Questioning can help us identify the fears that may be influencing decisions and behaviors. “It can be hard to figure out what you’re really afraid of,” says Khemaridh Hy, a popular blogger and podcaster who CNN has dubbed “an Oprah for millennials.” “But often, once you do identify it and verbalize it—for instance, the fear that I’ll end up broke or dead or both—you can start to come to grips with it.”

Phil Keoghan, a lifelong adventurer and fear conqueror who hosts the television series The Amazing Race, agrees that asking probing questions about one’s fears is a good starting point for overcoming them. Keoghan has coached people to help them conquer a range of fears (from the fear of heights to the fear of sharks), and he says he often begins by asking: What is your earliest memory of this fear? How do you react to it? What has it kept you from doing? How might things change if you were able to overcome this fear? In dissecting the fear, “we talk about the irrationality of it—and about real versus imagined risks,” he says.

Notice Keoghan’s last two questions focus on the positive benefits of overcoming a fear. The life coach Curt Rosengren points out that it’s critical to emphasize the Why? when trying to overcome fears—as in, Why would I want to do this thing or make this choice, even though it scares me? “Rather than focusing on what you are going to do (the thing inducing the fear), focus on the positive energy of the desired outcome,” Rosengren advises. That outcome may be a personal benefit or it might involve having a positive impact on others. Either way, when the answer to Why am I doing this? is about making a difference, “that inspires you and pulls you forward”—and it becomes easier to move past the fear.

When you’re deciding on a possibility that makes you uneasy, focus on the positive feelings associated with taking a risk. Adam Hansen, coauthor of Outsmart Your Instincts, suggests clients ask themselves: Within this scary possibility, what excites me?

But it’s also important to examine the negative feelings that may be associated with taking a risk—which can be based on legitimate concerns about what might go wrong if you pursue a risky possibility. Rather than avoiding thinking about these, it’s generally better to come right out and ask: What is the worst that could happen?

That’s a familiar question and a fairly basic one—but that doesn’t make it any less valuable. The question is a favorite of not only professional risk managers but coaches and psychologists as well.

And though it may seem like a negative question because it evokes worst-case imaginings, as long as it is paired with a more positive follow-up question—And how would I recover from that?—it can actually end up lessening your fears and giving you the confidence to take on the risk.

The author and entrepreneur Jonathan Fields notes that often when we think about failure, “we do so in a vague, exaggerated way—we’re afraid to even think about it clearly.” But before embarking on a high-risk challenge, if you visualize what would actually happen if you 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 scientist and decision-making expert Gary Klein is a proponent of using “premortems” (doing a postmortem in advance) to envision what a potential failure might look like, so that you can then consider the possible reasons for that failure. To put the premortem into question form, you might ask: If I were to fail, what might be the reasons for that failure? Decision researchers say using premortems can temper excessive optimism and encourage a more realistic assessment of risk. Here again, the main benefit of thinking about failure in advance is that it tends lessen the fear and uncertainty surrounding possible failure; if you can begin to envision it, you may see it’s not necessarily catastrophic and that there are ways to respond if it actually happens.

While you’re envisioning the possibility of failure, be sure to consider the opposite, as well, by asking: What if I succeed—what would that look like? Jonathan Fields points out that this question is important because it can help counter the negativity bias. Fields recommends visualizing, in detail, what would be likely to happen in a best-case scenario. The reality may not live up to that, but that vision can provide an incentive strong enough to encourage taking a risk.

That still doesn’t make it easy to actually move forward with a high-risk decision or course of action. The consensus among those who’ve studied and worked on overcoming fear seems to be that questioning, envisioning, and advance planning can take you only so far—at some point, there’s no substitute for action. (The person with a fear of water inevitably must enter the water.) But even at this action stage, there is a useful question to ask: How can I take one small step into the breach? Phil Keoghan finds that when he’s coaching people on overcoming fears, he develops a plan that starts with small steps and limited exposure to the source of the fear. For someone conquering a fear of heights, he logically starts with going to the top of a low structure before moving to a higher one.

A similar strategy can be used with almost any high-risk venture. In business, concerns about introducing a new product can be eased by starting with a limited introduction of a low-cost “beta” version of the offering before diving in with a full-scale rollout of a finished product. Almost any business trying to be innovative today has to become practiced at asking two questions: How can we generate more ideas? and just as importantly, How can we quickly and inexpensively test those ideas? Knowing how to answer the second question makes it feasible—and less risky—to pursue the first.

One of the powerful things you can do with a question is use it to temporarily shift reality. The question What would I try if I knew I could not fail? is a great example of a reality-shifting question, and it’s one I’ve been sharing with audiences for the past few years. I’m not the only fan of it—it’s been a popular question in Silicon Valley ever since a similar version was quoted in a 2012 TED Talk by Regina Dugan, a technologist who has worked with Google and DARPA. But the question goes back way before that: More than four decades ago, the American pastor Robert H. Schuller used it in inspirational sermons and books.

A reality-shifting question can permit us to see the world through a different lens. “In order for imagination to flourish, there must be an opportunity to see things as other than they currently are or appear to be,” explains John Seely Brown, a technologist and futurist who works with the Deloitte Center for the Edge. “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.”

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 questions to remove real-world limitations and constraints as a means of encouraging people to think more boldly and imaginatively. For example, product developers sometimes use the hypothetical question What if cost were not an issue? in order to temporarily remove practical limits on thinking. Once the cost restraint is set aside, it allows for a much wider exploration of ideas.

Of course, in the real world, constraints do exist: Budgets are limited, and the possibility of failure is very real. The ideas that emerge during the “What if I could not fail?” stage of thinking may have to be tempered or even discarded later. But the point is to open up more possibilities (in this case, bolder and riskier ones) for consideration.

An interesting variation of the “What if I could not fail?” question was explored in the New York Times by the writer Ron Lieber. He shared the story of Daniel L. Anderson, who’d grown bored with his real estate job in Reno and was trying to decide between an offer for a “safe” job in Houston and a riskier one in San Francisco. As Anderson was grappling with the decision, a mentor asked him the question: “What would you do if you weren’t afraid?”

Anderson said that question “caused me to re-examine my situation to make sure I wasn’t doing what was easy and comfortable,” adding that he also thought of stories his mother had told him about retired friends with regrets. “I didn’t want to be that person,” he said. He ended up taking the riskier San Francisco job, where he’s now thriving. As for that “safe” job offer he turned down in Houston? It was “from a company named Enron.”

Published with permission from The Book of Beautiful Questions

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