Got a question today from someone asking how I managed to achieve the lifestyle I did and asking for tips on having to do the same. In order to impart this wisdom, I am deeming it necessary to brag a little.

As many of you probably know, I live in the Bahamas and work from home. I’ll throw tact out the window and add that my condo is about 100 feet from a private beach and also has a pool and tennis courts. At night, my wife and I sit on the balcony reading to the sound of the ocean. Thanks to a side burner, we barbecue almost everything year-round, even pancakes. When I can get away with it (which is more often you might think, you’d be surprised what you can get away with by asking), I like to work only 3 days a week. Last weekend, my daughter and I jumped into the canal off the ocean with some neighbours’ kids for a while and when that got boring, we played baseball on the beach.

It’s probably a coincidence that I’ve just started reading The 4-Hour Workweek because this kind of sounds like something from the opening chapter. But the difference is: Tim Ferriss put some thought in achieving his lifestyle. As much as I would like to translate my own experience into a multi-million dollar empire, I came by my good fortune mostly by accident.

How it happened

Before moving here, my family and I lived in Calgary and I worked as an employee for a consulting company. My wife works for an international consultant and he decided to move to the Bahamas for whatever reason. We basically came along because he asked us if we wanted to. The decision was harder than you might imagine primarily because our daughter was three at the time and moving her away from family to a country where we knew little about the education system was a big unknown. I was also worried about the work situation.

But we did it and I, of course, had to quit my job. For the next two or three years, my career was very much in flux. I found contracts in the US but they required me to be onsite (i.e. away from my family). A couple of them paid room and board but for the ones that didn't, I had to rent a place on my own and live a college life, except that I couldn't date anyone. For the first two years alone, I was away from home for 13-14 months. I also tried a couple of permanent positions locally but that didn't take very well. I'll leave it at that and just say it'll be a long, long time before I accept a permanent position locally.

Really, it's only been in the last two or three years that I've been able to get some stability in my career to the point where I don't automatically panic when a contract ends. But having said that, it's a *LOT* of work trying to find a contract where they will let you work remotely. Chances are, I'll have to travel for work again in the future. In the meantime, the main reason I started blogging and speaking at user groups and attending conferences was self-serving. I need my name out there so people have at least some idea who they're talking to on the phone in the Bahamas. And even then, they're still leery. I feel like I have to be twice as productive just to prove myself. Which isn't too hard given that at most places, they're half as productive as they could be anyway.

So that was my master plan for living such a life: I said yes. And I don’t mind admitting that those first two or three years were tough and involved a lot of soul searching, to the point where we actually went house-hunting back in Calgary. Maybe it would have been different if we consciously decided to move here and follow our dream. But instead, the opportunity arose and we took it. So anytime something inconvenient happened, it was easy for us to say, “We didn’t have to deal with this back home.” And the fact that we still considered Calgary home at the time did not go unnoticed.

But gradually, we worked out the kinks. We learned the ins and outs of our new home and, most importantly, took stock of what was important. Only after doing that did we really start to realize that we were wasting a whole lot of time and energy on the wrong things. Since then, we’ve re-prioritized to take advantage of what we gained from our move (more sporting climate, proximity to beaches and other islands, more relaxed lifestyle) rather than focusing on what we lost (regular access to Multi-Grain Cheerios).

Planning it out

But that doesn’t mean I don’t have anything useful to say on the subject. I can help to avoid the same pitfalls I ran into. While the first couple of years had their challenges, I suspect people might be underestimating how easy it is to accomplish it. You’d be surprised at what you can accomplish through trial by fire. And if you put more thought and planning into it than we did, it’ll go that much smoother. Besides, it’s not like moving to another country is an irreversible decision (unless you’re dream is to visit the front lines in Iraq).

One of the most important things you will need is a safety net. You don’t want to have to worry about money so as much as you can secure a regular source of it, do it. Make sure you have a good list of contacts for people who could potentially hire you or help you find a job. Like I said, that’s what I went into blogging and community work. And it should be noted that I do love doing it. If you don’t, find another way to get your name out there because you won’t help anyone by faking interest in community work.

Also, start planting the seeds of working remotely now. Work from home a day or two a week if you can and try to increase it. If you can keep your current job when you move, that's gold. We were kind of okay because my wife had a pretty good job but it was a bit of a struggle with me being away all the time while she had to learn the ropes of a new country. Even if you do find a job working remotely, expect to have to leave home for work on occasion. Hopefully, you won't have to but it helps to prepare just in case.

When you do move, scope the place out first. Find expats who can give you the lay of the land for things like finding decent tradespeople. Splurge a little on the place where you’re living. It may be easy to say you’ll just start out in a small apartment next to the main road but you’ll be robbing yourself. What you want is some place where you can kick back at night with a malt-based beverage and say, “Now, THIS is more like it.”

Finally, realize that while your career is important and it's easy to get caught up in it, don't forget the reasons why you move. Even now, I still suffer from “just one more test, honey!” syndrome. Yes, by all means, be dedicated and good at your job and work on OSS projects and that side project that will get you on the cover of Time. But make sure you treat them for what they are: hobbies. You didn’t move to make yourself rich, you moved so you wouldn’t have to make yourself rich.

In short, if you’re already living your dream, don’t waste your time and effort pursuing it.

Kyle the Coached