How I Moved My Career Online to Travel the World and Enjoy Wine (Juleen’s Story)

This post is brought to you by Juleen’s tech essentials while traveling: her phone (especially necessary for Google Maps!), laptop, and a battery pack.

This is the latest interview in a series featuring digital nomads talking about their lives and lessons (click here if you want to be interviewed). The goal is to help demystify the process of making money online, wandering the world, and living an unconventional life!

Juleen grew up in Jamaica and went to college in the US. While studying abroad, she realized the traveling lifestyle suited her. She now has a remote career that allows her to nomad for part of the year while exploring one of her passions: wine! Be sure to check out her Instagram for awesome wine reviews!

Thank you for sharing your story with Freedom Is Everything, Juleen!

Key takeaways from Juleen’s interview:

“Is it cheating to say one of my favourite places I’ve lived is actually Jamaica? Oh, well! Jamaicans are amazing, and I love my people. The thing is, travel has helped me to appreciate my people and my culture so much more. Now, whenever I go home, I try to explore my country as if I’m a tourist, more than I ever did while I was living there. I’ve become more adventurous and confident through travel, so I feel more confident to try new things there when I go home.”

“Visiting friends and family in other cities is a great way to save on costs such as accommodations or maybe even food. There are many budget-friendly options such as Couchsurfing, hostels, and using bus/subway instead of rideshares. Skyscanner’s cheapest month and flexible destination options, for example, help with saving on flights if you can be flexible.”

“We really need to learn to live in the moment more. We never know what the future holds but right now, maybe the sun is shining outside, or your favourite tv show is on, or you’re reading an amazing book (or blog). Enjoy that because when a rainy day comes, you might wish it was sunny, but you didn’t even go outside to enjoy the sun when it was there.”

Table of Contents

Introduce yourself! 🙂 Who are you? What do you do for work? And what is your nomadic story?

I’m Juleen, Jamaican, software engineer, wine and travel content creator, and most recently a group trip planner via my business Jump & Wine Travel. That’s the short answer.

The longer answer? I grew up in Jamaica and moved to the United States for college. Before then, I had never left my island, but I always wanted to travel. Going to college in the U.S. was a stepping stone to that. During my junior year, I studied abroad in Italy and Hungary for a semester each while also visiting other European countries and cities for a couple of days at a time. This was my first taste of how I really wanted to travel – slowly.

After college, I did a yearlong fellowship before starting my current job in software engineering. Though I moved to the city where my job is based (Baltimore, Maryland), about half of my team (and other teams we work with) was already working remotely. I slowly went from going into the office every day to sometimes only going in once a week or even just one week a month. Realising my newfound freedom, I started to travel and take advantage of the opportunity to visit other countries and cities for longer than a weekend (without being restricted by the amount of vacation time I have).

Since then (2019), I’ve taken several trips throughout the U.S. and the Caribbean. This has included going to New Orleans, Sonoma County, Trinidad, multiple trips to Jamaica, a few trips to New York’s various wine regions, and most recently Hawaii.

What inspired you to start nomading? And how has nomading changed your perspective on life?

While I was studying abroad in Europe, most of my trips to other countries were short weekend trips. These never felt like long enough. Since then, I’ve also known that I wanted to incorporate travel more into my life.

I like “slow travel.” Whenever I visit a place, I want to spend a minimum of 1 week there, but ideally, I’m spending a month or more. This allows me to adjust to the new place (climate, time zone, people, etc.) so I can actually start to enjoy myself and the place. I’m also not the most outgoing person, so traveling for longer allows me a better chance to make friends, discover my favourite spots, etc. I’m also more flexible about weather and work deadlines because I have more time in the city or country to enjoy the nicer and less busy days.

Along those lines, nomading has helped me approach life and travel with a more relaxed attitude. Before, if my trip was too short, I always had to decide between doing all the things I wanted in a limited time or actually allowing myself to relax. Now, I have more time to do all these things, but I’ve also learnt that even if I can’t do everything I want, I’d rather do fewer things and enjoy doing them more fully.

Please tell us your detailed story of how you got into your line of work and how you turned it into a remote career.

I studied Computer Science in college and intended to go into software engineering afterward before switching to product management. I did not have any interests in any specialised fields, so I only pursued general software engineering roles. I ended up doing a year-long fellowship after graduation. Afterward, I got a software engineering role which is my current job. I actually just lucked out that my team was already partially remote, so I was able to eventually start working remotely soon after college.

What does a day in your work life look like? Paint a picture for us :).

My team mostly works asynchronously, so for the most part, I can work during the hours that best suit me. We have a weekly team call to check in, and I also have a biweekly call for another project I’m on. Otherwise, I’m a night owl, so I find I’m most productive at night when others are asleep, and I sleep in late a lot.

My daily routine consists of checking emails and Github issues for anything related to my area. Then I work on either bug fixes or feature requests related to any issue that I might see in my email or on Github. However, most of my time is actually focused on implementing a feature related to the main project I’m working on at the time.

If I need help with anything, I can reach out to a team member, and we might message back and forth or hop on a call to debug or brainstorm together. I also spend a fair amount of time googling and on Stack Overflow to see if others have encountered similar problems or for advice solving a problem.

What are the 2-3 favorite places where you’ve lived/traveled to and why?

Is it cheating to say one of my favourite places I’ve lived is actually Jamaica? Oh, well! Jamaicans are amazing, and I love my people. The thing is, travel has helped me to appreciate my people and my culture so much more. Now, whenever I go home, I try to explore my country as if I’m a tourist, more than I ever did while I was living there. I’ve become more adventurous and confident through travel, so I feel more confident to try new things there when I go home.

Besides Jamaica, I absolutely loved living in Italy for about five months. I got to experience both living in the north and the south and seeing the difference in the culture. I also visited cities in ten of the 20 regions, and they all have something unique to offer. Living in Italy helped me to develop so many skills, especially to travel solo. It was the first place I had to navigate the public transportation system in a semi-foreign language (I was also studying Italy). It was the place I cried on the train because I was so lost and confused and eventually missed my train. Now, I look back at that moment and shake my head at myself. But it’s all the memories that flood my mind whenever I think of Italy that I loved. Italy was also the first place outside of Jamaica that felt like a home away from home.

Hawai’i also now has a special place in my heart. It’s another place that felt like home. The people and culture there are all about kindness and respecting the earth and each other. How can one not love that? In addition, there is just so much to do, and each island has so much to offer. I got to see an erupting volcano, walk on black sand beaches, go on hikes, eat amazing food. I only visited the Big Island and Oahu during my stay, but I can’t wait to visit again so I can see other islands. 

What advice would you give to someone who’s thinking about nomading?

One of the first things I think about when choosing the next place I want to visit is visas and the type of entry requirements. I have a Jamaican passport which means there are a lot of countries that require I get a visa before my trip or when I land. However, even if you have a stronger passport, you should still check the entry requirements for the countries of interest. Even if you don’t need a visa to enter, there might be requirements based on the length of your stay or if you will be working remotely while in the country.

Most of the time I travel, it is solo, so I always try to ensure someone knows where I’ll be going and check in regularly. I’m not the type to keep a strict itinerary, but that’s a good thing to share with friends and family if you are. If your phone allows, share your location with people you trust.

I’m in a number of travel-related and wine-related groups on social media. Before any trip, I’ll usually ask for recommendations on things to do, places to eat, and so on. I also ask if anyone in the group lives there or anyone else will be visiting during the time of my trip. Sometimes it works out that I have someone to hang out with for a day or meal. Before the pandemic, I also stayed in hostels, and that was a great way to meet other travellers.

Another way I’ve met people is actually through dating apps. I’m usually pretty transparent that I’m only there for a limited time, and it’s fine to say you’re just looking for friends or people to hang out with. At least one app (Bumble) has a section dedicated to finding friends. Otherwise, I just put it in my bio. However, please be wary of letting people know that you are traveling alone, and please meet in public places.

What is unique about the way you travel, and what advice do you have for someone that wants to travel with a similar style?

I just bought a house, so I have a home base in Baltimore now. As I mentioned earlier, I moved to Baltimore for work. I actually bought a house as an investment and intend to eventually turn it into a passive income source. However, for now, I’ve been alternating between traveling and being in Baltimore, so a couple of weeks-months traveling then a month or so in Baltimore.

If you’re a woman or person of color, what should other people who identify similarly (and who haven’t traveled much) know about traveling/nomading?

I identify as a questioning (Caribbean) Black cis-woman.

Being a woman while traveling, especially when traveling solo, has meant being more vigilant. Firstly, it has an impact on where I choose to travel since I research places that are usually safer for female travelers. I’ve also avoided or minimized doing things like clubbing alone for safety reasons. For the most part, you’ll be fine, but sometimes, someone might see a woman traveling alone and not respect your space or see you as an easy target.

Similarly, I’ve had great experiences traveling while Black. However, I have had incidents happen that were obviously racially motivated. I refuse to let them ruin my trip or experience for me, and fortunately, my experiences are more good than bad. I will say that sometimes I’ve been the only Black/BIPOC person on a beach, in a restaurant, or another space. It’s a balancing act between trying to learn to live with it and trying to encourage or find more Black people to travel (to certain places). At the same time, there are countries and cities that I’ve decided never to visit (alone) because of race because safety first. You need to make that personal decision for yourself after doing your research and asking people who look like you about their experiences.

If you had debt/student loans when you started nomading, how did you handle or think about this, and what advice would you give to other people with a similar situation?

I actually had student loan debt up until I bought my house. I bought my house using a state program that paid off my student loans a few months ago.

Fortunately, my student loans payments were relatively low. Being able to make my loan payment every month was always more important than travel, and that is the approach I’d always recommend.

If you can’t afford a major trip while paying off your loans, maybe consider something more lowkey, such as a road trip to a neighboring state or a trip via bus or train to another city. Visiting friends and family in other cities is a great way to save on costs such as accommodations or maybe even food. There are many budget-friendly options such as Couchsurfing, hostels, and using bus/subway instead of rideshares. Skyscanner’s cheapest month and flexible destination options, for example, help with saving on flights if you can be flexible.

There are ways to travel cheaper without compromising your financial status. Alternatively, you could save for one major trip a year or every two years until you can afford more. At the end of the day, it is about knowing how to budget and knowing what you can and cannot afford at the time.

What digital tools do you use for your work?

My team uses Slack, Zoom, Github, Gitter, and the other GSuite apps such as Drive and Calendar. 

For someone interested in getting into your field of work, what’s the best advice you would give? And what books, podcasts, thought leaders, or other learning resources do you recommend?

My route to software engineering was relatively traditional: college then job. However, there are so many resources, websites, and companies to help you learn to code these days. Bootcamps seem to be a popular option. Otherwise, you can use sites such as Codecademy, Coursera, or Udemy to learn to code and Leetcode and Hackerrank to practice for interviews.

Tell us about your content creation journey and share some of your favorite content that people should check out!

I actually do wine and winery reviews on Instagram via my IGTVs. My goal is to inspire more people to enjoy wine and present wine in an approachable and interesting way. I use my Instagram to share my travel, including funny travel stories, cause sometimes my life really feels like a movie.

I recently created Twitter and TikTok accounts as well, so I’m excited (and a bit overwhelmed) to navigate those spaces. Content on those accounts have been more broadly focused, including my experience getting the Covid vaccine and buying my house.

If you only had a few minutes to live, what are the most important life lessons you would share with the world?

We really need to learn to live in the moment more. We never know what the future holds but right now, maybe the sun is shining outside, or your favourite tv show is on, or you’re reading an amazing book (or blog). Enjoy that because when a rainy day comes, you might wish it was sunny, but you didn’t even go outside to enjoy the sun when it was there.

What do you travel with that you couldn’t imagine traveling without?

My phone and my laptop.

My phone because when I’m lost, Google Maps comes in clutch (most of the time), even when I’m offline. Let’s just say travel would be significantly more stressful without my phone. A battery pack also comes in handy sometimes.

My laptop because of work. Doing research on my laptop is also easier than on my phone, so when I want to make a last-minute plan for the day or evening, it’s easier to navigate the different websites or articles.

Tell us about a deep passion of yours! What has your journey been like, and what advice/resources would you recommend for someone interested in learning more about this topic?

  • Be outside on a nice day
  • Drink wine
  • Beautiful drives, since most wineries are in suburban or rural areas surrounding by lush greenery

One great way to learn more is by joining me on one of my Jump & Wine group trips since they are meant to be both educational and fun. I also do wine reviews on my Instagram page. I’d also recommend just looking up wineries in your area or nearby and doing wine tastings. You get to learn what types of wines you like while supporting local businesses. There are tons of resources about the winemaking process and industry, but I definitely prefer the more hands-on approach. 

How can people learn more about you and your work?

To learn more about any of my carnival or wine-related group trips or join one, details are on my Instagram and website. You can find my content on wine and travel on my social media and website. Sometimes I share random things like adding a garden to my new house, lol.

Websites: https://www.juleenmeetsworld.com

Instagram: https://www.instagram.com/juleenmeetsworld/

Twitter: https://twitter.com/JuleenMW 

TikTok: https://www.tiktok.com/@juleenmeetsworld

YouTube: https://www.youtube.com/c/JuleenMeetsWorld

 

Lauren Allain
Lauren is a freelance journalist from Seattle. She travels the globe in search of the best grocery stores, bouldering gyms, and snorkeling locations. Her mission at Freedom Is Everything is to help others make the transition into location-independent lifestyles.