Why you should think twice before quitting your job to travel

Every day there seems to be a new story about an overworked office slave who broke free and now lives an inspirational life of travel. Or someone who quit their job to travel in an RV. Or a tiny house. Or a couple whose travel blog supports their vagabonding.

It sounds nice, doesn’t it? Save some money, then spend your days in sun-soaked Spain or meeting fellow ex-pats in South America. But blog posts and social media can be deceiving. The harsh reality is that quitting your job to travel isn’t as easy as getting a WordPress site and a selfie stick.

Just ask Chanel Cartell and Stevo Dirnberger, who quit their advertising jobs to travel, and wound up scrubbing toilets to be able to eat.

So what’s it really like to leave it all behind and live an international life of leisure? We asked some travelers who’ve made the jump to weigh in on some of the realities they’ve faced.

For most, the obvious was most important: financial planning. But there are other things to consider as well, from psychological effects to adjusting to uncertainty. While nearly everyone we spoke to was grateful for the experience they’d had, and glad they made the decision to travel, some of their experiences might be cause for pause if you’re thinking about taking the leap yourself.

If you’re dreaming about leaving it all to travel, start saving right now, and keep these considerations in mind:

You’ll never really feel settled

“It does get stressful trying to figure out where you’re staying next and constantly unpacking and packing,” says Steph De La Garza, who left a two-decade-long career in IT to travel. She chronicled her preparation for long-term travel in her book, Two Brauds Abroad.

De La Garza has stretched her travel dollars significantly by taking on housesitting gigs or odd jobs in exchange for a room. She estimates she’s lived at least 25 months rent-free, but admits that she’s grown tired of never staying in one place very long.

“I miss not having a home that I can decorate, and I’m really tired of sleeping in uncomfortable beds,” she says.

Issues at home can pull you back

Andrew Davis, author of Magic Travel Blog, is currently on his third long-term travel stint. His first two trips were cut short when issues at home, including death in the family and tenant problems at his apartment, called him back.

“The tenant in my apartment back in Perth decided to stop paying rent,” he remembers about the first time he hit the road. “After a year, I moved back into my parents’ home.”

The lesson Davis learned? “If you are renting out a property,” he says, “get landlord insurance.”

Losing touch with “home”

Greg Rodgers didn’t have any international travel experience when he quit his job at IBM in 2006 and bought a one-way ticket to Bangkok. Now, he writes about the “location independent” lifestyle on his site, StartBackpacking.com, and is working on a book on the subject.

But this lifestyle, says Greg, comes with a healthy amount of “the bad and the ugly” along with the good.

“The most unexpected challenges are the quiet ones that people don’t often talk about,” he explains. “There are psychological aspects of dealing with the widening rift between you and loved ones.”

He says that the nomadic life becomes a Catch-22.

“After too much time on the road, you find that you aren’t really ‘at home’ anywhere—including your hometown,” he says. “The only solution seems to be to keep moving.”

Friends and family won’t understand

“It’s terribly lonely out there, as friends and family from back home don’t understand this lifestyle and won’t be receptive to any complaints,” says Paul Kortman, who travels the world with his wife and four children.

Kortman runs the site NomadTogether.com, a community for traveling families.

“There’s a growing minority out there of families who think and live like this,” he says, recognizing that families who live on the road encounter different challenges than individuals. “We can empathize, and help.”

No regular paycheck

When Suzanne Wolko hit the road after a job layoff this year, she planned on writing a travel blog and picking up freelance work. “I planned on being that nomadic travel blogger I read about, bouncing from city to city, enjoying cafes and writing my stories,” she explains.

“The reality is that I failed miserably,” she admits, noting that she had a hard time finding time to write or a Wi-Fi connection to regularly update her blog. And though she had vacation savings, points, and friends’ houses to stay at, living without a regular paycheck was a tough adjustment.

“At the heart of it, I was unemployed and worried about money and spending every day,” she says.

After a few months of “travel sabbatical,” Wolko returned to Philadelphia.

“My taste of travel freedom from this experience made me realize that it’s okay to have a full-time job, a mortgage, and savor your vacation time,” she says.

Work can be a challenge

“To return to a regular job, even if it’s merely to help me save for the next adventure, can be very frustrating and depressing,” says Kimberly Blagrove. “You become all too aware of the fact that you’re in a cage.”

Blagrove, a self-defined “extended traveler” since 2009, takes annual trips to Europe, usually for one to four months at a time.

“Every time I leave, I hope to figure out how to stay for longer,” she says. “But I always end up returning stateside where I accept contract work and plot to leave again.”

“When you do take the leap and follow your hunch, it doesn’t mean things will work out as smoothly or quickly as you’d like,” advises Travis Levius, who wound up broke and homeless in London after quitting his teaching job in Atlanta. “I felt like my inner gut failed me.”

Eventually, after months of sleeping on couches and chasing work, Levius landed a job as a freelance travel writer and editor. His new job is now what he left his old job to do.

“It did eventually pay off,” he says of his decision to quit and move.

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