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Jun 11, 2019 18:49:38

The end of an era

by @hum | 1332 words | 🐣 | 417πŸ’Œ

Sarah Hum

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Andrew tweeted the other day that we are slowing down traveling. It's true. After two years living the digital nomad life, we are settling down for a while. The city we chose is Toronto, my hometown. I don't think it's really hit me yet but I think now's a good time to reflect. I can definitely feel reality creeping in.

We're in Toronto now for two and a half months. We're subletting so it doesn't feel permanent yet. We're off to Seattle for a short stint after this but then we're coming back. At that time, we'll look for more permanent housing. Insane!

I can see me being happy here. My family is here, I have friends here. Toronto is a really cool city. The whole thing feels kind of bitter-sweet. Either way, it's a new phase and something to be excited about.

Leaving SF was mostly my idea. I enjoy seeing the world and I would continue to do so if it was just me. That said, it's not just me. Andrew has made compromises for the last two years so I think it's fair that I make some now. I completely understand the tradeoffs he's had to make and the reasons he wants to settle down. 

First, a quick summary

During these last two years, we’ve lived and worked from 26 cities in 16 countries. London, Lyon, Budapest, Berlin, Madrid, Valencia, Barcelona, Seville, Las Palmas, Lisbon, Dubrovnik, Split, SF, NY, Seattle, Vegas, Toronto, Vancouver, Hong Kong, Saigon, Bangkok, Malapascua, Taipei, Kaohsiung, Fukuoka, and Seoul. We usually stayed in each city for about a month. The most memorable were Valencia, Lisbon, Split, and Seoul.

We worked on Canny full-time the entire time. We also started growing our team. We grew from just me and Andrew to a fully remote team of five. In Lisbon and Split, we held our first two team retreats. The lifestyle is definitely not for everyone. There's a lot of planning ahead, moving around, and adjusting to unfamiliar places. It's exhausting for a lot of people. I, however, love that stuff. Seeing how locals live, walking around new neighborhoods, discovering hidden gems. All while not having to pay rent at home. Of course, there are challenges but nothing great comes easy.

Not everybody can do what we did or has the means to do it. Desk jobs are called that for a reason. Although our time is ending, I am so grateful for the opportunity to travel for these last two years. 

Remote work continues

Our lifestyle as digital nomads and remote workers have largely overlapped these last two years. We felt the pros and cons both as individuals and as a team.

Remote work is a pretty hot topic these days. Buffer and Zapier are both big proponents for remote work. The remote workforce is continuing to grow. Of course, remote work also comes with its issues. Ryan Hoover wrote a post on the challenges of remote work. There are countless guides on building a remote team

Our team is fully remote and I don't think we'd have it any other way. Without it, we wouldn't have the stellar team that we have now.

Being remote-first meant that we were mindful of the challenges from the beginning. We are still continuing to iterate on our team meetings. We will continue to have team retreats. All we're changing is adding a personal home base.

Nomads write extensively about why they're ending their nomad journey. We've come to experience similar struggles that we'll talk about below.

While we're transitioning out of our digital nomad lifestyle, we're continuing to work remotely. With that, we're leaving some of the struggles of nomad life behind.


Andrew tweeted:

The thing I miss the most is camaraderie. When you're constantly on the move, it's really difficult to make lasting friendships. Especially for an introvert like me. 

I'm an introvert as well. Pushing ourselves to go out and meet people was tough. Especially when you're traveling with someone else so you're even less motivated to seek out new interactions.

Relationships take time to developβ€”usually longer than one month. When we landed in a city, it took us a while to get set up. Then, we'd be working a lot of the time. There wasn't much opportunity to make connections. Maybe that's just an excuse. It always felt like we'd be leaving in a couple weeks so what's the point?

We were lucky to meet a few awesome people. Those are actually the most memorable moments of our trip. Sadly, we probably won't see those people for a long time. 

Not only was it hard to make new friends, we lost touch with old friends. When we left San Francisco, we left friends we've known for years. Any time we were back stateside, it felt like we were always catching up with people. Now that we're back in Toronto, we have the chance to reconnect for the longer term.


The language barrier is a big deal too. It's now so nice to be able to have random small talk with people in the grocery store, or understand what the barbers are joking about while I'm getting my haircut.

I found the language barrier difficult at times too but also fascinating. Learning how to communicate with basic hand gestures or even by using Google Translate. There were moments we were able to connect with strangers that only knew basic English. I did yoga classes in Spanish and learned how to order groceries. Language is fun, I wish I knew more of it. Maybe we would have built more friendships if we had pushed ourselves more.

The search for a routine

Andrew tweeted:

It's also been hard to keep a productive routine. Every time we'd arrive in a new country, it'd take us a few days to find a good place to work, a grocery store, a gym, a sim card, etc. Then a few weeks later we'd leave and have to start all over again.

For someone who needs a routine, the nomad life wasn't ideal for Andrew. When you're moving every month, you find yourself having to relocate all your necessities. We bought a lot of the same staples in every city: salt, pepper, oil, cheese, garlic, butter, bread, peanut butter, jelly, onions, etc. Most of it we wouldn't even finish by the time we left.

Places to work were hit or miss. Sometimes we'd look for a co-working space. Sometimes we opted for coffee shops. With the latter, we get to explore more of the city. We also have days where no coffee shop has everything we need: outlets, bathrooms, and, most importantly, wifi.


We made a list of cities we might want to live along with things we cared about: people, weather, activities, and cost of living.

We eliminated New York for its high cost of living and bad weather. But also, neither of us could really see ourselves living there.

We eliminated San Francisco for its high cost of living but also, we already lived there for years.

Seattle came really close. Andrew's family's there and we have some friends there. Seattle winters aren't like Toronto winters.

In the end, Toronto won even though the weather here is probably the worst out of the list. My family is here and we have friends here. We also like the feel of Toronto. It's up and coming for tech but not overwhelmingly so. The Canadian dollar means an instant 25% discount. Being in EST is ideal for our team and customer set up.

We can see ourselves being happy here.

Originally published at canny.io

From Sarah Hum's collections:

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  • 1

    @hum How about them Raptors, eh?

    Gabriel Greco avatar Gabriel Greco | Jun 12, 2019 09:12:46
    • 1

      @gabrielgreco Game 6 let's go!! πŸ’ͺπŸ’ͺ

      Sarah Hum avatar Sarah Hum | Jun 12, 2019 17:30:12
    • 1

      @hum πŸ™

      Gabriel Greco avatar Gabriel Greco | Jun 13, 2019 16:01:09
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