Best Of/Worst Of:
Quitting Your Job to Travel

Surprises

Long term travel leaves room for the unexpected. A vacation, by its nature, needs structure. Who knows when you’ll next come back to Peru, and seeing Machu Picchu, the Nazca Lines and Lake Titicaca all in 10 days takes planning. Travelers who have months to spare can ditch that structure and embrace the unplanned experiences that make all the dorm beds, unwashed laundry and shoestring budgets worth it.

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Opportunity

I’ve lost count of the expats, bartenders, NGO workers and couples I know scattered around the world who just went away “for a while” and ended up doing something extraordinary. This is a chance for a reboot and a chance to ask that all-to-rare question, “what do I really want?” Whether it’s changing careers, changing cities or never coming back at all, it’s a lot easier to reconsider life back home from a little bit of distance.

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People

Vacations tend to be pretty insular. With a lot to see, we usually keep to ourselves and our traveling companions. Long term travel, especially solo, changes that. As days stretch into months there’s more opportunity to reach out to strangers. It’s raw necessity. Over time even people who brought a friend need someone else, and a good thing too. Getting to know new people is the single best part of this experience.

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Risk

Teddy Roosevelt once said, “far better is it to dare mighty things, to win glorious triumphs, even though checkered by failure, than to rank with those poor spirits who neither enjoy nor suffer much, because they live in a gray twilight that knows not victory nor defeat.” Quitting, for any reason, is a big roll of the dice. That goes double when you add travel into the mix. You never know where the road will take you, how it will end or into whose bed you’ll trip along the way. Walking out that door is Courage 101, which is sometimes exactly what we didn’t know we needed.

Worst Of

Risk

But you may still fail. Risks that end well make it look like the only thing between you and happily-ever-after is a little bit of courage, but things don’t always work out. It’s why millionaire drop outs make great stories but terrible role models. One Harvard evacuee went on to found Microsoft, yes, but the rest spend a lifetime fudging their resumes. It’s the same with quitting your job to see the world: breathtaking during quiet evenings watching the sun set over the Tonle Sap, not so much when that story ends in Mom and Dad’s basement eight months later. Risks, it turns out, suck when they fail.

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The Myth

Who doesn’t want to run off across the world? This is the myth of travel as a cure-all, the belief that anyone with the stones to walk out of a 9-5 can become Indiana Jones. Unfortunately it is a myth. Travel will not cure you. It can do a lot, but at the end of the day it’s still up to each of us to find happiness and pursue it. That’s just as true on a beach in Thailand as an office in St. Louis. Unless you spend time looking for meaning alongside the killer photos and comely backpackers your problems will come back over and over and over again.

They’ll just hurt worse when even Paradise couldn’t fix things.

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Money

Need I say more? Traveling with a job is awesome because nice things are, well… nice. Don’t get me wrong, you’ll find some of the best things in life on the shoestring. Street food is awesome, hostels are more fun than the Four Seasons and I’ll take a corner pub over Sky Bar any day. All that said, it’s a lot more fun to eat dollar noodles by choice and maybe wash them down with a pint of good beer. Plus, hostels may be fun but every now and again a private room with a nice shower is better than an open bar, a great party and all night epiphanies rolled into one.

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Aimlessness

The problem with not having to do anything is it’s far too easy to do nothing. For the first few months after I left practice opening up my laptop was next to impossible. There were cities to visit, people to meet, beers to drink. Over time it got easier, but never actually easy. (Getting up before noon is still one of the hardest parts of self employment.) Having a job means structure and deadlines, all the things that make actually getting stuff done happen. Take that away, mix well with a permissive environment, and it’s hard not to answer “what did you do last year” with “welllllll…”

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Real Life

I know a man who owns a bar in Chiang Mai. He’s a British expat who spends his days in town and his evenings drinking with friends on the patio he owns. Travelers meet plenty of these people along the expat trail, and we all stare with envy at the folks who left real life behind to carve out something new. They make it incredibly hard to come back to jobs, bills, gym memberships and taxes. Yes, there are many reasons to come home and build a life, but it’s hard not to sit back down behind a desk and think “there are people who don’t have to do this every day. I’ve met them.”

“I could be them.”