“I’ve Always Been Obsessed with Questions, and with Asking the Right Question.”

Interview: Jim Ryan (or should I say James E. Ryan?).

I’ve been friends with Jim for a long, long time. It’s interesting, as you get older, to see how people appear and re-appear during your life. It’s reassuring to realize that even if you don’t see someone for years, when your paths cross, you still have that same deep friendship to rely on.

We once hung out in the Silliman courtyard at Yale — now Jim is the Dean of the Harvard Graduate School of Education, and he’s also a very distinguished lawyer.

I was very excited to read Jim’s new book. It’s already a bestseller, which is not surprising, given that it was based on a wildly popular commencement speech he gave that went viral. (You can watch an excerpt here.) Wait, What? And Life’s Other Essential Questions is a very engaging, thought-provoking book about the five essential questions that can help us build a happy, productive life.

Spoiler alert — the five questions are:

• Wait, what?
• I wonder if . . .
• Couldn’t we at least?
• How can I help?
• What truly matters?
• (plus there’s a bonus question)

As you can tell from the description of the speech and the book, Jim is a very wise person — which is an odd thing to say about someone, perhaps, but it’s true.

In fact, if you want to hear me tell the story of how Jim gave me some very wise advice when I was applying for my clerkship with Justice Sandra Day O’Connor, listen here. Jim probably doesn’t even remember that conversation! Which was so helpful to me, and which I’ve remembered so many times.

If you’d like to watch Jim’s terrific interview on CBS This Morning, it’s here.

So I couldn’t wait to hear what Jim would say about happiness and habits.

Gretchen: What’s a simple habit that consistently makes you happier?

Jim: Running.  I used to hate running when I was younger.  I played a lot of team sports, and we only ran to warm up or if we were being punished.  Over time, though, I grew to love running and about eight years ago started training for marathons with my wife, Katie.  We will be running our seventh consecutive Boston Marathon this April.

What’s something you know now about forming healthy habits that you didn’t know when you were 18 years old?

You have to focus on what you will gain from the habit and not focus solely on what you might have to give up.

Do you have any habits that continually get in the way of your happiness?

Absolutely.  The single worst is checking email more than I need to or should.  I know it’s a distraction, but I have a hard time breaking the habit.

Which habits are most important to you? (for health, for creativity, for productivity, for leisure, etc.)

I would say the ones for both health, productivity and creativity, and in some ways they are connected.  I mentioned running earlier.  This habit is related to health, for sure, but it also keeps me productive and creative—I find I think most clearly while on a long run.  The idea for my commencement speech about questions, which became the basis for my book, came to me while running.  I also carve out time a few mornings each week for writing, which is easiest for me to do first thing in the morning.

Have you ever managed to gain a challenging healthy habit–or to break an unhealthy habit? If so, how did you do it?

I started eating much healthier about 8 or 9 years ago.  I stopped drinking a coke every day, and I started eating a lot more salad, including at breakfast.

I committed to trying it for a month, and it made me feel much better, so it became pretty easy to adopt.

Would you describe yourself as an Upholder, a Questioner, a Rebel, or an Obliger?

I am definitely a Questioner—as you can probably tell from my book! {Yes, it’s so obvious that Jim is a Questioner — in fact, his whole book is designed around questions! I love seeing the Tendencies play out like that.]

Does anything tend to interfere with your ability to keep your healthy habits? (e.g. travel, parties, kids)

Travel, for sure.  I find travel for work disruptive of a lot of good habits, including eating well, getting enough sleep, and exercising.  I have yet to figure out good travel habits.

Have you ever been hit by a “lightning bolt,” where you changed a major habit very suddenly, as a consequence of reading a book, a conversation with a friend, a milestone birthday, a health scare, etc.?

Yes!  I  read Raymond Carver’s haunting short story, “A Small, Good Thing” [in the collection Cathedral] which is about a baker who harasses parents who ordered a birthday cake for their son but never picked it up or paid for it—because the son, unbeknownst to the baker, was hit by a car and died after the cake was ordered.  It made me break a bad habit of assuming I knew enough about other people to make judgments about them and their performance across a lot of contexts.

Do you embrace habits or resist them?

I embrace them, but it’s an ongoing process, for sure.  I’m not yet a creature of habit, for better and for worse.

Has another person ever had a big influence on your habits?

My grandfather.  Whenever we visited him, we participated in his morning routines—of going into town to get the paper, check the mail, etc.  I loved the regularity of it, and I admired how his following this routine or habit seemed to give him both a sense of calm and a sense of purpose.

So what inspired the speech that became the basis for the book?

I have always been obsessed with questions, and with asking the right question.  I’ve always thought of questions like keys—just like using the right key, if you ask the right question, you can unlock all sorts of mysteries about yourself and others.  The five essential questions I described in my speech and in Wait, What? are, to me, like five crucial keys on a key ring.  You will need other questions from time to time, but you never want to be without these five.  in fact, asking these five questions of myself and others, I realized while preparing the speech and writing the book, has become a habit of mine.

If you’d like to see Jim’s interview on the CBS Morning Show, watch here. [TK]

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