How to Quit Your Job and Travel the World (from Someone Who's Done It)

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Photo: Jupiterimages

Ever feel like telling your boss to “take this job and shove it,” so you can drop everything and travel around the world? Well, really, what’s stopping you?

Some of you may find this hard to believe, but the idea isn’t that inconceivable. In fact, in many countries other than the United States, long-term global travel is so much a part of the accepted culture that it’s just normal. For example, in the UK and Australia, most late teens and twenty-somethings take “gap year” — the year between high school and college, or between undergrad and grad — to gallivant in remote parts of the world away from home. Israelis often travel for a year once they finish their military service requirement. The Germans, Danes, Dutch, Canadians, Japanese, French, etc., many of them (of varied ages and socioeconomic status) are out there in the world, traveling like most of their fellow countrymen.

But I’m a hard-working American, you say? But I’m not young anymore, you think? At the expense of using a cliché, if there’s a will, there’s a way, and it’s never too late to do it if you really want it; I’ve met a woman pushing 70 years of age, hiking the Inca Trail in Peru just because she wanted to. More and more Americans have been embracing the idea of long-term travel and following their around-the-world dreams in recent years. Here are some steps for how to get started.

 

Step 1: Take the idea seriously.

Photo: Erik R. Trinidad

You may have read the title of this article and thought, Yes, how do I do that?! You might have even read similar articles elsewhere but haven’t been proactive about the notion after the fact. Maybe you entertained the idea for a brief moment, only to be sucked into Facebook and have forgotten about it. Or maybe you brushed it off as a lofty pipe dream that you could never do for any number of excuses, usually starting with the word “But…” Well, this is the most important tip that should be the mantra of everything you do from here on out: Focus, and take the idea of quitting your job to fulfill your dream of traveling the world seriously. It’s not as crazy as you think.

Admittedly, I used to think the idea was crazy myself, until I really embraced it, took it seriously, and made plans to go on my own sixteen-month trip around the world in between cubicle desk jobs, mid-career. If you’re resourceful, you can find a way to do it too, as long as you stop making excuses and get it out of your head that it’s an unattainable fantasy — others like you have already done this. And from experience, I can report that when you come back, not much of the world you left behind will have changed; you can definitely pick up where you left off if you want — only enlightened with a new conception of the world.

 

Step 2: Recognize that the world is not a scary place.

News flash: the world isn’t as scary a place as the media portrays it. In fact, violence and turmoil often make the news because it’s dramatic, and that sells. Sure there are war zones and crime-ridden places, but peace-keeping places outnumber them in the world, and they do just that: keep the peace (but don’t make the news). And if it’s not violence that you’re concerned about and have a fear of being out in the wild, you should know that the perils of nature are also often dramatized. TV adventure hosts often accentuate the danger of a situation for the sake of drama (and their ego), but let it be known that in most scenarios, what you’re watching had been planned and staged with the logistics of traveling with a camera crew in mind; it’s not that extreme, nor does it have to be.

Fasilidas Castle in Gondar, Ethiopia. Photo: Erik R. Trinidad

Many television shows feed into the myth that other places are so foreign that they’re inaccessible; however, the world is currently more accessible than it has been in decades. Long gone are the times where it took days or weeks to get from Point A to Point B; many developing nations now have travel infrastructure — in fact, they depend on it for most of their economy. Remember when there was a war in Vietnam? The southeast Asian nation is now a sought-out beach destination. That War on Drugs in Panama? They’ve turned it around with their beaches and city culture. The famine in Ethiopia? It’s now a destination to explore a unique cuisine and medieval African castles. Safaris in sub-Saharan Africa, for example, are not as dangerous as your imagination might lead you to believe; I used to be intimidated myself until I went on one in Botswana and realized how organized everything is, with lodges, park ranger stations, and everything else you might find in operations at Yellowstone in America — only those are the things they usually edit out of most television shows.

So you’re a woman

To women concerned about traveling independently in certain countries, I respond with examples of all the fearless solo female travelers I’ve met on the road. In fact, Marie Javins is on her second independent world tour, and Jodi Ettenberg of Legal Nomads has been continuously traveling independently since 2008. Both of them can attest that you don’t need to be a guy to travel the world.

Don’t worry about it if you don’t speak a foreign language

Don’t speak a foreign language language? Don’t sweat it. Fortunately for Americans, the default language for most parts of the travelled world is English; Germans, Italians, Spaniards, French, and others often have to learn English as a “base” language to get around, even in non-English-speaking countries. Granted it’s always best to learn a foreign language before hand, and that is definitely preferrable — I’m just saying don’t let a lack of foreign language skills inhibit you from traveling; you’re not going to be the only one without them. (Still afraid? Get the “Point It” book to communicate by pointing to pictures as a backup.)

 

Step 3: Plan your escape from work.

Chances are if you’re seriously thinking of doing this (remember the mantra of Step 1), you already hate your job and want to quit. But maybe you love your job. If that’s the case, find out if your company is willing to let you go on sabbatical or a leave of absence. (It will probably be unpaid, but travel might not be as expensive as you think — more about that later.) You’d be surprised at how many companies will let you do this — in fact, you might actually be doing them a favor in our shaky economy; perhaps they could use a temporary lapse in salary payouts until things pick up. Try to negotiate something. However, if they won’t let you leave nicely, revise your opinion of your job: You now hate it — continue reading.

So you hate your job, or perhaps are just bored with it, and are ready for something new. Quit! (Just don’t burn that bridge severely. Who knows if you’ll run into your boss later on in life?)

What will you do for money?

Well, if there’s a will, there’s a way. Personally, I saved for months before leaving my job, sold my car, got rid of my apartment, and moved back to my parents for a few months — anything I could to stock up on funds. It may have seemed inconceivable and unbearable if not for remembering what I was doing it for. Everyone’s situation is different, but the options are out there if you look for them, as far-fetched as they may seem. Remember the mantra and you’ll find a way to make it work.

And who says you can’t make money on the road? Maybe there’s even a way you could work remotely for your current job, as much as you hate it. (If that’s the case, revise your opinion; you now like your job.) If not, don’t fret; many globetrotters I’ve met have financed their travel by teaching English abroad or volunteering with an organization. GoAbroad.com is a huge resource for exploring those options.

Family of four, off the beaten path at the Peruvian/Bolivian border. Photo: Erik R. Trinidad

So you’ve got a family

In my travels in the world, I’ve seen families travel together, particularly one Danish one off the beaten path in Bolivia with a four-year-old boy and a twelve-year-old girl — and they were more behaved than you would think. Pull your kids out of school, or just go during their summer break — whatever you can logistically make happen. Or redefine your conception of travel and try relocating somewhere else with them; I know of someone who left his New York life, took his wife and kids with him, and moved to a beach house in the Caribbean where things were a lot cheaper than they are in the Big Apple. The important part of traveling with your family is making sure everyone is on board to do so; it’s not going to work unless everyone follows Step 1. And if they’re not willing to travel, perhaps they’ll be supportive of you going solo anyway, just like Jean Béliveau of Montreal who walked around the world with the encouragement and support of his wife and sons.

So you’ve got a mortgage

No one says you have to leave your place forever; if you figure a way to come up with funds to cover your monthly costs for the time you’re away — no matter how far-fetched it may be (without committing any crimes, I mean) — then you’re golden. If not, here’s an idea: use a home rental site like HomeAway or AirBnB and rent out your place while you’re away. You can use the rent money people pay you to pay your monthly mortgage payments — and maybe even make a surplus amount in the process.

 

STEP 4: Plan your trip, but don’t overplan it.

Okay, so you’ve made arrangements to leave your job and have figured out some means to support yourself for the time you’re away, may it be a couple of weeks, or a year (or more). Now the fun part: get planning! There are plenty of on-line resources about independent travel — Lonely Planet being probably the most recognized one. Along with their guidebooks, I’ve found that BootsnAll.com is also an invaluable resource for the independent traveler, with a special section for RTW (Round The World) travel if you’re so inclined. If you really want your money to stretch, independent travel is the way to go, although if you don’t think you can hack it, there are tons of travel agencies out there — including Discovery Adventures — that can come up with tours if you want to see parts of the world in a series of convenient multi-day packages.

But you’ve quit your job; you have the luxury of time and don’t necessarily have to rush through structured day-to-day activities. When you travel independently over a longer period of time, you can get to know a place, and eat and travel as the locals do. Believe me, it’s a lot more culturally rewarding — and a hell of a lot cheaper. (Just remember to bring some Pepto Bismol, and stick to bottled or purified water where necessary.)

As for accommodations, you don’t have to stay in the fanciest hotel, or the diveiest shared hostel; in some places you can get a private room for as little as $15 per night, sometimes less. If you’re traveling with a partner or in a group, all your costs are split as well. Admittedly, I used to travel on the super-cheap, slumming it in hostel dorm rooms years ago ($3 per night in some places in South America), but have since outgrown those with age. I still go to hostels when traveling independently, but now I reserve a private room. This has the benefits of a hostel, including lower rates and the opportunity to meet other solo travelers almost automatically — something that nicer hotels don’t necessarily have — but with some privacy too.

Hostels are usually pretty clean. Photo: Erik R. Trinidad

On hostels and young, dirty, hippie backpackers

Some, but certainly not all, hostels have them. If you seek to avoid them, opt to reserve your own space. Usually in very popular destinations, there’s one party hostel, which is fine if that’s your thing, but most often there are quieter ones for the older crowds — hostels aren’t exclusively “youth hostels” anymore. In destinations with more than one hostel, there’s competition, so a hostel is generally clean; owners know they get better business if they stick to some sort of cleanliness standard. The same goes for small hotels.

Other affordable housing options

But hostels and small hotels aren’t the only places in town when traveling independently; let’s not ignore the B&Bs, the chain hotels, and the occasional 5-star resort — all of which I’ve embraced from time to time. There’s the prospect of renting someone’s place (you can use AirBnB as a renter instead of a rentee, for example). Also, there are homestay arrangements that can be made, like with the non-profit hospitality network CouchSurfing, where you stay with local hosts who voluntarily open their doors and their couches for travelers to crash.

Figure out your comfort zone in terms of food and accommodations, and mix it up if you can. This will save you money and let you extend your time out in the world if you opt on the lower end; in fact, I’ve found that “real travel” happens when you leave your comfort zone — although I do enjoy being pampered too from time to time. Just know what you’re comfortable with, what your tolerance is for inconveniences, and how much wiggle room you have in your budget and itinerary.

How to plan your trip — and when to go with the flow

When I was planning my big 16-month itinerary, I meticulously used guidebooks and the internet to figure out each and every place I’d stay, the site I’d see, the restaurant I’d eat at, etc., from day one. But I learned the first week of actually being on the trip that it’s not an advisable way to do things; from experience, I now recommend that you do not overplan, especially if you’re on a longer trip. You’re traveling long-term so you can be flexible; use it to your advantage. Inevitably, sometimes things will happen that are out of your control and if you have a tightly-planned itinerary, it can’t happen as planned. Overplanning just sets up an expectation that may or may not be met — many times not — which may ruin the experience for you. I’m not saying don’t plan — maybe you’re the planning type — I’m just saying don’t overplan.

My advice from my years of travel experience is to get a general sense of what you want to do and leave buffer time to let experiences in a destination evolve. And then, if you decide, you can embrace them. Lately when I go on a trip (if only for a couple of weeks), I simply book the flight to and from a destination (not necessarily the same airport so I can go from one place to another), and reserve a room for the first two nights. That’s it (unless there are vaccinations or visas needed). The itinerary evolves from there, based on what I hear, who I meet, etc. I have a general sense of the things I want to do, and where I want to go, but when they will happen I will figure out when I’m there; often a travel plan comes together naturally.

As for that initial flight to first get you to a destination, there are several sites out there to shop and price compare airfares; almost everyone knows about the regularly advertised travel sites like Travelocity, Expedia, Priceline, and Orbitz. Kayak and Hipmunk are also great tools for figuring out the best deal on airfare that works for you. For round-the-world (RTW) tickets, there are programs out there that offer deals; airline networks like Star Alliance have special RTW fares, albeit with some restrictions. Also I’ve had a positive experience with AirTreks, which specializes in inexpensive international and RTW tickets.

 

Step 5: Know what should be on your pre-flight to-do list.

Aside from any loose ends you have to tie up in your personal life, there are few basic things you need to do before you go:

Your passport becomes your portable booklet of bragging rights. Photo: Erik R. Trinidad

Get a passport and make sure it’s going to remain valid

According to a CNN article, only about 30% of Americans have passports, which is an embarrassingly low percentage compared to the other G10 nations. If you don’t have one, don’t be embarrassed; it’s never too late to get one, and it doesn’t take too much effort — all you need is 110 bucks, a couple of passport photos, and the patience to wait a few weeks for it to arrive. (Or pay more and get it quicker.) If you have a passport already, make sure it’s got a least 6 months left before the expiration date; many countries will not let you in if you don’t.

Find out if you need a visa

Check the US Department of State website for the visa requirements for specific countries you wish to visit. If you’re traveling long term, keep in mind the expiration dates on them; there’s no sense getting a visa that only lasts 90 days ahead of time if you’re not going to arrive until six months after you’ve left home. If that’s the case, remember that there are embassies in other major cities in the world that you can go to for visa applications, closer when you expect to arrive in a visa-requiring country.

Find out if you need vaccinations

Check the Center for Disease Control website for vaccination recommendations for the specific countries you wish to visit. Set up an appointment with your doctor and get them. If you can do this before you quit your job and can take advantage of health benefits, plan accordingly.

Consider travel insurance

Some people opt not to do this, but if you’ve quit your job and no longer have medical coverage, it might be a good idea — especially if you think you might end up having to get air-lifted off the Everest trail in Nepal because of altitude sickness. Surprisingly, travel insurance can be a lot less expensive than the monthly premiums you pay out of pocket simply by being at home. (For about 200 bucks — less than half of my monthly insurance premium in the USA — I had a multi-month travel policy which covered my $4,000 Everest rescue.) Shop around for what suits your needs. American Express Travel has a travel insurance program that includes medical benefits, albeit on the pricey side. For a less expensive policy, check out World Nomads Travel Insurance, which specializes in medical coverage for long-term travelers, and has been recommended by Lonely Planet, Rough Guides, National Geographic, and BootsnAll.

Get your ATM and credit cards in order

Gone are the days of travelers checks. Sure they’re available, but in most parts of the world, they’re a bit of a hassle to use, or come with a hefty surcharge. Cash is easier these days; ATMs are in most parts of the developing world now, and are almost always a part of a global network that you’re already associated with. (There are exceptions though; I was once in Zambia where all but one available ATM in the country was on the MasterCard/Cirrus network — the rest were on Visa.) With all your ATM and credit cards, make sure you remember to call your company and notify them that you’re traveling abroad; the worst thing is to have your cards reported as fraudulent or stolen when “mysterious” charges that are yours come from overseas.

Pack light

Most, if not all, experienced travelers can agree on this: Pack light! When you travel long-term, you obviously can’t pack for your entire stay. Long-term travel is different from a short vacation; you are inevitably and regularly going to do laundry on this trip, so there’s no sense trying to bring clothes for the entire time. I usually just pack a week’s worth of underwear, a week’s worth of socks, two pairs of quick-drying pants (one to wear while I’m washing the other), a few shirts, a quick drying towel, and a few toiletries. And you need not pack everything; remember that despite what you may see on television, you really aren’t going to the middle of nowhere; stores exist for basic necessities — as well as plenty of other things — and you can simply get things as needed when you’re away. (Plus, you might be surprised about what you can do without.)

 

Step 6: Go see the world, and have the time of your life!

If you’ve got this far, you’re making your dream a reality! If you’re still buying into excuses, please go back to Step 1.

Now quit that job, plan that trip, get your documents in order, pack your bags, board that plane, and travel the world! You won’t regret it; it’ll be the best decision you’ve made — that’s the general consensus of everyone I know who’s taken the leap. And if you’re still a little afraid, don’t worry; that only means it’s going to be good. Hell, it’s going to be great as you face your fears, conquer your qualms, meet new people (you’re never really alone when if you travel solo), explore new cultures, eat new foods, and learn new things about the world — and yourself.

You can make your peace with the planet in Patagonia. Photo: Erik R. Trinidad

“I’ve never met a person who did a RTW [Round The World trip] and regretted it,” says Sean Keener, CEO/co-founder of BootsnAll.com, and fellow world traveler. “It’s the best investment in yourself and perhaps the best way to get a real education. Forget grad schools and the overpriced MBAs; the long-term indie travel experience is worth far more in beginning to understand the world — and your best fit within it.”

Need more travel advice? Follow and/or contact me via twitter @theglobaltrip. You can also read about my past adventures at TheGlobalTrip.com.