Travel Interview: Jessie on a Journey


On an underwater snorkel adventure

Jessica Festa is a full-time travel writer who is always up for an adventure. She enjoys getting lost in new cities and having experiences you don’t read about in guidebooks. Some of her favorite travel experiences have been teaching English in Thailand, trekking her way through South America, backpacking Europe solo, road tripping through Australia and doing orphanage work in Ghana. Here she shares her story and advice: ‘stop making excuses’; she believes you’ll find the many gifts of travel if you just leap.

1.When did you get started traveling? I’ve been traveling my entire life, as my family was always very into it; however, while growing up I would typically go on road trips around North America and on Caribbean cruises, now I enjoy solo and adventure travel much more.

2.What made you decide to make the jump to a location independent/travel-based existence? After graduating with my BA/MA in Communication & Rhetoric from the State University of New York at Albany, I realized I did not want an office job. That would mean giving up traveling every month and for extended periods of time. So, I worked as a waitress — which allowed me to take off when I wanted and always come back with a job — until I figured myself out. I started researching travel jobs and when I saw normal backpackers just like myself making a living on their websites, I knew I’d found what I wanted to do with my life.

3.What benefits do you feel you get from this lifestyle? How do you handle the nay-sayers in your life? The major benefits are the ability to travel, experience new cultures and do something with my life that makes me truly feel like I’m living. Of course, for years my friends and family thought I was crazy, and I couldn’t find a boyfriend because nobody wanted to date someone who was never around; however, I knew traveling and travel writing were two things I loved and I made it my mission to show everyone I could succeed in this industry. Eventually as I started getting more opportunities and making more money — and when I moved out of my parent’s house — my family and friends realized I was doing okay. I also met a guy who is proud of my ambition and what I do and travels with me when he can. While I’m far from rich, I’d say I’m much happier with my job than many of my friends. That all being said, the lifestyle isn’t for everyone. People just see the photos and posts and think “wow, she gets to do so many interesting things!”. What they don’t see is how after every trip I lock myself in my bat cave and hunker down to spend hours writing, editing and answering the 1,000 emails that came in when I didn’t have wifi.

India kayaking

Kayaking in India

4.How did you save money to be able to afford living ‘on the road’/traveling often? How long did it take you to make the jump to a location independent/travel-based life? Travel doesn’t necessarily need to be crazy expensive if you choose destinations where your dollar stretches far. Unless it’s a trip where a destination or company is sponsoring me through a work partnership I stay in hostels (many of them now offer private rooms), cook my own meals and eat at little mom and pop eateries, and spend a lot of my time doing free/low-cost activities like complimentary walking tours, hiking, cycling, wandering parks with my camera and just getting lost in a new place.

5.How do you choose your destinations and for how long you’ll stay? What type of accommodations do you typically choose? Are there any specific resources you recommend? I don’t really have a method for choosing my destinations. Sometimes I’ll get invited for work, other times I’ll hear a story from another traveler about a place and become obsessed with the idea of going there and book a ticket. I enjoy the social nature of hostels, as well as the cultural immersion factor of homestays. My number one resource when traveling — I typically travel solo — is CouchSurfing. While you can use it to sleep on peoples’ couches free of charge you can also use its forums to plan meetups with locals and other travelers. I once celebrated a birthday in Mendoza when I was traveling alone and I went on the CouchSurfing Mendoza forum, posting that I didn’t want to celebrate alone. I had about 10 locals take me out for dinner and drinks. It was really touching to realize the kindness of strangers.

6.How much money do you traditionally need annually to support this lifestyle? That’s hard to answer because it really depends. If you travel for a living you’ll get paid to travel, through travel partnerships and for travel articles you produce, so in that way you don’t need to worry about saving money as much as making enough money to live. If you don’t travel for a living but instead work at home and then set off around the world once you’ve saved enough, it will really depend on what kind of traveler you are. If you don’t mind CouchSurfing, choose inexpensive destinations like Ecuador, Guatemala and Thailand and can live on home-cooked meals and street food, you may need less than you do at home. My home-base is Brooklyn, so I know that’s definitely the case for me where rent and food can be ridiculously expensive.

7.How do you make money on the road and save for retirement? If you don’t have a 401k or retirement fund through your employer you’ll need to set something up for yourself like an IRA. I would advise getting an accountant to handle all of that, as for many people who live and make money in an untraditional manner doing taxes can be much more complicated than for someone who simply makes money from one employer and doesn’t have many work expenses.

Inca Trail

Hiking Peru’s Inca Trail

8. What advice do you have for others trying to make the jump to a location independent/ travel-heavy lifestyle? Stop making excuses. You’ll never have enough money, your boss will always be pressuring you and you’ll never feel 100% comfortable with taking the leap — that is, before you do it. Do it and see for yourself the rewards of traveling and living life to the fullest. The worst thing that can happen is that you hate it and return to a more traditional lifestyle.

To follow Jessie on her adventures: check out her travel websites, Jessie on a Journey and Epicure & Culture.

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