This one’s been in the works for a while. Five years, at least. Over that time, it appears I’ve created something of a tradition. Around November, I decide that it would be a Great Idea to fly my own plane down to the Bahamas. This is not a particularly challenging flight aeronautically; basically you fly to Fort Lauderdale and make a left. It only becomes non-trivial when things like money and time become factors. In other words, in the Real World.

So at the appointed time, usually a bit before Thanksgiving, I continue the tradition by sending $10 off for the appropriate charts, after which I start drawing lines, looking at hotel rates, and adding up numbers. And then, after a while, I look at my bank account and my work schedule, and I quietly fold the chart up and put it on the shelf.

But last year, I decided to do something different. I set up an automatic monthly transfer to an unused bank account, and three months before the target date, I started informing my clients as to when I’d be out of town. So in principal, this should actually work. Two weeks, 2500 miles, two countries, six cities, ten airports, and at least one mouse (we’re stopping at Disney World on the way back). Doubtlessly there will be some anomalies along the way, but that’s okay – I’ve built a few extra days into the Master Plan.

More as it unfolds.