How Do I Get to Live on an Island?

When people find out I live on a tropical island for half the year, the first question they often ask is, “wow, how do I do that?” Short answer, it’s not easy. So, I’ll tell you a story about how we did it, and then I’ll try to give you a better path.

I’m not well suited for being an employee. I have been called unsupervisable at times. (I was also called a joy to have around, who knew?) I don’t do company politics well, and don’t have patience for foolishness. I have mellowed with age, but large companies are definitely not for me. I was, however, a successful employee for some 20 years, although not always a happy one. In 2002, I was working for a company that was a Microsoft Visual Studio partner, so I was getting all the earliest betas. At that time, the compact framework came out to support Microsoft’s PocketPC. Palm and Microsoft were actually dominant in handhelds at the time if you can believe that.

Pelican_SmallI believed that mobile would be huge. This may be a case of a blind squirrel finding a nut, but I pursued it. I thought that mobile would be a great addition to the company’s product. We were busy, though, and there wasn’t going to be time for another development. My wife, Cindi, had the smart idea of doing it as a side job in off hours. I put together a proposal, and the owner of the company accepted. This was the starting point of my business.

Now, there are a few things here that are really unusual. First, the owner of the company accepted the proposal for me to work on a contract basis instead of just adding it to my workload. He really wanted to encourage me being an entrepreneur – go figure! Second, we negotiated that I would keep some of the intellectual property (IP) rights for use in my business in the future. This essentially doesn’t ever happen, but he liked people who wanted to start businesses and he encouraged me.

So, Mooseworks Software was born from that contract. The IP was used in the first offerings. It was a second job, or micro-ISV for many years. Virtually every penny from Mooseworks was used to pay down our mortgage. I can’t stress this enough, pay off your debt, and don’t build up credit card debt. When we bought our first house, the realtor drove an old Mercedes sedan. It was in great condition, and was really comfortable, a perfect car for a realtor. He bought the car used, and said something that I will always remember, “Don’t spend big money on depreciating assets.” In other words, don’t spend $40,000 on a hot car. It will only be worth $20,000 in three years. Was that three years worth it? So, the most I have ever spent on a car is $16,000, and that’s for a new car. I run my cars into the ground, I’ve had three cars with over 200,000 miles on them.

Save Your Money!

Sorry for beating this into the ground, but managing your personal finances wisely is essential if you want to reach your long-term goals. We’ve sacrificed over the years. We don’t have great furniture, we don’t have expensive cars, we have never re-decorated (that would require decorating in the first place). Some would say I was cheap. I won’t deny that. I have different goals. The small sacrifices along the way are worth it to me. OK, enough of that.

So, through the side business of Mooseworks, we were able to lower our debt, and build up a significant amount of savings. I also had stock options in that company, and they did come to fruit to the tune of about $50,000. Not a million, but not bad. I moved onto another company, and got shares of that company. I got the shares because I made a similar proposal for extra work. In this case it didn’t go into Mooseworks, but it was something extra the company really needed at the time, and it was going to have to wait a year if done on a normal schedule. So, instead of cash, I got company shares. They have turned out to be worth more than the cash I initially asked for.

We used the money from Mooseworks, the shares, and the equity in our house to buy land and build the house on the island. It has no debt, it is ours free and clear. There are no property taxes in Turks and Caicos, so we really own our house. As I mentioned in why you’ll hate your boss, if you want to work from an island, you need to be your own boss. If you are an employee, eventually they will start thinking you spend “their” time on the beach. It’s just human nature. All the time building Mooseworks was pointing to this end. I now get to live where I want, and work the hours I want.

The Price

So what was the price? For 10 years, I have worked 6 to 7 days a week. I worked 90 to 100 hours a week for 6 months, and a normal week was 60. Some of you might say you are working 60 hours a week in your day job, and I don’t doubt it. You might want to evaluate whether that is going to get you where you want to go. I got the shares primarily because I was available 24×7. I wouldn’t do that for a “normal” job. I should also note that just working hours isn’t enough. You need to produce. Software development has a well-earned reputation for not delivering on time. Be different. Do what you say you will do.

I was chatting with a very nice fellow from Xamarin (I love Mono, btw), who said, “Being your own boss takes a lot of work”. Yes, it does. Instead of just developing, you are responsible for marketing, customer support, hosting, accounting, and Lord help you, subcontractors and employees. Let’s go back to that reward, shall we?

Empty Beach

Ok, that makes it worth it. So, that’s my story, but it is unlikely that it is reproducible. Is there a better way?

Ok, How Do I Get to Live on an Island?

First off, I don’t believe you can do it and remain an employee. That is not to say quit your job immediately. It means start laying pipe to get where you want to go. (The island, of course, can be seen as a metaphor for your particular long-term goal. After all, you may not like fish :-)). Look at your present employment. Does it help you beyond being a paycheck? Are there opportunities with the employer? Are you learning things that are marketable? Is there flexibility that would allow you to start a side business? If the answers are no, you probably need to address that first.

Ok, so now you have a good job. Start building a portfolio independently. Be in the position where you can show people not only what you can do, but what you have done. This is useful even if it’s just a resume item for future employment. It would be great if your portfolio included items you could sell. Mobile apps are an obvious choice, but there are certainly other markets. Pick a small, under-served market. Try to be significant in that market even though it’s small. Do something that other people don’t want to do, but is useful. I see lots of people who want to create social networking apps. They all want to be the next Facebook. It is really unlikely they will succeed. Shooting for the huge, take over the world, killer app is essentially going to the casino and rolling the dice. The odds are against you, but if you can find a niche that doesn’t have a big player in it, and you can provide a useful service, you can have success that you can build upon.

One thing to be wary of is your employment contract. Do make sure that your company doesn’t own anything you do regardless of where or when you do it. Also, don’t violate any non-compete clauses. Don’t make the lawyers richer; just pick something that’s unrelated to your employment. It’s cleaner that way for everyone. (Oh, yes, that deal I made with keeping the IP? Yep, when the company was sold, it was a problem in the non-compete. I had to leave, and that was fine, but it could have been uncomfortable).

So, now you have a portfolio, and maybe are selling some things – excellent. You’re moving in the right direction. Save your money, pay down any debt, and keep your eyes open for opportunities, new markets, possible contracts, partners, anything that gets you closer to your end goal. One thing to consider is to provide subscription based services. You can sell an app once. You get paid, and that’s it, you have to sell another to someone else. If you can provide something that has a monthly or quarterly fee, then you sell once, and you get an income stream for a hopefully long time. Then, each sale builds your income stream. If all goes well, that income stream replaces your employment income, and you’re really on your way. So, think about how your product or service is going to monetize, the effort you’ll need to put out for a sale, and what that sale brings in.

Ending Notes

I wish I had started earlier. I “wasted” years in a job that really didn’t go much of anywhere. That said, everything I’ve done has built up my knowledge, resume and skill set. That’s why I ask, are you learning things that are marketable at your job? In my mind, there is an interesting trade-off as to when to start a business. When you are young, possibly single, and don’t have obligations and responsibilities, you can take more risks because you have less to lose, and it’s only you who will be affected. You can also work ridiculous hours, and you won’t be neglecting anyone (except your social life). It’s harder if you have a family and a home. That said, there is evidence that would indicate that more experienced people are more successful in starting businesses. That makes sense, of course. More experienced hopefully means they have learned from their mistakes. Ideally, you start when you have gained some experience, but have not acquired a lot of responsibility in your life. It’s not necessarily an easy balance.

So, yes, it’s more work being your own boss, but for me, it’s worth it. The independence that it brings is the key. I am rewarded fairly directly for my efforts. If I slack off, sales tend to follow. If I bust tail, the business tends to do well. As an employee, that incentive feedback loop was often broken, if not inverted. Now, I alone can determine when I work, how hard, and if that walk on the beach is worth it.

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