photo: richard whittaker


First, let’s do the math. In the last 15 years of my career-life that ended ten years ago, I averaged one plane trip a month. In fifteen years, that’s 180 flights, assuming one-way flights. So with the return flight, that’s 360 trips! At this moment of this writing, not having been on a plane trip for two years due to the pandemic, that seems like an almost impossibly large number.
     After we sold our regional real estate appraisal company to a multi-billion dollar national/international corporation in 1997, I soon realized that regular plane trips would be part of my job. I pondered how I might utilize this remarkable perk - paid plane travel including all amenities - as a learning opportunity.
     My base of operations was Logan Airport, Boston, about an hour from my house. I made three rules for myself that I thought would be useful to achieve my goals of being a more gracious and attentive human being.

Rule 1 – Arrive early
Generally, this meant getting to the airport an hour before it was necessary. I made this rule because when I arrived just on time, I found myself tense, like so many other tense travelers hoping to make their flights. When I was early, I could be gracious to others, and more observant about the goings-on around and within me - and even have a leisurely cup of coffee.

Rule 2 – Take a limo or park in the reserved area 
Before I’d discovered that such a section existed, it sometimes happened that all spots in the airport garage were full. I’d spend the next half hour or more in a slight frenzy driving all over the place, thereby failing Rule #1.

Rule 3 – Be open to whoever or whatever crossed my path
During this time of my life, I was also becoming Catholic and Mother Teresa’s injunction spoke to me. “Seek the face of God in everything, everyone, all the time, and His hand in every happening. This is what it means to be contemplative in the heart of the world.” 
     The trips varied in duration from one-day jaunts on the East Coast, to many cross-country trips to California, and occasionally longer international flights. Fortunately, I find it very easy to meet and talk with other people, and sometimes their dogs. It is simply in my DNA that the rhythm and timing of meeting others flows naturally. Second, when entering a plane, or even an airport, I feel safe. I just do. It’s like entering a womb or a cave, and I somehow feel protected. This is a lovely gift to have since, in reality, one has no control whatsoever of the actual safety of the plane. My emotional receptivity allows me to relax deeply. I am aware this is not the case with everyone.
     I met people everywhere, from the waiting area, to Starbucks and on the plane itself. The normal conversation would usually begin involving where we were going and why. While that was fine and friendly, what I found myself wanting was something deeper, more genuine and more surprising. If there was enough time in the waiting area, sometimes those more intimate and real conversations happened. This was especially true if there were delays. I discovered that the anonymity of a stranger in the airport allowed for heartfelt discussions. A simple question like “What matters to you?” would open the floodgates. I practiced listening and sharing with the best quality of attention I could muster. My personal aim was to allow the energy of curiosity to simply take over. After that, it was easy.
     I met hundreds of people along the way – all sorts – all ages. I occasionally thought that the purpose of my “career job” was really the plane flights, and the actual job was simply a prop that allowed these encounters to happen.
     There are so many stories. Let me share three of them…

The Influence of Joanna Macy
It was 2008 and I was coming home after a challenging week at corporate headquarters in California. By this time, I was president of the appraisal division. I had also spent the prior evening and day visiting our daughter, Liz, who lived near Portland. In truth, I was tired and was looking forward to a short flight from Portland to Seattle, and then the red-eye from Seattle to Boston. I went to the waiting area and let my intuition find a seat. It was next to a woman who was sitting quietly. I looked at her and said to my own surprise, “You look tired.”
     She looked back, “So do you.”
     I told her little about my week. “And you?” I asked.
     “I’ve just been on a two-week retreat with Joanna Macy. Do you know who she is?” she asked.
     “She is one of my heroes”, I said. (From Wikipedia) “Joanna Rogers Macy (born May 2, 1929), is an environmental activist, author, scholar of Buddhism, general systems theory, and deep ecology. She is the author of twelve books.”
     Boarding was announced and we agreed to meet in Seattle since we were both catching the same night flight to Boston. We had a three-hour dinner together in Seattle. She told me she and her husband were part of the founding group of a sustainable community in Vermont. Many of the members of the community had been brain researchers from MIT (including her), but they felt that the climate issue was so pressing that they changed their focus.
     We kept in touch, and a few months later, I visited and enjoyed a wonderful communal dinner, where I chopped many onions. We arranged to meet the next morning with the “brain trust” of the community. This group had already worked with large international corporations to bring the issue of planetary sustainability to the fore. Their models were so well respected that they were utilized in the 2009 Copenhagen climate change conference.
     I’d previously wondered if it might be possible to include concern about the impact of climate change in the property valuation process in the country. If it were possible to do this, I thought I might be able to make it part of my own mission in the appraisal industry. However, after spending a few hours with this utterly remarkable group of thinkers, it became clear that my own industry was not ready for that kind of change at that time (or even now). The woman I met on the plane kept in touch for a number of years.

Want to Play a Fun Game?
I remember the date of the flight – March 7, 2007, because my 60th birthday was one day later, and I would be in Disney World at a real estate appraisal convention. It was the only time I remember not being with Catherine on my birthday, but I had previously agreed to do a presentation.
     The flight from Boston to Orlando is three hours. For my first self-birthday present, I decided simply to enjoy the ride, read a magazine I liked and relax into the experience. As a frequent flyer, I was seated early. My preferred space, as usual, was an aisle seat. A mother and her five-year-old son were my traveling mates with mom taking the window seat.
     After reading the magazine, I took a nap. I woke up toward the end of the flight and noticed that the boy had a very large bag of toys, some electronic, some not. One after the next, he switched playing with the toys. He seemed incapable of picking one toy and staying with it. It was disturbing to watch. None of his toys captured his attention sufficiently, nor was he able to focus intentionally. There was something about the way he handled the toys that gave me the impression that he had LOTS of toys at home, but perhaps no one played with him. Or maybe he was burdened with attention deficit disorder. I did not know, nor did that matter to me.
     And then, in my mind, I heard the Mission Impossible tag line your mission should you choose to accept it and even, this tape will self destruct in five seconds.
     Should I attempt to engage this child’s attention and imagination? I did not have any specific plan, but I figured that would emerge in the interaction. When our daughter was young, we played all sorts of games for memory, attention and imagination. In addition, I had been part of a “magic company” when I was younger and knew a variety of tricks. “Want to play a fun game?” I asked the boy.
     His mom looked suspiciously at me. I continued, “Oh, I think he will enjoy it. The game is even a bit challenging and nothing like the games he has in his bag.
     She tentatively agreed.
     I took the laminated card showing the plane’s exits from the back of the seat and, very slowly, pulled it up from my chest to cover my face. When I pulled the card down, I had a funny face with my tongue sticking out, and the boy laughed. “OK, you try it now,” I said, handing the card to him as if it was a magical card that could change faces. “Please, make a “funny” face,” I said. Pulling the card over his face and then bringing it down, he did just that.
     “OK, now you hand me the card and tell me what kind of face I should make.”
     And on we went, passing the card back and forth, and asking for different faces – happy, mad, confused, ice cream, peanut butter, and so on. After a little while, I asked his mom if she wanted to play, and passed the card to her saying “caring.” 
     When she pulled the card down, she looked at her son, and her face was filled with so much love that it was palpable.
     The three of us played for a little while longer. Then, as if on cue, the pilot announced that we would soon be arriving. I took the card, ceremoniously placed it in the back of the seat, and we all thanked each other for a very nice game.

The Texas Pastor
This encounter occurred around 2008 when I was 62 and quite sure that this was the final lap of my career with First American. First American made significant corporate changes every few years and we were in the midst of one of them. The appraisal division was to be merged with another division and someone else would be running it. I was OK with that but not at all clear on how to make my transition, either into another part of First American, or out completely. I had helped many others through their transitions and now it was my turn. This would be my last flight to Dallas where First American had a large campus and my current boss was located.
     Our direct flight from Boston to Dallas was not fully booked. Typically, the middle seat would be the last to be filled and the person on the aisle (me) and the person by the window silently hoped that no one would fill that middle seat.
     When the doors closed and we both realized that the middle seat would be empty, we acknowledged our good luck and readjusted our things to spread out a bit. He was around 50 or so, had a pleasant way and a deep Texas drawl. He had his reading material and I had mine, and we did not connect for quite a while.
     After a while we chatted. He was a Pastor for an Evangelical Christian church. I told him of my business life and - to my own surprise - shared about my anxieties around my coming transition. 
     He listened carefully as I filled in some details of my life, marriage, financial fears and other concerns. He had a nice way of feeding backing what I was saying. I liked him and, remarkably, felt safe in his presence. After I'd finished, he asked if he might offer a prayer for me. He spoke “Christian” - a language I'd been learning -  and I understood the meaning behind the words. I then asked, “and you?”
     He was quiet for a while, as if deciding how much to share. He told me of his “growing flock” and his fears of losing the intimacy that he really valued. There were the practical decisions, like bigger building and technological advances, and also the spiritual side of the need for something genuine. He went on for quite a while and I listened, occasionally asking questions. We had clearly connected.
When he finished, I asked if I might say a prayer. I know Psalm 23 by heart and as I began, to my surprise, all the pronouns became plural. I spoke very slowly, as if listening to it the first time myself:
     The Lord is our Shepherd, we shall not want. He makes us lie down in green pastures. He leads us beside still waters. He restores our souls. He leads us in right paths for his name's sake. Even though we walk through the valley of darkness, we fear no evil for You are with us. Your rod and Your staff, they comfort us. You prepare a table before us in the presence of our enemies. You anoint our heads with oil. Our cup overflows. Surely goodness and mercy shall follow us all the days of our lives. And we shall dwell in the house of the Lord forever.
     After I finished we were quiet for the rest of the trip. I left the airplane first and it took him a bit of time to get out. I waited for him and saw him looking for me. We both wanted one final hug sending us on our way as newfound brothers.