A few years ago, I got my hands on a copy of Tim Ferris’s book The Four-Hour Work Week, where the author described what he dubbed the “new rich,”— a generation of workers and entrepreneurs that leverage the internet to make an income while filling their lives with travel and experiences. This is a generation less tied to material possessions and the obligations that arise from owning a lot of stuff. I was hooked. At the time, I was in the throes of my corporate marketing career, having left my company for a new management role. It didn’t seem like the right time to be experimenting with digital nomadism or as a friend of mine called it “instagrammable homelessness.” And yet, I couldn’t let go of the idea. A seed was planted in my mind and with each passing day, I sowed it. With each morning train ride into the heart of the concrete jungle that is Toronto’s financial district, I stoked the embers of this flame that turned into a roaring fire I could no longer ignore.
The “work online, travel the world and live your dreams” angle has been explored to death. Remote work and a location-independent lifestyle have exploded over the last decade, driven both by social media and by globally skyrocketing costs of living (thank you Boomers). One of the things I realized when learning about digital nomadism and entrepreneurship is that most of the content is around the dreamy side of this lifestyle — the beaches, the hammocks, the sunsets, and the beautiful vistas. So, I want to talk about another aspect of the quit your job and wander life; the sacrifices involved with living in another country, working for yourself, and trying to build a creative business. The personal sacrifices and internal work before you even book a ticket, set foot on an airplane, or set-off on your next adventure. The list below strips away some of the glamour and gets to the heart of what it takes (or what it took me) to make this lifestyle a reality, and the work started long before I ever set foot in Costa Rica.
I gave up the weight of other people’s expectations
When my husband and I decided to sell our beautiful Toronto townhome along with many of our possessions and move to Costa Rica, we were on the receiving end of a lot of worry and skepticism. Concerns ranged from the perfectly reasonable (how will you sustain yourselves financially and build new careers?) to the utterly ludicrous (I heard peanut butter is expensive in Costa Rica, how will you eat peanut butter?!). I spent many nights tossing and turning over what people would think of me until one day I sat with my messy feelings and asked myself the only question that mattered — what did I think of myself and if I didn’t like what I saw, how did I plan on changing it? Once I answered that question (the answer was, I wasn’t loving things the way they were), what anyone else thought ceased to matter, and I began moving forward.
I gave up trying to hack life
We live in a world of hacks — the most optimized, engineered, and efficient way to do things that will get us the fastest results. Unfortunately, some things in life just aren’t hackable and I would count selling your home, starting multiple businesses, and moving to Central America in a global pandemic among them. Shortly after we started our business, my TikTok ForYou page was full of videos of people talking about how they 10xed their growth in two months and how if I copied their exact strategy I would too. I learned the hard way that some things are not hackable and there are no shortcuts.
Starting our own business, living a location-independent lifestyle, and making that work takes a lot of planning, preparation, and mental fortitude. It took me a long time to shift from the mindset of an employee to that of an owner and entrepreneur. Patience is not my strong suit and becoming a business owner is nothing if not a test of patience and resilience.
I gave up focusing on results and began focusing on the process
We are a results-focused world. We obsess with tracking, analyzing, and ranking. But results are overrated if you don’t enjoy the process. The process is where the magic happens. It’s where you fall flat on your face. It’s where you learn skills, lessons, make new friends, develop new relationships. The truth is that none of us ever actually reaches our goals. When was the last time you met a goal and thought now I am done, I can relax and throw my feet up and watch Love Island for the rest of my life? Chances are, likely never. It’s more likely that you reached your goal and thought yeah, but wouldn’t it be great if I could also do … The goalposts are always shifting. So why not enjoy the journey down the pitch as you move towards them?
I gave up prioritizing my wants and nice-to-haves and focused on my needs
In a culture of you need everything and you need it now, it’s tough to distinguish between needs, wants, and nice-to-haves. An example I like to use is how we settled on Costa Rica as a launchpad for the digital nomad lifestyle. When my husband and I were trying to settle on a destination to move to, we divided up our life into needs, wants, and nice-to-haves. We then started categorizing our choices.
One of our top priorities, a need was that we needed to move somewhere that was politically stable and relatively safe. Safety and stability are a need. We wanted it to be somewhere coastal and close to gorgeous beaches, a preference. A nice-to-have was that it should be relatively close to home (Toronto, Canada) which would allow us to make frequent visits back. While we chose a place that met all the requirements, I use this same approach to almost every problem or project. For example, we briefly toyed with the idea of moving to Peru, a country with more amenities, and a lower cost of living than Costa Rica. And while it was tempting to consider it as a destination, (and we were very tempted having spent our honeymoon in Peru three years ago), political stability was something we aren’t willing to compromise on for more amenities (Peru, although very safe hasn’t always been politically stable). This approach clears up a lot of the cobwebs in my head and takes a lot of the guesswork out of decision-making.
I gave up trying to be someone I am not
Or at least I am trying to. Most of us don’t really know who we are. To be fair, a lot of who we are is shaped by other people — our parents, friends, communities, and the culture we grow up in. By the time we make decisions for ourselves, we have this long history of doing what is expected. But part of trying new things or living life on your terms is realizing, accepting, and embracing who you are.
I realized that try as I might I would never feel completely happy, fulfilled, or at peace working in the corporate world. I have friends who are excellent at their jobs, they excel in big companies and thrive in that environment. But it wasn’t for me and making it fit felt like jamming my feet into shoes designed and made for somebody else — a square peg in a round hole. Figuring out who you are isn’t easy. It’s a trial-by-fire process. You will burn. You are going to mess up. But it’s the only way to figure out what lights you up inside.
Here’s the thing — there is no secret to living life on your terms. There are no shortcuts, no life hacks, no efficiencies, none of that. Ultimately life although not endless, is repetitive. It is routine. A set of days, weeks, months, and years of habits and choices that push you towards your goals. You need to chip away at it. Like a sculptor revealing the statue underneath, the life you want is already there. You just need the hammer and the chisel to uncover it.
