A More Beautiful Question (32 page)

But even though the question has some mileage on it—and even though some people believe it’s a flawed question—it exemplifies a beautiful question in its ability to inspire and spark the imagination. And it’s an appropriate follow-up to the “make one small change” recommendation. While that’s about encouraging modest actions, this question is about giving yourself permission to think big.

We’ve seen that companies sometimes use a hypothetical What If question to temporarily remove constraints that can inhibit ambitious thinking (
What if cost weren’t an issue—how might we do things differently?
), and the same principle applies when people are pursuing new ideas or embarking on change in their lives. Often the biggest constraint is fear of failure.

When I asked Sebastian Thrun why the
What if you could not fail?
question resonated with him, he responded, “People mainly fail because they fear failure.” A central tenet of Thrun’s approach to bringing about radical change, whether that involves reinventing cars or college courses, is “the willingness to fail fast and celebrate failures.” Thrun added, “Innovators have to be fearless.”

That was the message Dugan conveyed in her TED speech featuring the could-not-fail question. “If you really ask yourself this question,” she told the audience, “you can’t help but feel uncomfortable,” because it becomes clear 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.”

The notion that we should embrace failure has been a popular credo in Silicon Valley, though more recently the “failure is good” message has gone mainstream,
³⁸
showing up in, for example, a 2013 commencement speech by Oprah Winfrey. In fact, the sudden ubiquity of this idea prompted a mini-backlash from a writer on the website Big Think, who used the term
failure fetish
³⁹
to describe the trend. The writer pointed out that failure, despite all its current good press, is in reality often painful and sometimes devastating.

Nonetheless, many are pushing the “embrace failure” message. The writer Peter Sims pointed out
⁴⁰
that fear of failure has been drummed into us, starting early in life: “Your parents wanted you to achieve, achieve, achieve—in sports, the classroom, and scouting or work. Your teachers penalized you for having the ‘wrong’ answers,” Sims wrote in
Harvard Business Review
. And if anything, it only got worse as you moved into the business world, where, Sims noted, “modern industrial management is still predicated largely on mitigating risks and preventing errors.”

Meanwhile, in the more entrepreneurial and creative sectors, failure has come to be recognized and appreciated as an unavoidable—and often highly useful—step on the road to creativity and innovation. Mick Ebeling, the Eyewriter inventor, observes, “When we hit failure, I start
⁴¹
to laugh. It’s almost like checking off a box—great, we got that out of the way. Now we’re that much closer.”

Experienced creators have always known this. The poet John Keats wrote, “Failure is, in a sense, the highway
⁴²
to success, inasmuch as every discovery of what is false leads us to seek earnestly after what is true.” Those not comfortable enough to laugh at failure might start by questioning its nature, and how we perceive it.
What does failure mean to me: Do I see it as an end state, or a temporary stage in a process? How do I distinguish between an acceptable failure and unacceptable one?
(Not all failures are equal—and not all help you to move forward; some can shut everything down.)
Can I use productive “small failures” as a means of avoiding devastating “big failures”?

The author, blogger, and serial entrepreneur Jonathan Fields has known his share of setbacks and more than his share of successes; along the way, Fields has developed some interesting ideas about the questions we should ask ourselves about the possibility of failure.

Fields doesn’t particularly like the
What if you could not fail?
question. “It proposes a fantasy scenario,” he told me. “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 thinks that as we embark on a new endeavor, we should begin by confronting that possibility of failure via this question:

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. He suggests that anyone undertaking something with an element of risk start by visualizing what would actually happen if it failed and what would be needed to pick up the pieces from that failure.

This tends to clarify that failure in any endeavor is rarely total. There is a way back from almost anything, and once you acknowledge that, you can proceed with more confidence. The psychologist and author Judith Beck told me she
⁴³
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?

This underscores that when we undertake an important change, it’s often because we
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 get worse. “There is no sideways,” Fields says; generally, in life, if you’re not moving forward, you’re moving back.

Lastly, Fields says, 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,” Fields says. “So in order to give your mind a chance to latch onto something positive, something that will actually fuel action rather than fuel 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 put yet
⁴⁴
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?
”

How might we pry off the lid and stir the paint?

Considering Guillebeau’s question of what’s worth doing even at the risk of failure, the challenges that may be particularly worthy of that kind of investment are those that spark imagination, speak to the heart—and bring people closer together. The late Fran Peavey, a social activist, excelled
⁴⁵
at what she called “strategic questioning,” which I would characterize as questioning with an open mind and a caring heart. Peavey’s questioning left a mark in various far-flung corners of the world: in the slums of Bangkok, in war-torn Bosnia, in the water of India’s Ganges River, and in her adopted hometown of Oakland, California.

Peavey (who died in 2010) was, to put it mildly, a character. An oversize, exuberant woman (a journalist who interviewed her wrote that when she laughed, “her flesh wobbles . . . her chest heaves,
⁴⁶
her ears bob”), she was a sometime absurdist comedian as well as a full-time activist. When she traveled, she brought with her a handheld sign, which she’d hold up as she sat in train stations and other crowded gathering spots, reading american willing to listen.

It was an odd come-on, but it worked—people would approach Peavey, sometimes warily, to find out what she was up to. Over a couple of decades, she conducted thousands of interviews this way. “I refined my interviewing technique,”
⁴⁷
she told the
Melbourne Age
, “asking open-ended questions that would serve as springboards for opinions and stories—questions such as
How would you like things to be different in your life?
”

Peavey believed that by employing the right kinds of questions—open, curious, slightly provocative at times, but never judgmental—one could have a meaningful dialogue with people who are very different from you, culturally, politically, temperamentally. Such questions could slip under and around the barriers between people; they could help identify common ground and shared concerns. And eventually, if the questioning and the discussion went deep enough, they might begin to resolve conflicts and problems.

Peavey used her “strategic questioning” to work with people on all manner of problems. As one news report noted, she helped Thai prostitutes who were facing eviction from their neighborhood; worked on a program to feed the homeless in Osaka; got a botanic garden replanted in the Croatian city of Dubrovnik; and even helped California skateboarders who were being chased off their favorite skating places. One of her more interesting projects
⁴⁸
was a public awareness campaign about cleaning up the Ganges River. She used a series of questions to gain a better understanding of the issue, asking local residents questions such as:

How do you feel about the condition of the river?

How do you explain the condition of the river to your children?

Peavey said she chose her language carefully, trying not to use the word
pollution
(which might offend people who believed the river to be holy) and instead framing the questions and the discussion around “taking care of the river.” She could tell that people were daunted by the enormity of the task—so she began to focus the questions on a more long-term, ongoing objective:

How are you preparing your children to clean up the river?

When Peavey asked that question, people were forced to admit they weren’t doing anything in this regard. “Their love of the river, their love for their children, and the void in their answers to that question could not long exist in the same minds,” Peavey wrote. “The dissonance was too great.”

Parents responded by organizing a poster-painting contest for the children, around the theme of the health of the river. The plan was to hang the paintings in public venues so that “adults will see what the children see and be embarrassed.” In the years that followed, the contest became a large annual event. But as Peavey writes, the idea didn’t come from her—it came from the residents themselves—though it seems to have been sparked by Peavey’s question.

To Peavey, a question could serve as the lever to pry open the stuck lid on a can of paint. “If we have a longer lever, or a more dynamic question,” she wrote, it can also be used to “really stir things up.” In this metaphor, what’s being stirred are the ideas and potential answers that people already have in their heads; they just need a little mixing to help those thoughts come together. But Peavey’s approach to questioning also aimed to break down the “separation” between people based on differing cultures or views—which seems highly relevant in these polarized times.

When people are looking at issues from very different perspectives, it becomes problematic if one side tries to impose an answer on the other. Conversation either becomes argument or shuts down altogether. Perhaps the only way to break the stalemate on even the most divisive questions is to put the declarative statements on hold and try working on the following:

If we don’t agree on an answer yet, can we at least come to terms on a question?

What would you do to reach yourself?
⁵⁰

As a pastor of a bible church in a drug-riddled Philadelphia neighborhood known as the Badlands, Joel Van Dyke was determined to reach the youth of that community—but for years had no luck figuring out how to do so. Then, after stumbling upon the E. E. Cummings line about “beautiful questions,” Van Dyke decided to use questioning as an outreach tool. Instead of trying to tell local youths that he knew what they needed, “I decided to ask, ‘
What would you do to reach yourself?
’” Van Dyke’s willingness to immerse himself in the community and ask that question led to a surprising conversation. Community youths (including gang leaders) told him they very much wanted a place to play handball, but had been locked out of the local facilities. “Throw a big handball tournament,” they told Van Dyke, “and we’ll bring all our friends.” Van Dyke’s church went on to sponsor four tournaments a year, which also provided a venue to share the ministry’s message.

Former-adman-turned-activist Jon Bond,
⁴⁹
along with his wife, Rebecca, recently formed an anti-gun-violence movement called Evolve in response to the 2012 school shooting in Newtown, Connecticut. The group is working to reframe the conversation around gun control to focus on the larger question
How can we save lives?