What It Actually Takes to Move to A Tropical Island

Ever daydreamed about giving up all of your worldly possessions and moving to a beach in the Caribbean? Of course you have. Everyone dreams about it, and no one actually does it. What would it take to actually go through with it?

Here's what.

The first thing you need to take a look at is your personal finances. This isn't as scary as it sounds, don't panic if you don't have much (or anything) put away, but you do need to assess what kind of resources you have. Make a spreadsheet as we move forward and keep track of your numbers for easy review. We'll start with liquid assets: How much do you have in checking accounts? Savings accounts? Don't touch your retirement accounts, that's off limits. Write "Cash" in the first box in your spreadsheet, and fill in the amount.

Next, let's take a look at your monthly cash flow. In your spreadsheet, label cells for each of your fixed monthly expenses (house payment, car payment, Netflix, etc.), and fill in the amounts. Write in a final box for your estimate discretionary costs each month. Now add them up and write in the total at the bottom. This exercise, incidentally, is useful for everyone, not just those of us dreaming of pina coladas. All right, now for the revelatory moment: copy and paste the breakdown of your monthly expenses next to your original list, and now go through and knock out every expense that you will no longer have. This will, of course, be almost all of them, as you won't need a Suburban to get around your little beachside paradise. What's the new total? Keep in mind, of course, that you'll need new lodging, but we'll get to that momentarily.

Hopefully you've just realized how inexpensive it can be to live simply. But, of course, cheap isn't the same as free, and you'll still need money. And what about all of the junk out in the garage? What about the house itself? And the car?

Sell the car to Carmax. Give away the old dresser in the garage that you'll probably never use again. If you want complete independence from your former life, sell your real estate through a realtor you know. Or, if the poor housing market disturbs you, lease it out. The point is, you DON'T NEED most of your things, they merely serve to weigh you down and remind of what other things you think you want.

If you haven't thought much about where you actually want to move to, now's a good time. Consider the following:

1. Transportation - this may mean walking, or it may mean bicycling, or even a metro system (Singapore is both tropical and modern - food for thought), but you need to know how you'll get to the grocery store.

2. Economy - depending on what kind of work you want to do, you'll have to consider the opportunities in various local economies. Tourism is always an option, but go beyond the obvious, and research where there's a demand for a skill you can provide. Maybe you're an auto mechanic; where is there a shortage?

3. Cost of Living - There are realities to living right on the beach, including heavy prices and astronomical insurance. But perhaps there's a nice cottage half a mile from the beach that you could buy or rent dirt cheap? Or you can research where a local housing market is depressed from too much condominium speculation. The point is there are ways of making it affordable, you just have to dig a little deeper.

Finally, as mentioned above, you'll probably have to do some form of gainful employment, but depending on your skills and trade, there is almost always a demand for intelligent, educated people in poorer countries. And, of course, a quick look at any job site will reveal the massive demand for telecommuting jobs that can be done from anywhere.

The hardest part is simply letting go of your anchors, both physical and psychological, that hold you where you currently live. Your job, your house, your car, your lifestyle... let them go. Lease your house to a family, sell everything else, and go. If you decide after a year of being a beach bum that it's not for you, then simply return home: it will still be there waiting for you.