Should I Quit My Job to Travel?

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Should I Quit My Job to Travel?

Dear E. Jean: Should I leave everything and go on a road trip? I’m 27, with an okay job (but no promotions or salary increases in five years), and I’m still living with my parents. Last year, I read Cheryl Strayed’s Wild and started fantasizing about driving across the country on a great American adventure. My mom quit her job at 26 to backpack through Europe. I want to quit my job and travel while I’m young and single—but the risk! Wouldn’t it be smarter to flood the market with my résumé and focus on finding another 9-to-5 that pays better? —My Youth Is Slipping Away

Slipping, My Kumquat: Ha! I just returned from a hilarious 4,000-mile road trip traveling with my dog, Lewis Carroll, and I am still whooping it up. Cheryl Strayed’s goal in Wild was to come to grips with the death of her mother and hike the Pacific Crest Trail. (And this paragon among women hiked 1,100 miles of it with a pack she could barely lift!)

What’s your quest? A road trip will fire your brain, open your heart, calm your spleen, force you to be flexible, help you figure out where the hell you are going, and teach you to stop fearing “the risks” of going there. And when you return, not only will you be 10 times smarter and 30 times happier, you’ll have a pretty good idea how to mash up your interests and make a career out of it.


This letter is from the Ask E. Jean Archive, 1993-2017. Send questions to E. Jean at

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