A lament for Skype

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By now I’m sure you’ve all heard the sad news: In May, Microsoft will shut down Skype, the Internet phone service that, starting in 2003, became vital to connecting people around the world. In its place, Microsoft wants us all to use Teams, the Auschwitz of virtual workspaces:

As my work colleagues know all too well, I could spend the next thousand words simply dunking on Teams, but instead I want to recall the era of travel that made Skype so important. This one, I guess, is nostalgia for us old folks, perhaps informative for the younger travelers.

The first decade of the twenty-first century was an exciting time to travel. Despite the wars in Iraq and Afghanistan and the paranoia around terrorism that was transforming airport security into a Kafkaesque theater of absurd rituals, it was rapidly becoming easy and cheap to go almost anywhere in the world. Low-cost airlines, especially, but also high-end bus services put within reach countries and cities most of us had never considered visiting before, including huge swathes of Asia and Eastern Europe, where new hotels, restaurants, shops, and art galleries were opening seemingly every week.

Alongside these material manifestations of the world’s interconnectedness was the intangible version: the Internet, which if you can believe it still felt new, unfinished, unexplored. Yes, we had had booking sites like Expedia since the mid-1990s, and Google was an essential tool for digging up information about destinations, but much of the travel world still ran on paper: guidebooks, plane tickets¹, cash. Those of us who were already living on the Internet, and relying on email to stay in touch with friends, family, and work, had to seek out cybercafes, which were thankfully popping up in every city, town, and village around the world. There we’d sit at dusty Windows machines with sticky keyboards, paying a few dollars, đồng, or rupees an hour to login to Yahoo or Hotmail and catch up with the rest of the timeline. If we had photos to send—to pals or to an editor—we had to pop SD cards out of our digital cameras and into desktop card readers, and hope there was enough bandwidth to fling the images into the void before the hour was up.

If you had a cell phone back home, you weren’t necessarily using it abroad—and it was almost certainly a flip phone, not an iPhone, which was introduced only in 2007. Roaming fees charged by service providers were egregious, and stories abounded of travelers returning home to bills in the thousands of dollars. Our phones were often locked as well, tied to a specific provider in a specific country, so we couldn’t simply switch them over to affordable local SIM cards.

This was a big deal because—horror of horrors!—you needed to make phone calls all the time. You needed to call hotels to check on reservations, airlines to make flight changes, tour providers to see if there was room, museums to see if they were open. Sure, maybe all those institutions had email addresses, but you couldn’t be sure anyone there was monitoring them on a regular basis. You had to call.

This was the world into which Skype emerged—and which it transformed.

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Put simply, Skype allowed you to call almost any phone number, anywhere in the world, from a computer, for almost nothing. Calls to the United States, Canada, and (I think) Mexico were a penny a minute, and few countries cost more than ten times that, which was still easily affordable. Calls from one Skype account to another were free. Connections were reliable, the voice quality was high. For a small monthly fee, you could even set up a local number connected to your Skype account, so people with regular phones could call into it. The Estonian engineers who built the product were geniuses² !

It felt like a true breakthrough. It felt like the culmination of world-historical forces: We could now speak with anyone, anywhere, at any time. Long-established borders—physical, political, financial—were disintegrating at last. Staying connected felt like freedom.

When I became a travel writer, and was suddenly on the road for weeks or months at a stretch, I took all of this about as far as anyone could. I had found a way to “unlock” my cell phone, removing AT&T/Cingular’s restrictions on its use, and whenever I entered a new country I acquired a local SIM card. Then I would tell AT&T/Cingular to forward all the calls to my home cell phone number over to my Skype number, and I’d have Skype forward all of those calls to my local SIM card phone number. That meant that if my mom or an editor called my regular 917 number in the U.S., it would get routed, for no cost to them and almost no cost to me, to my local number in, say, Kyrgyzstan or Hong Kong.

This was pretty cool.

Again I’ll say it: Staying connected felt like freedom. It meant that you could share the day’s doings, whether that was kitesurfing in Mui Ne or jazz-clubbing in Shanghai, with loved ones halfway across the Earth. It meant you could live two lives at once—one away, the other at home—without sacrificing either. It meant we could all learn and understand more about our world and its people and not go broke in the attempt. The technology opened us all up.

I don’t want to over-romanticize this era of travel, only to capture how revolutionary it felt. And how brief. Because by the early 2010s, none of this felt special anymore. It was exceedingly normal. We all had iPhones and Android phones by then, Wifi was everywhere from Bangkok hotel lobbies to Polish gas stations to Dubai McDonald’s, and we’d started to give up on calling one another. Now we texted. So much easier, less intrusive. You texted your friends, your parents, the airline, the tour guide. They responded when they could. It no longer mattered where you were, where they were. We were all everywhere anyway, so what did it matter? When you traveled, you weren’t living two lives—it was all the same life, and in that life you maybe didn’t actually want to be interrupted by a phone call, which was likely a scam or a robo-call. After a decade or so of glorious interconnectedness, we travelers wanted nothing more than isolation.

This was, of course, when Microsoft decided to buy Skype, its biggest acquisition ever, for $8.5 billion in 2011—right before it would become unnecessary, obsolete.

That didn’t have to happen, I suppose. Skype could have become Zoom, a friendly, easy-to-use, reliable videoconferencing platform that worked well with other pieces of software. But, you know, Microsoft. That wasn’t going to happen.

Does it matter that Skype is now going away? Nope! We don’t need it anymore, and haven’t needed it for much of the last decade. My Skype call history, alas, only goes back to 2017, when for some reason I had calls with Mark Bowyer and Lauren Seligman. (Are you guys reading this? Do you remember what we discussed?) In July 2018, I Skyped with Jada Yuan, who was then in the middle of her stint as the New York Times’ “52 Places” traveler—and who had just visited Tallinn, the capital of Skypeland, a.k.a. Estonia. That must have been a grueling trip for her, and at 6:05 a.m., I offered her moral support, plus advice on how to navigate a life of perpetual travel (not to mention the labyrinth that is the New York Times). The call went on for precisely 12 minutes and 33 seconds, and it was the last time I had a Skype call that felt like the Skype calls from its golden age, when two people, who knows where, needed to connect across the gulf of time and space.

Skype is going away, but really it’s been gone for years now, so I won’t mourn its death. I don’t even mourn its golden age, which coincided with my own golden age of travel. Things are, by the way, much better now for travelers! But I do want to remember what that was like, how and why we all tried to stay in touch, the lengths we went to, the joy we felt at hearing the voice of a spouse, a parent, an airline customer-service worker. It rooted us, made us all citizens of the same planet, and for about a decade we were new beings, living in the future. Now such connections are so normal that they feel beneath our acknowledgment, a benefit we take for granted, ripe for misuse.

But that’s just right now, and if the travel world of 2005 was vastly different from that of 2015, perhaps 2025 will mark the start of another new era, in which we’ll come to think differently, once again, of our ability to connect and to disconnect. And while I won’t be on Skype anymore, I do know that wherever I am, I’ll be right here. 🪨🪨🪨

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1  Paper tickets came to an end on May 31, 2008.

2  Skype arguably put Estonia itself on the travel map, establishing it as a progressive, high-tech destination.