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Thinking aloud

(@Kenny B.)
Posts: 4
New Member
Topic starter

Hello All,

I’ve been lurking on the site for some time now reading as much as possible with regard to the pros and cons of living on an island. I’m 42 years old and fed up (really fed up) with the corporate world and the unavoidable BS.

My brilliant mind says: “Just move to an island and everything will be peachy.” Permanent holiday!!! But, I have a difficult time committing and risking everything to do so. The fear of dropping out to some degree is heightened by the fear of the possibility of having to drop back in. Or worse, move to the islands, hate it and going broke in the process.

My girlfriend and I are seriously looking at buying a small business (due diligence underway) in USVI and I’ve got an endeavor, albeit a risky one, that I am investigating.

Reading the posts has been, to say the least, very educational. One must enter into this with the rose colored glasses removed.

We would like to live on St. John, but the cost of living just seems to be dangerously close to outrageous. With that said, St. Thomas may be more of a reality and could provide more opportunities with regard to earning a living. Although, St. John sounds very romantic indeed.

I think I’d miss my social circle more than anything else.

Hmmm, no questions really (yet anyway), I was only thinking aloud.

If anyone has any comments, though, good, bad or otherwise I’d certainly appreciate the feedback.



Posted : August 25, 2005 7:56 pm
Posts: 29
Eminent Member

It is indeed a bit scary to pickup and move lock, stock and barrel. I've been in one place for 16 years. In my case, I believe I can do what I do from anywhere since most of my work is around the country and not where I live. Airplanes are great equalizers. That said, there are times I feel like I may lose the clients I have if it is perceived that I am too far out of pocket. My desire to move to STX is based on how we feel when we're there and a desire to explore this world and live life to the fullest. I mean, does'nt everyone dream of living in the Caribbean and giving the heave ho to the rat race. Reality is you still have bills to pay and a house to take care of. It's the intangibles that make it worth it. A walk on the beach or sunset cocktails with new friends and a chance to get a little closer the dream.

Posted : August 25, 2005 8:10 pm
Posts: 3030

Hello Kenny,

Welcome to posting on the board. 😀

Another good section of this site to read is the What to Expect section. It contains about 40 stories written by people who made the move (and stayed or left) or wrote an account of their pre-move visit (why they are going ahead with the move or why they decided against it)... you might find more insight there.

All the best with you plans.


Posted : August 25, 2005 11:12 pm
Linda from Michigan
Posts: 550
Honorable Member

For what it is worth....
Life is short. Do we know what is going to happen or when?
My best friend from college died last Nov. in his driveway. The weekend he moved into the house he dreamed of and finally got to build. That was the first thing he really got that he wanted to do in life.

I decided - you never know - and I can't any more justify the "some day" thoughts. I decided to live life. I came down on a 30 day pre-move visit (after spending 18 years being in love w/ STX from afar) and 2 years worth of heavy research. I haven't left. I came with 3 suitcases. I have my other "stuff" in a storage unit back home.

What if I only last 6 months - or 6 years. At least I got off my butt, followed a dream and did something! I love it here. There are problems - don't get me wrong - but I truely love this island and I promote it to everyone - to at least check it out.

Island life is not for everyone. There are a lot of concessions that you make living on a rock - but for me - I could be like a lot of the others I went to school with 25+ years ago and still be in the same little town, doing what everyone expects me to do.

For what it's worth....


Posted : August 26, 2005 12:11 am
Posts: 0
New Member

Thanks for the replies. We're certainly giving this a lot of thought. My largest concern is the financial risk. At 42 years of age ending up broke after 2 years would be very unnerving.

We'll see how it plays out. I'm reading many of the posts as hearing real life experiences are priceless.

Hope this finds everyone healthy and happy...


Posted : August 29, 2005 3:02 pm
Posts: 8
Active Member

Hi Kenny,

I don't have anything substantial to say other than I completely empathize with your post. My husband and I are mid- to late-thirties (I'm the 'mid' - he's the 'late'-- haha) and we've talked about moving to the islands for the past ten years. Earlier this year we had yet another discussion about whether we can make this plan a reality someday, and together had an epiphany moment of "if not now, when?" Kinda like what Linda said -- you never know what life has in store, or how long any of us will be here. So, why not now??

And then the somewhat-rhetorical "what have we got to lose?" question comes up, except that it's not so rhetorical. Financially, we could lose, well, everything, in a worst-case scenario. It gives me a lump in my stomach to think about it. So we're trying to take off the rose-colored glasses like you, do our research and planning, and we're giving ourselves another year before the proposed move -- trying to be careful in the risk-taking (a paradox?). There are days when I think we should just stay in our comfortable, predicable, suburban life. But then that gives me a bigger lump in my stomach.

On the same journey,

Posted : August 29, 2005 4:41 pm
(@STT Resident)
Posts: 114
Estimable Member

KennieB and AngieS.

For what it's worth, I came to St. Thomas 21 years ago at the age of 39. My PMV (a term that certainly wasn't coined back then!) consisted of a four day visit with friends of mine from Connecticut who had moved here. During those four days I was offered a job in an area where I had no expertise whatsoever.

Upon my return to Connecticut, I mulled over the job offer on STT and then got a 'phone call from a previous boss (Yale Uniersity School of Medicine) about a job in the medical field at Duke University Medical Center in North Carolina. Betwixt and between, I accepted the offer of an all-expenses paid trip to NC and had a wonderful weekend there. meeting some wonderful people and looking at a state of the art medical facility which was just awesome. In the meantime, the prospectve STT employer kept upping the ante.

There was one major problem and it took me three weeks to figure out something that I'd never even been aware of before in my life. It suddenly hit me hard. I was born in England close to the sea, I was raised by the sea. Wherever I grew up as a child (and my mother schlepped me around a lot!) it was always by the sea. When I left home I was by the sea. When I moved to the USA I was by the sea.

A strange epiphany. Durham, NC was about a five hour drive from the ocean and murky lakes were there but they were bodies of water that I just couldn't get excited about. So I came to STT.

What a very long and sometimes very arduous 21 years it's been but that's another tale. I sometimes wonder what would have happened if I'd ignored that "epiphany" and taken the job in NC. Possibly, probably, I would have segued into middle age and older with a nice pension, maybe even a wealthy physician for a husband and naturally a penchant for gathering people together for dinner parties!

But I moved to STT and here I be to this day, so many years later, and poorer in $ than I've probably ever been in my entire life! Am I bitching about it - no.

There are no guarantees in life. Some are content to live their whole life in one small community in which they feel comfortable, others decide to spread their wings either sooner or later. You have to simply do what your inner self snidely tells you to do and then, if you decide to make a move, you have to understand and learn the old adage which goes, "when in Rome do as the Romans"...

Paradise is paradise is paradise and is all dependent on what's in your soul.


Posted : August 29, 2005 7:39 pm
Posts: 17
Active Member

Kenny B.,
Our dream is similar to yours and we both have been researching and scheming to move to STX. We have visited STX and absolutely love it. We will wait 2 years until his youngest is out of high school and in a little better financial state of mind.
I just wanted to comment about your statement that you would miss your social circle. I had visited this message board and the vacation message board for about a year before our trip to STX. If you will notice they do have get togethers on all of the islands quite frequently and it is a great way to meet people. We just happen to be visiting STX when there was a get together and it was a great time. We met many people while on our trip to STX. We met those at the get together, at restaurants, or just sitting at a bar. There is no doubt in my mind that once we move to STX and I hope it happens, we will develop a circle of friends.


Posted : August 29, 2005 7:59 pm
(@Kelly M)
Posts: 2
New Member


I guess I will also add by two cents worth...

My husband (just turned 49) leaves in 10 days. Our son (8) and I (38) will leave later this year. We have been self-employed for 28 years and are ditching it all. We don't have a "sellable" business so we are liquidating and paying off the massive debt incurred since the Enron problems and 9/11 which affected our business greatly. We will have very little left and yet with this decision feel a lighter burdon on our shoulders than we have in years. We are planning to buy a small business ourselves as well as make ends meet by continuing a smaller version of our current business on island. We came to the realization that life is too short and if we don't do this we will never forgive ourselves for not being brave enough to do it. If you decide to make the big move, I am sure you will have a tremendous support system that you didn't realize was even there.

FYI-We are moving to St. John. For us, it's the only option. And our social circle that is non-existant here is wonderful on island. We already have several very close friends who we can really count on and enjoy being with. The rental housing on STJ isn't really all that bad. You just have to be there or have one or more really helpful friends on island to help you. We've found a very nice, very new, 2/2 for $1500/mo.

Just some more thoughts for you.

Posted : August 30, 2005 1:15 am
Posts: 3
New Member
Topic starter

Firstly, thanks to everyone for sharing their thoughts. It’s very helpful to hear others thoughts and experiences. We’re diligently doing our research and planning a reconnaissance trip as early as October. If all goes well, who knows what might happen.

I must add too that this is a bloody great site. I’m not 100% certain, but I think a guy called “Islander” started it, is that correct? Anyway, thinks to whomever started this site as it was a great idea.

Best regards,


Posted : August 30, 2005 9:09 pm
Linda from Michigan
Posts: 550
Honorable Member

Unless you had hit a major windfall, think how many times most millionaires, super business people have had it all, lost it and rose to the top again. I've read some of these guys' stories. They were able to re-build because they knew how they did it before.

I know that no one wants to lose everything they worked hard for - to move to a place that there are so many unknowns - but what do you gain if you don't take opportunities? Everything in life has risks involved. There is nothing to say you couldn't have been in New Orleans and just lost absolutely everything!

Do a thorough pre-move visit - don't do it blindly. Know what you are getting into and make a decision. But do the PMV. It is critical. This is not paradise without problems. But for some of us, it is the only place to be....for right now.

Just my 2 cents -- I know it's not for everyone. But don't lose out on something you might regret the rest of your life.

Posted : August 31, 2005 10:41 am
Posts: 2
New Member

I too am in a similar position, for a long time talking about the move and now finally getting in gear to actually do it. I have been visiting the islands for over 20 years and over the past 2 years have really accepted the fact that life is too short.

I hate the corporate life although I have been successful in it and do not want to end up tired, frustrated and unfulfilled. So I too am ready to give it all up to at least try...

Do it, follow the dream....... I am

Posted : August 31, 2005 11:12 am
Posts: 532
Honorable Member

Just a word to the wise - you may well find yourself tired and frustrated here. Every day living can be quite a challenge on island - DMV ( to name a famous source of aggravation), out of stock parts, slow and poor service, no recycling etc.
The people who seem to do well here, are those who tolerate frustration and inconvenience well, laugh and move on. You will give up a lot of concrete things that you take for granted for an intangible gain. We think it is definitely worth it, but we are a hardy bunch - lol!

Posted : August 31, 2005 7:18 pm
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