The Lost Art of the Airport Conversation

Of all of the different kinds of conversations we’re not having that were all too commonplace in the past, and indeed taken for granted; the one I miss the most is the airport conversation. In the past week I’ve reflected on how many great airport conversations I’ve had that have gone on to create lasting friendships and even business opportunities years later. What is it about airport conversations that makes them so powerful? I’m not sure, but I’m curious to examine my experiences and hear yours too. 

John Steinbeck documents his conversations with strangers as he crossed America in ‘Travels with Charley’. I must recommend this book straight off the bat for the magnificent writing that earned him a Nobel prize for literature. It seems to be filling a particular void for me that used to be filled with travel and meeting strangers in different places. Also his dog, Charley, sounds like a whole lot of fun. The closest I get to owning a dog is watching the cute dogs running through the snow in the park across the road from my apartment. But more than anything, the novel nudges me to reflect on conversation. 

I can’t speak for everyone, but the number of people I’m having conversations with has lowered significantly since the beginning of the pandemic. I’ll assume that this is not the case for everyone. Perhaps your social circle has broadened using any number of digital communication tools. Remember the early days? HouseParty was a flash in the pan from my perspective. It offered some fun gimmicks but didn’t ultimately serve conversations so my willingness to open it up again waned pretty quickly. 

Other new discoveries like MeetButter and Wonder allow for more of a ‘real’ conversation to take place, where connections can be made in an informal setting. This is what makes me think that Clubhouse, while I haven’t entirely wrapped my head around it yet as it begins to gain some early traction in Europe, may be a way that people can access and participate in more conversations than they normally would. This fills me with optimism for the platform, but of course, time will tell! 

The Art of the Airport Conversation is an effortless one. At least for me. I’m pretty chatty after all, and would rather strike up a chat then sit alone in silence while unforeseen delays rob me of my remaining youth. I have made some incredible connections in airports over the years. But I haven’t had any airport conversations, or any that I feel the same gravity around, for so long! 

Travel used to be quite a pillar of my life. I was shipped all over the place during my time at Tesla. But I liked to keep my occupation to myself most often when meeting people in airports. Most people had some kind of opinion formed on Tesla, or at least Elon. So I would usually just mention that I worked at a 'tech company’ which would usually arrest people with the fear of boredom if they asked much more than that. If they did, conversation was usually brilliant and people came with a curiosity about Tesla’s mission and what role I played in it across Europe.

The other reason I’m partial to an airport conversation is because occasionally I would be travelling between Australia and Europe and 24 hours or more of travelling does fry my brain to a degree. So I’m always up for a chat with somebody along the way. One such occasion was when I met Sarah Wilkin at Changi Airport in Singapore. We were the only two patrons of a Chinese restaurant in the middle of the night. Sarah shared with me some of the early work she was doing at her company Fly Green Alliance and we’ve become good mates here in Amsterdam since. You can see what Sarah’s been doing since then by reading her edition of our Amsterdam Founders Series. 

Another sure-fire way to dive into a quality airport conversation is to combine the inevitable delays that may inspire desperation in some travellers with the oldest social lubricant of all, booze. I like to think I’m in the more experienced bunch of travellers, and I believe the evidence is in the time it takes to find the nearest bar (or fridge at least) when delay is called. Travelling back home from a multi-stop work trip on a Friday night from Stockholm to Amsterdam is where I met Stephan who pulled up next to me in pole position at one such airport bar. I offered the first round knowing that I was in for another spectacular edition of airport conversations. Stephan and I have stayed in touch since then. Other people I’ve met in airports have been tour guides, supporters of my work, teachers of subjects I was new to, and inspiration.

So what about the future of these conversations? There’s not doubt we’ll be travelling less from now on, and that travel ought to be far less airport/aviation-based than before. So where will I be getting my fix of unexpected, inspirational, and truly enjoyable conversations from? I can’t say for certain. But I will share that since beginning working on Troopl full-time, I’m absolutely thrilled that my calendar has become far more populous with interesting people offering their time to chat and share ideas and wisdom with me. It seems the airport behaviour of willingness to chat to someone based on very few credentials does indeed continue. Instead of a suitcase and a Crumpler laptop bag (always a good conversation-starter), we now merit a conversation based more than ever on someone’s online activity and behaviour. I suppose it’s undeniable, and I’ll admit it makes me a little uncomfortable. I’ve never been one to contribute to an ongoing online ‘persona’, and I find myself feeling awkward from time to time as I come to grips with how and where conversations will take place from now on. 

Of course, life will fall into a new kind of normal rhythm once again. And I get to experience the multitude of shifts through the lens of an ambitious, yet fairly clueless entrepreneur. I’m anxious to travel again and will be so excited to discover new places and people when the time is right. So in the future if you see me wandering through an airport or train station, be sure to ask me about my bag. 

Benjamin Webster.