5 Essential Questions in Life

Guest Post by Dean James Ryan

Note from Bob:  It is Graduation Season! Here is an incredible commencement address to the graduating class of 2016 by Dr. James E. Ryan, who was then the Dean of the Harvard University Graduate School of Education.  Today Dr. Ryan is the President of the University of Virginia.  Dr. Ryan offered remarkable advice to graduates eager to make their mark on the world. The key to achieving emotional connections and social progress he told them, can be found in “5 Essential Questions in Life.”  Below is both the video excerpt and transcription of Dr. Ryan’s address.   Dr. Ryan’s book: “Wait, What? And Life’s Other Essential Questions” .

My final suggestion is that there are five truly essential questions that you should regularly ask yourself and others. My claim is that, if you get in the habit of asking these questions, you have a very good chance of being both successful and happy, and you will be in a good position to answer “I did” to the bonus question at the end.

The first is a question my own kids are fond of asking, and it’s one you may have heard other teenagers pose — or maybe you still pose it yourself. The question is “Wait, what?”

My kids typically pose this question when I get to the point in a conversation where I’m asking them to do a chore or two. From their perspective, they hear me saying something like: “blah, blah, blah, blah, and then I’d like you to clean your room.” And at that precise moment, the question inevitably comes: “Wait, what? Clean what?”

“Wait what” is actually a very effective way of asking for clarification, which is crucial to understanding. It’s the question you should ask before drawing conclusions or before making a decision.  The Dean of Harvard College, Rakesh Khurana, gave a great master class this year, where he emphasized the importance of inquiry before advocacy. It’s important to understand an idea before you advocate for or against it. The wait, which precedes the what, is also a good reminder that it pays to slow down to make sure you truly understand.

The second question is “I wonder” which can be followed by “why” or “if.” 

So: I wonder why, or I wonder if. Asking “I wonder why” is the way to remain curious about the world, and asking “I wonder if” is the way to start thinking about how you might improve the world. As in, I wonder why our schools are so segregated, and I wonder if we could change this? Or I wonder why students often seem bored in school, and I wonder if we could make their classes more engaging?

The third question is: “Couldn’t we at least…?”

This is the question to ask that will enable you to get unstuck, as they say. It’s what enables you to get past disagreement to some consensus, as in couldn’t we at least agree that we all care about the welfare of students, even if we disagree about strategy? It’s also a way to get started when you’re not entirely sure where you will finish, as in couldn’t we at least begin by making sure that all kids have the chance to come to school healthy and well-fed?

The fourth question is: “How can I help?”

You are at HGSE, I presume, because you are interested in helping others. But you also know, from your time here, to be aware of the savior complex, of the stance where you are the expert or hero who swoops in to save others. We shouldn’t let the real pitfalls of the savior complex extinguish one of the most humane instincts there is — the instinct to lend a hand. But how we help matters as much as that we do help, and if you ask “how” you can help, you are asking, with humility, for direction. And you are recognizing that others are experts in their own lives and that they will likely help you as much as you help them.

The fifth question is this: “What truly matters?”

You can tack on “to me” as appropriate. This is the question that forces you to get to the heart of issues and to the heart of your own beliefs and convictions. Indeed, it’s a question that you might add to, or substitute for, New Year’s resolutions. You might ask yourself, in other words, at least every new year: what truly matters to me?

So these are the five essential questions:

  • “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 really matters” gets you to the heart of life.

If you ask these questions regularly, especially the last one, you will be in a great position to answer the bonus question, which is, at the end of the day, the most important question you’ll ever face.

This bonus question is posed in many ways, and you have surely heard a version of it before.

To me, the single best phrasing of this question is in a poem by Raymond Carver, called “Late Fragments.” It’s one of the last poems he wrote. I came across it recently on the very sad occasion of a memorial service for one of my dearest and closest friends, my former law school roommate Doug Kendall, who died in September at the far too young age of 51. The poem was printed on the back of the program for his memorial and it starts with this question, what I’m calling the Bonus Question:

“And did you get what you wanted out of life, even so?”

The “even so” part of this, to me, captures perfectly the recognition of the pain and disappointment that inevitably make up a full life, but also the hope that life, even so, offers the possibility of joy and contentment.

My claim is that if you regularly ask: wait, what, I wonder, couldn’t we at least, how can I help, and what really matters, when it comes time to ask yourself “And did you get what you wanted out of life, even so,” your answer will be “I did.”

So the poem asks “And did you get what you wanted out of life, even so,” and then continues:

“I did./And what did you want?/To call myself beloved. To feel beloved on the earth.”

The word “beloved” is important here as it not only means dearly loved, but also cherished and respected. And while I promise I’m very near the end of my speech, let me just say that when I read these lines, it’s hard for me not to think about students. We spend a lot of time, here and elsewhere, thinking about how we might improve student performance, which is how it should be. Yet I can’t help but think that schools, and indeed, the world, would be better places if students didn’t simply perform well but also felt beloved — beloved by their teachers and by their fellow classmates.

To tie this all together into one slightly misshapen package, and to bid you a final farewell: As you leave Appian Way and head into a world that desperately needs you, let me express my sincere hope and belief that: if you never stop asking and listening for good questions, you will feel beloved on this earth, and, just as importantly, you will help others, especially students, feel the same.

Dr. James E. Ryan


Dr. James E. Ryan is the 9th President of the University of Virginia.  Before coming to UVA, Dr. Ryan served as dean of the Harvard Graduate School of Education. He received his A.B., summa cum laude, from Yale University and his J.D. from the University of Virginia, which he attended on a full scholarship and from which he graduated first in his class. After law school, Dr. Ryan clerked for Chief Justice William H. Rehnquist, and then worked in Newark, N.J. as a public interest lawyer before entering into teaching. Jim and his wife, Katie, have four school-age children.  His  book, “Wait, What? And Life’s Other Essential Questions” can be ordered by clicking “Here.”


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