Since September 2018 (how long ago that seems now!), I’ve spent nearly a year traveling the world and more than three years as a digital nomad. Both lifestyles have a lot in common – I don’t have a permanent home, I own very few clothes, and I spend a lot of time writing at cafes over a strong and sweet coffee. And I’m sure lots of people have rolled their eyes at my Instagram feed during both phases (digital nomad is such a cringe term!).
But the transition has been an interesting shift.
As the coronavirus pandemic rages on, I’ve talked to more and more people who are considering transitioning to the digital nomad life themselves.
After all, if you can now work from anywhere (and it turns out many white-collar professionals can), why wouldn’t you work from a beach or a foreign city or a little mountain cabin? But long-term travel and digital nomad life are very different. Here’s what I’ve found, what I’ve learned, and what I’d recommend if you’re thinking about one lifestyle or another.
Exploration is Harder
When I was just traveling with no job, I could go see anything at any time. That was great for getting into fancy or tiny restaurants, for exploring crowded museums, and for generally wandering and truly getting to know a place in just a few days. But that was the long-term travel life.
Now, with a living to earn again? I’m not chained to certain working hours like I was at a corporate job. Being a freelancer is great that way. But it also means sometimes I’m working on a Saturday afternoon – and I’m almost certainly working on a Wednesday morning.

When I’m in Europe out of the US timezones, sometimes I can get in some exploration on a weekday morning when my clients aren’t awake and asking for things yet. But generally now, if it’s a weekday, I’m working.
Local Life is More Real
When I was just traveling through a place, I was a tourist having fun. That was great! I could still visit small local restaurants and tiny museums, remote archeological digs, and all the major sites. But usually I’d move on within a few days. (I did spend that heavenly month in Paris and now I can die happy.)
Now as a nomad, I stay in places longer because I need to. I make more local friends, I rent a real apartment and learn about the local plumbing and electrical quirks, and I do normal things in an exciting place.
Grocery shopping and market visiting are now regular events – and they’re still thrilling, because it’s all new. Don’t believe me? Try grocery shopping in Greek. I can get the real feel of a neighborhood from months spent strolling the streets daily – like the little wine caves of Exarchia in Athens, or the bus system of Great Britain.
A Few More Needs

Since I’m spending more of my days working – and some in meetings with potential clients – my glamour standards are a little higher now than they were in my long-term travel days. Sometimes I need to look like a respectable writer and businesswoman.
There’s no room for my pilled yoga pants on those days. Also I can’t go two weeks without brushing my hair anymore (though I do love sneaking into fancy hotels to glam up pre-date).
I also need a few more things to help me work. Freelance writing is pretty light on the equipment, but I do have a new MacBook that has changed my life after not owning a laptop for 6 years. Work is much easier with it – but when I ws just traveling (and for a few months as a digital nomad) my iPad sufficed just fine and traveled easy. Traveling with a 35-liter backpack makes you realize how much every single tiny item takes up – never mind a laptop.
For a while as a digital nomad, I was living with a little bit more luggage. I went from just the backpack to the backpack + a tiny roll-on to just one big suitcase. We all only wear three outfits anyways, so I’m making my life very simple again.
A Little Less Time
During my year of travel, I went to 30 different airports. Just thinking about all that back and forth now makes me tired – but when I didn’t have a job, I had plenty of time to sleep off the tiredness! Seriously though, I went to so many airports, sometimes at insane hours of the night.
Now I have to be more conscious of my time, since I’m using it to earn money again. I spend less time on planes, train, buses, and the occasional ferry, since I stay in places longer now. And I often prioritize forms of transport now where I can get work done if it’s a weekday, like trains, since I can’t read or write anything on buses or in cars.
Related: How I stay in Europe for more than 90 days as an American
A Few New Priorities
While I was traveling, all I had to consider when thinking about where to stay was the price, and where I wanted to stay. A little hut in Thailand’s jungle-filled north? Sure! Just watch out for the noisy lizards in the thatched roof. A hostel in the remote south of Crete with almost no wifi? Sounds like heaven!
Now I am free – I can work from anywhere that has wifi. But that means my life now revolves around decent wifi. And that’s not a given everywhere. I stayed in one beautiful Art Deco apartment as a digital nomad in Athens with a whole room just for my clothes and yoga mat that only had wifi in one little corner.
I joined a coworking space to make sure I could get decent internet during my working hours. I also now prioritize a space with a working area, like a little desk or a comfy couch, and am always on the lookout for cafes with great wifi where I can hang for hours.
And I’m looking to meet more permanent friends, if I’m in Greece or England where I am spending more time these days. I’m less interested in meeting people in hostels, since they’ll just be gone in a few days. I want friendships that will last in person more than two days – and that’s a bit harder to come by. (Dating is its own challenge as a nomad!)
A Different Perspective
My year of travel was incredible – a break from the slog of normal daily life, an exploration of parts of 24 countries on three continents, and a deep dive into what I truly love and value. It was life-changing and perspective-altering, and I’m so grateful for that. I spent so much money and wasted a year of my career and I regret not a single thing.
And that trip inspired my digital nomad life. In the last week of my trip, spent walking across the whole of England, I thought and thought about what I wanted from my life now. It wasn’t going home to Boston and an easy, conventional life. I wanted to keep traveling and live abroad and work on my own terms.

So that’s my perspective now – where do I want to spend significant time in my digital nomad life? So far that’s Greece, and England, and Ireland, and Croatia too. Some of it is cultural, a lot depends on visas, and the general cost of living is a big factor too. And of course, the weather, because winter is not my friend.
I’m fortunate enough to be able to travel the world for a year without working, and now to have spent a year abroad working as a freelance writer. Both have been amazing, but different in their own wonderful ways.
Thinking of becoming a digital nomad yourself? Here’s how I made the transition – and what I would do differently now.
More digital nomad resources
- How I Find Housing, Pay Taxes, and More in My Digital Nomad Lifestyle
- My Minimalist Digital Nomad Packing List
- The Challenges of the Digital Nomad Lifestyle
- A Guide to Housesitting as a Digital Nomad