How to Quit Your Job and Travel the World

Hate your job.

You forget about travel for weeks. Your boss gives you a promotion. No raise, but a better title, more responsibility. Your job seems like it’s going to get better. During a happy hour you tell your boss that you actually enjoy working there. The company finally understands your potential. But you quickly discover that these new responsibilities aren’t worth it. You have to micromanage a team of interns, you have to work longer hours, you have less time to sit in front of your computer eating turkey sandwiches and living vicariously through your friends. Shit stays the same. Nothing will ever change. You want to quit your job and book a flight — but it just seems so distressingly overwhelming!

Questions run through your mind each night obstructing you from sleep: What would your family say? What would you do with all of your possessions? Would you ever be able to reenter the workforce? Would this affect your permanent record? Will you have to cancel your Match.com account? In a rare moment of slumber you have a dream that clarifies everything: There is no alternative to the life you want to live. You have to jump off the corporate ladder. And with a little planning this will all come together so easily.

Set up a timeline.

In a daydream you walk up to your boss, a real dickhead who slyly worked his way into middle-management, and tell him to “fuck off!!!” You imagine yourself holding each syllable as you spit these words into existence. You think about how awesome that would make you feel. But being pepper-sprayed and dragged out by security might make you wish that you’d reconsidered your word choice, and that you’d become better friends with the security guards. You recognize that it’s probably better not to be spontaneous about leaving the workforce. You decide to plan things out. You buy a travel guide, research your destination, and set up a timeline.

3 months out: save money.

You give yourself three months to strategize and save money. This will make your travels come easily. You discipline yourself. You put aside every dollar that you’d regularly spend on “Prohibition-era” cocktails knowing that it will go towards another night of accommodation in Chiang Mai. You rarely go out at night anymore.

You drink $3.75 bottles of wine and read through a friend’s copy of Southeast Asia on a Shoestring. The next morning you feel like shit — too many bottles of cheap wine. You consider staying home to recover, maybe read some more. But you know that every sick day you accumulate will be transferred into cold hard cash. One sick day in America is worth a week in Thailand.

You are traveling to find paradise, and the brochures insist that where you’re going is paradise, but you know they’re just trying to exploit locals and tourists for a quick buck — kind of like what your company does. You also know that paradise is anywhere outside of your office.

2 months out: buy your ticket.

You learn that buying a ticket a couple of months in advance (and booking on a Tuesday) will save you money. But you buy your transcontinental flight as more of a deposit. Having that ticket in your hands is insurance that you won’t wimp out and stay with that job you hate.

You worry that someone on your Facebook feed might inadvertently alert your boss to your departure. You make sure to only tell the closest of your confidants about your trip. You halfheartedly try to convince a few friends to come with you. No bites. You know this is a solo journey. You’re worried that you’ll get lonely. A friend who just returned from Guatemala assures you that if you stay in hostels you’ll never really be alone.

1 month out: vacate your apartment.

You know that you’re only supposed to spend 25-35% of your income on housing, but this is New York City: Half of your paycheck goes to rent. There’s no way you’ll be able to afford this while you’re abroad and unemployed.

You think about pulling an epic vagabond move: Selling everything you own. You go on eBay to see how much your shit is worth. That process exhausts you. You figure you’ll just sublet your apartment. You calculate that it’s better if you just get rid of your place. That security deposit will cover the cost of your flight. You leave all your clothes and furniture at various friends’ houses. You know you’ll probably never recover any of these things. You don’t care.

You’ve done all of this a month before your flight leaves. You’re still bringing in an income from that job you hate. But now it’s going to directly into your bank account for you to spend in emerging economies.

You crash on friends’ couches. Once you even sleep under your desk at work. You know this is temporary, but this homelessness will help ease you into the nomadic nature of travel.

1/2 month out: leave office.

Two weeks before you quit, you follow the standard practice of putting in your notice. It’s not as jarring as telling your boss to “fuck off.” But that confusion on his face is great. “You’re quitting to go on vacation?” You want to tell him this isn’t vacation, this is a monumental moment in your life, but you just nod your head and smile.

You spend the next two weeks at your desk posting humble brags onto Facebook: “Just decided to quit my job to traverse the jungles of Borneo,” “I guess I won’t have to fill out that annual evaluation sheet,” “I won’t have dental insurance anymore — but at least I’ll be in Bali!!!

Now you’re really traveling!

Your old roommates throw you a goodbye party at a bar around the corner. A girl you used to have a crush on shows up. You talk to her for a few hours about your plans. She’s just gotten back from a trip around the world. You start to wonder if you’ve made a mistake.

Your former roommate and best buddy looks at you and can somehow tell what you’re thinking. He whispers into your ear, “Don’t worry, the best women are already on the road.” You know that he’s right, plus you already bought a non-refundable ticket. You enjoy your last night on the mainland.

You’re sitting at the terminal, overwhelmed with an excited anticipation. You haven’t felt this level of exhilaration about the unexpected since you saw your freshman dorms for the first time.

You know that you’ll be away for a long time. You did the right thing. You’ve reclaimed the freedom that you’d been selling to that soul-crushing organization. Eventually you’ll want to come home (possibly) and rejoin the workforce. But you know that this trip will help you to return on your own terms. You quit your job to travel because you decided to control your life, and that’s exactly what will happen.