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What Are You So Afraid Of?

Ask yourself these “courageous questions” to overcome fear of failure.

Warren Berger
Source: Warren Berger

As a questionologist, I have a tendency to think that asking questions can help with just about anything. But can questioning enable you to contend with a force as primal and powerful as fear? Unquestionably, yes.

To begin with, questioning can help us identify unspoken fears that may be influencing decisions and behaviors. “It can be hard to figure out what you’re really afraid of,” says Khe Hy, who often writes about fear (and other issues) in his popular Rad Reads blog. Hy told me that in his previous career as a high-flying hedge-fund manager on Wall Street, he was often wracked by restless anxiety without understanding why.

Then one day, a life coach posed a simple question to him: What are you so afraid of?

When he actually thought about that question, Hy says, he realized that fear was a driving force behind his need to keep earning more money and attaining higher levels of success in the financial world. No matter how much money he made, he was still afraid of ending up broke. He also feared that he’d die before he could leave his mark on the world. And he worried he’d fail to live up to expectations of others.

In Hy’s case, thinking about that question set him on a journey that led to a career change and a whole new way of life (his blog, podcast, and Snapchat messages have become so popular that CNN dubbed him “an Oprah for millennials”). Most importantly, he was able to tame those unspoken fears by acknowledging them.

“It can be hard to figure out what you’re really afraid of,” says Hy. “But often, once you do identify it and verbalize it—in my case, it was the fear that I’d end up broke or dead, or both—you can start to come to grips with it.”

If What am I afraid of? is the first question to ask about fear, the second may be, Why I am I so afraid of it?

My friend Phil Keoghan, a lifelong adventurer and fear-conqueror who hosts the television series The Amazing Race, often coaches people to help them overcome a range of fears, from fear of heights to fear of sharks. He finds that asking probing questions can help in gaining an understanding of why one has certain fears. Keoghan says he begins by asking someone: What is your earliest memory of this fear? In dissecting the fear, he says, “We talk about the irrationality of it—and about real versus imagined risks.”

He also asks: What has this fear kept you from doing? How might things change if you were able to overcome this fear? Those questions focus on the positive benefits of overcoming a fear.

Feeling Like You’re Making a Difference Makes a Difference

The life coach Curt Rosengren points out that it’s critical to emphasize the motivation for 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 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 can inspire you and pull you forward”—and it becomes easier to move past fear.

When you’re deciding on a possibility that makes you uneasy, try focusing on the positive feelings associated with taking a risk. The business consultant Adam Hansen says that when his clients are considering a choice that makes them nervous, he advises them to consider: 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 this, come right out and ask: What is the worst that could happen?

That’s an old, familiar question (perhaps your mom used it long ago to encourage you (I know mine did). But that doesn’t make it any less powerful. The question is a favorite of professional risk managers, coaches, and psychologists, as well as moms. 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.

Imagining the Way Back from Failure

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 “pre-mortems” (doing a post-mortem 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 pre-mortem into question form, you might ask: If I were to fail, what might be the reasons for that failure? Decision researchers say using pre-mortems 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 lessens 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 natural tendency to give too much weight to negative possibilities. 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 on 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 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 fear of heights, he logically starts with going to the top of a low structure before moving to a higher one.

Using Questions to Shift Reality

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 it was quoted in a 2010 TED Talk by Regina Dugan, a technologist who has worked with Google and DARPA. But the question goes back way before that: more than three decades ago, the American pastor Robert Schuller used it in inspirational sermons and books.

A reality-shifting question can permit us to see the world through a different lens. 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 on 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 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.

TAKEAWAYS: ‘Courageous Questions’ to overcome fear of failure

  • What would I try if I knew I could not fail? Start with this favorite Silicon Valley question to help identify bold possibilities.
  • What is the worst that could happen? This may seem negative, but the question forces you to confront hazy fears and consider them in a more specific way (which usually makes them less scary).
  • If I did fail, what would be the likely causes? Do a “pre-mortem” on a possible failure, listing some of the potential causes; this tells you what pitfalls to avoid.
  • … and how would I recover from that failure? Just thinking about how you would pick up the pieces if you did fail tends to lessen the fear of that possibility.
  • What if I succeed—what would that look like? Now shift from worst case to best-case scenario. Visualizing success breeds confidence—and provides motivation for moving forward.
  • How can I take one small step into the breach? Consider whether there are “baby steps” that could lead up to taking a leap.


...CNN dubbed him “an Oprah for millennials”… Heather Long, “Meet Khe Hy, the Oprah for Millennials,” CNN Money, Dec. 31, 2016.

...often coaches people to help them overcome a range of fears (from fear of heights to fear of sharks). Keoghan’s tips are extracted from my interviews with Keoghan for the [CE1] book, No Opportunity Wasted, by Phil Keoghan with Warren Berger, (New York: Rodale, 2004).

“… focus on the positive energy of the desired outcome,” Rosengren advises … Curt Rosengren, “8 Fear-Busting Questions,” Passion Catalyst (blog),

...“Within this scary possibility, what excites me?” … From my interview with Adam Hansen, who also discusses this in his book, Outsmart Your Instincts: How the Behavioral Innovation Approach Drives Your Company Forward, by Adam Hansen, Edward Harrington, and Beth Storz (Minneapolis: Forness Press, 2017).

...The author and entrepreneur Jonathan Fields notes that often when we think about failure… From my interview with Jonathan Fields in 2013 for A More Beautiful Question. A couple of Fields’s comments here originally appeared in that book.

...The scientist and decision-making expert Gary Klein is a proponent of using “pre-mortems” … Gary Klein, “Performing a Project Premortem,” Harvard Business Review, Sept. 2007,

...a 2012 TED Talk by Regina Dugan, a technologist who has worked with Google and DARPA” … Regina Dugan’s March 2012 TED Talk, “From Mach 20 Glider to Hummingbird Drone”

...the American pastor Robert Schuller used it in inspirational sermons and books... Pastor Robert H. Schuller, Possibility Thinking: What Great Thing Would You Attempt. . . . If You Knew You Could Not Fail? (Chicago: Nightingale-Conant Corp., 1971[CE1] ).

...An interesting variation on the What if I could not fail? question was explored in the New York Times by the writer Ron Lieber… Ron Lieber, “‘What Would You Do If You Weren’t Afraid?’ and 4 Money Questions from Readers,” “Your Money” column, ˆSept. 2, 2016,

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