So You Want To Live on an Island

As you may have read in Living the Dream, I live half-time in North Caicos, a small island in the Caribbean. When finding this out, fellow developers want to know how I managed to make it happen. I’ll talk about some technical considerations later, but the question is really about how you can position yourself to work in paradise. “You may ask yourself, well, how did I get here?”1 Lots of folks work, as an old co-worker of mine once said, their ordinary job in their ordinary way for their ordinary pay. It is the seemingly safe thing to do, and I fell into that pattern as well. Often, however, people want more, and when presented with proof that it is actually possible, the wheels start turning.

When I was growing up, I wasn’t ambitious. My family didn’t come from money, and most everyone I knew worked their ordinary jobs. I grew up thinking you went to college, and then you worked in a profession until you retired. The idea of starting a company never occurred to me. Why, I’m not sure, because a close friend of the family was an engineer who owned his own company. Yep, I had a mentor right there in front of me, and yet didn’t see it. I was constrained by my ideas of a normal life.

That’s the first step. Create the intention in your mind. I spent about 10 years of my career working a job. It wasn’t until we got the notion to move to Cape Cod that I began to move forward. Cape Cod is an odd place for a software engineer, but I was drawn to the beauty and the simplicity of that life. It took a few years for that intent to turn into a move, but it only happened because I started envisioning and looking for it. I also took a major risk.

There are not a lot of technology companies on the Cape, but I came across a write-up in the paper of a job fair where two companies were looking for engineers. I interviewed with both, and one was interested. The job required Delphi and C++, neither of which I knew at the time. I was honest about that, and said I could learn. They checked my references, called me up, and said, “Keith, we really like you, your references love you, but we haven’t found anyone who can tell us about your code.” This was logical, because I hadn’t written a lot of code. Some VB testing code here, some assembly there, but I was good at it when I did write it. I said, “I write solid, clean code, and I’ll show you.” They hired me, and panic ensued. “You may say to yourself, my God, what have I done?”2 They had fired two previous developers, and there probably wasn’t another job on Cape for me. McDonald’s was my back up plan. I busted my tail, and didn’t need to flip burgers. I learned tons about how to be a professional developer. It was very exciting, rewarding, and terrifying for a bit.

So you need to establish an intention, and then you may need to take a risk. The Cape was great, but somewhere along the line we got the notion that we wanted to avoid winter on a tropical island. I had started Mooseworks Software shortly before, primarily to pay off the mortgage. It was a part-time company for a number of years. I believe creating a part-time software company is a great place to start. You have to be very careful with your day job however, making sure the intellectual property is yours. I had started with the encouragement and aid of the owner of the company I worked for. That company was later bought out by another, much larger corporation. I competed with their products. We tried for months to negotiate a deal, reducing my product line, having them buy me out, etc. In the end, they said that I had to close if I wanted my job. I didn’t want my job that badly, and I quit. This was risk number two.

I saw an ad in the paper (can you believe it?) for a .Net developer right down the street. I figured it would be a little mom and pop, and I could get a nice consulting contract to help me over the hump. It was indeed a mom and pop, only after my interview, pop had a meeting about partnering with IBM. I had stumbled into an international data consulting firm that was growing like crazy, and needed to build a software team. I learned a lot about big data in that job, and acquired a significant amount of company shares. We also built the house on North Caicos. Things went well for a while, but I eventually grew restless. That old boss who had helped me start Mooseworks called. He was creating a start-up, a consumer social website. This was risk number three.

The start-up hasn’t exploded quite as planned, but maybe some day my shares in that one will prosper. I figured out it was time for me to go out on my own. Risk number four. One of the major factors in deciding to be independent was the ability to live on the island. Both of my previous bosses agreed to me working from here, but in the end, they just couldn’t bear it, and it caused a fair amount of friction. I no longer need to worry about that. Freedom is an important concept for me. Freedom to create, freedom to live where I like, and freedom to work the schedule that best fits me. No one has ever challenged my work ethic or what I produce, yet something in a boss makes them need to control hours and location. Yahoo has shown this recently. It’s maddening to me. (For more on bosses, see Why you’ll hate your boss).

Each step of the way was crucial for me to get here. Each stop built upon what I had learned before, and I’m using everything I learned about technology and business. As you can see, there were a number of risky steps along the way. I’m married, and it’s nerve wracking to think that my failure would hurt my wife. If it were just me, that’s ok, but I feel a greater responsibility to her. Of course, she’s always supported these changes, and the island house was her silly idea, otherwise this wouldn’t have worked at all.

For us to get here, we needed to start with an intention or vision, we needed to take some risks, we needed to learn and grow, and ultimately, we needed to be independent. Your idea of a dream may not involve a remote tropical island, but the elements to get to where you dream of are probably very similar.

Other questions devs ask:

  • Does the power go out a lot?
    • The Caribbean does have issues on some islands. We’re lucky in that TCI has fairly reliable power. It’s really expensive, though, at greater than $0.50/kWh. We have a whole house backup generator as well. Being without power is not an option for me. We’ve looked into solar and wind, and will likely put in solar at some point.
  • How about internet?
    • Ah well, that’s been a bit of an issue. We have DSL, and had to pay to string the wire out here. The speed is not amazing, but is adequate. The reliability has not been great, but is improving. I do, however, know the line tech personally, having called him so many times. We added satellite internet as a backup. It’s not good for VOIP, but is ok otherwise.
  • Cell phones?
    • Yes, we have them, and we have hopes of being 4G in a couple of years. I would love it if it was 3G now. That’s right, it’s edge. Better than nothing.
  • How much is a call to the states?
    • It varies, but the standard rate is $0.40/minute. I use Skype.
  • How do you collaborate?
    • The same way you do. Skype, WebEx, TeamViewer, remote access. I have clients who have no idea where I am.
  • Can you get equipment?
    • Yes, but no. There’s not much available here in stock. I can order things and have them shipped, but the cost is astronomical. I had a server power supply blow out. The power supply cost $110, the shipping cost $150. I have spares of spares of everything, and I backup religiously.
  • Do you work from the beach?
    • No, it’s really bright out there, and sand gets into everything. I think on the beach. It’s really good for that. It seems a lot of folks think I spend all day on the beach. If it were only so.
  • What do you do at night?
    • Work. I implement what I thought about on the beach. I’m a nighttime person, and the quiet here is great for having uninterrupted code runs. I’m more productive here than in the states.
  • Is it expensive?
    • Short answer – yes. Perhaps not worse than New York City, but a lot worse than Austin.
  • The big one – Would you do it again?
    • It’s not always easy here. Building was painful. It can be difficult to get what you need. It’s not completely stable politically, and we are reminded regularly that it’s not our country. So, hell yeah, I’d do it again!
[1] Talking Heads, Once In A Lifetime lyrics © Warner/Chappell Music, Inc., Universal Music Publishing Group
[2] Ibid

3 thoughts on “So You Want To Live on an Island

  1. Wow, congrats! You really have what I want and you answered lots of questions for me. I want to do the same thing but for me it is my home country: Bolivia. Right now I live in Switzerland and I always wondered if all those problems you mention had an acceptable solution.

    May I ask you two questions?

    1) Is satellite internet as a backup expensive? Do you pay only when you need it, or you have some kind of monthly bill?
    2) With the internet connection over there is it possible to rely on webapps for handling critical task? (I use asana [for team management] and I wonder if with your setup it is possible to depend on such a web app)

    • Hi mundacho, Thanks, and I wish you luck. Infrastructure can be a challenge. Some answers:
      1) My satellite is $89 USD/month for a 1M download/200k upload. The upload speed and latency (1 second) make Skype unusable, but other things work, and it’s just a backup. I do have a 24 month contract, and had to pay for the equipment, so it’s not cheap. There are other faster, more expensive plans.

      2) I have DSL and I use TFS, SVN, remote desktop, and video conferencing over it. I also write mobile apps that interface with web services. It’s not up to US speed standards, but it works.

      The above is specific for my location. On a more “civilized” island, I might not have the satellite back up. The main island, Provo, has more reliable communications. We paid for the last mile of telephone wire, so we’re at the end of the line. A funny thing. We just moved to New Hampshire, and around here there are roads without DSL or cable, so it’s something to check wherever you go.

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