Wait, What?

"...questions are just as important as answers, often more so. The simple truth is that an answer can only be as good as the question asked. If you ask the wrong question, you are going to get the wrong answer."

- Wait, What?, page 12

As children, we ask questions to gain an understanding of the world around us. James E. Ryan was no different. Or perhaps he was. His curiosity as a child was rarely sated (“In short, I was annoying,” he jokes) and, unlike many of us, he never lost his inquisitive nature. If anything, it’s continued to flourish over the years, and has held him in good stead in his career as a lawyer (the vocation his father predicted for him many years before) and now as the dean of Harvard University’s Graduate School of Education.

When he delivered a commencement speech on life’s five essential questions, Ryan was astonished when it became a viral sensation. He expanded the lessons into book form, and Wait, What? is the result. It’s a wonderfully poignant manifesto on how staying curious and learning to “cultivate the art of asking good questions” can, quite literally, transform your life.

The Big Idea

The Big Idea: The biggest takeaway from the book

Life’s Essential Questions

"These are the questions you should ask yourself and others on a regular basis. If you get into the habit of asking these five questions, you will live a happier and more successful life. You will also be in a position, at the end of the day, to give a good answer to what I will call the bonus question—which is probably the most important question you will ever face."
- Wait, What?, page 1

Ryan acknowledges that this claim might “seem grandiose and even a bit outlandish.” However, hear him out. He has narrowed down five questions that he deems life’s most essential. They are:

“Wait, what?” is at the root of all understanding.
“I wonder…?” is at the heart of all curiosity.
“Couldn’t we at least…?” is the beginning of all progress.
“How can I help?” is at the base of all good relationships.
And “What truly matters?” helps you get to the heart of life.

There is also a bonus question, perhaps the most important one of all: “And did you get what you wanted from this life, even so?” This quote is from a poem by the great American writer Raymond Carver, who was suffering from cancer at the time he wrote it. It’s an important question, Ryan says, because while it acknowledges life’s challenges, it speaks to our power to rise above them to attain “joy and contentment.” It also helps you “consider now what will likely matter to you when your time has run out.”

While we don’t have the space to delve into each of the questions individually, the remainder of the summary will go into a deep dive on two of them: “Wait, what?” and “What truly matters?”

Insight #1

An actionable way to implement the Big Idea into your life

Wait, What?

"‘Wait, what?’ is first on my list of essential questions because it is an effective way of asking for clarification, and clarification is the first step toward truly understanding something"
- Wait, What?, page 26

The question that inspired the book’s title is an important one, both in our personal and professional lives. It is, as Ryan writes, “remarkably flexible.” It can be used to ask someone to repeat what they just said, or to express incredulity. Its lack of grammatical correctness can be compensated for by its power to illuminate something we don’t understand, which is at the crux of what makes this question so crucial.

So many of us are reluctant to ask clarifying questions. I’m certainly guilty of it from time to time, and I bet you are, too. We don’t want to appear dumb in front of our colleagues, or our boss, so we keep our mouth shut and nod our head in assent rather than put our hand up and ask for clarification. The next time you don’t understand something, or want to understand something better, politely interrupt with “Wait, what?” You’ll be surprised how it can improve not only your understanding of any given situation, but your relationships with others.

And, as Ryan reminds us, “it is better to ask clarifying questions first and to argue second,”  something else we’ve all been guilty of on occasion.

Words to live by!

Insight #2

An actionable way to implement the Big Idea into your life

What Truly Matters?

"...you should ask this question of yourself, and you should answer it honestly and fearlessly. If you do, this question won’t just help you get to the bottom of an issue or problem. It will also help you get to the heart of your life."
- Wait, What?, page 125

“What truly matters?” is perhaps the question that resonated most strongly with me. It cuts to the heart of what’s important in any situation. On a deeper level, it’s a question that many of us spend our lives attempting to answer (unfortunately, many of us in vain or until it’s almost too late). Ryan, who has read more than his fair share of obituaries and memorials, has noticed a common theme that seems to run throughout each of them, and believes “what matters” boils down to four categories:

  1. Family
  2. Friends
  3. Work
  4. Acts of kindness

This sounds deceptively simpleor perhaps even monotonous. As he explains, “within these broad categories, you still have to figure out for yourself what truly matters.” It’s going to be entirely different for each of us, and that’s a beautiful thing.

James E. Ryan’s Wait, What? is a slim volume, but its size belies its potencyit packs a mighty punch and speaks to the importance of crafting good, incisive questions. If you still need more convincing on the necessity of cultivating the art of asking good questions, I’ll leave you with this quote from the book: “[Albert] Einstein, who was a big believer in the importance of asking questions, famously said that if he had an hour to solve a problem, and his life depended on it, he would spend the first fifty-five minutes determining the proper question to ask.”

Are you going to devote more time thinking about the right questions to ask?

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Andy Budgell

ABOUT Andy Budgell

Andy is the Managing Editor at Actionable Books. A graduate of the University of Waterloo's English Rhetoric and Literature program, Andy brings a love of words to Actionable, and complements the team with his distinct writing ability, amazing customer service, and a passion for film.
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