Boing 747 London - BangkokThose of us who fly often have learned that it pays to stay observant and opportunistic when you’re on flights and in airports. Most people are in their own little world — focused on their laptops, Kindles or iPads, or immersed in their smartphones. I enjoy looking around and experiencing what’s going on around me — you never know who you may bump into.

One of my mentors, Alan Weiss, has been to virtually every country in the world; I think they need to create a new class of frequent flyer status to accommodate his many millions of miles. Needless to say he travels all the time and always first class. On one of his trips to Australia I believe it was, he wound up seating next to Dolly Parton. That’s a long flight and they had a terrific time getting to know each other — he had a blast and loves to tell that story.

I’ve had plenty of these types of experiences myself over the years — I’m up and down between Silicon Valley and LA all the time; I even have my own gate agent at Southwest at the San Jose airport (no joke — for over 25 years now!). During my tenure as Apple’s original music and entertainment exec, I developed relationships with many artists and industry execs — one of whom was Peter Gabriel who lives in Bath, England.

Peter and I had probably been ‘pen pals’ and were in touch virtually for decades before we finally met at the San Jose airport of all places on one of my regular flights to LA. To the untrained eye, Peter is somewhat unrecognizable at this stage of his life — and he was with his manager Mike Large. But of course I knew him right away and approached him discreetly to avoid drawing unnecessary attention his way. He had just met with Google and was headed to LA to meet with Danny Hillis of the Long Now Foundation (fascinating!). Peter and I had a real blast catching up during the flight, connecting dots and laughing at some of the more absurd items in the now defunct Skymall in-flight catalog. It was a truly memorable experience I won’t forget.

Another time I spotted celebrity chef Kerry Simon (who has sadly since passed) on a flight from LA to Vegas. He invited me to be his guest for dinner at his restaurant at The Palms, which I did; and subsequently I invited him to be a presenter at one of the award shows I produced — which he did. And that was the basis for a great friendship between us that lasted until his passing.

Just this past weekend, I was returning to the Bay Area from Hawaii, and because of some last minute changes with my schedule — wound up re-routing myself through Maui airport where I had maybe a one hour or so layover. As I was sitting in Sammy Hagar’s restaurant there having an iced tea and a snack, I happened to look up and spotted some familiar faces across the room. They were former clients of mine from at least a decade ago who I’d mostly been out of touch with for that period of time — a highly entrepreneurial couple working on some initiatives I very much resonated with (as I did with them!). They almost fell on the floor when I approached them they were so stunned — one of them said they had just been talking about me not 30 minutes earlier.

We had a brief catch up and they demo-ed their latest groundbreaking tech venture for me; we talked about ‘getting the band back together’ and re-grouping around it. We may have a second bite at the apple in terms of doing business together again. I wasn’t even supposed to be at the Maui airport; what were the odds of us running into each other like that in that restaurant at that fleeting moment when they were headed to Sweden and me to San Jose — and all of us with very limited time on the ground?

So bottom line: stay alert, pay attention, be opportunistic, and look up from your smart devices once in awhile when you’re on flights and in airports. You never know who you may come across in a chance encounter at the hands of fate; you could meet a future client or a future spouse — or someone who somehow makes your day — or even changes your life.

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