Becoming a Digital Nomad: How I Did It, And What I’d Do Differently

in 2019, I finished my world-wide travels and was faced with some very real questions. What would I do with my life? How would I get a job? Where in the world do I want to live now? And how do I want to live?

Long-term travel has an uncomfortable way of opening up your worldview, and a whole lot of questions along with it. I needed a job – but I wasn’t ready to come back to the United States or the 9-5 corporate life. 

So I became a digital nomad. 

Writing that line, it sounds like I wrapped myself in a little chrysalis and emerged as a fully-fledged, terribly trendy remote worker with a fancy title. Of course, it’s a lot more complicated than that. 

So how, exactly, did I do it? And what has it been like so far? I’ll tell you all about it so you can learn from my successes and my mistakes.

Greece beach in Crete with clouds at sunset
The digital nomad dream is to work from a Greek beach, right?

Why did I become a digital nomad?

In my year of traveling to 24 countries and not working at all, I enjoyed myself immensely. If it were financially possible for me to retire at age 33, I would have done it in a heartbeat. But since I had financed my travels from two years of savings from the highly-paid corporate job that I quit, and spent most of that, it was time to go back to some form of work. 

In my final fortnight of travel, I took my time walking across England. I picked my way over rolling fields covered in skittish sheep and shallow puddles, thinking about what I wanted my life to look like. Most of my old life – expensive apartment, the city of Boston, a 9-5 corporate desk job – wasn’t calling to me any longer. 

I had fallen in love with the excitement of new places, with this free rootlessness I’d found. Everyone back in my old life seemed to be getting more and more settled: having a second or third kid, buying big lovely suburban houses, being promoted to managers and executives. When that’s what you want, it’s delightful – but it wasn’t what I wanted now. 

I needed a new plan. And I decided I was set on becoming a digital nomad.

Becoming a digital nomad: how to make it happen

I’d gotten a guest post published on Be My Travel Muse a few weeks before, and it started the wheels in my head turning. After all, I have over a decade of professional writing experience at this point – a series of corporate communications jobs and non-profit fundraising work. 

Writing is a notoriously low-paying field. But maybe I could wrangle some freelance corporate work – it wouldn’t have to pay much if I lived somewhere cheaper than Boston. (Nearly everywhere is cheaper than Boston.) 

I’d also noticed that many of the cheaper places I’d visited – Greece, Bali, Cambodia, Malaysia – were also very warm. My little cold-blooded body can’t stand the five-month-long winters of Boston, full of grey skies and grey slush and air so cold it hurts my face. 

Solo female traveler in Kuang Si Falls, Laos
Warm and happy in Laos

The wheels started turning. 

When I finished my trip and got back to Boston, I started looking for a freelance writing job in earnest. I found lots of job boards but got very few responses – probably because I didn’t know how to pitch myself yet. 

Then I found Andrea from It’s a Travel OD on Instagram. She posts remote jobs (legit ones that she vets) on Fridays – an invaluable resource. And if that weren’t enough, she gives plenty of tips on how to land that first remote job. She’s a game-changer. 

I applied for a digital marketing job, reasoning that my aptitude for quick learning and writing skills would translate to copywriting and blogging pretty swiftly. And after a few interviews, ContentFirst.Marketing brought me on as a freelance writer and editor, and that was the start of a business I’ve been building for almost three years now.  

If I’m making this search sound much too easy, maybe it was from the outside. But I had reached a point in my career where I had over a decade of experience – and some well-respected companies on my resume. It can often seem from Instagram like all the digital nomads are glamorous 24-year-olds, doing vague jobs for a lot of money.

Really, being a freelance writer is a great career path when you’re in your 30s or above as well. You have the experience to land a decent job without too much fuss – 24-year-old me would not have been qualified to do what I’m doing now. 

That’s my job, sorted (at least the first one). 

Finding a place to live

Once I had signed that contract, it was time to figure out where to live. Greece was at the top of my list – no surprise, as I’ve written a whole bunch about how much I love it there. (I really love it!) Athens is such a great spot for digital nomads too – cheap, safe, fun, and social. I bought my ticket for a few weeks later and started to work on the logistics of the move. 

AirBnB certainly has its issues as a platform, but I found it really valuable for getting a month-long place to stay. Hosts will often give you a good discount for a stay more than 28 days, and when you aren’t on-site to vet potential apartments before moving in, the reviews are critical.

I found a huge but affordable apartment ($600 for two bedrooms!) in the artsy Kipseli neighborhood of Athens and started getting excited to have my own space for the first time in months. 

An iced coffee at a cafe in Athens Greece
Freddo cappuccino immediately, please.

Getting accessorized for the digital nomad life

I had a job and a place to live for at least a month – look at that relative stability! 

But the packing proved a little difficult. I decided I needed to bring my little purple suitcase with me as well as my backpack – I’d be living a more stable and social life and needed a wardrobe that had more than three outfits in it. I packed mostly clothes that were comfortable for working from home and doing yoga and going out to dinner – trying to blend in a little as a local. No huge Thailand pants, and Tevas only on beach days. 

For getting my work done, I decided not to spend $1k on a new laptop just yet. My iPad was been perfectly functional for getting work done – after all, as a writer I need very little technical equipment. I have the Microsoft suite on it, all the Google apps, and Dropbox – that’s all I need. I did buy a Bluetooth keyboard to make my typing a hell of a lot easier. But that was pretty much it. 

These days, three years into living as a digital nomad, I have some additional equipment. But it still all fits in a suitcase and backpack.

After living so minimally (that 35L backpack did not fit a lot), I wanted to stick to possessing as little as possible. At least for a while. 

And sooner than I expected, I was off again. I took the ferry across Boston Harbor on a sunny September afternoon to the airport as the city gleamed over the still water, and said goodbye once more. 

Greek island of Delos with a cat in the ancient ruins
Greek cats know how to live.

What I would have done differently

Hindsight is 20/20, they say, but trying to figure out what your future self will want is a much more difficult game. It’s easy to say now what I would have differently, but really I don’t regret any of my choices in my travels and my digital nomad life. 

But for your benefit – maybe you’re thinking about making the remote leap too – let’s get into the details. 

  1. Started my job search earlier. This has a couple of layers. I could have dipped a toe into freelancing before I left, to put less pressure on starting from scratch when I returned. If you’re not taking a long time totally off work like I did, that’s my biggest recommendation. Start freelancing before you quit your day job, if you’re thinking of going down the freelance path. 
  2. Figure out exactly what freelancing entails. I didn’t do this before I started – I just jumped in enthusiastically like I usually do. Freelancing can be tough – the ups and downs in income flow, the need to do your own complicated taxes, health insurance woes if you’re an American citizen. I’ve actually found I love it, but if you’re in need of more stability, a full-time remote job can be a better option. 
  3. Find a digital nomad community wherever you are. I took a while to do this – I didn’t join a co-working space until my second month in Athens and I wish I had done it sooner. Writing is already a lonely occupation. Writing alone in my big cool dark apartment in a foreign country was even lonelier. But once I found a few people I connected with, the world opened up. I had sailing invites on weekends and dinner plans on weeknights, and a whole bunch of people who were doing the same thing I was. There was advice, commiseration, and a lot of wisdom shared. That was worth the $150 a month in coworking space fees for sure. 
  4. Find a good way to describe what you do quickly. I get a lot of people asking me where I live, as I toss my hair nervously and tell them I’m kind of homeless “but in a cool way.” This feels like a vaguely offensive and also incorrect way to say it, so I need to workshop that a little. People in general have a LOT of questions about the semi-nomadic lifestyle, so get ready to have some thrown at you when you start. It’s a relatively new way of working, so their curiosity is natural. 

Leaving my old life behind

I’ve been back to Boston a few times since I left, spending time with my family and friends and eating cookies from my favorite and much-missed bakery. It’s been great, but it also reaffirms that I love my new digital nomad life. I miss a few things about a stable life – space to keep my beloved books, casual dates with old friends, seeing my family regularly – but I love too much about my nomadic life to stay still right now. 

And if that feeling wears off? It’s easy enough to go back – it’s a lot harder to leave an old and comfortable existence. 

More digital nomad resources:

Want to get my latest blog posts, news, and updates right in your inbox a few times a month? Sign up for my newsletter!

2 thoughts on “Becoming a Digital Nomad: How I Did It, And What I’d Do Differently”

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.