[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.