This Lawyer & Best Selling Author Shares Her Insights On How She Was Able To Travel The World Solo While Also Maintaining A Full Time Job
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Jen had always wanted to travel the world but made excuses for not doing so because she had a serious job or it was pointless to travel so far for such a short time.
17th Jul | 9 min read

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    At GAFFL, we love to publish inspiring travel stories from adventurers around the world. You can connect with adventurers from 170+ countries on GAFFL, meet up, and explore destinations together. In this article, we are featuring Jen.

    Jen had always wanted to travel the world but made excuses for not doing so because she had a serious job or it was pointless to travel so far for such a short time. Before her 30th birthday in 2017, Jen set out to take 12 trips in 12 months despite working full-time as an attorney. She took 20 trips in a year and discovered a new career path. 

    She is now a solo female traveler and entrepreneur, five-time Amazon bestselling author, three-time TEDx speaker, and solo travel expert who teaches young travelers and digital entrepreneurs how to work from anywhere and explore the world. 

    You can find her advice on her blog, Jen on a Jet Plane, and you can follow her on Facebook, Instagram, YouTube, and Pinterest to keep up with her experiences.

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    My Inspiration To Start Solo Traveling

    As a young professional, I found it difficult to plan trips with others. No one ever had the money or the time off, so I kept putting off making plans.

    One day I decided to stop waiting for others and start seeing the world on my own. It was the best decision I ever made. I found that I enjoyed having the freedom to explore on my schedule, stopping at any shop or restaurant, taking a mid-day nap, etc.

    I also found that I could better connect with people abroad when I was by myself because I didn’t have the safety blanket of a companion who spoke my language or could help if anything went wrong. 

    How Do I Decide On My Next Destination  

    I used to go where the flight deals took me, and still if I see a bargain to a destination that maybe wasn’t at the top of my list before, I’ll consider it.

    Now, though, my main focus is knocking out bucket list sites and destinations, so World Wonders, UNESCO Heritage Sites, seasonal and natural displays — anything that is extraordinary. And bonus if there’s a cheap flight to get there.

    Duration Of My Trips

    My trips can range from a few days to 2 weeks. I try not to travel for more than 3 weeks at a time since I crave having a home base and sense of normalcy. 

    Once I decide on a location, I research all the top things to see and do there so I can make sure I don’t miss the highlights. I make any necessary reservations so I’m not scrambling for in-demand tickets on the ground. Then I look for hidden gems, especially searching for terms like “off the beaten path.” Finally, I put together all the places I most want to visit on the itinerary like puzzle pieces, rearranging based on availability, expected crowds, opening dates, winter hours, and more. 

    How I Pack For My Trips

    I always carry a pen — sounds simple but they’re impossible to find when you need one to fill out customs forms or other paperwork on the road. I pack a collapsible water bottle and try to keep it filled on my journey as an emergency backup. I take cash and hide cash and cards in different compartments in my bags, in case one gets lost. I use packing cubes to separate the types of clothing I’m bringing and always have a tripod for taking my own pictures. 

    Beyond that, I go light on equipment, usually relying on my iPhone to be a map, translator, currency converter, alarm, and means to contact friends and family back home. Since I use my phone for so many things, two other essentials are a backup battery and a local SIM card. 

    Favorite Memories Of Meeting New People & Exploring With Locals 

    When I was in Meteora, Greece I went to explore monasteries. I ended up on a tour with a 9-person Italian family. They essentially adopted me for the day and after put Lorna t tour was over I hopped into their van and we went to hit up other local sites. I remember being in the backseat, squished between the brother and sister while everyone talked a foreign language, and having that be a surreal moment. 

    In Bali, I was at home for 3 weeks. The family lived on-site and immediately took me in, inviting me to pray with them at their home altar and bringing me to a local ceremony where I was the only non-Balinese person in attendance. The mom lent me her ceremonial attire and helped me get dressed, finishing the outfit with a flower in my hair. We’re still in touch over social media. 

    How Jen On A Jet Plane Comes In

    I started a blog as a creative outlet because as an attorney I was doing mundane, routine paperwork every day. At first, I was writing general lifestyle pieces. It wasn’t until a travel editor from Paste Magazine reached out to me that I considered focusing on travel specifically, and rebranded to Jen on a Jet Plane. 

    Like me, my site has evolved. Initially, I talked a lot about cheap flights and how to travel with a full-time job because I was underpaid and overworked and trying to find solutions. 

    Now I focus more on the transformative power of travel and helping others build a career that gives them the freedom to travel and empowering women to ignore societal expectations and timelines.  

    My Inspiration To Write Books

    I have written 5 books — 3 are about travel and 2 are about digital entrepreneurship. I wanted to share my knowledge and found that quick DMs or even social media videos weren’t cutting it — I still had people asking for more information. Books are a great way of sharing all my knowledge through one easy to consume, affordable product. 

    If you want to start flying for less check out my book, “The Affordable Flight Guide.” It’s a #1 Amazon Bestseller with more than 40 websites, apps, and links to help you start traveling more without breaking the bank.

    I also wrote a book to help you travel more even when you have a “real job,” called “You Need a Vacation! How to Travel with a Full-Time Job” and one on how you can travel the world fearlessly on your own called “The Solo Female Travel Book.”

    As a full-time remote worker, I know how scary it can be when you’re first making the switch. This is why I published my bestselling book, 25 Ways to Work From Home, with details on exactly how you can turn your passion into a legit and profitable online business.

    Countries I Have Traveled So Far

    I’ve traveled to 35 countries, many more than once like Italy and Mexico. I would love to visit Turkey, Japan, and Ireland. I want to sleep in a cave hotel in Turkey, ride Super Mario go-karts while in costume in Japan and see the Trinity Library in Ireland. I’d also like to make it to Easter Island. 

    Best Solo Travel Experiences

    I spent 10 days on my own exploring Jordan recently. This trip blew my mind — every day was another epic adventure. From floating in the Dead Sea to sleeping under the stars in a glass dome in the desert, I felt completely safe and in awe of this beautiful country. 

    Another memorable solo trip was to New Zealand. I remember walking along Hobbiton thinking, “do places this peaceful actually exist?” It was an incredible trip. I dug a natural jacuzzi in the sand at the beach. I saw glowworm caves. I visited the only McDonald’s in the world inside a plane. It was a 7-day road trip throughout the North Island and was an easy trip to make. 

    How I Manage Travel Costs 

    I like to use Scott’s Cheap Flights for flight alerts. They tell you when there’s a price drop or mistake fare to your destination. I also swear by points and miles and will open a new credit card with the sole goal of getting the sign-up bonus.

    For lodging, I check sites like Agoda and I never assume a place will be less expensive just because it’s on Airbnb — by the time you factor fees in that might not be the case so I check all options, including third-party sites and booking directly with the hotel. 

    How I Think GAFFL Can Help Solo Travelers

    It’s great to connect with travel buddies abroad! It can help solo travelers ease into a new location. It’s also useful to have a friend if you’re exploring the nightlife in a new city.

    Other apps I use on my travels include WhatsApp to stay connected with tour operators and people I meet, Clear for expedited airport lines, and Google Photos to back up all my pictures. 

    Challenges I Faced & Compromises I Had To Make To Start Living As A Digital Nomad

    I was lucky because when I transitioned to being a digital nomad, I had a job teaching English online. That was enough to pay my bills every month and could be done from anywhere so I didn’t feel as much pressure. It has been challenging becoming a digital entrepreneur because you have to learn about different income streams, create content constantly and wear many different hats, from photographer to agent. 

    I’ve had to make compromises in terms of where I live — I couldn’t afford to stay in Florida without my attorney salary. However, moving to Puerto Rico turned out to be a blessing and there are tax incentives here for digital nomads that want to do the same. I’ve also had to make compromises on the brands I work with, occasionally taking a campaign that isn’t the best fit because I needed the income.

    Advice For Aspiring Travelers

    Start small! A day trip 2 hours away can work wonders and reinvigorate you until your next big vacation. Don’t feel guilty about requesting time off — you’re given those days for a reason and can use them as you see fit. Have a work buddy that can step in for you and cover emergencies. When you finally take a vacation, disconnect. Don’t make it a point to be available at all hours.

    You need to have a way to make money online if you're looking to pursue a full-time traveling lifestyle. That can be anything from a steady job working remotely for an established company to passive income from cryptocurrencies. Once you have this, you can be location independent and work from anywhere. You also need a good WiFi connection. 

    Things I Wish I'd Known When I First Started Traveling

    I wish I’d known about local SIM cards when I started — I cringe thinking about how much I spent on roaming fees and international data plans. 

    I wish I’d known that World Wonders only ever have less public access, not more. I wouldn’t visit Chitchen Itzá when I was able to climb or go inside the pyramids. 

    I wish I’d known that the way the media portrays “unsafe” countries is often drastically different from day-to-day life on the ground and that I shouldn’t be afraid to travel someplace new. 

    I wish I’d known that the only thing you regret about travel is not starting sooner. 

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