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🌍 Q&A: How to take 3 months off/year, Nomad Cruises, & The remote island hiring a manager

More Q&A with veteran nomad Mashon Thomas

January 21, 2025

This week, we’re covering:

  • Reader questions for Mashon, continuing last week’s special Q&A

  • Digital Nomad Cruises: A different way to travel that’s growing in popularity

  • SĂŁo Paulo Spotlight: A Redditor’s report on this misunderstood gem

  • Unique Job Alert: Be the manager of this remote island with no residents

  • The 11 best destinations for solo travelers


And lots more. Let’s dive in! ⛔

đŸ’» Mashon is back to answer YOUR questions

Last week, we introduced Mashon Thomas, a seasoned nomad who shared how she got started after being laid off, and what her life is like as she continues the nomad lifestyle at 40. Today she’s back to answer the follow up questions you readers wrote in with.

Missed the first interview? You can catch up on her story here.

Q: “How did you make so many friends abroad and build so many big social circles while traveling? I've always wanted to do more solo travel but I’m pretty introverted and don’t think I’d have the same experience as you, meeting new people everywhere I go.” – I.M.

A: I'm actually an introvert too, I need lots of time to recharge from social situations—in a given week, I’ll have like four days of downtime, then go out the other three. And I’ve found that making friends while traveling is much easier than meeting friends in my home town. 

People notice you look different or hear your different accent, ask where you’re from, and they’re usually eager to practice their English or show you around their neighborhood.

In many places, locals don’t meet many travelers. I was just in Yorkshire and everyone would say they said they don’t get many visitors since everyone goes to London. When I was living in Montenegro, locals would say, “You’re the first American I’ve met!” People are friendly, and connections can start with a simple conversation. Maybe you’re an introvert, but you’ll come across excited extraverts in plenty of places.

Meetup and expat Facebook groups are also great ways to meet like-minded people. Frequent travellers are actually more likely to use these – I’ll visit non-nomad friends and they’ll be amazed that I have a wide circle of multiple friend groups where they live while they only know a few people. It’s just easier when you’re not from there—people want to learn more about you.

Q: “Can you say a bit more about what you do exactly as a VP/Director of Operations? It seems like an exciting job, but I’ve never thought of that as a potential career.” – A.S.

A: I sort of stumbled into this field by accident too. It started with a client giving me a small random project, and after handling it well, they just kept giving me more responsibilities until I became their go-to person for getting all sorts of various things done. I didn’t really need any special training to be a Director of Operations—it was more about taking on whatever was thrown at me, and handling it with a “can-do” attitude.

If there ever was something I didn’t know how to do myself, I would just hire a specialist to do it for me. Clients are usually happy to pay you to handle that process of finding and vetting and hiring other people – many founders don’t want to have 20 different people reporting to them, constantly bothering them to ask for logins and feedback and approvals or whatever. 

As I handled more tasks, the trust I built with clients grew. They started seeing me as someone they could rely on to manage the day-to-day operations of their businesses, and eventually, they handed over the reins completely, saying, “You’re killing it. I don’t want to manage all this anymore; you take over.” Then they’re freed up to work on whatever is most exciting/fulfilling to them.

Q: “How do you balance taking such extended time off, like three whole months a year? What’s stopping clients from replacing you with someone more available, especially if their teams are able to do all their work without you for so long anyway?” – M.F.

A: Well I usually don’t take all three months off at once, typically it’s three months total throughout the year – but yes, this time it really is a straight three-month “sabbatical”.

Keeping clients happy comes with time and good work—they trust me because of my reliability. Clients often appreciate my time off because I always ensure things are covered in my absence. Every time I plan to go away, all the company’s systems have to improve to make that possible. As long as there aren’t a bunch of new responsibilities being dumped on them, they’re more than happy to let me make those process improvements.

They don’t need to replace me because once I’ve set up the right teams and processes, they don’t need me as much day-to-day. That may sound like a bad thing, but a growing business always has new needs to replace the old ones. The same exact role I left may not be there any more, but I’m still around to handle the higher-level tasks, be the go-between, and lead the next big project the founder thought up. 

Plus, when I’m away, it’s great peace-of-mind knowing I’ll eventually come back to handle everything. Training a brand-new person to take over all those responsibilities from scratch would be so much more work than they want to deal with.

Thanks Mashon, this was super insightful!

Remember, you can find all the details about Mashon’s freelancing course, The Escape Hatch, here if you want to learn even more about how to support yourself with remote work like she does. Be sure to use the code “NOMADCLOUD” at checkout to claim the special price before it’s gone forever!

Again, this is NOT an affiliate link, we’re just genuine fans of the course ourselves. Several of us on the Nomad Cloud team are actual customers who went through the material to build our own careers.

P.S. Next week will feature the final Q&A with Mashon, so make sure to reply to this email with any last-minute questions! We’ll pick the best ones for Mashon to answer.

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Digital nomad cruises are transforming the way remote professionals work and travel, blending productivity with exploration aboard fully equipped ships. These cruises are tailored for those who want to work while traveling, offering essential amenities like high-speed internet, dedicated coworking spaces, and flexible itineraries. Whether navigating the Mediterranean or cruising through the Caribbean, these voyages cater to the needs of digital nomads, making it easier to balance work and leisure.

The appeal of these cruises lies in their all-inclusive nature. Accommodations, meals, and fitness facilities are provided, eliminating much of the stress involved in planning travel. The convenience of having everything arranged for you is a major selling point. Onboard, passengers can connect with other like-minded professionals, making it an excellent opportunity for networking and collaboration. The community-focused environment allows digital nomads to share experiences, offer advice, and forge valuable business relationships.

However, there are challenges that come with this type of travel. The reliability of internet connections can vary, and the costs associated with these cruises tend to be higher than standard vacations. For some, these factors may outweigh the benefits, especially if stable internet access is a priority or if the price point is too steep.

Despite these drawbacks, digital nomad cruises represent an exciting trend in the travel industry, reflecting the growing shift toward location-independent work. They offer an innovative solution for remote professionals seeking a blend of work and adventure. As the demand for this lifestyle continues to rise, it’s likely that more cruise lines will expand their offerings, creating even more options for digital nomads around the world.

Skellig Michael (Ireland). Also doubles as Luke Skywalker's retreat/pity palace in Star Wars

Handa Island, a remote and uninhabited Scottish island, is hiring a manager for ÂŁ25,000 ($31,000) annually. The role involves overseeing the island's nature reserve, managing seasonal staff, and ensuring smooth operations for the thousands of visitors who flock to see its stunning landscapes and diverse wildlife. The job offers a rare opportunity to live and work in a serene, nature-filled environment, appealing to those seeking an escape from traditional work settings. With no permanent residents and a focus on conservation, the position is perfect for someone craving solitude and a meaningful connection with nature.

This Reddit post by a nomad goes in depth on their trip to São Paulo, Brazil, highlighting the city’s walkable neighborhoods, vibrant atmosphere, and safety, debunking common misconceptions. While lacking Rio’s beaches, São Paulo excels with its urban vibe, affordability, green spaces, and coworking options, making it ideal for remote workers.

🌐 Elsewhere on the Web

Entering 2025, the digital nomad lifestyle flourishes in Asia with cities like Bangkok, Phuket, and Chiang Mai offering vibrant cultures, low crime rates, and favorable visa conditions. These locations provide affordable living, excellent infrastructure, and/or strong expat communities, making them ideal for remote work and exploration.

This list from The Times isn’t necessarily ranking the cheapest, but they’re some of the safest. The top 5 include:

  1. Tokyo, Japan – A vibrant metropolis with friendly locals, efficient transport, and endless cultural attractions.

  2. Copenhagen, Denmark – Known for its safe environment, bike-friendly streets, and cozy cafes.

  3. Reykjavik, Iceland – Gateway to stunning natural landscapes like geysers, waterfalls, and the Northern Lights.

  4. Queenstown, New Zealand – Adventure capital with activities like bungee jumping, hiking, and scenic drives.

  5. Lisbon, Portugal – A historic yet modern city with great food, sunny weather, and affordable living.

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🔗 This Week’s Quick Reads 

Digital Nomad Visas Gain Popularity Post-2024 US Elections: Interest in digital nomad visas has surged among Americans since the 2024 election. See where you can get one here.

Remote Work Statistics And Trends In 2025: Forbes outlines 2025 remote work trends in this report. If you aren’t already working remotely, maybe sharing this might convince your boss to let you start.

Swim with 12-meter whale sharks (and 500 fish species) at hidden reef paradise: This reef offers an underwater paradise with one of the world's largest concentrations of whale sharks, as well as over 500 species of fish.

That’s all for this week. 

Before you go, don’t forget to check out Mashon’s freelancing course, The Escape Hatch. Make sure to use the code “NOMADCLOUD” to unlock the special price before it’s gone.

🚱 Until next time, keep exploring,

The Nomad Cloud Team