Digital Nomad Lifestyle: “Try jumping in.” An interview with Jackie Leavitt.

This week I had the pleasure of interviewing Jackie Leavitt, the chief editor of Cloudwards is a publication focused on cloud-based technology and software, with a fully remote team of editors and writers. Jackie has been pursuing a digital nomad lifestyle since 2015, when she left San Francisco to sail through the Caribbean. Since […]

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This week I had the pleasure of interviewing Jackie Leavitt, the chief editor of Cloudwards is a publication focused on cloud-based technology and software, with a fully remote team of editors and writers. Jackie has been pursuing a digital nomad lifestyle since 2015, when she left San Francisco to sail through the Caribbean. Since then, she has worked remotely as an editor, writer and online English teacher as she lived and traveled all over the world, including Mexico, Portugal, New Zealand, Australia, and Indonesia.

What was your inspiration for living and working nomadically? What factors inspired you to leave the stationary lifestyle and start earning money remotely? 

My inspiration for living and working remotely started back in 2015 when I left my job in San Francisco and decided to spend a couple of months with friends who were sailing through the Caribbean. It was on this trip that I met some amazing women who were pursuing the digital nomad lifestyle. For example, it was my first day on the sailboat in the Dominican Republic when I met my now good friend Julie Diamond, who had founded her own tutoring company in Canada, Teachers to Go, and was able to work remotely and abroad. She was a big inspiration, and over the years we’ve continued to meet up, including living together for a couple of months in Ensenada, Mexico. 

This first trip opened my eyes to alternative ways of living and working beyond typical office life, and I kept delaying my return to San Francisco. Ultimately, at the end of seven months abroad in the Caribbean and Colombia, I had spent all my savings and needed to find work, but I also made the decision that I did not want to return to life “as normal” in the United States. I realized that, with the advances in cloud-based software, I could do a lot of jobs from anywhere that had a decent WiFi connection. So I started pursuing remote work, using my skills with editing, writing and teaching.

What unexpected challenges and hurdles have you encountered so far as a digital nomad?

The biggest challenge as a digital nomad is the most obvious: reliable and strong internet. If you don’t have good WiFi, it can have major professional complications. As a digital nomad, you can go to most major cities and find decent internet, but if you want to go into less touristy areas, the connection can get sketchy fast. However, there are some great tools people can utilize. Get a local SIM card with data so you can hotspot yourself if the internet goes out or isn’t strong enough. Look into remote WiFi devices, like the Skyroam, which picks up on many local services all around the world.

However, a less obvious challenge with this lifestyle is on the personal side of things: building community. You can meet many amazing like-minded travelers, as well as interact with many different cultures, but being in motion from location to location can have a toll on relationships back home. It might be hard to call friends and family because of time zones or simply being busy. Plus, if this becomes a long-term lifestyle for you, some relationships might not be able to survive catching up by phone. A few of my friendships have faded over the years, but I’m lucky to have many of them still thriving with video calls every month or two and the occasional visit in person. 

Do you have any personal anecdotes or stories about the hardships you’ve faced as a location independent worker? How did you overcome them?

A good example of a time when I’ve faced challenges while working abroad was when my boyfriend and I spent two months in Indonesia. We visited many locations that had very iffy WiFi, so I ended up relying on my local SIM card and hotspot device to make video calls with clients in the U.S. The other hard part about that was the time difference. I was on the other side of the world from these clients, so my meetings happened in my early morning or late evening. Working on that schedule was exhausting, but I made it work so that I could spend a long time in new areas.

Another anecdote that comes to mind was last year when the WHO declared an international pandemic. I was in Western Australia at the time, working remotely as a copy editor for When borders started closing around the world, my boyfriend and I knew we needed to return to the United States to be closer to family. But that meant we needed to drive cross country (about 2,000 miles) for five days to return a borrowed car, then hop on a plane home. I worked from the passenger seat, hotspotting myself when I could, as we drove through the Outback, which is essentially a desert and in general does not have phone or WiFi service. It was pretty stressful, and we arrived in Melbourne the day before our flight, with just enough time to return the car and pack. 

Has any aspect of the lifestyle and career been easier than expected? Is there anything that you thought would be difficult but, in reality, hasn’t been?

I thought finding remote work would be the hardest part of this lifestyle. But luckily it hasn’t. When I first started pursuing the digital nomad life, I was able to find work as an editor with companies that support remote work, and I was also able to fill in extra time with teaching English online. 

Then, of course, more opportunities evolve from existing ones. So the remote copy editing job for a coffee publication evolved into copy editing for, an online publication focused on cloud-based software and technology. That copy editing led to other editorial tasks, and now after several years and many different travel locations, I’m the chief editor of the site—still working remotely and now living on a sailboat off the coast of California. 

What character traits would you say are the most important or essential for successful digital nomads?

As a digital nomad, you need to have a nice combination of flexibility and adaptability, but also have the ability to stick to a schedule to make sure you meet your professional responsibilities. Some people get lost in the joy of travel and don’t prioritize their career. Others are the opposite and lose themselves in work to a point where it’s not even worth being abroad—you might as well be in an office back home. 

If you were starting over from scratch today, what would you do differently?

I’m not sure I would do anything differently. It’s been a long and wonderful journey since 2015 that has led me to many different parts of the world. I have no regrets, and I feel thankful for all the experiences, whether they were challenging or not.

What would you say to aspiring digital nomads looking to get started on a similar career path? Any words of wisdom or cautionary tales?

For aspiring digital nomads, I say go for it! I think a lot of people grow up thinking that you pursue a profession in one certain way, when the reality is that it’s easy to step outside the box and find alternative lifestyles. And it’s getting easier every day, as more and more companies realize the benefits of remote work. For example, is a fully remote team of writers and editors. Why would we need to work in person at an office?

However, I do think that some people might pursue the digital nomad lifestyle because it looks “Insta-perfect.” I can say right now that this lifestyle is not as easy or as “perfect” as what you can see with some influencers. Before you begin, ask yourself some hard questions about how you want to live your life. Do you actually want to live and work abroad, or do you just want to go on vacation? Are you really OK leaving your friends and family behind to travel for long periods of time? Are you flexible enough to handle WiFi outages and things not going to plan? But if the answers are yes, don’t wait too long. Try jumping in.

What were some digital strategies that originally helped get your business or service off the ground, and what were some of the challenges you faced regarding digital marketing?

With a digital nomad lifestyle, there is sometimes a disconnect between how you want to work and how you actually work. For example, when I first started, I thought I could be a freelance writer. But the reality was that I’m not very good at pitching articles and staying on top of the hustle. I do much better with a reliable schedule, which is why freelance editing and online teaching was a much better avenue for me. 

As for digital marketing, my freelance work has been largely word of mouth. For example, when I helped a student with his college essays, he had an uncle who needed someone to edit his dentistry site. Other students have connected me with their friends, who also need help applying to medical school, nursing school or counseling programs. One time I was even on an airplane flying from Boston to Portugal when the woman next to me had a son who planned to apply to medical school the next year. I gave her my email, and a year later they asked me to help edit his essays. 

Do you have a preferred platform for gaining exposure for your business or service?

I thought about marketing my freelance editing business, but I ultimately decided that I was busy enough that I didn’t need additional work. Now as the chief editor of, I think about my employees and the publication, rather than how to promote my own personal editing business. 

To follow Jackie’s digital nomad journey, connect with her on LinkedIn.

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