Greg Forbes Siegman: Conversations in the Sky

Local Life, Travel Tips
Greg Forbes Siegman and a fellow traveler talk during a flight from St. Louis.

Over the past decade, as an increasing number of people have read The Silhouette Man (and its condensed edition for students, The First Thirty), its real-life subject, Greg Forbes Siegman, has been invited to speak with audiences in different states and countries. While in transit, the former educator has made a conscious effort to learn about—and learn from—flight attendants, pilots, airport staff, and other passengers on his trips to and from these events. The results reflect what is possible when we focus on the journey, not simply the destination. After meeting Siegman on a flight from San Francisco, Julia Huebner interviewed him about his “be curious” approach to travel and its ripple effects.

What inspired you to start chatting with other passengers on planes?

I like to learn, and I think we can learn something from everyone—no matter how we meet them. I also think the best way to bridge divides is to sit with someone who seems different, set aside assumptions and ask questions. Flights give us a chance to do that.

Describe some of the people you’ve met on your flights.

All ages, races, faiths, careers and nationalities imaginable. People who grew up on farms. A rapper on his way to a concert. A Veteran heading home from Afghanistan. A couple carrying the baby they just adopted. A man set free after being wrongly convicted of a crime. A cancer survivor. People between jobs. A CEO who—literally—had a box full of gold. Students commuting to campus. Lots of grandparents.

What have you learned from people of such diverse backgrounds?

The conversations have given me a chance to learn about different eras, industries and ways of life. I’ve learned about relationships. I’ve had the chance to hear different perspectives on issues and events that impact our world. The conversations have reinforced my belief that people who seem different on the surface actually have a lot in common, and my belief that we ought to give the benefit of the doubt to the people we meet. There are a lot of good ones.

Have any of these conversations continued beyond the flights?

Definitely. One time, the whole row – all strangers when we departed – went to dinner together when the plane landed. Many of the passengers and crew I’ve met on planes or in airports have become Facebook friends, and we stay in touch.  In some cases, in the months and years that followed a flight, other passengers and I have met for meals, visited each other’s homes, shared a birthday or holiday, or even taken a later trip together. New friendships don’t have to end just because the flight does.

Where else have your favorite interactions on flights led you?

In some cases, the new friendships have led to adventures and great learning experiences. On a flight from Miami, I met a mixed martial artist who arranged for me to spar for one round. I sat between two chefs on a trip to Aspen. They invited me to shadow them for a day at their restaurant. It was fascinating to see how much care they put into every meal. On a flight to Chicago, I met someone who worked at a food company. He gave me a tour of a plant where they make cereal. I loved it. It was like the Willy Wonka factory. On a flight from MSP Airport, a conversation I had with a passenger sparked a chain of events that led me to receive an offer to serve as Scholar-in-Residence for a program in Africa. A few months later, I packed my bags for Cape Town.

What if the other passengers prefer to work or sleep, or simply don’t seem interested in getting to know someone?

I sit quietly and read.

You just won a round-trip ticket to fly anywhere in the world. Where do you go and why?

London. My biggest regret is that I declined a chance to study abroad in London when I was in college. To this day, I have the offer letter framed on my wall. A constant reminder to always get on the plane.

For more on The Silhouette Man and The First Thirty, visit

Julia Huebner is a writer based in Chicago.

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