Sitting Next to Me on the Plane
Excuse me, I'm curious about...
A couple of essays back, I shared the story of sitting behind a celebrity and finally gathering the courage to ask her for a selfie on behalf of my wife. That moment got me thinking. What if I hadn’t been seated a couple of rows behind her? What if we had been seated next to each other? What’s one question I would ask her, and why?
My mind works that way. As an executive coach, my stock in trade is asking clients questions of curiosity that help them clear away the brush that stands in their way of achieving the life and leadership they desire.
And as the host of a weekly podcast, Getting Unstuck–Cultivating Curiosity, I have the stated mission of of bringing guests to the microphone who will make us think, “I didn’t know anything about that,” or “That’s something I hadn’t considered,” or “I might be able to apply that to some aspect of my life.” I end each episode by allowing my guest to ask me the last question.
“Context” is my number 1 StrengthFinder skill. I’m always curious to know why someone said what they said, behaved a certain way, or thinks a certain way. I love people’s back stories, how life’s twists and turns brought them here. I’m not saying we have to become forensic reporters with those we meet, but being genuinely interested in someone breeds respect and empathy—both of which are in short supply these days.
So, after publishing the Substack, I was curious how colleagues, friends, and family would respond to the questions: “Who would you want to sit next to on a plane? What’s one question you would ask them and why?” I was curious about who they would ask, but even more so about what they would ask and why. What were they curious about?
Here are some of their responses to the scenario, edited for brevity.
Julie I. I would love to sit next to my Grandma Lena, because I never got to meet her. I would have enough questions to pass the time on an overseas flight: Why did you come to America at that time? What was it like to be on the boat leaving your home? What did you feel the first time you saw America? Why did you settle in Chicago?
Neil H. I’d want it to be Sir Tim Berners-Lee who gave the world the World Wide Web. I’d love to ask him, “If you were redesigning the web today from scratch, knowing everything you know about misinformation, surveillance, and walled gardens, what would you build differently, and how do you keep faith that the web can still live up to its original promise?” It’s a curiosity that reflects my work on unpacking how technology solves real problems while staying rooted in values that serve everyone, not just a few.
Christine M. I would be sitting between Barack and Michelle Obama. I’d be curious to know how they'd help the United States regain a kinder, more compassionate, and more intelligent leadership position in the world, because that’s what the world needs from us.
Paul M. I’d want to be seated next to Winston Churchill historian Andrew Roberts. And I‘d be compelled to ask him two questions: 1. With so many books already written on Winston Churchill, what inspired you to write another? (His book is universally considered one of the best written on Churchill, by the way.) And 2. What is the great topic that has so far eluded you?
Sarah E. I’d love to sit next to Sally McMullin, the Instagram host of “Black History We Should All Know.” She appears to be a fun, warm, thoughtful, and approachable person. I could learn a lot from her, perhaps, as she answers my question: “I’m curious if you had a few moments in the early days of posting ‘Black history we should all know', when you considered giving up on the idea. If so, what prompted that thinking, and what specific thing happened afterward that made you decide to continue?
Charlotte W. I think having Iain McGilchrist available for a long flight would be a real treat. I just finished his book, The Master and His Emissary. It’s a book about the differences between our brain’s right (the master) and left (the emissary) hemispheres, and how those differences have influenced culture and history. I’d ask him, what would it take to rebalance the power between the master and the emissary? Heavy reading, but lovely for a nerd like me.
Melissa H. I’d love to be seated next to Dan Ariely. I’ve read everything he’s written, and I’ve listened to every recording of him out there. I have this fantasy of sitting at the bar and sharing a bottle of wine, digging into behavioral economics and quirky psychology studies. I think it’s partially because he seems so down to earth and approachable and funny…and SMART! If I have two more picks, I’d add Daniel Pink and Daniel Kahneman to the list for pretty much the same reasons. And now that I’m seeing all three are men named Daniel, I’m wondering what that says about me!
Penelope T. If I had an opportunity to sit next to someone famous on a plane, it would have to be Eric Kripke, the creator of the show I became a superfan of: “Supernatural.” I would ask him where he got his ideas about leadership, which he appears to understand at a biological level.
Dennis P. If I could sit down next to anyone on a plane, it would be Brian Wilson. I'd love to hear how he translated his internal musical visions into iconic recordings and the stories that inspired his songwriting. Beyond the music, I'd be curious about how Brian navigated mental health struggles amidst his groundbreaking work. It would be an unparalleled opportunity to learn from a musical giant who profoundly influenced my life.
Rich G. I was on a flight to San Diego with my family last month when our plane was delayed. A fellow passenger who was also going to miss his connecting flight showed me how to use the airline's app to reschedule. Thanks to his help, I was able to book a later flight with five open seats for my family before they filled up. I was so grateful for his kindness and was inspired by his stories of traveling the world on a whim. I’d be curious to ask him, Where to next and why there?
And then, of course, there’s me. My father was the first person who came to mind. I knew he had emigrated with his parents from Europe in the early 1900s, that he grew up in Chicago, and that he met my future mom during the early days of World War II, where he managed a war production factory, and she was his assistant.
My dad was hardworking and a good provider, but if our lives together were illustrated by a paint-by-number canvas, there would be a lot of white space and numbers yet to be filled in. Both he and my mother were very private. I’d love to ask him what he loved about my mom beyond her outward beauty. Would it be for the same reason(s) I would share? That question would tell me a lot about him and her.
I’m curious, who would you want to sit next to on a plane? What one question would you ask them and why?
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Episode 338 is one of my all-time favorite conversations. Anthropologist Elizabeth Keating, PhD, wrote a powerful book on the questions we could be asking our elders now. Don’t wait until it’s too late.
Intriguing idea here and interesting to read people's reflections. Interesting that we're both interested in life's twist and turns today, eh?! I can think of a lot of people I'd want to sit next to, but maybe Stephen Sondheim or Leonard Bernstein would be great? Only if they'd be willing to spend the entire time talking about their creative process. Or maybe the two of them together? Wouldn't that be fun?
A rather pedestrian response from me, but I'd love to fly & share thoughts with Igor Sikorsky. As a helicopter pilot for 35+ years, I'd love to ask the inventor of those quirky, noisy, unstable, and absolutely fascinating aircraft what his inspirations were along the way, and about his biggest challenges solving each aeronautical riddle. I suppose I'd have to thank him for facilitating my flying career, and for allowing me to have such a damn good time at work!