A conversation with middle school teacher turned nomad

How she travels the world while working just 20 hours a week

January 14, 2025

Today we’re starting with something new: An original interview with veteran nomad legend, Mashon Thomas. 

Mashon has been living the nomadic lifestyle since 2018 and, having just turned 40, proves that adventure knows no age.

Several of us here on the Nomad Cloud team are big fans of hers, having followed her blog and podcast, Live Work Travel.

Currently in Ecuador before her next trip to “probably England?”, she’s answering all our questions about how she supports herself, what her first trip was like, and more.

Let’s dive in! 

Q: What’s life like for you right now as a nomad?

A: I prefer slow travel, usually staying in one place for 3-6 months. Ecuador here is one of my “home bases” — this is where I spent the pandemic, so I made a lot of close friends. I started learning Spanish when I started nomading and can speak fluently now, so it’s very comfortable.

I’m probably going to England next which is a second home base (because why have only one?). It’s really easy to easy to connect and travel from either of these to new places, wherever else I want to go.

I’m originally from Columbus, Ohio, but I’ve only been back twice since 2018. I prefer having people come to me—like I had my parents join me in Medellín for a while, and I’ve taken them touring through England and Scotland. 

Q: Here’s what everyone’s dying to know: How do you make it all work financially? What do you do to support yourself while traveling?

A: I’m a remote freelancer—all my client work is entirely online. Officially, they’ll call me a VP or Director of Operations, but in simple terms, I just help founders get shit done—helping run their businesses, managing their teams, and being their right-hand person.

When I first started out I was just doing random odd jobs like organizing email and stuff—whatever I could with my limited skillset. I wasn’t in a “real” field like programming or design, so I had to find a way to make the basic things I could do into a high-value thing.

Q: It sounds like you’ve really made it work! With all those responsibilities, how do you juggle work and personal life while living the nomadic dream?

A: I work about 20 hours a week with a few long-term clients and take at least three full months off each year. I don’t have email on my phone, so I can truly enjoy traveling without constant interruptions. It gives me the freedom to explore, travel, and live the lifestyle I’ve always wanted, on my terms.

Q: Let’s rewind a bit—what was your life like before you took the leap into nomadism?

A: I spent seven years as a middle school teacher, then took a remote copy editing job for an online education company. It sounded cool at first since it was remote, but it paid pennies and had no real career growth. At that point, I was still in Ohio.

Q: And what was the turning point that inspired you to leave it all behind and embrace the nomadic lifestyle?

A: Well I actually didn’t make the decision myself—I was laid off out of the blue. That sparked a fire in me to build a life where I was truly free and in control, not just struggling while in a home office. I’d always dreamed of traveling, and at the time, I was diving into digital nomad blogs and newsletters like this one.

Q: How did you land your first clients, and what was the timeline like from being laid off to becoming a full-fledged digital nomad?

A: I researched a few small businesses I thought I could help and basically just sent these very carefully crafted emails where I pitched myself for whatever work it seemed like I could do. I sent a first batch of 9 emails in like a week, and five hired me right away (with a sixth coming back later). I immediately bought a one-way plane ticket on Dec 8, 2018 and never looked back!

Q: Where did you go first, and what was that initial trip like?

A: I went to Medellín, Colombia because other nomads said there wasn’t much English spoken—I wanted to challenge myself to learn Spanish right away. I stayed for 5 months, enrolling in a Spanish school for 20 hours a week and working another 20 hours for two of those first few freelance clients that had steady work.

Everything was new, even something as simple as a grocery trip felt like an adventure. I’d sit on my balcony in the evenings, looking at the skyline, thinking, “Holy shit, I did it—I’m living abroad!” That trip was pivotal for me; I made so many close friends there, both locals and fellow nomads—I think the raw excitement of being on my first trip just attracted a ton of incredible people to me.

Q: That’s such a beautiful story. I have a feeling this next question might be tough, but what’s been your #1 favorite experience as a digital nomad?

A: Obviously there are TONS, but if I have to pick one… I took a solo trip to Iceland in 2021 where I was entirely offline for two weeks. I rented a camper van and just drove around by myself—just cooking, hiking, waking up next to waterfalls, and seeing the northern lights. I always make sure to structure my work so I can freely take off like that—I just told my clients I’d be unreachable and made sure their teams knew what to do. That trip was one of the most memorable experiences of my life, just so peaceful and perfect.

Q: Alright last question: You’ve been teaching people how to do what you do for a while now, since before the pandemic even started. I know we have some readers who aren’t “full” digital nomads yet, and some who haven’t even made their first trip yet (like how you said you were reading digital nomad newsletters while still in Ohio). 

With those readers in mind, what’s one piece of advice you have to help them get started with this kind of life?

A: Hmm… I’d say it’s super helpful to have the “what you’re doing for work” part figured out first. I started freelancing while still in Ohio and only started travelling once that was secured. Trying to juggle both at once would’ve been incredibly stressful and hectic. For me, having clients and a clear income gave me the confidence to buy that one-way plane ticket. For your first trip, you want to be fully focused on living and exploring—not stressing over finding work on top of everything else.

And that’s a wrap for today’s interview! But we’ll be back next week to answer reader questions (keep reading for details).

But first: Several of us here at Nomad Cloud are former students of Mashon’s freelancing course, The Escape Hatch, which is packed with everything you need to build a fully remote career—copy/paste-able scripts, client-ready templates, tons of real examples from her career, and much more.

After much begging, Mashon was kind enough to let us give a special discount that’s exclusive only to Nomad Cloud readers—the first price reduction of any kind she’s EVER offered on this program.

This is NOT an affiliate link—we just genuinely believe this this information should be in the hands of more nomads (and aspiring nomads).

All the details on The Escape Hatch are here. Just use the code “NOMADCLOUD” before the end of the month to unlock the special price!

Nomad Cloud Readers: Have any additional questions for Mashon? Just reply to this email, and you might see your question (and Mashon’s answer) featured in our next issue!

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🌐 Elsewhere on the Web

Looking for a change of scenery? The Ambroz Valley – a rural Spanish region just under 3 hours from Madrid – is offering $16,000 to remote workers willing to relocate to its picturesque (but depopulating) villages. And Spain isn’t alone—more countries are rolling out incentives for digital nomads.

This Wired article covers how “Virtual Villages” like Slack groups, subreddits, WhatsApp chats, and more are helping nomads deal with challenges like loneliness and isolation. By fostering connections and providing spaces for digital nomads to meet, collaborate, and form real-world friendships, these communities are creating a much-needed sense of belonging for remote workers around the globe.

Unfair reality facing thousands of young Australians

Young Aussies are fleeing high house prices and cost-of-living pressures in search of more affordable places to live. Government stats show a sharp rise in migrant departures, with an 8% increase to 221,000 in just one year. 

🔗 This week’s Quick Reads 

Our next sponsor has a guide on using ChatGPT to make your work as a digital nomad effortless, which includes 100 prompts you can use to start. Our favorites are on creating pitch decks (#3), managing a social media calendar (#46), and collecting testimonials (#70)!

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That’s all for this week!

And don’t forget—there’s still time to snag Mashon’s course, The Escape Hatch, and take a big step toward achieving your nomadic dreams (or continuing them). As a Nomad Cloud reader, you get an exclusive special price—just use the code “NOMADCLOUD” at checkout before the month ends. All the details are here!

✈️Wishing you endless adventures,
The Nomad Cloud Team