneurs, and leading creative thinkers to explore the art (and innovative potential) of asking the right questions.]
Here’s a question: What would you attempt to do if you knew you could not fail?
If that question seems familiar, it should. One of the hallmarks of a powerful question is that it gets passed around, and among innovators I spoke with in the tech industry, this one has been making the rounds perhaps more than any other—quoted by everyone from Google’s Regina Dugan to Sebastian Thrun at Udacity and Airbnb co-founder Joe Gebbia.
Interestingly, the question did not originate in Silicon Valley. It can be traced back three decades to the American pastor Robert Schuller, who used it in inspirational sermons and books. But its popularity was jumpstarted a few years ago by Dugan, who featured the question in a widely circulated 2010 TED speech (Dugan was a creative director at DARPA at the time).
"If you really ask yourself this question," Dugan told the TED audience, "you can’t help but feel uncomfortable." She explained that the question tends to make us aware that fear of failure "keeps us from attempting great things . . . and life gets dull. Amazing things stop happening." But if you can get past that fear, Dugan said, "impossible things suddenly become possible."
When I asked Thrun, who often quotes the question and has shared it on Reddit, why it resonated with him, he said it was because it touches on what may be the biggest issue for innovators—fear of failure. "Innovators have to be fearless," he said. "People mainly fail because they fear failure."
But how can a question help with something as primal and powerful as fear? It has to do with the power of hypothetical "what if" questions to enable us to temporarily shift reality—allowing us to look at the world through a different lens. According to John Seely Brown of the Deloitte Center for the Edge, "In order for imagination to flourish, there must be an opportunity to see things as other than they currently are or appear to be. This begins with a simple question: What if? It is a process of introducing something strange and perhaps even demonstrably untrue into our current situation or perspective."
So by asking What if I could not fail?, we create a mental landscape in which the constraint of failure is removed. It’s actually quite common, and effective, to use "What if" questions to remove various kinds of mental constraints—to allow for thinking freely, without some of the mental baggage that can weigh down the imagination. Product developers sometimes use the hypothetical question What if cost were not an issue? to temporarily remove practical limits on thinking. Similarly, a favorite question of Airbnb’s Gebbia that he uses to jumpstart thinking on projects is, What if we could start with a blank page? The question removes the constraint of having to deal with what’s already been done.
But while "what if" questions can help you imagine a world without failure and other practical problems, the author, blogger, and serial entrepreneur Jonathan Fields recommends using hypothetical questions in a different way—one that can help you anticipate and come to terms with real-world problems, including failure. Fields told me he doesn’t particularly like the What if you could not fail question because "it proposes a fantasy scenario. I’m more interested in taking people through a series of questions that will actually empower you to take action in the face of the reality that you might fail." Fields suggests that we use questioning to confront failure head-on by asking: What if I fail—how will I recover?
Often when we think about failure, Fields says, "we do so in a vague, exaggerated way—we’re afraid to even think about it clearly." But if before embarking on a high-risk challenge, you visualize what would actually happen if it failed—and what you’d likely have to do to pick up the pieces from that failure—this can help you realize that, as Fields says, "failure in any endeavor is rarely absolute. There is a way back from almost anything, and once you acknowledge that, you can proceed with more confidence." (The psychiatrist and author Judith Beck told me that she uses a similar question with patients—If the worst happens, how could I cope?—because, as she explained, "People’s anxiety goes down once they realize they will live through their worst fear, and that they have internal and external resources that will help them get through it.")
Another important question Fields thinks we should ask: What if I do nothing? The point being, when we take on a major challenge it’s often because we really need to change—and if we don’t go ahead with it, we’re likely to be unhappy staying put. Whatever problem or restlessness already exists may, in fact, get worse. "There is no sideways," Fields says; if you’re not moving forward, you’re moving back.
Lastly, Fields suggests, ask yourself: What if I succeed? "That’s important because the way our brains are wired, we tend to automatically go toward the negative scenario. So in order to give your mind a chance to latch on to something positive, something that will actually fuel action rather than paralysis, it’s helpful to create some level of clarity around what success in this endeavor would look like." In other words, give yourself a strong incentive to want to risk failure.
The blogger Chris Guillebeau is getting at a similar idea in this post, wherein he puts yet another spin on the Schuller question. "Instead of thinking about what you would do if you knew you wouldn’t fail," Guillebeau writes, "maybe a better question is . . . What’s truly worth doing, whether you fail or succeed?"
Of course, if failure does become a reality, as it often does when taking on worthwhile challenges, a whole new set of questions become important—the kind that can help you analyze the failure, learn from it, and figure out how to use it to keep moving forward on the challenge. There are many such questions, but here’s one, in particular, to keep in your back pocket and use when needed: In this failure, what went right?
It’s a question people rarely ask about failure "because they’re completely focused on what went wrong," says Stanford University’s Bob Sutton, author of Scaling Up Excellence. But by paying attention to the small successes within a failure, we’re reminded that failure often is not absolute, nor is it an endgame—it is an instructive stage, and one step on a longer journey.