Wait, What?: A Thought-Provoking Guide To Asking The Right Questions

by James E. Ryan

If you commit to asking “I wonder why?” you can prod yourself to remain curious. Even if others get tired of hearing it or cannot answer the question, you should never stop posing it to yourself.

Thoreau observed: “We are never prepared to believe that our ancestors lifted large stones or built thick walls. How can their work be so visible and permanent and themselves so transient? When I see a stone which it must have taken many yoke of oxen to move, lying in a bank wall . . . I am curiously surprised, because it suggests an energy and force of which we have no memorials.” What started as largely invisible walls turned into a local history lesson and a set of existential questions from Thoreau,

Everyone has a unique story. To hear these stories, and to understand the world around you, from the beliefs and values of a community to the experiences of the people in it, you simply have to take the time to notice and to ask “I wonder why?”

Curiosity, it turns out, is conducive to health and happiness, as scores of social scientists have documented. Curious people, not surprisingly, are likely to learn more and to retain more of what they learn. Curious people are likely to be more attractive to others, as people are attracted to those who seem interested in them.

Just as asking “I wonder why?” will keep you curious about the world, asking “I wonder if?” will keep you engaged in the world. Nearly every adventure I have been on, and nearly every new thing I have tried, began with the question: “I wonder if I could do that?” The answers have not been uniform.

to ask “I wonder why?” about the present naturally raises the question “I wonder if?” about the future.

de facto segregation, the legal term for segregation “in fact,” meaning segregation that does not arise because of laws compelling it, but is instead caused by a range of other factors. This type of segregation continues to exist.

Desegregation decrees, which were always meant to be temporary, are being lifted by courts, so programs to integrate schools are being dismantled; neighborhoods remain segregated, so neighborhood schools remain segregated; and charter schools tend to focus on serving poor students of color, not on creating integrated schools.

the very first step toward altering what you see is to ask “I wonder why?” and then to follow that question with another: “I wonder if?”

This is not a story about changing the world, of course, but it did change my world, in a remarkable and meaningful way. And this leads to the final point about asking “I wonder why?” and “I wonder if?” These are questions that are useful to ask not simply about the world around you, but to ask yourself.

I believe it’s healthy and productive to remain curious about yourself. Why do you have certain habits? Why do you like certain places, foods, events, and people, and what if there are others you would like just as much, if you gave them a chance? Why do new experiences make you nervous? Why are you quiet in meetings or shy at parties? Why are you easily distracted? Why do you sometimes lose your patience with certain members of your family? And what if you tried to change those things about yourself that you would really like to change? Or, just as importantly, what if you just accepted some of those things as part of who you are?

Asking “I wonder if?” is equally essential because it is the way to remain engaged with the world and to begin thinking about ways to improve your corner of it. If you fail to ask these questions, you risk missing out on joys and possibilities that you don’t even realize exist

Like the second essential question, “Couldn’t we at least . . . ?” forms the core of a series of questions rather than one specific and complete question.

Regardless of the variety of ways this question can be posed, at its core, asking “Couldn’t we at least . . . ?” is a good way to get unstuck. It is a way to get past disagreement to form some consensus, as in, “Couldn’t we at least agree?” It’s also a way to get started even when you’re not entirely sure where you will finish, as in: “Couldn’t we at least begin?” No matter its specific form, asking questions that begin with “Couldn’t we at least . . . ?” is the way to make progress.

“Couldn’t we at least agree?” is a way to fin...

Asking “Couldn’t we at least agree?” especially in the midst of an argument, is a good way to pause, step back, and look for some areas of agreement.

After taking a step back and finding some consensus, you might have just what you need to take two steps forward, which is just how progress often works: one step back, two steps forward.

Our virtual worlds are becoming so segmented that we can even choose from different broadcasts of the same sporting event—one that favors the home team or one that favors the visiting team.

More and more, we can choose to see only what we want to see.

“group polarization.” When like-minded individuals get together, online or in real life, they tend to reinforce each other’s views. They not only increase the strength of each other’s convictions, but they often lead each other, intentionally or not, to take even more extreme positions.

“Couldn’t we at least agree?” is a way to push back against polarization and extremism, because it is an invitation to find some areas of consensus.

“Couldn’t we at least agree that everyone should care about the actual meaning of the words in the Constitution?”

“Couldn’t we at least agree that a lot of important provisions in the Constitution are open-ended and establish general principles rather than concrete and specific rules?

And couldn’t we at least agree that the application of those general principles might change over time as circumst...

finding some common ground was a first step toward persuading others to their views. And both were remarkably effective in doing just that.

Finding some common ground, in other words, can help isolate true areas of disagreement.

As the astute philosopher Mary Poppins recognized, “A job begun is a job half done.”

Too often—whether because of procrastination, fear, or a desire for perfection—we hesitate to begin a project at home or at work if we cannot see precisely how or when it will end.

German writer Goethe, is this: “Whatever you can do or dream you can, begin it. Boldness has genius, power, and magic in it.”

Asking “Couldn’t we at least take a look?” can nudge you and others to do just that.

When you ask “Couldn’t we at least . . . ?” you are essentially suggesting that you and others try to do something, whether it is to come to some agreement or to get started on something. If you don’t ask this question, you are less likely to try. And failing to try, I believe, is the source of some of our deepest regrets—indeed,

I believe that what we don’t do often haunts us more than what we actually do.

That’s the problem with not trying—you will never know what the outcome might have been. Even if you think the result would have been the same, that’s only a small comfort. When it comes to helping your friends and family, what you want most is to believe that you tried everything you could to help.

If you fail, often the worst thing that can happen is that you will have a funny story to tell. I have never heard a single funny story about failing to try.

the question “Couldn’t we at least . . . ?” sparks movement.

It is the question that nudges you and others to the starting line. It is the question, as I said at the opening, at the heart of all progress, and for that reason—as Phebe and our entire, complete family can attest—it is absolutely essential to ask.

You are recognizing that others are experts in their own lives, and you are affording them the opportunity to remain in charge, even if you are providing some help.

The Moth is a radio program and podcast that features true stories, told live by people from around the world.

She then recounted how her neighbors often came by to talk and emphasized with gratitude that, when they offered to help, they always asked how they could help. By asking her how they could help, she explained, they were allowing her to retain her independence and dignity.

bike trip from Nairobi, Kenya, to Victoria Falls, Zimbabwe.

Asking how you can help is also an effective way of nudging others to identify, express, and confront their own problems. This is sometimes understandably hard to do, as Atul Gawande describes movingly in Being Mortal, in which he recounts the difficult choices advanced cancer patients must make about their own care.

With each suggestion, he became more disagreeable, until completely exasperated, I finally asked, “Okay, this isn’t working, so maybe you can tell me how I can help you?”

To my surprise, that question made him pause. He looked around, and then he very quietly said, “I’m still hungry.” I made him another PB&J sandwich and sat with him while he ate. He was definitely hungry, but I also think he needed a mental health break. I didn’t anticipate it at the time, but by asking him to tell me what he needed, I shifted the burden to him to identify and begin to address what, exactly, was bothering him.

Yet sometimes offering solutions simply fuels the anxiety or stubbornness that your kids or students are feeling, just as occurred with the boy in ski school.

You are showing both sympathy and empathy, which is sometimes all someone needs. Put differently, in asking how you can help, sometimes you already have.

Down syndrome, whom I will call Cindy.

and I were married, I asked my friend Roger to read Robert Frost’s “A Prayer in Spring” at the ceremony. Roger had been with me in Kentucky, and it was there that I first came across this poem, which captures well what Cindy and the other kids had taught me. The poem begins: Oh, give us pleasure in the flowers today; And give us not to think so far away As the uncertain harvest; keep us here All simply in the springing of the year After encouraging the reader to enjoy the orchards, bees, and birds surrounding her, the poem ends: For this is love and nothing else is love, The which it is reserved for God above To sanctify to what far ends he will, But which it only needs that we fulfill.

“How can I help?” is an essential question. It is the question that forms the base of all good relationships. It is a question that signals that you care. It signals a willingness to help. But it also signals respect, humility, and the likelihood that, in the end, it is you who will be helped just as much.

“What truly matters?” This is the question that can just as effectively guide you through a meeting with colleagues as it can guide you through the biggest decisions in your life.

It forces you to get to the heart of issues at work or school, and to the heart of your own convictions, beliefs, and goals in life. It’s the question that can help you separate the truly important from the trivial and can help you maneuver through the minutiae in pursuit of the momentous.