Digital Nomad as a lifestyle: CozyCal

Kat and Chris are a couple working on bootstrapping CozyCal, a scheduling software for small businesses and freelancers. They went on a three-month trip in Asia to experience the digital nomad lifestyle. Here’s the story of their adventure.

People often say that the world is your oyster. When Chris and I were working full-time in New York, our oyster was only as big as an 8 miles by 2 miles rectangle. We had always dreamed of travelling the world while working on something we love. But our fast-paced work schedules left us little time to plan out how to turn our dream into reality. Quietly, we shoved the dream under the rug.

About a year and half ago, we decided to quit our jobs in New York and moved back home to Vancouver, Canada to bootstrap CozyCal together. Our vision is simple. We want to build the most design-oriented and user-friendly scheduling software out there. We want to help freelancers and small businesses to generate leads, book meetings and collect payments all in one place.

Hitting the road

As we began to get into the rhythm of bootstrapping a business, the dream of combining work and traveling resurfaced. We were surprised to learn how digital nomadism is a rising trend across the world. Seeing others sharing their journeys of travel while working made us realize that there would be no better time than now for us to try out this completely new lifestyle.

In early 2018, we embarked on a three-month sabbatical of being digital nomads in Asia. We spent a month making our way from North to South Thailand, leaving footprints in Chiang Mai, Chiang Rai, Bangkok and Ko Lanta. For the rest of the trip, we visited Siem Reap in Cambodia and Taipei where we fell in love with both cities.

In each city, we immersed ourselves in the local culture, tasted delicious food, and even made connections with other digital nomads. To our surprise, we found many co-working spaces have been sprouting up in these cities.

When we stayed on Koh Lanta, a tropical island near the tip of Southern Thailand, we got to work at a co-working space called KoHub. Just imagine typing away on your laptop being surrounded by chattering of monkeys and the smell of the ocean. I had to pinch myself hard to be convinced that I was not in a virtual reality studio.

Along our trip, we got to chat with other people from all over the world. Some are newly minted digital nomads like us, while some have been on the road for several years. The types of projects people work on also vary. They range from side-hustle projects, contracting work, cryptocurrency trading, to working remotely for startups or bootstrapping a business full-time. It’s no doubt that the world is becoming more remote friendly.

It’s cool to see the possibilities of merging travel, work and living in one lifestyle. Another interesting observation we’ve had is seeing that digital nomads are bringing positive changes to local economies. The co-working hubs we visited in Thailand and Cambodia have hired local staff to help run the business. If we were to stay a bit longer in each city, we’d love to chat with local entrepreneurs and hear their stories.

Balancing work and traveling

During the three months of travel, most of our days were divided evenly between exploring and working. When we first arrived in a new location, we usually spent the first several days sightseeing and scouting for coffee shops with stable wi-fi.

After getting used to our surroundings, we transitioned to a more regular schedule. In the morning, we would kick off the day with a brief all-hands meeting (yup, just the two of us), and block out chunks of time throughout the day to focus on tasks of the day. By dusk, we would wander into the night markets hunting for authentic, local cuisine.

Sometimes, we needed to stay up late to answer support tickets or take demo calls from other timezones. But that didn’t bother us at all. I think this is the magic of bootstrapping a software business. With all the amazing tech tools, we can choose to work from anywhere, at anytime.

The flexibility of the digital nomad lifestyle allows us to balance work and travel in a way that would not be otherwise possible with an office job. We are happier, healthier, and in general feeling more free than ever. More importantly, we are in control over our own schedules and locations.

It’s not to say that there were no stress or challenges at all of being digital nomads. We still feel the pressure of bootstrapping CozyCal to ramen profitability. The frictions between two people who are in each other’s presence twenty-four seven could be tense. But traveling to new places and seeing new things make us more open-minded, humble, and grateful. Our perspectives in life have changed as we are spending more time reflecting who we want to be and what we want in life. Less is more.

My favorite toolkit

As a small two-person team, we try to run things in a lean and efficient manner. While Chris is the developer, I focus on the non-technical side of operation including marketing, customer support and sales. Here is a list of some of my favorite tools:

• appear.in: My go to tool for demo calls and customer feedback interviews. I love how I can easily share my room link on my booking page with the guests. Skipping the need of dialing in or entering a unique code, they can join me with just one simple click. More importantly, the video quality is consistently stable and reliable.

• Canny: Canny is a customer feedback management tool that helps collect feature requests. We have created CozyCal’s roadmap in Canny that displays the list of feature requests our users have submitted. We love how Canny‘s simple interface helps us capture feedback in one organized place.
• Focus Keeper: Focus Keeper is a productivity app that uses the Pomodoro method. Pomodoro Method is a time management technique that divides work into 25-minutes intervals, separated by 5-minutes breaks in-between. As someone who can be easily distracted, the Pomodoro technique helps to keep my attention-span in check.
• Notion: Notion is a note-taking application with markdown support that also integrates tasks, wikis, and databases. We use Notion both for managing CozyCal operation as well as personal affairs. Besides equipped with powerful features, Notion’s design is beautiful.

What’s next?

We hope to make Europe and South America our next destinations. And Norway is on our list!

Another dream of ours is to build a camper van and drive across North America while continue growing CozyCal! Got any tips living a camper van life? Let us know!

Check out CozyCal’s website and follow us on Twitter and Instagram. 🙌