The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead

by Warren Berger

With “capital P” Purpose the question is, Am I making a difference? With “small p” purpose the question is, Am I making a contribution?

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How might I apply my signature strengths to a pursuit that is of natural interest to me and helps others? By addressing all three “passion” elements—strengths, interests, purpose—it can help guide you to something that both engages you and enables you to use your gifts to make a difference.

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Considering how hard it is to do anything worthwhile, perhaps a good question to keep in mind is this off-color one,85 shared by Mark Manson: What is your favorite flavor of shit sandwich? As Manson explains, “Everything sucks, some of the time … So the question becomes: What struggle or sacrifice are you willing to tolerate?”

In trying to figure out your sentence—which could also be thought of as a personal mission statement—try asking, How would I like to be remembered? What matters most to me? What change would I like to create?

What was I put on this earth to do?

How can I help as many people as possible rediscover their creative confidence?

Tom’s words, “creativity has a way of spilling over into your whole life,” making it more fulfilling and productive.

In light of Sternberg’s findings, perhaps the first question any of us should ask about creativity is: Am I willing to decide in favor of it? And if so, why?

As the productivity author Phyllis Korkki puts it, “Creativity is yoga for the brain.”

If you can create, you are now more likely to be in demand. For example, creativity was never thought of as a leadership skill in the past but recent surveys rank it as a top skill of business leaders.

Many have suggested that schools train creativity out of students, though social pressures play a role, too. “As you get older, you become more aware that not everyone loves your crazy ideas,” Burkus says.

Kelley reassures students that whether they can draw well, for example, is not a measure of their creativity; that’s a specific skill, which can be developed over time. Creativity, on the other hand, is not a skill but a “mindset” or a way of looking at the world. And we all have the ability to look at something—a problem, a subject, a situation, a theme—and bring forth our own ideas and interpretations.

IF YOU WANT TO BE MORE CREATIVE, STOP ASKING THESE 6 QUESTIONS These are wrong questions that people often ask about creativity. Read the answers below—then stop asking them. Am I creative? If you’re human, you are creative. There is no “creativity gene” that some have and others lack. It’s a gift that is available to everyone. How creative am I? It’s difficult to measure or answer this (and besides, it’s not a competition). Better to rearrange the question and ask: How am I creative? You will likely find many answers to that question. Where will I ever find an original idea? (Hasn’t everything been thought of already?) You don’t have to create from whole cloth; almost every new idea consists of fragments of existing ideas. And the fragments are everywhere. Where will I find the time to create? Start by turning off your iPhone (unless you use it to create). How can I come up with an idea that will make money? Don’t begin with the outcome in mind. Find and develop a worthy idea; the money will follow (maybe). Where do I begin? You don’t need a perfect starting point. To quote the composer John Cage, “Begin anywhere.”

If you’re trying to decide whether to pursue a project and want to make sure you’re doing it for the right reasons, ask yourself, What if I knew at the outset that there was no possibility of fame or fortune from this work—would I still want to do it?

Fear of getting started—of taking that first step on a creative endeavor—is also a major obstacle, the Kelleys say. This fear is expressed in many ways, but three questions, in particular, tend to be used to avoid actually doing something creative. Beware of the three “where”s: Where will I find the time?; Where will I find an original idea?; and Where do I begin? We’ll get to the “time” issue in due course, but as for the last two, the short answers are: 1) everywhere and 2) anywhere. A longer answer follows.

To be inspired by things that already exist in the real world—that are all around us, waiting to be noticed and then reimagined in a whole new form—is the way most original creations come into existence, notes Myths of Creativity author David Burkus. But that’s not the way we tend to think about creativity.

Burkus cites the “originality myth”—the notion that creativity must come from completely original ideas or sources—as one of great misconceptions about creating. “Almost all new ideas are combinations of preexisting ideas,” he says. He points to the iPhone as a prime example—in 2007 Steve Jobs combined elements of the cell phone, Blackberry, camera, and iPod into that highly original combo package.

What is lacking here? What is happening that doesn’t make sense? What is the story that is not being told? How might the whole thing be reinvented or turned upside down? And the most critical question: Why might I want to take on this problem and make it my own?

TO FIND YOUR BIG IDEA, ASK THESE QUESTIONS What stirs me? To find a “problem” that’s worth devoting your creative efforts to solve, start with a high interest level—meaning it touches on something that matters to you. What bugs me? Frustration is the starting point for many innovations and creative breakthroughs. What’s missing? Whereas the previous question may focus on existing problems or inadequacies, this one focuses on the absence of something—a product that doesn’t exist but should, a need not addressed, a perspective that is underrepresented. What do I keep coming back to? Pay attention to recurring themes that keep coming up in your work or even in your conversation. It may be a sign that your big idea is trying to find you. What is ripe for reinvention? It could be a product but also a classic story, a theme, or a genre.

TO SEE THE WORLD DIFFERENTLY, ASK What might I notice if I were encountering this for the first time? Apply this “fresh eye” approach to your job, the people around you, your everyday path to work. What if I stand on the desk? Not necessarily to be taken literally, but try changing the angle from which you view things. What is in the background? Try to focus on that which is usually obscured or ignored. What here would fascinate a five-year-old? Or a ninety-year-old? What would Seinfeld be amused by? Use a comic observer’s eye to look for inconsistencies. What would Steve Jobs be frustrated by? Use an innovator’s eye to notice inadequacies.

The simple reason most of us don’t notice the details of what’s going on around us is that we “stop looking too soon,” says Tom Kelley. It’s not just a matter of how long we look but where we focus as we’re looking.

How would a five-year-old child see this object or situation? What would the child be likely to notice?

Listening is as important as looking. When trying to “find problems” in business, keep in mind that “customers are always beautifully, wonderfully dissatisfied,”26 according to Amazon founder Jeff Bezos. They will find the problems that exist within any business offering, and they are inclined to express that dissatisfaction in some way. But if no one at the business is listening, the problem will remain “unfound.”

When am I most resonant? What are people responding to in my work?”

Just because you’ve found a problem (or it has found you), does that mean it’s the right problem for you to pursue as a creative endeavor? Grant says that when he’s deciding on a creative project, “The first thing I ask is, Do I look forward to thinking about this topic? I can get interested in a lot of things, and often the initial energy is due to the fact that new things are always fun. So I ask myself, Will I want to commit to this six months or a year down the road?”

If others are pursuing the same idea, what’s my twist? How might my approach differ from others?

BEFORE COMMITTING TO AN IDEA, ASK Can I own this problem? The best kind of problem is the one that you, alone, have noticed. But if others are pursuing it, then the question becomes: What is my special twist? What can I bring to this that others can’t? This is not so much about the approach you have in mind (that’s your special twist), but more about your talent, perspective, expertise—and how all of that can enable you to make a unique contribution to this creative challenge. Will I still love this problem tomorrow? This is a “crystal ball” question: It requires you to try to envision how well the subject, and the work itself, is apt to keep you engaged and enthused over time. What is the potential upside? Not to be confused with trying to predict hard outcomes (Will I make a million bucks on this idea?), but rather trying to envision the positive impact this project could have in a best-case scenario.

Framing a challenge as a question can help initiate the flow of ideas—because your mind (including your subconscious mind) can’t resist trying to answer a question that has been posed.

It may seem that sudden “Eureka!” insights have come out of the blue, but “they don’t come into existence from nothing,”32 notes psychology professor John Kounios of Drexel University. “Your ability to make new connections is limited—or empowered—by the amount of knowledge you have. So if your goal is to be struck by new ideas, you first have to do the relevant homework in whatever field you hope to be innovative.”

While doing research, focus on “Why?” questions to try to gain a better understanding of the problem or issue at hand. Why does this problem matter? Why does it exist in the first place? Why hasn’t someone solved it already? Why might that change now?

ASKING THESE “FOUR WHYS” WILL HELP YOU UNDERSTAND ANY PROBLEM Why does this problem matter? Use research to clarify what is at stake by digging deeper into who is affected and how. Consider the significance of that, in terms of overall effect and future ramifications. Why does the problem exist? Try to get to the root causes that put this problem into motion. (This may necessitate additional “whys” to get all the way down to the root.) Why hasn’t it been solved already? This will make clear the obstacles you are up against (and may uncover past efforts that hold lessons). Why might that change now? What are the conditions and dynamics that might bring about a desired change?

John Cleese, the great British comedian and one of the original creators of Monty Python’s Flying Circus, has had a successful second career as a creative coach to business leaders. A few years ago, while watching one of Cleese’s creativity talks,34 I was struck by his insistence that any creative person who wants to actually create must regularly escape to what Cleese called a “tortoise enclosure”—a quiet, secure place where one can be alone with one’s imagination. Cleese advised going into that shell for a designated period of time—and, he said, “you mustn’t come out until the time’s up.”

A place where there is no contact with the outside world. A place where you can be with your own self and just do or try to find out what it is that you love the most. A place where you can be distraction free.

So after asking, Why do I want to create? and What might I want to create?, be sure to ask: Where will I actually be able to create?

“Focus is the new IQ,”36 says Cal Newport,

Cal Newport suggests we flip the ratio of online time versus disconnected time. “Instead of taking breaks from digital media,40 we should allow ourselves occasional breaks to indulge in it,” he says. In other words, get into the habit of asking the reframed question, When should I take a break to connect?

The reverse psychology thing where you connect instead of disconnect. Set aside a period of time everyday to indulge in your online needs. Use only that time to do it.

IF YOU CAN’T FIND THE TIME TO BE CREATIVE, ASK YOURSELF THESE FIVE QUESTIONS If I began to see my attention as a precious resource, how might I better protect it? How can I shift from a “manager’s schedule” to a “maker’s schedule”? The former tries to fill every hour with appointments; the latter is designed with multi-hour, uninterrupted blocks. Am I pruning the vine? If you’re juggling many projects and pastimes, consider cutting back lesser ones to provide more time for the primary ones. What if I trade the morning news for the “morning muse”? The morning can be a prime time for creative thinking, so skip the morning news and march straight from the bed to the tortoise shell. Instead of taking breaks from social media, what if I reverse that? Spend more time disconnected and think in terms of taking breaks to social media.

Boredom leads to daydreaming, which is associated with creative epiphanies. We actually don’t do enough daydreaming these days, the psychologist Sandi Mann says, because “we try to extinguish every moment of boredom in our lives with mobile devices.”43 (It’s “like eating junk food,” she adds.)

We need to stop using our phones when we feel bored. We just have to feel bored from time to time to make sure that we are having moments of epiphany. These days we don’t let our mind wander off into the unknown like before. That is why there are very less ideas we have these days.

If you aspire to do more “making” (creating), consider the question, How can I shift from a manager’s schedule to a maker’s schedule?

We need to be makers. We don’t need to managers when we are making. Not saying that managing is any less thing to do. But when we do the work of making properly, we can be good managers as well is my humble opinion.

Dan Ariely points out that when we do this, we leave no time for deep creative thinking. “You open your calendar and you see a blank space45 and that seems like it’s the wrong thing,” he says. “The reality is, blank spaces are the spaces where you’re supposed to do the most meaningful work.” It’s all those other things filling up the calendar that should be seen as expendable. So the challenge is: How can we resist the urge to fill in the blank spaces?

Being busy is not the same as being productive. Sometimes we are just busy and not doing any meaningful work. So it is important that we are doing meaningful work instead of just being busy doing something that doesn’t help us or others in any meaningful way.

When scheduling creative time, another question to be addressed is: When is my creative “prime time”?

One study of successful painters, writers, and musicians found that 72 percent of them did their best work in the morning.48 And there may be good reason for that. As neurological research shows, amazing things are going on in the subconscious of your brain—mental connections are being forged, ideas are constantly forming and transforming. Your unconscious mind comes alive when you’re sleeping and dreaming. So what better time to tap into its creative power than when you’re just waking up?

Back in the 1930s, the writing teacher Dorothea Brande wrote a persuasive argument for doing creative work in the mornings, when we’re in the midst of the “waking dream.” As Brande put it: “To have the full benefit of the richness of the unconscious”49 you must begin your creative work “when the unconscious is in the ascendant.” In the mornings, Brande advised, get up a half hour earlier than usual and—“without talking, without reading the morning’s paper”—begin to write. This advice can be extended beyond writing to any creative endeavor: Get up, go someplace quiet, and start thinking and capturing ideas. Try to take advantage of what Brande calls the wonderful “twilight zone between sleep and the full waking state.”

Even before getting up from the bed, you can maximize that awakening period by summoning what Tom Kelley calls the “snooze muse.” When your alarm clock goes off, hit the snooze button and instead of going back to sleep, use that ten minutes to thi...

How can I fight through that initial period and not give up?

When we sit down for doing some creative work, we give up too easily when it doesn’t happen immediately. Instead we need to be patient with ourselves. We need to be patient not to give up too early, or sometimes we never should be giving up. The reality is creative ideas are not common. We need to let our mind wander off. We are currently in a phase where there is a shortage of focus, shortage of patience.

A creatively stimulating environment exposes you to inspiration, yet still leaves room for you to think about your own ideas. And—best-case scenario—it may result in you connecting someone else’s ideas to your own. A number of places can provide this kind of stimulation, such as a bookstore or a library. Creative advertising legend George Lois suggests this foolproof option: Go to the museum. “Museums are custodians of epiphanies.”55

It is a time to escape from “the cacophony in which it is impossible to hear your own voice,”56 as author William Deresiewicz says. It’s a time of being “unplugged,” when you can feel as if you’re plugging into your best self—the one who imagines, reasons, connects, builds.

This is one thing that the younger generation needs these days. Kids need a better place to be free from distractions and be free from all the distraction magnets like social media and other online stuffs.

Can I live with this discrepancy between imagination and reality? Or, to paraphrase Patchett, If I can’t create the thing I dream of, can I at least create the thing I’m capable of making?

It is something like don’t be disappointed with yourself. Be patient ‘bout what you can do and don’t stress more about what you want to do. No dissonance between what you can actually do and what you want to do. Understand your reality and rest assured about it.

IF YOU’RE HAVING TROUBLE GETTING STARTED ON A CREATIVE PROJECT, ASK THESE SIX QUESTIONS Am I chasing butterflies? Meaning you keep thinking of new ideas instead of moving forward with an existing project. To develop an idea, you must pick one butterfly and pin it down. Who will hold me accountable? Share your idea with someone–and schedule a series of small deliverables. Am I rearranging the bookshelves? This refers to the act of “preparing to create.” It may involve setting up a workspace, taking lessons, or doing research—each of which is fine until the point it becomes a stall tactic. How can I lower the bar? Instead of trying to begin with greatness, be willing to start off with something merely okay or even bad. What if I begin anywhere? If you’re stuck trying to think of a beginning, start in the middle, at the end, or somewhere in between. Can I make a prototype? Find some way to give rudimentary form to your idea (outline, rough sketch, collage, beta website).

IDEO’s Tom Kelley suggests this starter question: What if I lower the bar? Give yourself permission to start with something rough, imperfect, maybe even lousy. Kelley cites a favorite scene from the indie film Ruby Sparks in which a writer suffering from creative block is advised to just begin writing anything. “Can it be bad?” the writer asks. When told yes, he starts writing whatever nonsense comes into his head. But quickly he starts changing and improving what he wrote, turning it into something good. This often happens in real life, says the neuroscientist Robert Burton. If you shift to the “editor off” mode of your mind64 “and you’re willing to write anything, without regard to whether it will work or not, new ideas will emerge,” Burton explains.

The very first idea about anything is always a boring idea. It is not the best one. Think about all the devices that Apple brings out. Their first version always sucks. Always.

Grant sometimes tries to see through the lens of people who might have a particular connection to the issue at hand. But he also tries to tap into the perspectives of a “standard set of original thinkers I admire,” he says. “Some of my favorite research projects have started with asking, What would Lincoln think in a situation like this?” Grant also tries to time-shift his own perspective: “Another question I use is, If I would have tried to tackle this problem ten or twenty years ago, how would I have approached it differently? Then I’ll mentally time travel forward as well and ask, If I were to imagine future me, ten or twenty years ahead, how do I imagine I’d look at this problem differently? The past one helps me shed assumptions I’m making. I like to go ‘past’ first, then ‘future.’