An Honest Look at the Pros and Cons of Digital Nomad Life

Every now and then, it’s important to sit down and reflect a bit. We just returned to Puerto Vallarta – the place where our digital nomad journey took off six years ago.

Now seems like as good a time as any to reflect on this digital nomad lifestyle and share some of the pros and cons we have experienced.

Our Digital Nomad History

For those of you landing here for the first time on a Google search – welcome! That means we’ve actually learned something about SEO, which one would hope we have at this point…

In case you’re new around here, let me lay out our nomad life story in a concise manner.

We started out by teaching English in China, first in Beijing and then in Kunming. We traveled any chance we could get, but that still wasn’t enough.

On a trip to Bali, we decided to work our tails off until our teaching contracts ended in order to save money for a gap year. Once you spend a year traveling and experiencing that freedom, it’s hard to put that genie back in the bottle.

bali sunset
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Life in Bali

I applied for and got accepted to the Darmasiswa program in Bali, where I got tuition, a year-long visa, and a meager scholarship to cover some of my expenses.

During our nine months on the island, I did a bunch of freelance writing, managed a few Facebook pages, and made videos for a language company when I wasn’t in my Indonesian language and culture classes.

It didn’t take me long to learn the freelancing advantages and disadvantages.

On the one hand, I was able to get a relatively stable paycheck that went quite far in Bali. On the other, I had to rely on the unstable internet and the frequent power outages during the rainy season.

For the record, this was back in 2015 when the term “digital nomad” wasn’t yet a buzzword. Bali is now a nomad hotspot and there are plenty of coworking spaces with super-fast WiFi. I’m sure the power outages still happen, though.

Meanwhile, Rachel was doing everything she could to learn more about blogging, social media, and running a business. We were both determined to not go back to the grind of working for someone else.

We found out about teaching English online, applied, got the jobs, and did a trial run of the digital nomad lifestyle while visiting friends and family in the US for a few months.

digital nomad benefits,remote work pros and cons,work from anywhere drawbacks
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Traveling through the USA in summer 2016

This was another good lesson about the pros and cons of remote work. We got to work from an Airbnb in Vegas before going out to see a concert, but we also had to teach at 3 AM in a friend’s kitchen while in Bend, Oregon.

If we planted the seeds of our nomad life in Bali and watered them in the US, then we truly watched those plants grow once we moved to Mexico.

We felt confident enough in our abilities to balance travel and work, so we followed the lines going south and have been going strong ever since.

Remote Work Pros and Cons

Since we started traveling full-time as digital nomads, we’ve had our fair share of ups and downs. We’ve come up with a remote work pros and cons list.

We don’t want to scare you away, so let’s start with the good stuff! There are plenty of digital nomad benefits that this lifestyle affords.

For us, the biggest benefit to the digital nomad lifestyle is far and away the freedom. Neither of us liked asking a boss for time off, and we didn’t particularly like the fixed schedule. Even the 1-9 PM schedule we worked in Beijing wasn’t for us.

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We go where the wind blows us

This is a big reason why we haven’t applied for actual remote jobs and have been living as freelancers. Having a remote job that still has a set weekly schedule wouldn’t really be conducive to our lifestyle. However, this works for many people including lots of our nomad friends.

We love being able to sit down, look at the map, search for flights and Airbnbs, and pick a place to go live for a few months. That’s what we just did in Buenos Aires and we had an incredible experience there.

We worked hard (and played harder, of course) in the city, but we also had the chance to take two full weeks off to go to Patagonia for some epic hiking.

Oh yeah, and we also got to walk with wild penguins! All without asking for a single day off. Another one of the many digital nomad benefits.

sasha and rachel patagonia penguin selfie
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Hanging with penguins in Ushuaia, Argentina

Taking a remote job with a fixed schedule allows you to potentially take the show on the road, but it depends on a lot of factors. For example, your company may require you to stay within a certain time zone, or they may just not allow you to log in from other countries at all for tax purposes.

If you are able to travel with a remote job, though, you can enjoy the stability of having a guaranteed income and a routine. Those making an American or European salary in Latin America or Southeast Asia can also live the high life for a fraction of what it costs at home.

Meanwhile, we freelancers and entrepreneurs ride the roller coaster of life with its many twists and turns. Some months are great, and then the next you lose your biggest source of income.

That’s exactly what happened to us when China introduced new regulations in the fall of 2021 essentially banning online tutoring and overnight that industry went poof. Bye!

On the plus side, we were able to pivot our efforts into getting private students, growing our YouTube, starting new affiliate programs, and doing other things to generate income that didn’t require waking up with the roosters to sing the ABCs. Sometimes you need a good kick in the pants to make a change.

That being said, the instability of the freelancer life definitely isn’t for everyone. We’ve been doing it for years and are pretty accustomed to the ups and downs, but it’s starting to wear thin for us as well.

We’re currently looking into other remote work opportunities and may be making some changes in the next year, so we’ll definitely keep you posted on our progress.

Work From Anywhere Drawbacks

Whether you have a remote job or you’re a freelancer, it’s likely you’ll eventually deal with burnout and loneliness. We have dealt with both and we’re a traveling couple.

rachel and sasha blue ridge parkway
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The digital nomad lifestyle can be lonely sometimes

Moving around often isn’t very conducive to building friendships, which is why we’ve chosen to spend several months a year in places like Puerto Vallarta where we’ve developed a community.

Thankfully, there are all kinds of online forums, social media groups, blogs, coworking/coliving spaces, and nomad-friendly events these days. It’s definitely a different scene now compared to when we started.

Take Puerto Vallarta for example. When we first got here in February 2017, the usual crowd of retirees and snowbirds were surprised to hear we were staying a few months and working from our Airbnb apartment.

There’s now a Facebook group with thousands of people and it seems like every other person you meet here is working remotely.

While places like PV are quite developed and have the infrastructure for digital nomads, it takes more than fast internet to be productive and effective.

We’re back here at the moment, and while it’s great to be back, the dogs, roosters, construction, mariachi bands, and fireworks really make it difficult to have classes, take calls, or even just write and edit videos.

It’s also a bit difficult to travel with a nice desk, an ergonomic chair, and all the bells and whistles that make for a comfortable remote work setup.

Once upon a time, I worked on an ironing board and a plastic lawn chair for several months in Colombia. These are the sacrifices we make to be able to live this lifestyle.

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Sasha using an ironing board as a desk in Medellin

At this point, we get legitimately excited when we see a picture of a decent desk and a chair on an Airbnb listing. If there’s also a screenshot of the WiFi speed test, there are high fives involved. It’s the little things that do it for us nomads, really.

Digital Nomad Insurance

Understanding the ups and downs of digital nomad life will help you deal when you experience these low points yourself. These are some of the things we wish we had known when we were starting our location-independent lifestyle.

One thing that has always given us peace of mind is having solid digital nomad insurance.

Before hitting the open road with your laptop and a dream, you’ll want to make sure you’re covered in case anything happens. It will help you enjoy your travels much more and will also help put family and friends at ease.

Since we started our digital nomad journey, we’ve been using SafetyWing and their Nomad Insurance policy. It’s a travel insurance company created by nomads for nomads, so we fully support their mission.

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Best of all, you can purchase a policy even if your trip has already started. We were so busy in the run-up to our Argentina trip that we forgot to sign up before our flight out.

It was a relief to find we could still sign up after we had already arrived in Argentina and know we’d also be covered in Uruguay, Chile, Panama, and Mexico for the rest of our trip. They actually cover you in 185 countries and you don’t even need to let them know about your itinerary in advance.

SafetyWing really saved our butts in 2020 when we got stuck in Medellin during the pandemic lockdowns. They covered our humanitarian flights back to the US no questions asked and were pleasant to deal with. You can read that story in our SafetyWing review.

Check out their options on their website, which start from $42 per person for four weeks.

As such, we’re proud affiliates and repeat customers.

Final Thoughts

To sum it up, the digital nomad lifestyle is quite the wild ride. It has its benefits and drawbacks just like any lifestyle, its good days and its bad. Sometimes you’re on top of the world, and other times it feels like the world is squishing you.

All that being said, we wouldn’t trade our experience living and traveling as digital nomads for anything.

Being able to immerse ourselves in so many fascinating cultures, learn new languages, try all the local food, and meet so many incredible people is something we’ll always be grateful for. And it’s certainly not something we could have learned in an office in, oh, say, Scranton, PA.

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Hiking in Cinque Terre was a huge bucket list item that we ticked off in 2022

Now that we’re the Grateful Gnomads, we’re hoping to bring you lots of new content that’s relevant to the digital nomad lifestyle.

Whether it’s your first time here or you’re a 1.0 fan, let us know what kind of stuff you’d like to see on the blog, in newsletters, and on YouTube.

Happy nomading,

Sasha (& Rachel) 🙂

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