How to Sell Everything You Own And Move to the Caribbean

[Originally published in November, 2012 at Manarchy Magazine]

First, you have to realize this is life: Nobody gets out alive. If you’re like most people, you hate your job almost as much as you hate the drudging commute that makes you late on a semi-regular basis. Sure, you’ve got your TiVo and that super fast internet connection, but when was the last time you spent three hours on Facebook and felt good about it afterward? There must be more to life than merely passing the time between birth and death with vapid entertainment and forgettable distractions.

Junk mail, leaf blowers, telemarketers, MPG estimates that never add up and political ads that go on for months: What’s the point of a high life expectancy if you’re not enjoying yourself? First world problems may sound petty, but the ulcers they induce don’t hurt any less on account of their source.

Aim for blue skies and white sand beaches, where rum is cheaper than milk and there are more holidays than you know what to do with, and don’t work unless you absolutely have to. Do this for a year or so, and if after that you decide to return to the first world grind, you’ll have amazing stories to tell and your outlook on life can only have improved.

Consider a few places where the cost of living is low, where the exchange rate can give you an advantage. Don’t be worried about language barriers; pretty much the entire Caribbean speaks English. You can compare the cost of living with your current city and your destination side by side on sites like, and this is invaluable for setting up a monthly budget and the planning the overall longevity of your stay. And if you think paradise may eventually bore you before you run out of money, check out work visa requirements. A part-time gig tending bar or selling sun screen like it’s liquid gold at a touristy gift shop beats punching a clock in Anytown, USA. (Also, remember to pack a lot of sunscreen before you fly out.)

Now is the time to buy your ticket, while the idea is fresh and you have momentum. Departing on a Wednesday or Thursday is best, as tickets tend to be cheaper. Buy a round trip ticket, but set the return for six months or so with the knowledge that you can change this at any time to extend or cut short your trip and that change fees aren’t all that bad. is great site for airfare, as they check many other sites for the best fares and list all the results on one page. Book your departure date out about four or five weeks to give you time to sell everything, as this will build a sense of urgency without looming for too long.

After that, it’s time to realize that almost everything you own is replaceable, stuff you won’t even remember in five years. This one’s easier than it seems at first. Look at all those dusty boxes you’ve kept in your closet since high school. I bet you can’t name half the things inside without peeking, and that’s a good thing. Keep this in mind going forward, because almost everything you own right now is just as fleeting and meaningless to you. Be sure to enjoy the nostalgic moment as you decide the best way to dispose of these things, but dispose of them you must. Keep your high school yearbook, throw out your graduation robe, burn old love letters.

Anything you’ve collected that holds real monetary value, say old comic books, Beatles LPs, or Coca-Cola memorabilia, can be handled one of two ways: You either cut your losses, since you haven’t unpacked that collection in nearly five years, and sell it to a nearby antiques shop, or you leave it with a friend or relative to look after while you’re getting yourself together down south. They’ll understand.

Now take a stroll through your place thinking, “If there was a fire, a storm coming, if there were flood waters rising, what would I absolutely have to grab?” As you decide what to throw in your suitcase in a few weeks (and you may need to buy some luggage, but keep it simple), these few items go to the top of your list.

This is actually the most liberating part of the process because you end up with a tangible representation of your priorities. Things like your laptop and backup disc, a couple books, photos (if you don’t save everything digitally already), and maybe your favorite coffee mug. After this, airline baggage limitations will dictate whatever else you bring based mostly on weight and extra baggage cost. Marble bookends will not make it past this step, and neither will that clever bread machine you never use. Don’t pack a coat, but don’t get rid of every last one, either. You’ll want to leave at least one with the same person who’s holding on to your coin collection.

Now is the time to check sites like for long term rentals on your island of choice. Short-term rentals tend to be vacation oriented and expensive, but many places have a nice range of furnished two or three bedroom houses and apartments for a few hundred dollars a month. If you’re going it alone, single bedroom places are even cheaper. Find an island where you won’t need a car, that way you open up a huge chunk of the monthly budget you’re accustomed to. You’d be amazed how much cash this frees up. Cars are nearly pointless in most of the Caribbean anyway. They’re expensive to ship over, even more expensive to buy once there, and gas and maintenance are just ridiculous. And many of these islands are only dangerous if you’re behind the wheel. If your car is paid off, selling it can give you another month or two in your destination, easy.

Week number two is when you start listing the bigger things on Craigslist and schedule any appointments with your dentist or eye doctor while you still have your work insurance. Plan a yard sale for your last weekend in town, and keep in mind that anything that doesn’t sell can be given to a friend or donated to charity. If you call ahead many organizations will schedule a pickup time and send a truck to you (which is great if your car sells sooner rather than later); set this up for the Monday or Tuesday after your yard sale. However, don’t sell your microwave or washer and dryer until that last week unless you have an awesome neighbor who won’t mind letting you use theirs.

Once you’ve done your research, booked your ticket, listed your TV and your couch online, it’s time to call the utility companies to schedule the shut-off dates, give your landlord thirty-days notice and plan a going away party. Don’t call it a going away party, of course, but plan it for the Friday night before your yard sale, and set aside a couple things here and there you might want to give to a close friend or two. You can start telling your friends now that things are in motion, but keep it off the social network until you let your employer know, just to keep things professional. There’s no reason to burn any bridges unless your job is so soul-crushing you’d rather die than go back. If that’s the case, give your two weeks notice and count down the days with a smile. Otherwise, talk to them about taking a leave of absence. Tell them you’re going to go finish that novel you’ve been putting off.

Finally, it’s time to call your parents. They may love or hate the idea, but by now there’s no turning back. You’re an adult; you don’t need their approval. This is a cause for celebration, so it wouldn’t be classy to let your parents find out from some random relative third-hand.

For the next three weeks or so, you’ll spend your time listing things online, taking less money than you think your stuff is worth (don’t worry, it all adds up) and hitting up all those restaurants you’ve been meaning to check out but never found the time. You’ll be amazed how your schedule opens up despite how much time this sort of planning takes.

Do this. Do it because it’s been too long since you took a real worthwhile risk. Do it because you need to get to know yourself. Because few things can define the distance between who you are and who you want to be like holding on to those things you cannot live without and letting everything else slide.

Even if you don’t really plan to leave the country and do the Caribbean thing for six months or a year, going through these motions is a healthy exercise. All the clothes that no longer fit, DVDs you’ll never watch again, all the extra channels you don’t need and all the countless hours you waste on pointless entertainment that gets you nowhere near any sort of contentment; all these things will come into sharp focus. Even if you only work it all out on paper and use this as an exercise to realign your priorities, you’ll likely be blown away by how much better your next year will be. Just working out your monthly budget with all this in mind can be eye opening, so even if you decide to stick it out on the mainland, keep all this information close at hand. Because if (or when) the economy tanks again and you find yourself out of work, or if you ever get so fed up you feel like there’s no point in going on, you’ll know where you can head, how much it will cost and how long you can stay. You’ll have it all worked out on paper and the only big barrier will be buying that plane ticket.

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