Most of the die-hard travelers I know have, at one time or another, thought, “I want to live abroad!” Very few, however, do much more than take extended vacations. Why? Because the journey between having the idea to move to another country and actually making it happen it can be long, cumbersome, expensive, and just plain frustrating. It’s a big challenge – but it’s absolutely something that can be achieved.

At the moment, I’m in the process of getting a visa to move abroad to Italy. I’ve buried my nose in countless books, contacted numerous current and former expats, and perused dozens of websites, all offering advice about living in Italy. In short, I’m up to my eyeballs in information, in the middle of the process of becoming an expat, myself.

My goal here is to present some of the things you should think about before making the move to a foreign country. I’m not trying to scare you out of it; I want you to be aware of some potential problems that could arise before they come up and smack you in your jet-lagged face. Unforeseen dilemmas are a given, but the fewer of them you encounter, the better. Those of you daring enough to show up somewhere and just stay on without legal papers can skip on to our Indie Travel Guides for our best tips on wherever you plan to end up.

For some, picking a country is straightforward – it’s not just that you’ve dreamed of living abroad, you’ve already set your sights on a particular place and nothing else will do. For others, it’s simply the idea of living in a foreign country that’s appealing, and you haven’t figured out the “where” part yet. Honestly, those in latter camp, may be better off. It’s much easier to pick and choose from the countries that things easy for expats, rather than getting your heart set on a country where there are major roadblocks to becoming an expat.

Whichever camp you fall into, there are a few things to do before picking the country you’ll be adopting as your new home.

• Check out the visa process While I’m jumping through countless hoops to become a legal resident in Italy (as I would in any EU country), a former BootsnAll employee who lives in Bali merely has to leave his island every couple of years and pay the government some cash in order to stay. Another colleague of mine who lives in Costa Rica just had to make sure he had a way to support himself before moving. It’s important to know how involved the process is, and how long it will take, before you start packing up house.
• Use a scouting mission to learn more. A two-week vacation doesn’t give you an accurate picture of life at a destination. So before you make the big move you should take time to spend a month or two renting an apartment in the city you think you want to live in – preferably in not the best weather or the busiest season so you aren’t duped into thinking it’s always beautiful and sunny and full of energy. An extended, single-location stay will let you settle into a routine and get used to things like grocery shopping, cleaning the house, and paying the bills.
• Talk to current and former expats. Your goal here should be connect with people who either live or used to live in your destination. Their perspectives will give you the most complete picture of what it would be like to live there. Remember, you’re bound to get some overly positive feedback as well as some that’s overly negative. You’ll need more than one or two opinions to consider yourself informed. Websites and online forums frequented by expats can also be handy.

As mentioned above, depending on the country you’ve chosen, the process for becoming a legal immigrant can be anything from overwhelmingly challenging to almost nonexistent. I like to say (and I’m not alone here) that the Italian government invented red tape – this after barely dipping my toes in the bureaucracy that’s required to get my visa.

While current and former expats can be a good starting resource for visa information, in some countries everyone is going to require something a little different. Your best bet is to find out what you need directly from the horse’s mouth, so to speak.

• Find your nearest embassy or consulate. It’s possible you’ll have to make multiple trips to the nearest consulate representing the country you’ve chosen, so hopefully it’s not too far away! The official website is a good starting point for information, and you can call or email for additional information as well. There’s a list of the embassies and consulates in the US here.
• Find out about different kinds of visas. You may find that there are several different kinds of visas available, depending on your situation. There are working visas, visas for retired people, visas for students, and what I call “famous/rich people visas.” This latter category is one that allows people that are wealthy enough to have second (or third, or fifth) homes in a country besides their own come and go as they please. The reasoning is that because they’re rich, they’re not going to be a drain on the local economy. If you’re reading this article, my guess is that you don’t fall into that category, so you’ll just need to figure out which visas you qualify for – and which are easier to obtain.
• Find out about family visas, if necessary. If you’ve got family who’ll come along with you, it’s important to know what kinds of visas are available to them and what they can do on those visas – sometimes they’ll be allowed to work using their visas, and sometimes they’ll be strictly prohibited from working. For example, I’m getting a freelancer visa, and my husband will have a family visa through me that allows him to work legally in Italy. His dreams of lazy days in Italy courtesy of a sugar mama are, therefore, going to stay dreams. Sorry, honey.

The question of whether or not you’re allowed to work in a place is largely – if not entirely – determined by the type of visa you acquire. Some visas give you the freedom to legally accept just about any job that’s offered to you. Others pretty much force you to work illegally when you need the income. This is an important thing to find out at the consulate when you’re assessing your visa options. Some visas are specific to a job opportunity with a particular company, which means you’re somewhat trapped in that position unless you find another company to sponsor your visa.

It’s also important to note that in my experience, student visas often don’t allow for legal employment, so if you’re planning to work your way through your studies and don’t want to work for cash, you might be out of luck.

If you don’t mind bending the law to make ends meet, you’ve got more options. Most countries have a thriving market for under-the-table employment, although the pay can hardly be described as lucrative. In places like the EU, jobs, like waiting tables or teaching English, are easy enough to find, and offer flexible schedules that could be ideal for students, if they learn to live on a limited income.

I said this earlier, but I can’t stress it enough – the bliss you felt during your two-week vacation to Tuscany doesn’t mean that buying a farmhouse and spending the next decade restoring it is going to be bliss.

Real life in any country is nothing like a vacation in that country – you’re on vacation, after all. You’ve put all those mundane everyday real-life activities out of your head. You’re not cleaning the toilet, you’re not defrosting the fridge, you’re not taking out the trash – you may not even be making your own bed! To assume that living in a country will be the same as it was on your vacation is a recipe for disaster; you could end up sorely disappointed during your expat life there.

Many of the things you take for granted at home will be different in another country; these changes can cause culture shock. You’ll have to re-learn how to do all kinds of stuff that you’ve known how to do since you were 15. You may have to learn a new language. Everyday things like renting an apartment, getting a bank account, finding a doctor, doing the grocery shopping, paying the bills, voting, getting a driver’s license, and doing the dry cleaning may prove challenging. Even “fun” activities like shopping for clothes and books can be problematic, as you’ll need to figure out what size you are in this new country, and you may not have ready access to reading material in anything but the local language.

If you’re an internet junkie, you’ll need to make absolutely sure you can get online and get your fix as often as you’d like. I know a woman in Italy who has been fighting with the local telecom company for over a year to get high-speed internet (she’s been on dial-up), and that’s after paying for the connection to be installed in her house. In more rustic settings, online access can be slow or limited to internet cafes and other such internet points.

The situation only gets more complicated if you’ve got a family. Bringing your children will require you to figure out your options for the kids’ schools and doctors (and you’d better hope you don’t have a picky eater who doesn’t like the local fare!). Should your family includes pets that you want to bring with you, be sure to check into quarantine laws early because they can be onerous, especially in island countries.

Now, re-reading all of this, it feels like I’m saying, “You shouldn’t do this! Out there is totally different from in here, and different is bad! Stay home! Shut the doors and windows and never leave!” Okay, maybe it doesn’t sound that bad, but all of this cautioning isn’t to tell you that you shouldn’t move to another country.

In many ways, it’s all the quirks – the differences in everyday life – that make life in a foreign place so interesting. Who would have thought that after 20+ years of doing the grocery shopping on auto-pilot back home that going to the market would be something I’d want to write home about? And yet that’s just what happens to me every time I go to a market in Italy.

Only you can decide whether living in another country is going to be worth whatever hurdles that country puts up in your path; but if when you’re presented with hurdles and you still keep going then your chances of success are infinitely greater than if you’d just given up at the first sign of a bump in the road.

As a former expat I know once said to me, “Obstacles are just there to keep out the people who don’t want it enough.” And every time something about the process of becoming an expat in Italy seems more troublesome than it should be, I just go back to that quote and it’s full steam ahead.

Perhaps the best thing ever to happen to the expat community worldwide is the internet. It’s not only given expats a way to communicate with each other and share resources, it’s given them a way to communicate more easily with friends and family back home. The internet makes the world smaller and goes a long way in keeping important emotional ties from going cold.

Still, some of the resources I’m listing here are good, old–fashioned books! I can’t help it, I’m one of those people who likes books printed on paper now and then. They’re great on the go, no charger or internet required. So, here are a few of the resources I think are particularly useful for anyone contemplating a move to a foreign country.

• Online Forums – You’ll need to do an online search for the words “expats in” plus the country you plan to live in; there are sure to be at least a couple websites and online communities for most of the popular countries. Italy has several such sites, like Expats in Italy.
• “The Expert Expatriate” – This book may seem overly basic for some people who are further along in their plans, but it’s a great collection of some of the general things to think about before quitting your job and selling your house. There are several books dedicated just to living, working, and studying in Italy, too – many of which I’ve been reading – and my guess is that there would be a similar array of books for other countries as well. Check with your local bookstore or library to find out what’s available.
• The Culture Shock! Series – This series of books, covering most countries (and some cities) around the world is good at presenting a place not just in its best light, but in its most realistic. The books go over cultural differences so that you’re prepared for them when you encounter them, instead of just getting frustrated. (Not to say you won’t get frustrated. You will.) Here’s the “Culture Shock! Italy” book, which is – of course – on my bookshelf.
• Expat Bloggers – This is kind of an offshoot of the online expat forums, but I’ve found a great group of expat bloggers in Italy who have not only been really helpful to me in answering questions but we’ve also become good friends in the process. Beyond what I perceive as the natural openness of people who choose to live in another country, bloggers in particular are even more open to sharing their experiences – and the expat bloggers I’ve met so far have been incredibly forthcoming and helpful. I hope to pay the favor forward someday.
• BootsnAll Expats Forum – There’s a forum right here on BootsnAll for expats and expat–wannabes, including those who are just looking for a 1–2 year experience teaching abroad.
• Transitions Abroad – This magazine is great for people who are working or studying abroad, or are just dreaming about it. It’s not cheap, so it’s one of those investments that’s best when you’re pretty certain of an impending move. Check your local library or bookstore to get a sample copy.
• Escape Artist – Specifically for people who are living abroad, while working or retired.