In an era of remote work, people can live anywhere. Where will they choose to go? (Image: Guille Faingold / Stocksy)

Episode 13: Remote Work

Remote work could change not just the way we live in cities — but which cities we live in, too.

City of the Future
Sidewalk Talk
Published in
17 min readOct 30, 2020

“City of the Future” is a podcast that explores ideas and innovations that could transform cities. In this episode, hosts Eric Jaffe and Vanessa Quirk discuss how remote work is changing cities and interview professor of urban economics Richard Florida, Estonia’s digital transformation adviser Anett Numa, Tulsa Remote community manager Taylor Allen, and Topia’s Chief Product Officer Sten Tamkivi and Director of Product Management Chantel Rowe.

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Taylor Allen: As a remote worker, you sometimes find yourself isolated because your entire community is online. It’s really easy just to stay inside with your computer and not have a reason to branch out.

Eric Jaffe: That’s Taylor Allen. In 2018, Taylor was a recent college graduate who had taken a remote job, which meant she could live anywhere.

Vanessa Quirk: She went to Florida. But the glamour of working from the beach wore off fast.

Taylor Allen: I really had no reason to leave my house unless I was going to the beach or the pool.

Eric Jaffe: Taylor’s main source of community at the time was an online church.

Taylor Allen: I followed Transformation Church pretty religiously, no pun intended. I was captivated by the pastor and felt supported by the community, even online, and was curious about where the church was. I saw that it was in Tulsa, Oklahoma, and I was like, “All right, there is no reason I would ever find myself in Tulsa. I don’t even know where that is.”

Vanessa Quirk: Then, in November of 2018, she got an email with an interesting subject line.

Taylor Allen: “Work remotely? Get paid $10,000 to move to Tulsa.”

Eric Jaffe: It was an invitation to apply to something called Tulsa Remote, a program designed to entice remote workers from around the world to live in — you guessed it — Tulsa, Oklahoma.

Taylor Allen: The prospect of being able to have a faith community, to join in the community in general, was the impetus for me applying.

Vanessa Quirk: She sent in her application and waited. And then one day…

Taylor Allen: I remember exactly where I was. I was at a restaurant with my mom and stepdad, and I got an email from Tulsa Remote. I was like, “Oh my gosh, I’m hearing back.” The email said, “We have been overwhelmed with the response. We’ve gotten over 10,000 applications. We weren’t expecting that, but we want to invite you to interview.”

Eric Jaffe: Taylor really wanted that spot, so she got to work.

Taylor Allen: I’d really done my research about Tulsa and the organization’s initiatives, and I really spoke about my interests and my passions — ways that I could give back and be connected if I were to make Tulsa home.

Vanessa Quirk: She was accepted, and one short month later, she was moving.

Taylor Allen: I moved sight unseen. I’d never been to Tulsa.

Eric Jaffe: Without ever visiting? Wow.

Taylor Allen: Without ever visiting. I was number four to ever move with Tulsa Remote, so I was an early guinea pig. That forced me to really connect with the community and local Tulsans, starting from last March all the way to March of…what’s this year? 2020.

Eric Jaffe: I too would like to forget what year it is.

Taylor Allen: Yeah, March of 2020 was when my year was up with the program. I remember realizing that day, “Wow, Tulsa is home and I do not see myself leaving Tulsa anytime soon.” Tulsa Remote obviously wanted to keep me as well, because they offered me a job. That helps, but it was also that sense of community and connection. The opportunities are endless in Tulsa, and I love that.

Vanessa Quirk: This timeline is pretty remarkable, Taylor, when you think about it. March 2019 to March 2020, you were on the forefront of this movement. March 2020, COVID happens. Obviously the world changes, and this idea of remote work is now on everybody’s radar in a way that it wasn’t even a month before. How did COVID change the way you think about remote work?

Taylor Allen: I think a lot of people are remote forward now. I remember telling people that I worked remotely, and there was a huge question mark with what that meant. Now it’s the norm. It’s making me realize that as a remote worker, where you live matters. We see so many applications from people in New York and California who are ready to flee the coasts and higher costs of living, and then move to Oklahoma to have space, open air, clear blue skies, and an opportunity to connect with the community. COVID has made me realize how convenient remote working is, but also how it really is our future.

Eric Jaffe: Welcome to City of the Future, a podcast from Sidewalk Labs. Each episode, we explore ideas and innovations that could transform cities. I’m Eric Jaffe.

Vanessa Quirk: And I’m Vanessa Quirk. In this episode, we’re exploring an idea that could change not just the way we live in cities, but which cities we live in, too.

Eric Jaffe: Remote work.

Vanessa Quirk: Eric, we’ve been working from home for about eight months now.

Eric Jaffe: I hadn’t noticed.

Vanessa Quirk: So how has remote work been for you?

Eric Jaffe: In a lot of respects, it’s very challenging. My wife Jeneen has also worked from home this entire time. You know, our marriage is great!

Vanessa Quirk: You are still married, despite eight months of co-habitation and co-working, right?

Eric Jaffe: Yeah, I mean there are definitely challenges. But when it comes to the podcast — this has actually been a breeze. This was one thing that actually got better.

Vanessa Quirk: I agree, actually. Every single time we had to record a podcast, we used to make sure we had this one booth, and we would get in there. I would sometimes even jerry-rig it so the air conditioning wouldn’t come on, so we would get the perfect sound quality for our podcast.

Eric Jaffe: For you listeners.

Vanessa Quirk: Just for you guys. Then, as soon as we were recording from home, we were like, “Oh, we can just set up a mic in our bedrooms and it’s fine.”

Eric Jaffe: If there were a picture in the dictionary of a superspreading event, it would be that little podcast booth with four people crammed in, and stuffy air floating around for an hour on those tiny seats. So from a podcast-hosting perspective, remote work has been way better. In fact, I think we’d continue to do it this way even if the office opened back up — wouldn’t you think?

Vanessa Quirk: Yeah, I think so. It’s interesting because there are a lot of companies that we’ve been reading about that are starting to offer this option to their workers. You don’t have to go back. You could be remote indefinitely, maybe forever.

Eric Jaffe: What would you do if you had that option?

Vanessa Quirk: That’s a tough one. There is something attractive about going somewhere cheaper with more nature, and working from there. But I don’t know — even though I don’t miss the booth per se, I do miss the office. I think I would go back.

Richard Florida: To be honest, I’m not going back. I’m not going back to the old way. It was taking too much out of me. I’m not going to deal with it.

Image of man with glasses sitting in a suit
Professor of Urban Economics Richard Florida believes that cities will increasingly compete for talent in an era of remote work. (Image: Daria Malysheva / Creative Class Group)

Eric Jaffe: That’s Richard Florida, a professor of urban economics and an advisor to Sidewalk Labs. We wanted to hear what he thinks remote work will mean for the future of cities.

Richard Florida: I’ve liked being home. I find that I like my neighborhood and my life better. I mean, my kids are three and four, and it’s given me a lot more time to spend with my two girls. I’ve gotten to know my neighbors a lot more and have cycling buddies now. We set up a front porch and have people over there a lot.

Vanessa Quirk: For Richard, it wasn’t just neighborhood life that improved. Teaching classes got better, too.

Richard Florida: I taught my course online, so I was able to bring in people from all over the world: mayors, urban economic developers, people from technology companies. We had to learn how to do it, and we got better at it. It showed me that we have the ability to do remote teaching and have it go very successfully.

Vanessa Quirk: It’s interesting that your experience highlights two very different advantages of remote work. On the one hand, in your teaching, you’ve brought in more global perspectives than ever before. At the same time, you’re so much more keyed into the local — what’s happening outside your front door.

Richard Florida: After a 40-year career in urbanism, it’s made me appreciate the local in ways I never would’ve thought. The other thing is, my neighborhood was a commuter neighborhood for knowledge workers and corporate people. Before, as a remote worker and professor and writer, I was the only adult man in the neighborhood during the day, and I really felt like a freaking oddball. Now, there are a lot of guys my age in the neighborhood all the time with their kids or hanging around or going to the park.

Eric Jaffe: It sounds like the daytime population of your neighborhood has gone up dramatically, but do you have a sense of what the daytime population’s like now in the commercial districts of Toronto — in those corporate knowledge sector places that the folks you live around aren’t going to anymore?

Richard Florida: It’s terrible, because there’s not many people down there. I had thought more of those buildings were residential, and they’re not. Personally, I think the central business district is a historical relic. During the Industrial Revolution, beginning with manufacturing, we separated work from life. People used to work where they lived if they were artisans or producers, living above their shop. Then, as we added transportation innovations like subways and trains and transit, people started to commute more and more to factories and offices. We developed these giant commercial towers and stack and pack knowledge workers. I think a lot of that’s going away, and this shift to virtual or remote work is a big part of it.

Eric Jaffe: Richard told us that this forced experiment in remote work has hastened a process that was already in motion — not just for individuals, but for cities too.

Richard Florida: The future of economic development is talent. There is now no other economic development strategy. I’m talking to economic developers all the time, and it’s like light bulbs are going off in their head. If you want to talk about the new city competition, it’s been this shift away from the power of firms to the power of talent. Especially in an era of remote work, the location of talent will be even more important. In cities and suburbs and rural areas, the terms of the competition will be about competing for talent, competing for workforce, competing for people, and competing for remote work.

Eric Jaffe: So the big question is: in an era where every city now must compete for remote workers, what can cities do to attract them?

Vanessa Quirk: There is a place that has a really compelling answer to this question: Estonia.

Vanessa Quirk: Believe it or not, the small Baltic nation of Estonia is one of the most digitally enabled countries in the world. For years, I’d been reading about its remarkable transformation, and in the summer of 2019, I decided to go see it for myself. While I went before COVID, Estonia has only become more relevant in a post-pandemic, remote world. But, I’m getting ahead of myself. Let’s go back to 2019, when traveling was still a thing.

Sound of airplane taking off.

Flight attendant: “Ladies and gentlemen, welcome to Tallinn.”

Image of aerial view of Tallinn, Estonia
Tallinn, the capital of Estonia, one of the most digitally enabled places in the world. (Image: Julius Jansson / Unsplash)

Vanessa Quirk: The first stop on my journey was the e-Estonia Briefing Centre in the capital city of Tallinn. That’s where I met Anett Numa.

Anett Numa: My name is Anett, and I work in the e-Estonia Briefing Centre as a speaker.

Vanessa Quirk: Anett explained that to understand how Estonia got to where it is today, you have to go back to 1991, when the Soviet Union collapsed and Estonia gained its independence.

Anett Numa: It was very easy for us to build everything from scratch, as we didn’t have any kind of system here yet when we gained independence. Luckily, Estonia had a very young government. Our Prime Minister was in his 30s at that time. He said, “Okay, what about technology? Maybe technology can help us.”

Vanessa Quirk: The advent of the internet was very exciting to Estonia in the ’90s because it emerged just as this young country was building its government from scratch. The first service that they put online was taxes.

Anett Numa: In 1999, we put it online. It takes us one or two minutes.

Vanessa Quirk: Estonia didn’t stop there — they wanted every single government service to be accessible online. To make this work, they issued a mandatory ID card for every Estonian citizen. It’s like a driving license, a library card, a health insurance card, and a coffee shop loyalty card all rolled into one. You can even use it to vote online, wherever you are.

Anett Numa: The last time when we had elections, I was having my vacation in the Maldives, on a paradise island. I was lying on a beach and grabbed my laptop. We had internet connection there, so I was able to vote for the candidate I wanted to.

Vanessa Quirk: Has being so digitally enabled also convinced Estonians to stay and not necessarily leave the country?

Anett Numa: I used to live in France, and did my master’s studies there. The reason I’m back in Estonia is not the weather — it’s raining and it’s cold here, and I was living in a beautiful French city. The reason I came back was 100% the ease of life.

Vanessa Quirk: Anett’s not the only one. While I was in Estonia, I met another Estonian who had just returned home.

Sten Tamkivi: I just moved back from the US a few years ago.

Vanessa Quirk: That’s Sten Tamkivi. He’s the chief product officer at a company called Topia, a startup that helps companies manage their global workforce. He was thinking about the question of how to compete for workers years before COVID was on anyone’s radar.

Sten Tamkivi: We are in a world where every single government, city, and country is competing for every single citizen. The only question is do they know that, and are they doing something about it?

Vanessa Quirk: To Sten, “ease of life” — that’s Estonia’s competitive advantage for attracting remote workers who can choose to live anywhere.

Sten Tamkivi: The top talent in the world in any field is free to choose where they live and work. Where are they happy and fulfilled, and where can they make the most of their potential? People’s incentives are to find the best environment for themselves. If you screw up your environment, people will leave faster than ever before, and if you do something great, people will find you and go there faster than ever before.

Vanessa Quirk: In the early days of his company, Sten and his team did some research to see what draws talented workers to cities.

Sten Tamkivi: There were some criteria that are always high up. It’s like a Maslow pyramid. Clean air — staying alive kind of matters. And tolerance for minorities, because the people who move to a new place by definition are the minority and the immigrant. These basic human safety things are relatively high up, but from there it’s the Wild West. Someone might care about proximity to mountains because they’re a snowboarder. For somebody who has kids, education quality immediately goes to number one.

Vanessa Quirk: Sten became convinced that what cities truly need is something that makes them stand out and makes them unique.

Sten Tamkivi: What is your distinguishing factor? What’s your unique selling point that you have for the world? It might be your language, your culture, or your heritage. It might be something future-looking.

Vanessa Quirk: In Estonia, it’s definitely the latter. Thanks to its forward-looking digital infrastructure, Estonia is perfectly set up to attract remote workers — workers like Chantel Rowe. She’s lived and worked in a lot of places.

Chantel Rowe: I’ve lived in London and Bristol, and I moved to Switzerland for a year and lived in Geneva. I lived in Paris for five years and spent the last four years in San Francisco. And now Estonia. I’ve experienced the gamut of how easy it is to get set up in a country and what the pain points are. I bounce around every three to four years, so I know what’s annoying: Getting a Social Security ID number. Getting your health care set up. Getting a bank account set up. All of these things vary in terms of complexity.

Vanessa Quirk: But in Estonia, thanks to that ID card, it isn’t complex at all. To show me how it works, Chantel took me on Tallinn’s transit system.

Chantel Rowe: As soon as I got my ID card, I registered it and now it just taps through.

Vanessa Quirk: And it’s free, which is cool.

Chantel Rowe: It’s totally free.

Vanessa Quirk: So which stop are we going to?

Chantel Rowe: We’re going to Viru Keskus, which is a center stop.

Vanessa Quirk: Chantel took me to an ordinary supermarket for a not-so-ordinary shopping experience.

Chantel Rowe: The first thing I’m going to do is tag my card. It knows that I am English-speaking, so it puts my little gun in English, and now we can shop as we go along.

Vanessa Quirk: Wait, I’m confused. What is this? You called it a gun, but it looks like a remote control. What is it for?

Chantel Rowe: We use it to scan things as we go along, and then walk out of the store.

Vanessa Quirk: Oh, cashier-less.

Chantel Rowe: Cashier-less, correct. It’s super fast and easy, and trust-based, which I like.

Vanessa Quirk: It’s not just shopping that’s easy. Thanks to that ID card, Chantel has access to everything. It’s all easy.

Chantel Rowe: Having this identity that ties to just me, as a person who lives in Estonia, has made everything easier to get access to. It’s been an incredibly easy transition.

Eric Jaffe: It really sounds like Estonia is perfectly set up to attract remote workers.

Vanessa Quirk: Yeah, and remember that I visited Estonia in 2019. I think it’s even more attractive now post-pandemic. In fact, I called Anett back up a few weeks ago and asked her how Estonia has navigated COVID.

Eric Jaffe: And how’d they do?

Vanessa Quirk: She said it was surprisingly seamless. Because everything was already online, schools, offices, and government services all went remote basically overnight. The only thing that’s changed for Anett is that she now has a new title of digital transformation adviser, and she’s getting more interest from countries looking to have their own digital transformations.

Eric Jaffe: That makes sense to me, especially now that COVID has made more people see the benefits of going remote.

Vanessa Quirk: But I have been wondering: as much as digital infrastructure could attract you to a place, would it make you stay?

Eric Jaffe: It’s a good question. I think for some people, probably yes. But others are definitely going to need more. Think about Taylor Allen from Tulsa Remote. For her, it wasn’t about digital infrastructure at all. What took her to Tulsa, and what made her stay, was the social infrastructure — the people.

Image of buildings and streets in Tulsa, Oklahoma
Tulsa, Oklahoma recently started a program to attract remote workers to the city. (Image: W. R. Oswald / Wikimedia Commons)

Taylor Allen: If you think about Tulsa Remote, the skeleton of it is an economic development project. We’re moving people to Tulsa who already have jobs, and therefore they’re going to be investing financially and economically into Tulsa. But the skeleton in and of itself is not enough. The heart of this program is that community aspect: creating a really promising environment, not only for Tulsa Remote members, but also for the City of Tulsa.

Eric Jaffe: So far, they’re succeeding. Most people who do the program end up staying.

Taylor Allen: We’ve only had a handful leave. We’ve invited 320 people to move to Tulsa so far, and we just keep growing. It’s exciting.

Vanessa Quirk: The more these remote workers put down roots in Tulsa and invest in their new communities, the more Tulsa will be able to grow and improve — and attract even more workers.

Eric Jaffe: It’s a virtuous cycle, one that allows Tulsa to compete with other cities, but in a way that stays true to Tulsa.

Taylor Allen: We’re not trying to reinvent or make another San Francisco or Austin or Dallas or New York. Tulsa is Tulsa, and we’re looking for people who are passionate about what Tulsa has to offer and will help to cultivate what’s already here. We want people to feel like they are connected to a part of the fabric of Tulsa as a city.

Vanessa Quirk: It’s being a part of that fabric of Tulsa that has given Taylor the sense of identity and community that she’d been looking for.

Taylor Allen: After my work day is over, I have a community that I can go hang out with. I think the sense of community outside of the home really helps alleviate the feeling of being isolated and confined working virtually. Everywhere I go in Tulsa, I feel like I have a name. I’m not just a number on a subway or a number at a gym. There is that close, genuine connection and relationship building that’s being cultivated here. It makes you really proud to call Tulsa home, proud to wear your Tulsa gear and wave your Tulsa flag.

Vanessa Quirk: Before I spoke to you, I would have been like, “Okay, the city needs to have a brewery, a coffee shop, good wifi, and that’s what you need to attract top talent.”

Taylor Allen: Think about it: You show up to the brewery or the coffee shop, but what if people aren’t kind? What if people don’t want to talk to you? That completely strips the experience.

Eric Jaffe: I think New York only has those coffee shops.

Taylor Allen: Like I said, the small-town feel is that Southern hospitality, where you know your neighbor. It also has all of the city amenities, but that really comes secondary to the charm and the value of relationship building and community.

Vanessa Quirk: Which is what you were looking for when you applied: community. You were seeking it, and you received it.

Taylor Allen: Amen.

Eric Jaffe: Thank you for listening to City of the Future, a podcast from Sidewalk Labs. Your hosts are Vanessa Quirk and me, Eric Jaffe. We are produced by Benjamin Walker and Andrew Callaway.

Vanessa Quirk: Mix by Zach McNees. Special thanks to Taylor Allen, Richard Florida, Anett Numa, Sten Tamkivi, and Chantel Rowe.

Eric Jaffe: Our art is by the great Tim Kau. Our music is composed by Adaam James Levin-Areddy. If you want to hear more of Adaam’s work, you can check out his band, Lost Amsterdam.

Vanessa Quirk: To learn more about Sidewalk Labs, visit our website, where you can subscribe to our newsletter at the bottom of the page. You can also follow us on Instagram.

Eric Jaffe: A quick note to our listeners — our next episode will come out not in two weeks but in three, on November 20. Make sure you’re subscribed to City of the Future, and you’ll see that episode pop up in your feed.

Vanessa Quirk: See you in the future!