Over the years people have turned to me to ask my opinion on moving to key West and I am leery about offering advice, mostly because it is ignored and sometimes misinterpreted but at this late stage I suppose I can offer my thoughts especially by way of thanks to people who think I know more than I do.
The first question I have is why would you want to move to the Keys? Layne and I washed up here looking for a place to earn some money to continue sailing and I had friends here from previous visits and thus it all fell into place. If you want to move to the Keys you have to know why. It's a long way from nowhere and and as much as people promise to visit you shouldn't count on it. The Cuban embargo effectively makes Key West a dead end and you will have to learn to live separated from your former life. This isn't a frontier town in the traditional sense with a nearby open door to new cultures. It's a cul-de-sac for most residents.
The fundamentals of living in the Keys are the same as anywhere else. Except consider this: you have to drive north of Atlanta some 800 miles from Key West to see a mountain. I love the varied landscapes of the Florida peninsula but the terrain is seen as monotonous by most people. The other point to consider is Miami is a shithole. I used to hear other people characterize it thus and felt rather put out. My wife and I speak Spanish and we enjoy different cultures but Miami is a cross roads of incivility, indifference and cruelty. Of course there are people and pockets that buck the trend but it takes years to find the places you can enjoy and its a tough journey to find what you like in that city. Miami does not add nearly as much as you'd like to think it would to the experience of living in the Keys and it's a shame. That's my very personal subjective view of a city I wanted to love and that has spurned me. Like everything else I write you may have a very different experience and I hope you do.
You need to make a plan and part of that plan is understanding the limitations. At work you have to dump your ambition and your expectation. The best career positions are taken and you need to understand you are optional in the cog of career choices in the Keys. The best paid jobs are for permanent residents, people with connections and roots and you will be tolerated as long as you threaten no one. Innovation, over work and pushiness are fatal to your prospects. It may not be immediately apparent but you will be sidelined. If you live to work stay away. The best career move you can make in the Keys is to be reliable, show up and do things as you are taught how to do them. Become an old timer yourself...
Richard has lived on the streets of Key West for 46 years. I asked him once if he gets bored and he looked startled - in Key West? he said incredulously. I made the faux pas of offering money in my ridiculously suburbanite way -money cures all ills- but he looked at me again as though I were stupid. I've found street people like to pet Rusty, the non judgmental, silent soft ball of furry warmth. It's the human touch not easily found on the streets. And it comes from a dog. Remember the true value and meaning of Island Time. If you can stand an atheist quoting the Bible at you Island Time means Judge not lest ye be judged, for with what judgement ye judge ye shall be judged. Try and figure the difference between a criminal, a lunatic and a non conformist before you feel called upon to act.
In a way I feel like Covid has brought the rest of the country down to the level of service the Keys have been enjoying for years. The problem is you can't get a job that justifies spending the money required to buy a house. Professionals can manage but even so the work to pay ratio remains out of proportion and the only true compensation is joy in living here. For people not planning to be doctors accountants vets and managers the cost of living requires you work all the time so you don't get to enjoy the living in the Keys side of things. So you leave. Thus under staffing is a permanent issue. There is no shopping in the Keys compared to the mainland. If you don't like ordering stuff you are going to be living truly minimally. On busy weekends and during the winter my internet service routinely pixilates my Netflix on my television as the bandwidth is insufficient for the influx of people. See above: quit yer bitchin'. Layne and I developed a saying 20 years ago after cruising Central America on our boat. The Keys: First World Prices with Third World Service and none of the charm.