What a nice surprise to be featured in Islands Magazine this month in their “Ten Best Islands to Live On” article. Almost exactly one year ago Terrie and I purchased the Palmetto Guesthouse after living overseas for many years.
We are both originally from Massachusetts and we had the dream of owning our own business for many years and finally saw that goal come to fruition with the purchase of the Palmetto here on Culebra.
Our travels have taken us to Europe, Central and South America, the South Pacific, and of course, the Caribbean.
Chasing Coconuts - How I Went From the Cube to the Caribbean
March 6th, 2008
I am guest posting at AnyWired today:
In one of my previous guest posts here at AnyWired I discussed how to remove yourself from the office and take your show on the road. Today, I thought that I would give you a little insight and look into how I went from the cube to the Caribbean.
My story about searching for personal freedom might be a little different than most as I now live in the Caribbean and I am currently trying to develop my web presence from here. But, whatever your web worker dreams are, this story should hopefully resonate with many AnyWired readers because I am truly “everyman.” I do not come from money and have done every possible job from working as a waiter, landscaper, and warehouse worker to presenting data and policy to high level government officials.
To be sure, my goal to live in the Caribbean is most likely quite analogous to *your* situation, whatever your objective might be – starting your own business, telecommuting a couple of days a week, or traveling the globe, and most likely my journey was not too much different from what many who read AnyWired hope to achieve.
The Beginning of the Journey
Strangely enough, my journey out of the corporate world actually began when I was about fifteen (I turn 40 this year) and I don’t think I even knew what a cubicle was. During my second year of high school I had the chance to go to Hawaii with a friend and his family. To this day I can still remember stepping off the United Airlines plane and having my feet touch the sand and soil of the tropics for the very first time. Certainly, my life would never be the same.
5 Must Ask Questions On Your Quest For Personal Freedom
December 6th, 2007
Would you like to successfully Quit Your Job, Travel The World, Pursue Your Dreams, and truly do your life’s work?
Some of the most popular posts on the internet today seem to be about taking control of your life and removing yourself from the corporate setting to travel the world, become your own boss, and fulfill your dreams.
Really, it is all simply a euphemism for creating and living the life that you want rather than accepting the status quo of the commuter and workaday grind.

image source: jepoirrier
Because the ‘personal freedom’ topic is so broad and entails many aspects which are required to achieve success (unless you are rich) I am going to break this up into a series that will run every Thursday.
Today, I have a short post to kick everything off and I would just like to offer up five questions or thoughts for you to ponder and ask yourself to determine if you are indeed ready to “chase your dreams.”
1 Are you caught in a rut? Whether at work or personally?
2 Are you prepared to be an active participant in your quest personal freedom?
3 What would you ideally like to be doing with your life?
4 Do you have personal or familial obligations that you need to sort out?
5 Would you like to make a change?
Whether you are interested in moving overseas, changing jobs, or starting your own business. All of these goals require one thing, a positive mindset and a plan with room for flexibility. With that you can achieve anything.
Please join me on Thursday of next week for the first post in this series when we will look at “How to Remove Yourself from a Negative Situation.”
Now, I ask you, are there other questions that you ask yourself when thinking about pursuing an aspiration, or change? Let me know in the comments.
Editor’s note: in case you have recently noticed the new tagline above -
Living Overseas | Blogging | Inspiration and Motivation | Entrepreneurship
MyTropicalEscape has taken a slight turn to include more niche topics. For those of you that are interested in my new editorial calendar, every Monday I will have a post on blogging or marketing, on Tuesday’s there is the flagship “Ten Questions With” interview series, Thursday will focus on the new series about personal freedom, and Friday will be a day to give back where I will discuss social or humanitarian issues.
5 Tips For a Better Life Starting Today Based on Subsistence Living
November 30th, 2007
Those who lead a subsistence existence grow only enough food to feed their family, support their animal’s grazing area or farmland, and perhaps to provide a small marketable surplus.
Do you find yourself caught in a cubicle?
November 17th, 2007
Editor’s note: this is a re-post of an older article as I am going to be away without reliable internet for a few days.
Why its Important to Visit a Country Before you Move Overseas
November 9th, 2007
Do you dream of moving overseas? Perhaps to the South Pacific or Caribbean? When we lived in American Samoa many people would accept government contracts pretty much sight unseen. Upon accepting a position soon to be new government employees would sell every possession they owned and pack up and move to Polynesia.
Five Tips for Aspiring Expats
October 29th, 2007
For some it is hard to resist the allure of a move overseas and the thought of becoming an expat. Whether it is for work, or for other more personal reasons, living in a foreign country can be tremendously satisfying. However, going to another country to establish a new life, I believe, comes with some responsibility and below I would like to present five tips that every aspiring expat should know and think about before they pack their bags:
- do some research - make sure you can legally work in the country you wish to relocate to (this includes volunteering).
- realize that your life will not improve if you are trying to escape demons, whatever your issues are at home they will only be magnified overseas.
- respect local customs and cultural differences.
- remember you are not in your home country so try to go with the flow.
- no matter how long you live in a foreign country you are still a guest in someone else’s country.
These tips are not meant to be condescending or cynical. Unfortunately, we have seen many people move overseas only to be drastically disappointed because their particular brand of hair gel was not available. Or, because “things do not run like this in their country.”
If you decide to move overseas – GOOD LUCK - and for further information, you may wish to read Adjusting to Life Overseas.
Reverse Culture Shock
October 26th, 2007
If you travel, or spend an extended period of time overseas, then there is a good chance that you might encounter reverse culture shock upon your return home. Reverse culture shock is a funny phenomenon and if you have not experienced it, can be difficult to explain. As a means to prepare students’ who have been abroad the University of Iowa’s International Programs website has this description, “Reverse culture shock basically consists of feeling out of place in your own country, or experiencing a sense of disorientation. While everything is familiar, you feel different. Even walking through the airport and hearing American English spoken can be a very surreal experience.” I can still remember leaving Papua New Guinea and American Samoa and arriving in the United States and everything seemed foreign to me. Specifically, from the way people greeted each other to how people passed others in a crowded grocery store aisle is tremendously different depending on where you are. Sometimes reverse culture shock can be extremely overwhelming and the University of Iowa site goes on to further explain that, “Fitting your new life into your old one can be frustrating. Since every country has a unique approach to life, it can be difficult if you’re used to operating within cultural mode, or have made that approach to life a part of you, to return to the U.S. where the rules are different.”