Digital Nomad Interviews – Kelsey from the United States

Here’s our next digital nomad interview. With this series, I feature people of different cultural, professional and personal background and let them talk about their lifestyle, why they chose to become digital nomads and how they combine work and travel. Please don’t hesitate to get in touch if you’d like to be part of the digital nomad interview series.

This time, Kelsey from the United States was so kind as to answer my questions.

Kelsey is a location-independent ESL teacher and works with kids from China

Please check out Kelsey’s website and Instagram account to connect and follow her:



Did you miss the previous interviews? Here they are:

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Interview with Kelsey

Digital Nomad Interviews: Kelsey from the US

Hi Kelsey! Could you tell us a bit about yourself and your background?

Hi, I’m Kelsey! Once upon a time, I was a confused college student in California that loved to travel but wasn’t sure how to make that lifestyle a reality. I had no idea what I wanted to do but knew it would involve some sort of conservation work, teaching, and creativity.

Before I started out on my digital nomad journey, I worked in environmental education teaching people about birds and their importance. Now, I work as an online English teacher for VIP Kid and travel while I teach!

I’m still trying to figure out how to tie all of my interests together (and at times feel just as confused as I was in college), but I’m slowly figuring it out.

Does working as an online ESL teacher come with special challenges?

Yes, definitely! You really need to make sure that you have good wifi wherever you’re staying, and that you can either be alone or that other people won’t mind if you’re singing the ABC’s at 8AM.

You also really have to consider the timezone where you’re traveling to – I teach students in China, so I have to be conscious of their hours. It was a nightmare when I went back home to California and was teaching on PST – I had to get up at 3AM to teach! In Europe, it’s perfect – students are usually taking classes in the evening, so that means busy hours fall in the middle of 8AM-4PM my time, which I like a lot more!

You also definitely need to like kids, of course! I’m lucky that I do, but I think this job can be stressful if you don’t. It’s a lot of fun, but can also take a lot of energy – most of my students are wonderful, but I do occasionally have one that may test my patience.

I’m also an introvert, and have found that teaching too many classes really drains my energy so I have to be careful. I’ve found that my sweet spot is teaching 8-10 classes a day, and I try to take at least 1-2 days off during the week.

Why and when did you set up as a digital nomad?

When I left the US for the first time on a study abroad program in the UK in college, I was HOOKED. I’ve been in love with Europe ever since and keep finding myself back here. I have yet to actually apply for a visa, but hope to make my love affair more permanent at some point!

I left my location-based life in January 2019 (so it hasn’t even been a full year!) Becoming a digital nomad, or at least moving abroad, was always something I wanted to do since I’ve always loved to travel. I also just really like the idea of having the freedom to decide where I want to be and when. I like that if I feel like going somewhere, I can just pick up and go, and don’t have to answer to anyone about it!

Do you travel alone or with a partner/friend? Which advantages and disadvantages does this have?

I traveled with a friend for the first 3 months. For her, it was purely vacation, whereas for me it was a “test” to see if I liked the digital nomad lifestyle. We both went back home after that time was up, but I came back to Europe while she stayed in California. So, since June, I’ve been traveling alone.

I like both types of travel – when I’m with a friend, I like that I have a built-in sounding board and someone to share all my travel experiences with. Plus it’s nice have someone to watch your stuff when you need to pee in the airport (lol) or to commiserate with when you hit some bumps in the road (which you probably will, both literally and figuratively.)

I also enjoy traveling alone since I don’t have to make any compromises and can literally do WHATEVER I want without considering another person’s needs. I also find that I usually end up making more friends since I’m more willing to put myself out there. When I’m with a friend I tend to stay in my comfort zone a little more. However, it can get lonely at times, especially since I mostly house sit now instead of staying in hostels, which makes it a little harder to meet people.

Overall, I don’t necessarily prefer one style of travel over the other, and like to mix it up! I enjoy having some solo travel time, but also enjoy traveling with someone else. It is important to ensure that your travel goals are the same, though – as much as I loved traveling with my friend, it was a little difficult to focus on work while she was on ‘vacation mode.’ So, in the future, I’d prefer to either travel solo, short term with a friend on ‘vacation mode,’ or long term with another digital nomad. 

Digital Nomad Interviews - Kelsey from the US

Which continents/countries have you already visited? Do you have a bucket list of places you’d like to see?

I’ve pretty much just stuck to Europe during my travels! Like I mentioned above, for some reason it’s always just called to me. I have yet to go to any other continents as a digital nomad, but I’m honestly open to anything.

I have always been drawn to Arctic destinations (I visited northern Sweden a couple years ago and LOVED IT) so I’d like to explore those more! I also would really like to check out more of Eastern Europe, as well as Japan. And I’m dying to go to Antarctica (but that probably won’t be for a WHILE, haha.)

For now, I mainly just go wherever I can find a cool house sit, preferably in a small city/town that’s close to nature. I’d also really like to try out some ‘digital nomad hub’ destinations, because being a digital nomad can get really lonely! It can be too easy for me to end up hiding at home, working and not interacting with other people. I’d love to meet more people and collaborate on projects – I’ve really been missing that lately!

How do you handle work vs travel/sightseeing time?

I’m not going to lie, this can be tough at times since I feel the pressure to see everything but also still need to work. When I was with my friend, I definitely did a lot more travel stuff since we were only in each location for about a week or two. 

Now, I stay in places for at least a month but preferably more, and usually give myself 1-2 sightseeing days a week. I love this style of travel much better – traveling quickly requires way too much planning work for me!

How long do you plan ahead? What are the advantages and disadvantages of planning ahead, in your opinion?

This is a tricky one, and I haven’t found the perfect formula yet! I would ideally LIKE to plan ahead by 2-3 months, but sometimes it ends up being as short notice as a few days to a week in advance (although I’m trying not to do that anymore)…This can be really really stressful but can also lead to some pretty cool house sits! 

For example, in England I was asked if I could arrive earlier and stay longer, which worked great for me (all that moving around gets exhausting!) The house sit I’m currently at in Hamburg is AMAZING and worked out perfectly with my plans, and I found it about a month before. I was also asked to stay a month longer in the middle of the sit, which again, I wouldn’t have been able to do had I planned too far ahead.

Sometimes people put up amazing sits super last minute, and those are easier to get since less people are applying. I found a really cute apartment in London that way – like literally 2 days before! And, sometimes you can find cheap last minute plane fares, too!

So in sum – I wish I was more of a planner, but have had a lot of luck winging it (even if that can be a little more stressful.) On average though, I’d say I usually plan about a month ahead.

Digital Nomad Interviews - Kelsey from the US

How do you choose your accommodation? What kind of accommodation do you like best? Why?

I used to stay in hostels when I first started traveling in my early 20’s, but since starting out as a digital nomad I’ve done a combination of house sits and AirBnbs.

Hostels are a great way to meet people, but at this point in my life, sharing a room with 10 other strangers is not my idea of fun! I would still do it but would have to be in the right mood (but it also wouldn’t really work with me teaching during the day.)

I like AirBnbs since they have kitchens, and I also enjoy getting a private room to have some human contact haha. However, I know that in some places, AirBnbs have really negatively impacted the local economy so in the future I want to avoid getting them in areas where this is the case, or just make sure I get a private room. Now that my friend is no longer traveling with me I pretty much exclusively do house sits, and kind of just go wherever I find a cool one. I mostly house sit for cats, so it’s typically pretty easy and I don’t have to worry about a dog barking when I’m teaching.

In the future, I’m toying with the idea of getting an apartment of my own just so I can feel a little more ‘settled’ and have more control over the destinations I want to go/how long I can stay. We’ll see!

How and where do you like to work? Why?

I usually just work from home since I’m teaching and don’t want to bother anyone. However, when I’m working on my blog I usually prefer coffee shops or other public spaces, like libraries. It’s nice to be around people, because working by myself at home can get lonely!

Do you have plans to settle down one day? If yes, where?

Eventually, I’d like to have some sort of “home base” that I might be able to sublet when I want to travel. I still haven’t figured out where yet, but if I do, it will probably be somewhere in Europe or the Pacific Northwest in the US!

That’s probably in the far future, though – for now I’m happy to continue moving around as it suits my fancy.

Any recommendation for people who would like to start a nomadic life but are not sure how?

YES! Becoming nomadic is really not as hard as you may think. If you have an American or Candadian accent, a degree, and at least one year working with kids in some capacity (be it babysitting, teaching, etc.) you can teach English online with the company I work for, VIP Kid! Feel free to message me if you have any questions about it.

I guarantee you also have other skills even if you don’t realize it. I’d highly recommend joining Facebook groups for things you’re interested in as they are SO HELPFUL in finding jobs and networking. I found a freelance writing job that way. I’m in some groups for freelance writers, VIP Kid teachers, digital nomads, and other bloggers. Just search for whatever you’re interested in and you’ll find something!

If you want some digital nomad specific ones, my favorites are Female Digital Nomads, Digital Nomad Girls, and Digital Nomad Jobs.

You can also become a Virtual Assistant with a program called “90 Day VA” – I haven’t done it myself, but have heard nothing but good things about it! If you currently have a 9-5, you can even approach your boss and ask if there’s any way you may be able to transition into a remote position.

I’d also recommend looking into house sitting (I use Trusted Housesitters) – there are TONS of opportunities, especially in the UK! I’d recommend starting there if you’re new as it’s really easy to find sits there. You can also use Hostelworld to find hostels.

Also make sure to look up the Visa requirements and how long you can stay in each country/region. That’s very important, too!

I’d also really recommend following a bunch of digital nomad accounts on Instagram to give you the confidence to believe that it IS possible! That’s what I did, and I found it SO helpful. My favorites are @itsatravelod, @travelingfro, @temporaryprovisions, @lenapapadopolous, @mollyhostudio, @seenicwander, and @theoffbeat life. They all provide amazing value and advice and don’t just show you pretty photos with a one-liner caption. @itsatravelod even posts new remote jobs on Fridays in her story, and has a website with remote job listings!

You can also listen to podcasts like The Offbeat Life, Compass, and Women on the Road to hear about how other people have made their remote jobs/life a reality. It’s so important to surround yourself with other people living the lifestyle you want to create, as it will give you ideas, create connections, and just keep you going when you feel discouraged.

Feel free to reach out to me if you have any questions! I’ve been there, and I’d love to help you if you want some support. I’m still quite new at this “digital nomad life” so I understand what it’s like to start out – and facing pressures from family/society can honestly be tougher than figuring out all the logistic stuff. 

Digital Nomad Interviews - Kelsey from the US

Anything funny, dangerous or special which happened to you that you’d like to share?

The first couple of days into my digital nomad journey were a complete DISASTER and left me questioning whether I’d made the right choice and if this was horrible foreshadowing for what was to come. My friend and I barely slept on the flight over – it was a red eye, and I’ve never been good at sleeping on flights (even when armed with all the essentials – sleeping mask, earplugs, melatonin.)

When we arrived in London, the airline lost my friend’s bag that had all of our toiletry items in it. Which wasn’t a HUGE deal, we just bought new ones, but she was freaking out as it was her first time abroad and the airline couldn’t give us a clear estimate of when she’d get her bag back, and where they’d even be able to send it (they hinted that we may have to come back to the airport to pick it up, even though we had a bus to Glasgow the next day.)

We then arrived at our hostel in London and quickly found out why it was only £25 a night. It was January and there was a microscopic heater in our room that let out the tiniest puffs of heat, our window wouldn’t close all the way and we had to MacGyver it shut with my hairband, the mattress was thin and lumpy, and there was really loud construction outside All. Night. Long. I had earplugs, but it was not the most relaxing sound to listen to before I put them in and I could still hear it a little as it was literally right outside our window. (Note to all of y’all: earplugs are ESSENTIAL. Never go anywhere without them, even if it’s just to walk around the corner. You never know when you’ll need them.)

My friend ended up getting sick from the flight and spent the majority of the next day in bed. Then, we got lost on our way to Victoria Coach Station and missed our bus to Glasgow by literally a minute.

We rebooked another ticket, and immediately regretted taking an overnight bus after we’d both had 2 nights of terrible sleep – the first on the plane, and the second at the hostel. We both barely slept and arrived at our house sit not really knowing what year it was.

Luckily, things started looking up after that! Our house sit was in a gorgeous home in a perfect location with the most adorable dog. The people we were house sitting for were SO COOL and made us a home cooked meal that night. The airline sent my friend’s luggage to Glasgow and we had access to our stuff again!

I know these were the most first world problems ever, but it seriously felt like we were living in a Series of Unfortunate Events for 72 hours haha. Although we had some hiccups later on, nothing was as bad as those first few days!

Thank you very much, Kelsey!

Digital Nomad Interviews - Kelsey from the USA
Digital Nomad Interviews - Kelsey from the USA
Daniela Fries
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