15: Working from home? It may be time to take your office on the road

Many people have been stuck working from a spare bedroom or kitchen table for months because of the pandemic. And, while some companies are moving towards reopening offices, many are offering flexibility for employees to continue working remotely, at least some of the time. This shift, along with the increase in people doing freelance work, means workers who need nothing more than a laptop and strong Wi-Fi to get their job done are less tied to living close to a corporate office. Some are turning this into an opportunity to explore the world, living and working as digital nomads. In today’s episode, Liz talks to Kathleen O’Donnell who has been traveling the world solo for over two years about how she made the leap from full-time corporate gig to the digital nomad lifestyle.

Kathleen O’Donnell is a digital nomad who quit her corporate job in 2018 to explore the world while working as a freelance writer.

Maybe it’s because I just passed the one-year anniversary of my last time getting on an airplane – just weeks before the start of lockdown – but I’ve had travel on the brain lately. So, I was thrilled to have the opportunity to speak recently with Kathleen O’Donnell about her adventures living as a digital nomad – working as a freelance writer while she travels the world, with nothing more than a laptop and a small backpack of clothes. 

One of the silver linings of COVID-19 is that more people have increased flexibility in terms of where and how they work. If you have an office job, you’ve likely been working from home for much of the past year. Some companies are moving towards reopening offices. A New York Times article recently cited data from Kastle Systems that said about a quarter of employees across the US are going back into offices to work these days. But the articles said that many people would prefer to continue working remotely at least part time after the pandemic. And, some companies seem to be embracing this shift, allowing employees more flexibility than ever before. 

Some countries are actually courting digital nomads during the pandemic, welcoming travelers with special long-stay visas. The Washington Post reports that Hawaii, Barbados and Estonia all have special program for digital nomads now. Madeira even has a community with free co-working space that the Post likened to summer camp for adults. 

Until I can get back on the road again, I’ll have to settle for living vicariously through Kathleen. When I caught up with her for the Seven Plates Spinning podcast, Kathleen was hunkered down in Split, Croatia, where she’s been riding out the pandemic until travel opens up again. Croatia is also offering long-stay visas right now, and Kathleen is trying to get one. 

What follows are some highlights from our conversation. You can catch the full podcast episode here

Liz Serotte (LS): I’m fairly certain that lots of people think the idea of taking off and traveling the world sounds fabulous. But few of us find the courage to actually do it. What got you to actually take the leap?

Kathleen O’Donnell (KO): The decision had been something I had been kicking around for years and years. Someday I’ll quit my job and spend a year traveling. And I think a lot of us have that someday feeling, but life sometimes looks different than what you think it will look like. My mom was diagnosed with Parkinson’s disease in 2012 and so that really lit a fire under me.  Something like that reminds you that the future doesn’t always look like what you thought it would. That really inspired me to take the full-time travel leap and travel for a year. And then I thought, “Well, maybe after that I’ll come back to Boston and work another corporate job.” But the more I traveled, the more I thought, “No, that’s just not for me anymore.” And so, I decided I had to figure out a way that I could keep traveling and keep living abroad and still earn money to live on. 

LS: So, before you starting working from the road, you just traveled for a year? 

KO: Yes, I quit my corporate job in September of 2018 and just traveled full-time for a year. It was really wonderful. I was very lucky to be able to save up and do that, and just travel and not work at all. Also helped me figure out what I wanted to do after. But, of course, I had to eventually work again, because I was not in a position to retire at age 33.

LS: That sounds amazing. What surprised you most about the experience of traveling solo for such a long time? 

KO: I was surprised by how many interesting people I’ve met traveling everywhere. You meet so many people when you travel alone, which is great. And I met so many people who were living abroad and working abroad in so many different, interesting ways – like running their own companies, freelancing, doing seasonal work to fund their year-round travels, things like that. So it was really inspiring to see so many different possible lifestyles from people who were very similar to me. I wouldn’t have thought that I had that many options, but the more people I talked to, the more options I realized I had, and that was really encouraging.

LS: So now you work as a freelance writer. What gear do you need to work on the road?

KO:  For working gear, I found you don’t need as much as you would think. Actually when I started, I didn’t own a laptop, which was a bold choice on my part. I probably should have bought one earlier. I had like an 11-year-old MacBook that didn’t really work. So I started out writing on an iPad with a Bluetooth keyboard.  And, you know what, it worked okay while I was getting started. Other than that, being a writer, I am fortunate that I don’t need too much other equipment. I do have a good pair of headphones for video calls, and my Kindle, so that I can read books on writing and copywriting without having to find copywriting books in English in a Croatian bookstore. I live in a 1,000-year-old stone building, so sometimes the WiFi’s not great. So I always check with wherever I’m staying about their WiFi speeds. Or I work at a coworking space, because they tend to have very fast internet, even if you’re in a country where the internet is typically slow.

LS: What type of working hours do you keep? How do you balance work and play?

KO: Because since I’m in such a different time zone, I did have to divide up my work day. So I do a lot of my quiet, focused work, where I’m just writing, in the mornings from like 9:00 to 1:00. It’s a good focus time for me. But then I typically dedicate like 4:00 PM to 7:00 PM to answering live any questions that I have. That’s when I schedule all of my calls with clients. And there is the occasional workday that lasts until 10 or 11:00 PM when things come in late, especially with West Coast clients. But otherwise, it’s not too bad. I get a nice midday break to live the Mediterranean lifestyle. I spend three hours drinking coffee in a cafe.

LS: Not bad! I know you’ve been stuck in Croatia for about six months now because of the pandemic – and, let me just say, there are certainly worse places in the world to be stuck! – but you typically move around more often right? 

KO: Yes. I usually move around every three months, partly because I get a little bit bored – that’s why I live this way – and also due to visa restrictions. Most countries you can stay for 90 days without a visa, especially in Europe. And then any longer than that you have to go through the residency process, and that is quite difficult in lots of countries. So it’s easier to just go somewhere else.

LS:  Do you have a favorite place you’ve visited?

KO: I do. Athens, Greece is my absolute favorite place. I typically spend a lot of time there, but Americans have not been allowed in for the last year. So I can’t wait to get back. There’s a small but growing digital nomad scene. The cost of living is very low. The weather is beautiful. People are so warm and friendly. And, of course, Split, Croatia is also number two on that list now. I’ve grown very fond of it.

LS: What was the biggest lesson you’ve learned along the way?

KO: It’s that I’m capable. And I think most people are capable of so much more than we would ever think just living our normal daily lives. Because in your normal life, you don’t have to go too far out of your comfort zone generally. I certainly did not. And then traveling the world for a whole year, totally by myself, turns out I am capable of a lot of things.  Like jumping into freelance life. I had never thought it would be something that would appeal to me or something that I could find a lot of success in. And  I really have! And it’s been a huge confidence builder to realize that you are capable of doing a lot of things. If you really want to do them and you believe that you can do them, you usually can.

LS: One of my first podcast episodes, actually, we had a conversation about getting out of your comfort zone, and taking risks, and the fact that most people don’t. Like you said, we just get really comfortable with our day-to-day. And even if we might have dreams of doing something different, it’s really hard to take that first step and get yourself out of your comfort zone. But usually, when you do – even if there’s some failure that come with it – usually goodness ensues if you can manage to take that first step and get yourself out there. It sounds like that’s definitely been true for you.

KO: Absolutely. And you know what? Failure is not as scary as it seems most of the time. You learn a lot from it. Things that go sideways – like living a traveling lifestyle and then having a pandemic hit that shuts down the whole world. Did not see that one coming! But get through all of that, you discover all sorts of unexpected benefits as well – like landing in Croatia. Would not have thought I would have done that, but it’s been incredible. Taking the first step is the hardest part. It’s really hard. Once you take that first step, all the rest of the steps are a lot easier.

LS: It’s kind of like you’ve already jumped off the cliff, then getting into the water seems quite easy.

KO: Exactly.

LS:  Have you found it scary traveling alone as a woman?

KO: The reality is that there are risks and dangers as a woman doing anything anywhere in the world.  In Boston, I had scary experiences walking home from work at the end of the day. I just always make sure that I have a working cell phone. I get a local SIM card or a phone plan where I can access my data while I’m abroad, so that I can access maps or call someone. And that gives you real security. It’s definitely something that makes traveling easier in these times. I have met so many more kind, welcoming, very helpful people, than I have met people who are threatening, or scary, or even just unfriendly.

LS: Tell me about packing properly. And when I say properly, I mean packing light, which I struggle with all the time. You told me that you’re traveling around with just a backpack, right? 

KO: It’s a small backpack, too. I really went all in. It’s 35 liters, so it’s tiny. One of the things that I always remember is that out of all the clothes you own, let’s be real – especially, I think we have all learned this in COVID – we all wear the same three outfits over and over. So just pack those three outfits. Don’t pack anything else. Don’t pack your aspirational outfits, you will not wear them. Heels are a pain. Pack comfortable shoes. And then, also one of the things that I do to really lighten the load is I buy a lot of stuff when I get to wherever I am. I travel carry on only as well, so you can really not have many liquids. But everywhere I’ve been – except for Laos, where it’s hard to find much of anything – you can find sunscreen, makeup, body lotion, any of those big things that would normally take up a lot of space. I did a lot of sink laundry. That is the downside of traveling with so little is that I would basically have to wash whatever I wore in the sink that night and hang it up to dry for the next day. So that is kind of a pain, but the time saved in checking bags, losing bags, paying for checked bags, wondering where your stuff is, wondering if it will get damaged, it was worth all of the headache.

LS: So what does 2021 hold for you? What are you plans? 

KO:  Hopefully, tomorrow I get my four month temporary residency in Croatia, so I will have the next four months squared away staying here. And then, hopefully I’m able to return to Greece. I’d like to go back to the US to visit for a bit too. I left in July, so it’s been a long time. But then after that, I think one of the things I’ve learned from traveling is you just have to stay really flexible. You never know what things will look like. That’s true normally, and it’s doubly true these days. So I’m just staying open to see what happens, where I end up going. It will definitely be somewhere abroad, but I’m excited to see what that will look like once we have a few more options.

You can read more about Kathleen’s travel adventures on her blog My Lonesome Roads.