5 Truly Essential Questions in Life That You Should Regularly Ask Yourself and Others

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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. – Dean James Ryan

A friend of mine shared the below video with me a few days ago and I really liked it, and now I am sharing it with you, hoping that it ignites something new in you.

The short clip titled: “Dean James Ryan’s 5 Essential Questions In Life” is taken from Ryan’s remarks at the 2016 HGSE Presentation of Diplomas and Certificates.

These are the 5 truly essential questions that you should regularly ask yourself and others, according to Dean James Ryan:

1. Wait, What?

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?”

2. I Wonder, Why or If?

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?


3. Couldn’t we at least…?

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?

4. How can I help?

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.

5. What Truly Matters?

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.

..the bonus question is from a poem by Raymond Carver, called “Late Fragments.” that starts with the question, “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 myself
beloved on the earth.”

So my wish for you, myself, and all of us,is that we never stop asking and listening for good questions, to feel beloved on this earth, and to make this world a better place by helping others.

This is the full commencement speech he gave at Harvard a few weeks ago:

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