Tanel's office location at the end of Sõrve Peninsula on Saaremaa, Estonia

I'm standing just outside my friend’s remote office here on Sõrve Peninsula on Saaremaa. When growing up, this place with its far-reaching extension into the Baltic sea, always felt like the very end of the world to me. Little did I know then that Saaremaa is also one of the posited locations of Ultima Thule, a distant place located beyond the borders of the known world in classical European literature and maps during the Middle Ages.

Tanel, my friend from high school, is wiggling his way into a wetsuit with an uncontrollable smile on his face. He looks happy like a little kid. I'm left alone on the beach with "The wind is picking up; let’s talk later!" as he runs off with his windsurfing gear.

Saaremaa used to be one of the most western points of the former Soviet Union (USSR). Only a few decades ago you needed a permit just to get to this closed-off border zone island. Now you can walk to Paris from here without showing your passport (provided you can swim to the mainland). Sõrve Peninsula saw major battles in 1941 and 1944 between the Soviets and the Nazis, but now when Tanel is not busy windsurfing, he is helping German companies with their CMS integration and web frontends through his private venture.

As I watch him surf off into the distance, I’m left pondering the low likelihood of seeing your home country borders change during your lifetime, and whether optimism bias has anything to do with how unlikely we assume these things to be.


Discussing remote work after a windsurfing session.

Tanel is a location independent knowledge worker, his location does not matter for his work, yet he chooses to live here – on a remote island once home to Estonian Vikings. For someone who just spent four years in fast paced Silicon Valley, I find it surprising to hear his arguments: "I'm as close as I can be to my hobbies here; it's cheap, not crowded, and I can set my own pace here." He then proceeds to tell me how he scales down his working hours when he needs less money.


A view from Tanels remote office with a windsurfer in the background.

Still captivated by the view from his office window, I head back inland. Five miles later Jaak, a huge smile on his face, welcomes me to a tiny farm. His beard and heavy professional studio Polaroid camera in hand give away his artistic inclination. He works as a Senior Design Integration Manager for Skype and spends most of his summers here working remotely. He has lived on Trinidad and Tobago in the Caribbean as well as across the Baltic Sea in nearby Sweden and currently spends about two months per year travelling for business.


Jaak celebrating the completion of the wood-fired earth oven.

Seeing me stare at two of his relatives behind laptops seeking shadow from the sun he comments , "They're still working. What do you want on your pizza?" We walk over to a wood stove oven he recently built and he bakes me the best pizza I've had in years. Jaak continues to tell me about the wifi routers sharing the connection from the 4G antenna up high on the pole and how the 3G wasn't cutting it anymore. To my question Why here? Jaak responds: "First, this is the warmest place in Estonia. Second, I want my kids to enjoy the kind of summers I did when I grew up. And finally, it only takes a second here to disconnect from the digital to the analog world. I can just close my laptop, grab a shovel or a hammer and be totally disconnected.”


Wood-fired earth oven can reach temperatures required for baking pizza.

Our discussion continues around how innovation in communications enables remote places to reappear on the map, and on the topic of people (including Yours Truly) not realizing how technology is changing where we live.

As I ride off I can't help but feel some of the location happiness of my friends rubbing off on me as well. Not all remote workers are the same - some seek a constant flow of new adventures, switching places just for the thrill of it; others enjoy the same freedoms through technology to find their optimal place and stay put for years. Tanel and Jaak belong to the latter and have obviously taken the time to figure out what places make them happy.

It's surely something more and more people will start to think about.


Images courtesy of Kristjan Klementi, Jüri Parik and Silver Keskküla