How to Take a Permanent Paid Vacation

This is not a reprise of that old Dire Straits song. So I am not gonna tell you how to get your money for nothing and your chicks for free. Sorry about that.

However, if you’d like to see some parts of the United States and have someone else finance the trip then I can tell you something about how to get that done. It’s possible that the techniques I have used can even work with traveling overseas.

I work in IT. Although I myself have not done it, it is my understanding that if you have a skill that is in high demand, you can get someone to pay for you actual trip to say Hawaii or Toledo. I am a general web programmer so my skills are not that specialized.

The first thing you want to do to get someone else to pay for your wanderlust is to keep a detailed account of all your moving expenses including, packing, shipping, gas, mileage, meals, etc. As long as you don’t move too often you may be able to deduct some of these expenses off your taxes. So the first rule in our modern world is when you want someone else to pay for something, look at the government first. You purists are justifiably angry at this attitude but it is a truthful one. This is a consequence of our fellow citizens continually voting for representatives who want to tell us in detail how to blow our noses and wipe our bottoms. In theory, it is your duty as a good citizen to ask first: can I deduct that? And then decide whether you want to do it, whatever it is.

The next step is move to the city of your choice. And look for a job. If you have been following my advice carefully, step by step as you read this, it is entirely possible that you are now hosed. After all, what happens if you can’t find a job?

Fortunately, if your skills in IT are broad enough you won’t have much difficulty getting a job so I haven’t gotten you into too much trouble. But if you were perverse enough to want a paid vacation to Detroit—an economically depress area--you may be well and truly hosed. I hear they have houses for a dollar there or some absurdly low price so the economy, even for IT types is probably not that good.

So, before you pack up and leave some place, first check the internet to see if there are job openings in your field. You might even apply for some jobs before you move to see what kind of reply you get. If you never get any reply, you don’t want to move there. If they say they only take local residents seriously, that’s a green light. This means that while the move is not risk free—nothing in life is—the risk is manageable. At least you are not moving to marry some stranger sight unseen—now that’s a risk!

One thing that can help the transition is to get in contact with a headhunter or recruiter. This individual should be knowledgeable about the local work environment and they can help you look for jobs.

As an IT contractor with broad experience you can move to various parts of the country and take jobs either directly with tech companies or through recruiters. So you are using the jobs to earn money to finance your travel and you are actually getting to live in different locations. You can do this for fun if you just like sampling life in places as varied as Alaska, Hawaii, Arizona and Florida or you can use this kind of travel to make a serious study of where you would like to settle down and live. If you want some hints then consider the following. You are probably not going to want to settle in California because of the cost of living. Arizona is too hot and some will find Florida to be too humid.

Texas, at least at present has a good business climate and therefore lots of IT jobs. Texas also has no income tax and you can travel to the beach or live not far from it if you wish. Since Texas is a big state some of the beach travel might take longer than you bargained for unless you live in Houston as opposed to Dallas.

Even though California is expensive it has a nice climate and you can easily live not far from the beach there. It can be cheaper to live inland in California but then that drive to the beach can get a might long. For married couples California is definitely a two income state.

Kentucky and Oklahoma have a more rural feel to them than Texas and California. They both have a relatively low cost of living. They both also have IT work. This means that in both states you can make out like a bandit since IT tends to pay well. You do need to be comfortable with a more rural setting or with a college town setting in these states. Whereas in California you don’t have to know anything about the local cultural landscape and no one will think twice about it if you don’t; in Kentucky and even in some places in Oklahoma, no one will understand if you neither know nor care about how the college team is doing in athletics. In Kentucky in particular you may find college basketball championships being played live on the speaker in the grocery store. Yeah, they are that serious about it.

Yes, it is possible to join the military and see the world. However you do need to choose a branch of the military and a job in that branch that will enable to see the world. If you join the military as a statistical analyst for instance it may be hard to convince anyone to send you to Iceland so you can find out if Icelandic girls are nice. However, if you join as a military policeman, while I don’t know that the actual duty is any fun, but they can send you anywhere on the planet because there is need of security forces everywhere we have a military presence.

Another perk for being in the military can be additional travel opportunities. There is something called Space Available travel where you can hitch a ride on an airplane if they have a seat available. If you are stationed in Europe this can allow you to see European countries you are not stationed in without paying any travel costs. It’s not necessarily glamorous travel. The last time I rode on a military aircraft it was cold, noisy and I believe we sat on some kind of webbing not unlike a hammock.

If you can actually put up with being in the military or retiring from the military then some of travel benefits can be almost painfully cool. Again if there is space available, you can stay, during you off duty or vacation time at some beautiful places at a lower cost than some off base hotel. We stayed on a beach in a bungalow in San Diego once. And on that same trip we spent a couple of days in a military hotel with a view of sailboats on the bay.

You may have noticed that there are actually people working on cruise ships. Now not every cruise ship pays decent wages and not every job on a cruise ship is something you’d like to do, but if you could get paid to play music and flirt with pretty senioritas on a cruise ship, why not? There are also presenters, seminars speakers and entertainers of all sorts on cruise ships. If you want to be paid to travel, it’s at least worth looking into.

I don’t know if it’s still true, but it used to be that all you needed in some countries, like China, was the ability to speak English and you could get a job. Given that you could be stranded in a foreign country with no money and no job check this one out very carefully before you go. But it does point out that some American skills are in demand in some foreign locales.

This also cements the notion that if you really want the freedom to travel anywhere and have someone else pay for it, then it behooves you to perfect some rare and useful skill. I don’t know if it is still the case but at one time Cisco networking people commanded the big bucks. If you can climb your way into the IT stratosphere you may find yourself in demand. Look into computer architecture, planning and design for instance.

When you are looking at IT don’t forget to look at all of it. Database administrator and database programmer. System administrator. Programmer. Architect. Software engineer. Etc.

If travel is really your thing then consider jobs where travel is essential. Pilot, stewardess, traveling salesmen, truck driver, buyer, consultant, field service representative, field engineer, and consultant come to mind. There are also people who appraise property or art collections that do a certain amount of travel. Try to get a traveling job where the employer pays all travel expenses. If you can’t get that then deduct all work related expenses from your taxes.