The end of our digital nomad journey

· 9 min read
The end of our digital nomad journey

Andrew tweeted a few months ago 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.

Andrew and I met and worked full-time in San Francisco. We called it “home” for several years. Leaving the Bay Area to travel was mostly my idea. I enjoy seeing the world and I would continue to do so if it was just me.

Our first Instagram post about our travels

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.

We’re in Seattle now for our last leg of “travel”. In a month, we’ll fly back to Toronto and settle in more permanent housing. Insane!

I can see us being happy there. My family is there, we have friends there. Toronto is a really cool city. The whole thing feels kind of bitter-sweet because I really enjoyed traveling. Either way, it’s a new phase and something to be excited about.

A quick summary

During these last two years, we’ve lived and worked from 27 cities in 16 countries:

London, Lyon, Budapest, Berlin, Madrid, Valencia, Barcelona, Seville, Las Palmas, Lisbon, Dubrovnik, Split, SF, NY, Seattle, Vegas, Denver, Toronto, Vancouver, Hong Kong, Saigon, Bangkok, Malapascua, Taipei, Kaohsiung, Fukuoka, and Seoul.

Cities we've been
My travel map on RemoteHub

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.

Canny team photo
Team Canny in Lisbon

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. Although our time is ending, I am so grateful for the opportunity to travel for these last two years.

Choosing Toronto

We made a short list of cities we were interested in living in: New York, San Francisco, Seattle, and Toronto. Then, we scored each 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. The only reason we’d live in San Francisco again would be for our friends there.

Seattle came really close. Andrew’s family’s there and we have some friends there. Plus, Seattle winters are way nicer than Toronto winters.

Toronto was the winning city

In the end, Toronto won even though the weather there is probably the worst out of the list. My family is there and we have friends there. Toronto feels right.

It’s up and coming for tech but not overwhelmingly so. The Canadian dollar means an instant 25% discount. Being in eastern time is ideal for keeping in touch with our team and customers.

We can see ourselves being happy there.

Remote work continues

Our lives as digital nomads and remote workers have been one and the same 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, Invision, and Zapier are all big advocates 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 we wouldn’t have it any other way. Without it, we wouldn’t have the stellar team that we have now.

Canny team meeting via Zoom
Meeting Pippa in one of our biweekly Canny Cuddles

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.

While we’re transitioning out of our digital nomad life, we’re still working remotely. With that, we’re leaving some of the struggles of nomad life behind.

Here are some of the struggles that stood out:

Lack of comrades

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

Relationships take time to develop—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. It always felt like we’d be leaving in a couple weeks, so what’s the point? Maybe we’re just making excuses.

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.

Some late-night döner with friends Mary and Stephen

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’ll be back in Toronto, we have the chance to reconnect for the longer term. We’re excited to pick up hobbies again. Andrew’s playing in a soccer league and I’m getting back into a cappella!

Communication struggles

I found the language barrier difficult at times too but also fascinating. We learned how to communicate with basic hand gestures and 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.

My favorite Spanish power yoga class

Language is fun, I wish I knew more of it. Maybe we would have built more friendships if we had pushed ourselves more.

That said, the nomad community is also growing. When we were in Las Palmas, we learned about the Nomad Cruise. There are increasing opportunities to connect with other nomads.

The search for a routine

For someone who needs a routine, the nomad life wasn’t ideal for Andrew. Time zone changes, environment changes, everything changes. We went through an adjustment period every month.

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 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 former, we had a space optimized for productivity. With the latter, we got to explore more of the city.

Dojo Coworking for a day in Las Palmas

We’d also have days where no coffee shop had everything we needed: outlets, bathrooms, and, most importantly, wifi. That gets pretty frustrating.

We’ll have everything we need to build a routine again in Toronto. We’re looking into setting up a home office. A separate room in our apartment where productivity happens. Standing desks, ergonomic chairs, strong wifi, and no commute. It’ll be a nice change of pace.

Don’t have an office? Don’t worry. You can still be very productive.

We had a great time

Although there were challenges, we both really enjoyed our time on the road.

We got to see a lot more than some get to see in a whole lifetime. We experienced so many different cultures, cuisines, and climates. We know “hello” and “thank you” in many different languages.

We chased warmth and avoided the brutal winters back home. We got our open water diving licenses and conquered escape rooms all over the world.

Escape room winners
Literally set the record at this escape room

We’ve had the best pastel de nata, pineapple buns, and mango smoothies. Looking back through my camera roll brings so much joy.

We also got a lot of work done. Not knowing a lot of people meant we were usually on our own schedules. The hard work payed off too.

We left San Francisco as a team of two and we’re coming home a team of five. We’re still fully bootstrapped and profitable.

Now, we’re dedicating our travel to our team retreats. They’re so great for team bonding and shenanigans. We just got back from our third one in Denver! P.S. We’re hiring.

Settling down will mean several changes to our day-to-day. Less traveling, more family and friends. All things that we’re looking forward to.

Sarah Hum

Hey there, I'm one of the co-founders of Canny. As a founder, I dabble in pretty much everything but my expertise is in product design. Outside work, I enjoy digital illustration, a cappella, and hanging out with our dog, Emmy.

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September 18, 2019 3:38 pm

: ) I enjoyed your post. Congrats on your old and new adventures. I wish you guys the best!


September 26, 2019 3:25 pm

Great post! Thank you for sharing.

October 2, 2019 1:47 pm

I love this lifestyle soo different and i hope for u more happness and success 🙂

Will Hum
Will Hum
October 11, 2019 8:04 pm

Welcome home Sarah!

Eli Okii
Eli Okii
November 20, 2019 5:30 am

This is wonderful!

Sammy D Deleña
Sammy D Deleña
January 19, 2020 10:27 pm

Been remote working for 4 years now…so far so good. If you need help in software testing, I’m just an email away!

Josh McPherson
Josh McPherson
February 5, 2020 12:29 pm

Great post. It looks and sounds to me like you guys had a fantastic time playing and working hard. I love to see it

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