Since I started working remotely as a software developer a few years ago, I wanted to try out the lifestyle of a digital nomad. Between completing my Bachelor's and COVID-19, I couldn't find a good time to leap into the world of traveling and working remotely. That finally changed in 2021 when I managed to take 4 trips, and here's what I learned.
July 2021 • 3 weeks
The very first trip I took was to Mexico City when travel was slowly becoming more unrestricted and COVID-19 cases were falling. I ended up going with a good friend of mine who had already been to Mexico City before and was familiar with the area. We spent just over 2 out of the 3 weeks in Mexico City before heading to Yucatan & Quintana Roo. However, in Mexico City, many people didn't speak English and the only Spanish I knew was from 15 years ago when I watched Dora the Explorer. The language barrier was only a slight inconvenience, and I've since learned a lot more Spanish to assist me in my travels.
The main purpose of this trip was to see if I would be productive working in a new place or if I would be tempted to take time off to go explore. Additionally, I wanted to know if I would be able to see and do enough things when 8 hours of my day would be reserved for work.
Since I ended up taking many more trips after this, the answer was clearly yes. I was able to stay productive and I didn't feel like I missed a lot either. In fact, I enjoyed this type of trip more than a traditional vacation, since I wasn't tiring myself out every day doing different things.
An oversight during the planning of this trip however was the accommodation. While the location of our Airbnb was decent and the WiFi was fast & reliable, the practicality of the space inside wasn't. This apartment lacked an ergonomic workspace and the furniture was uncomfortable in general. This isn't always easy to see by looking at pictures, but in this case, it was evident in hindsight.
I stayed in Escandón which is a nice neighborhood and only a 15-minute walk from some grocery stores, restaurants, and bars. However, I found myself taking a lot of Uber rides to get to La Condesa or Roma, which wasn't too expensive but it added up. In retrospect, I wish I had coughed up a little bit more money upfront and stayed in La Condesa, which would have been partially offset by needing to take fewer Uber rides.
August 2021 • 2 weeks
Up until this trip, I had only traveled within Southwestern Ontario, despite living in Canada for over 22 years. That was my main incentive for spending 2 weeks in Vancouver, BC.
Being 3 hours behind my normal life didn't seem like a problem going into the trip but it proved to be a lot more challenging. First off, I'm far from a morning person, and waking up on days when I had 6 a.m PST (9 a.m. EST) meetings proved to be difficult. Since I was only gone for 2 weeks, I managed to reschedule some of these and started my workday by 8 a.m. PST (11 a.m. EST) which was when standup was. Thankfully, my working hours are flexible as we have team members all across the globe, so this was possible.
Additionally, by 2 p.m. PST (5 p.m. EST), most of my team had ended their day but I still needed to work for a few more hours. These quiet hours allowed me to zone in on my work and be very productive on some days. The downside to this was that most people weren't online, so if I had questions or was blocked, I had to wait until the next morning.
Personally, I couldn't work from Vancouver or any other place 2 or more hours behind the rest of my team for more than 1 week. Ideally, I want to be in the same time zone, or even a couple of hours ahead.
November 2021 • 2 weeks
My first ever solo trip started off in Panama City where I spent all 2 weeks. Panama ended up being a warm-up before the big 1 month Costa Rica trip that I talk about next. I met a lot more people here that spoke English so it made learning Spanish easier and less daunting. To make the most of my trip, I tried to meet as many new people as I could.
I ended up meeting some amazing, fun, and smart people on this trip and they're a big part of the reason why it was so memorable. As a child, I lacked confidence and was a shy personal overall. I'm glad that I was able to step out of my comfort zone because without that, I don't think I would have enjoyed it nearly as much.
Panama City is not considered a tourist or digital nomad destination but it's a super diverse city with lots to do, and I tried to take advantage of that as much as possible. I did do some of the touristy activities like seeing the Panama Canal or visiting Casco Viejo (old quarter), but I also explored the city on my own by renting Bird scooters. By doing that, I was able to see a different side of the city that you might not be able to if you're visiting for a few days or if you're on a business trip.
Panama City showed me what I wanted to get out of a new place when traveling, and that's a new experience. I've seen been actively seeking out something spontaneous, exciting, and adventurous whenever I'm somewhere new.
December 2021 • 4 weeks
After gaining experience living the digital nomad lifestyle, I was ready to take on Costa Rica. Being a small country, you could get to a lot of places in just a few hours. Knowing this, my strategy was to set up a base in the center, the capital city of San Jose. This is where I spent my time during the week, and I booked a place to stay along with a bus ticket to some other part of the country. Here's how my 4 weekends in Costa Rica
The first weekend, I spent exploring San Jose as well as getting myself sorted for things like a local SIM card, groceries for my Airbnb, and exploring the neighborhood around me. I also took part of this weekend to work on an overdue side-project of mine; a website redesign and a new blog. I ended up asking my host for some recommendations to places in the country I should visit.
This led to me booking a hotel and bus to Manuel Antonio, a famous national park mostly for locals on the Pacific side of the country. I ended up staying in a small but traditional hotel with a couple of pools and a restaurant on the property. That weekend I spent half my time on a beach with a drink or by the pool. The other half, I spent hiking through various parts of the national park and city center. I really enjoyed the balance I had between adventure, nature, and fun, and I wanted to keep that for my next trip.
Almost every local I talked to told me I had to visit Puerto Viejo, so that's I found myself on my third weekend. This little hipster town on the Caribbean side had tons of beaches, waves to surf on, and a young crowd. Since they ran out of rental scooters, I secured a bicycle for myself to explore the town and its neighboring places. Turns out, a lot of other people had the same idea. On the one and only road where everything happens, I met so many people using bicycles as enjoyment and a way to get around. I ended up taking a chocolate tour, had dinner with live music, and hung out at the markets with some new friends. To end the night, I had booked myself a quiet lodge in the middle of nature with no AC, WiFi, or signal.
Originally planning to go to Tamarindo, I made a quick change in plans and booked my stay in La Fortuna, this time in a hostel. I've never stayed at a hostel before so I didn't know what to look for. I went for the first one with good reviews in my budget. When I got there, I met some new friends right out front of the hostel. We ended up drinking beers and talking on the quiet, dark road next to the hostel. I ended up going out with everyone that night, so I got home quite late because I had forgotten I booked myself an 8 a.m. hike on the volcano that's the main attraction in town. I underestimated how physically exhausting the hike would be because, by the end of it, I had no interest in doing anything else that night.
There were a few key similarities between each of these weekend trips, but each one was memorable in its own way. I did something very different each weekend, which was probably my favorite part about how my trip to Costa Rica went.
If this is something you've been thinking about trying for yourself but don't know where to start, I hope this post gives you some more insight on things. I was able to take these trips while still working full-time Monday to Friday, only taking a day off at most for each trip. I did this by moving around on the weekends, going for a longer period, and using evenings to explore local attractions.
As you might have been able to tell, my first few trips ended up being the learning phase for myself, and how I wanted to travel and live. Towards the end of 2021, I found my rhythm and the experiences showed that.
I found my personal sweet spot between living the digital nomad lifestyle while not being away from home for months or years on end. After spending some time with friends & family, I'm heading to Colombia in March 2022. I'll be spending 2 weeks in Medellín followed by 2 weeks in Cartagena. If you have any recommendations for Colombia, let me know on Twitter or shoot me an email.
📸 All pictures were taken by me. Check out my Unsplash to see more.