Imagination at Work

What I Learned After 3 Years As a Digital Nomad

What I Learned After 3 Years As a Digital Nomad

This month marks 3 years since I’ve been a digital nomad and during that time I’ve learned a lot. I started my journey on the inaugural Remote Year program back in June 2015. You can read my full story about becoming a digital nomad here. Since taking that leap of faith, I’ve not only landed a remote job but started my own blog, The Remote Nomad, and my own company, WiFly Nomads. I would never have imagined just how much can happen in only 3 short years.

During these 3 years, I’ve learned some of my biggest life lessons. Before I became a digital nomad, I was seeking out something that I didn’t even know existed. Then, I finally came across the concept of working online and traveling the world. The decision to go remote has been the best decision I have ever made in my life. Here are the top 10 things I’ve learned over the past 3 years:

#1 – It’s the people, not the place, that make the best experience

When people ask me about my best travel memories, it always goes back to a moment with people. I guess the sad part of traveling so much for so long is that those ‘must see’ spots get old. In fact, if anything they are usually really crowded and because of that, they lose their magic.

Whether it was attending a local wedding in Argentina, being welcomed into a local home in Croatia for dinner, living with a family in Mexico, or lying on the beach watching the stars from Bali and realizing that the moon actually looks upside down… those are the memories I remember.

You can always go back to visit a place, but you can never recreate those memories with people because you can’t plan for these moments. No matter how beautiful a place is, if you have no one to share that experience with, it loses the allure.

#2 – Traveling, and the people you meet traveling, will be the greatest teachers in life. You’ll grow personally and professionally, at rapid fire.

Hands down this is true 110%. Don’t overlook what I am saying here. I never realized that 90% of who I thought I was, was actually just preconditioning of childhood and the environment and culture that I was raised in. Traveling, and the people I met traveling, challenged me. It made me look at myself in the mirror from a different perspective, it made me see and experience things that a book can’t teach you.

  • When you go to Kenya and see a family living in a hut you are humbled.
  • When you are swimming in the ocean in Bali and a piece of plastic washes up, you care about plastic and the ocean.
  • When you think you show your true self to people, then someone challenges you on the idea, that in fact you are closed off, you have no choice but explore if there is truth to the statement.

I’ve discovered new food, music, and language that I love that I would have never realized unless I was exposed to it.

You know that saying, “You don’t know what you don’t know.”? Well I’ve learned so many things that I simply didn’t know that I didn’t know.

I feel like now, after 3 years of being a digital nomad, that I have chipped away who I thought I was and have become more of who I really am. This is purely shaped by the people and the places I’ve traveled to. It’s as though you get to see and experience everything and pull from it what you choose to take with you.

#3 – This lifestyle isn’t just for ‘other’ people, it’s for those who work for it

So many people will want to live this lifestyle but will dismiss that it’s not for them. They think they need to be more technical than they are. Here’s the thing though, it won’t happen immediately. It takes a lot of patience and learning along the way. But those who are dedicated to the process will succeed. So many people give up at the first bit of resistance. Just to recap the resistance I faced…

  • I couldn’t land a remote job after 3 months (and it’s a bit of a crush to the ego, especially when you’re in a position to easily land a traditional job in no time)
  • I booked a one-way ticket to Prague with no job and only had 1 month to figure something out
  • My laptop died 2 weeks into ‘taking the leap’
  • All my savings were gone

After ALL of these things, pushing forward, it finally all came together.

It will not be easy but it most certainly will be possible. I was never born into this life. I great up in a small town in Canada BUT I was clear on what I wanted and everything I did was working towards that.

#4 – Shit will still happen

Just because you wake up every day in a Thai or Bali paradise doesn’t mean shit will just stop happening. What you don’t see on Instagram is when someone’s family member dies (thankfully not my case), people will still disappoint you or you’ll get heartbroken, you’ll have bad days, just as you’ll have good days. The point is, life still happens.

#5 – You must always prioritize taking care of yourself, before anything else

This is HUGE. When I started working online, I abandoned all good habits, and in fact, took up bad habits.

Instead of meditating, eating healthy, hydrating, eliminating sugar, exercising, getting a proper sleep etc I was I was drinking, and trying to see and do everything which meant I wasn’t sleeping, I started eating like shit and then I got to a low place. I was no longer thriving, I was just surviving. My energy levels were low and I was less able to handle stress properly. I was certainly not showing up as my best self.

I’ve been good at taking care of myself and as a result experienced some of the highest highs and I’ve also been shit at taking care of myself and as a result, experienced some of the lowest lows.

I know absolutely, for a fact and for certain just how critical taking care of yourself is on this journey. In a lifestyle where so many elements are constantly changing around you, you need to consistently always take care of yourself. I now have the awareness to recognize when I’m slipping, and immediately change course when that happens because that low sucked, hard, and I never want to get to that point again. So no matter what, always prioritize taking care of yourself first.

#6 – You’re trading one set of pros and cons for another

Just as I mentioned above, life doesn’t magically become perfect just because you’re globetrotting throughout paradise. The lifestyle comes with its own set of pros and cons. Sure you may not have the 9-5 grind, but you’ll face a new set of challenges, like the people always leaving, which makes it more difficult to establish friendships or form relationships.

#7 – Traveling won’t allow you to ‘escape your problems’, in fact, it’ll amplify them

I always thought I traveled because I liked it and I liked experiencing other cultures. Then eventually I realized that maybe in fact I was running from some of my deepest issues. The problem with that is that you can run away from your issues when you’re traveling. If anything, it will just amplify those issues. This means you have no choice but to finally address them. You can be a million miles away, but that shit is within you, so you really never escape it until you address it.

#8 – You can’t unknow or unsee what you experience. There will be no going back.

You don’t know what you don’t know, but once you know, you can’t unsee it. My participants from WiFly Nomads have even said the same thing. Once you grow up in a lifestyle that is based around the 9-5 you don’t really know anything different. But once dive into this digital nomad lifestyle, you understand a whole new way a living is possible. Not just that, but that there’s so much more too. You start to understand the opportunity of working for yourself, how you can earn a passive income, and how much more possible all of that seems because you see people living it first hand.

#9 – You’ll meet the most incredible people you would have never had the chance to meet otherwise.

My friends range from 20-40, come from all different countries around the world and have the most diverse set of skills. I have friends just scraping by and I have friends making millions. I have friends that are entrepreneurs and friends that work for other companies. I cannot express the diversity of my friends. The most amazing thing about this is that these are people you would have not had the chance to meet otherwise.

Had I not started this lifestyle, I would have never met Daniel DiPiazza from Rich20Something, or Joel Brown from Addicted2Success, or one of my now best friends, Johnathan, or Emile Steenveld, who helped me overcome some of the most challenging mindset barriers I’ve faced.

I’ve met people that I’ve learned from, people that I have helped, people that challenged my views, and people that I could just have fun with. Regardless, all of these people have had a profound impact on my life and they’ve helped shape me into the person I am today.

#10 – No matter how long you’re a digital nomad, you’ll still wake up every single day of your life so grateful that this is your life. You will always know, recognize and appreciate this incredible lifestyle you live.

This never gets old. No matter how busy life gets, at random points i’ll just pause, look around me and think, “wow. Is this really my life?”. If you asked me 5 years ago, this lifestyle would have been my ultimate life dream. If I could have achieved this lifestyle before 60 I would have thought I made it and I’m already living it now. I never forget that and I appreciate every bit of that. When you hear people complain about commutes, their boss, or office politics and you can no longer relate and you feel grateful for have putting in the work to make this lifestyle a reality.


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