The 3 Biggest Lessons I Learned From Becoming A Digital Nomad

In the dead of winter in 2015, I made a decision that some might call… impulsive, hasty, maybe even insane. My frustration with the cold and, honestly, the loneliness of freelancing from home through another Montreal winter had reached its peak. In what seems like a blur now, I applied to join a community of nomads called Hacker Paradise, booked a plane ticket, and left for Vietnam 3 weeks later.

Thus was the beginning of my life as a truly location independent entrepreneur and part-time digital nomad.

I’ve learned a lot since this adventure started; how to find cheap flights, how to live for 3 months out of a carry on, how to barter for a hotel room, how to discern the likelihood that a food cart is going to make you sick… All valuable lessons, of course. But there are 3 major life and business changing lessons that really stand out.


I’m sure this isn’t the first time you’ve read this. I know I heard this repeatedly but always made excuses about staying put in my apartment. It wasn’t until I was forced to get out of my room to work (hotels have notoriously crappy wifi) that I realized it wasn’t just a cliche.

When you travel, anything can be inspiring. New scenery, new culture, new people, new foods and smells, new languages and sounds in your ears. It is all stimulating and can get your creative juices flowing. It might inspire you to create something new, or to look at something completely differently. Or it might just inspire you to stop procrastinating so you can go exploring in the afternoon.

When you go somewhere new, chances are you’re hoping to spend more of your time away from your laptop than usual. This was a huge factor for me to get organized and get off Facebook. Parkinson’s Law says that work expands to fit the time available for its completion, so cutting my work day down didn’t actually impact my level of output, it just meant that I was able to fit more activities into a day.

Spending more time away from work can also be one of the most inspiring things you can do for your business. When I started doing things for fun, instead of only to make money and move my business forward, I started getting more clarity on what I really wanted and felt more motivation to get back to work in the mornings.


Going to Hacker Paradise reminded me of how important it is to surround yourself with remarkable people. If I am the sum of the 5 people I spend the most time with, I want those 5 people to be #killingit.

Another business (and life) lesson I have learned over the past couple of years is that I can’t do it all myself. Meeting new people has allowed me to form awesome collaborations with experts. I’ve hired a writer and developer for my startup, contributed marketing ideas and feedback for a hackday project that went viral, and will soon be releasing a podcast series with my travel bestie. Amazing people are everywhere and I want to work with them all.

The other freelancers and entrepreneurs I met have become friends, mentors, clients, travel buddies and huge inspirations in my life. They share my work with their networks and we all act as cheerleaders for each other.


When you meet new people a few of them are going to challenge you. You can choose to be stubborn with what you know and ignore them, or you can choose to open yourself up to new ideas, new ways of thinking about things, and new viewpoints on business, life, and the world.

If you’re reading the same types of blogs by the same kinds of bloggers, you’re only getting one kind of advice – the advice that works for that industry.

What if you took advice from a software developer who used growth hacking techniques to go viral with a side project and make $10 grand in a day? Or a serial entrepreneur who uses outsourcing so much that he has actually achieved a 4-hour work week? There is a lot to be learned from people with experience in fields and business models vastly different than your own.

When I started my adventure, I was working in the only niche I really knew or felt confident enough to work in. My work didn’t make me happy, but I knew how to do it. Over the past two years I have completely changed my niche to one that actually gets me excited about work, I’ve got new clients I love working with, I’ve completely changed my brand to something I’m proud of, and I’m now the CEO of a startup. Whoa.

There isn’t only one way to do things or one way to reach success.


It took me going halfway around the world to get out of my comfort zone, check my values, and get truly happy in my entrepreneurial journey. But you don’t have to leave your hometown to learn these things.

Join a coworking space. Go to meetups. Join a new Slack or Facebook group that isn’t specific to your niche. Start a mastermind with entrepreneurs from different backgrounds. Soak in new experiences and new ideas, make honest connections with new people, collaborate on projects just for fun, and get the hell out there.

Leave a Comment