Becoming “Digital Nomads:” Why We Quit Our Jobs to Travel

In October of last year, Ryan and I made the changes we’d been planning for months: we quit our jobs and left our apartment in Boston to pursue a life of traveling, writing, and freelancing online. Today, we have no jobs, no home, and no concrete plans, our possessions fit in our backpacks, and we earn money mostly from writing – oh, and we’re in Thailand.

Maybe I should back up…

Discovering the Digital Nomad Lifestyle

It was back in 2011, when I was in the middle of my Peace Corps service in Rwanda, that I stumbled across people on the Internet who were living what sounded like a dream life: traveling long-term and working for themselves, mostly online.

They were entrepreneurs or freelancers, and worked as writers, designers, programmers, or even admin assistants. They called themselves “digital nomads” and said they were “location independent,” and they traveled constantly, or lived for a few months at a time in places like Bali or Chiang Mai before moving on to the next exotic locale. They weren’t interested in the rat race; they were interested in living a creative life on their own terms.

Hearing about people who bucked society’s expectations to chart their own path was incredibly inspiring. It sounded unconventional and exciting and fulfilling. It was very different from the life I had planned for myself – one that included attending grad school and working full-time in international development – but this idea of working for myself from someplace like Thailand sounded like a dream, nonetheless.

The post-Peace Corps trip I took in Southeast Asia, including traveling around Thailand and Malaysia with Ryan, only cemented the idea that this dream life could be possible. The cost of living and traveling was unbelievably low, the places we visited were amazing, and I met people doing all kinds of interesting things to make their travel-filled dreams a reality.

Living in Boston

After ten weeks of traveling, we returned to the U.S., and I set down the path I’d planned on. Ryan joined me in Boston, where I was attending grad school, and got his first office job. But a seed had been planted in both of us.

Fast-forward a couple years: we were engaged, we had an apartment in Boston, we both had Master’s degrees and good jobs, and I was working in international development as planned.

But our day-to-day lives left us wondering what else was out there and wanting something more. We found ourselves constantly reminiscing about past travels, desperately waiting for a week or two of vacation per year, and fantasizing about giving it all up to do something different.

Starting Our Travel Blog

The weekend after I started at my last job, Ryan and I went hiking in Maine, and had a conversation that led us to realize we were interested in starting a travel and outdoors blog. I’d always loved writing, and Ryan was getting more into photography. We wanted to share our passion for travel and the outdoors, as well as the tips we’ve picked up along the way, hoping to inspire others to travel, get out in nature, and seek adventure.

Running this blog over the past year and a half or so provided a creative outlet when we needed one, and it’s already opened a ton of doors for us.

Why We Changed Our Lives

As much as we were committed to our life in Boston – working hard, finding an apartment we loved, exploring New England, spending time with friends, practicing at my favorite Boston yoga studios – those ideas of a totally different life were always in the back of our minds.

We spent so much of our free time learning more about different possibilities for traveling, freelancing, blogging, and working online – and eventually realized that we were, in fact, serious about making it a reality.

It really boils down to our belief that there’s another way to live – and in the age of the Internet, it’s easier than ever. While it might sound like a crazy thing we’re doing, just Google something like “quit my job to travel” or “work online in Thailand” for (literally) millions of search results that suggest it’s not so uncommon.

More and more people we know have made similar choices, and Southeast Asia in particular is full of Westerners pursuing the same things as us.

Over the last few years, I was so lucky to have the chance to work at places I’d long admired and that did exactly the type of work I was interested in. But I found myself resistant to the idea of working for someone else, bristling at the long and inflexible hours, and lamenting the lack of flexibility, creativity, and independence (maybe a delayed effect of growing up with self-employed parents?).

We wanted to leave the U.S. because what seems to have become a typical modern lifestyle – one that revolves around constant “busyness,” working yourself into the ground, sacrificing health and relationships, fighting for promotions and recognition, waiting a whole year for one week off, earning as much money as possible, spending it on big houses and fancy clothes, and consuming and then consuming some more – just isn’t what we want.

Money, power, material wealth, and conventional “success” aren’t our priorities. We wanted to be able to regain control over our own lives, do work we love, see the world, and have time for the things we’re passionate about.

Our time on earth is remarkably short, and we can, in fact, use it in any way we want. Why shouldn’t we spend it trying to make our dreams come true? And maybe it’s morbid to bring this up, but life is also utterly unpredictable.

You don’t know what will happen tomorrow or next month or next year, whether you’ll stay healthy, or how long you’ll live. What a tragedy to see people who put off truly living until retirement, only to not even make it to 65.

We don’t want that to be us. We don’t want to wake up one day in ten years (or forty years) and realize that fear or greed or society’s expectations kept us from going after our dreams. So, we’re going after them now.

We got engaged in December 2015, and it wasn’t long afterwards that we set fall of 2016 as our date for leaving – giving us enough time to save up more money, start experimenting with freelance work, and take care of some logistics (like getting rid of almost a whole apartment worth of stuff!).

Starting a Life of Travel

We got married last August, and in October, we finally quit our jobs in Boston. The next few months didn’t go quite as planned, owing to a host of health and family struggles, but it meant we were able to spend some time at home in Montana, seeing friends and family and even getting in some skiing.

We also cashed in a bunch of credit card and frequent flyer points to fly to New Orleans and take a two-week road trip through the South (which we’ll be writing about eventually as we get caught up!).

By the beginning of March, everything was finally in place, and we took a one-way flight to Bangkok. As I write this, it’s 81 and sunny, and we’re sitting on a balcony overlooking a river on the island of Koh Kood. Are our lives here perfect? Are all our problems gone? No. But here we are, finally living the life we’ve dreamed of.

Travel & Self-Employment

As any business owner can tell you, working for yourself has its own set of challenges. And as our own experience as ex-pats has made more than clear, living abroad poses certain difficulties, too. Even though this is our dream life, we expect there to be plenty of moments of fear, frustration, and uncertainty.

Working for yourself means taking on all kinds of tasks and responsibilities you’d normally never worry about (accounting, taxes, legal status, insurance, and website maintenance, to name a few), and it means a constant hustle to find new opportunities – and frankly, never being sure where your next paycheck will come from or how big it will be.

But by starting in a region of the world with a low cost of living, where just our savings will go a long way, we’re able to hedge against some of the financial risk. And to us, the lower standard of living here is more than worth the ability to pursue this. No doubt this lifestyle comes with some other sacrifices, too, but the creativity and flexibility it allows are more important to us than the money and security we’re giving up.

And as a caveat: no, we’re not rich. The idea that traveling has to be expensive is truly a myth. In a place like Thailand, it’s pretty easy to travel on under $50 a day between the two of us – over a month, that’s literally less than we paid for rent alone in Boston.

It’s such an amazing privilege to be in this position. We don’t know how things will go for us – how successful our work will be, how long we’ll travel, or what all we’ll end up doing – but we’re excited to take the plunge and give this new life a try.

Have you ever considered the digital nomad lifestyle?

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“Digital Nomads” photo credits include Laura Hoffman and Paul Sableman.