Introduction

The Genesis of a Stupid Idea

I was dead tired from being bashed around by the boat for the last few hours. I was soaked to the bone from the sleet storm that seemed attached to the boat. Georgia had the boat heeled over so hard that one railing was in the water -- water so cold that it was nearly slush. I was fascinated by that water, and by the railing that wasn't under water, because the only reason that I wasn't falling into the former was that I was hanging onto the latter by my right foot. While Christian was attempting to reel me in by grabbing the seat of my pants (perhaps the most delighted I've ever been at being groped), I was wondering to myself whether I was having one of those "peak experiences" that my psychologist is always talking about. Unfortunately, my contemplations were interrupted by Georgia's exclamation: "Hey guys, I have this really great idea!"

The rest is the stuff that regrets are made of.

I'm having a particularly hard time believing my life lately. I don't expect you to believe any of this, because I sure don't. Even so, I might as well spell it out to bolster all those claims that the psychiatric community has been making that I have delusions of grandeur.

Here I am, an unemployed post-Yuppie undergrad student, with nothing to my name but one paid-for car, a couple closets full of electronic gadgetry, and an ever declining bank balance, and I just spent the first Sunday of our new year driving all over New England with a Honda generator in the back seat of my car and a spinnaker from the "America3" in the trunk. Now, if the latter doesn't ring any bells for you, it's a sail from one of the most famous boats of the year, 'cause "America3" won the Americas Cup race this year. And, for those of you who don't know what the Americas Cup is, it's an event wherein a group of fabulously wealthy people from all over the world put together fabulously expensive boats, staff them with fabulously underpaid slaves, and enter them in a race with such fabulously refined rules that for all intents and purposes, the race itself is over shortly before the starting gun fires.

And, there I was with a sail from that fabulously expensive boat in the trunk of my fabulously bourgeois car, driving all over New England on a nose-hair-freezing cold winter day, using up what might well have been the last tank of premium unleaded that I could ever afford. What's worse, is that it all fits together in a sick, twisted sort of way. A sane person would ask why.

I have been asking "Why?", but to an entirely different set of questions than you might first suspect. The main one is "Why am I so stupid?"

Let me back up a bit. I have a friend, Georgia Hilton, a sweet, lovable megalomaniac, who came up with this really great idea. Actually, that idea might not have been so great after all. As a matter of fact, it felt to me like a big stupid idea, but then again, thinking that something's a stupid idea is how I generally feel right before I do something that I'm bound to regret for the rest of my life. I guess I'm just funny that way.

The big, stupid idea involved too much sun, too much being outside, too much water, too little land, too many boats, too little space, and too much of my money. The upside was that I got to record the event for all posterity, or at least for the sake of providing evidence for any future litigation. Georgia has asked me to put my fertile mind to use and write this up.

I'd like to say that the whole idea came in a moment of inspiration on Georgia's part. Picture a Mickey-Rooneyesque scene: Georgia finds a master sailor's license (made out in her name) in an old trunk in the attic, springs to her feet and exclaims "Hey, guys, we can use this! Let's put on a cruise!" Unfortunately, it didn't happen that way. Like all bad ideas, it had much more prosaic, if not somewhat sinister beginnings.

I don't know precisely where this all started, but where it started for me was one fine weekend, when Georgia, Kathy, Kathleen, Margie, Christian, Jerry-the-Geek and I were out sailing on Lake Champlain. If I wanted to, I could write a very lengthy, and gut-splittingly humorous piece about that weekend, which is to say that most of us had a perfectly rotten time.

See, we were getting our brains pelted out by an arctic wind, a sleet storm, and the slushy, near frozen waters of the Lake. At the time, we were "tacking", which is sailing speak for "getting nowhere, slowly and painfully." About half of us were sitting up near the bow, feeling soaked to the bone and miserable, and the other half were doing the work of sailing the boat (and feeling soaked to the bone and miserable). Christian had been sent on a suicide mission to try to adjust the wildly flapping sail (while the boat was tipped at about a 60 degree angle), and Georgia was sitting back at the helm with her typical shit-eating "I'm having a great time at your expense" grin frozen on her face. It was frozen there by a not-so-thin layer of rime ice from the sleet and lake.

It was sometime during this idyllic scene that Georgia floated the idea that we should all get together on a boat in the Caribbean for a week and a half, and make ourselves even more miserable. After all, if we merely wanted to kill each other after spending a mere two days together on an inland lake, just think of the psychotic rages we could all get into after a week of being cooped up together in a tiny little boat in the middle of nowhere on the open sea.

Most of us went along with the idea. I think we all figured that Georgia would dump us all at sea (at lake?) if we didn't humor her, so we all dutifully made out checks as a sort of offering for the captain. Or, at least we promised to. Everyone except for Jerry-the-Geek, which should just go to show how unreliable nicknames can be.

I don't know if Georgia was inspired by how easy it was to strong arm a half a dozen people participating in such a dumb idea, or if she was depressed that all she got was six people. Whatever her reasons, they compelled her to go searching for more fools with money in dire need of separation. And, while under normal circumstances, finding a collection of such people might be difficult, Georgia had one of the greatest fool detectors in the civilized world at her fingertips and she knew how to use it.

The tool was an electronic computer network that put her in touch with 100,000 other people. It stands to reason that somewhere in those 100,000 people, there are more fools with money, and that reasoning stood because that's exactly what she found. She wrote up an announcement of the trip and posted it to an electronic bulletin board devoted to sailing, and got a couple of responses. She posted the announcement to another bulletin board for singles, and got a couple more responses. Finally, in a master stroke of trolling, she posted it to an bulletin board devoted exclusively to being a fool with too much money, and got a whole bunch more responses. When all was said and done with, she'd found thirty people (most of whom were total strangers) to send her money, sight unseen.

At final count, that made thirty one people (including Georgia), all set to fly or drive from all corners of the western world, converging on Ft. Lauderdale, where we were to hop onto four boats and set sail for the Bahamas for a week's worth of fun, sun, and excitement -- the makings of once in a lifetime memories.

Right.

I should have called my shrink instead.

What's my part in this? Well, I'd like to claim that I was one of the original fools, but the truth of the matter is that I hemmed and hawed for about a month before I decided to send her a bunch of money. Why did I do it? Well, here are the reasons why I wouldn't:

Against that rather trivial list, I weighed the reasons in favor of doing it:

Of course, when I wrote those two lists out like that, it was obvious that it was something I just had to do. Sliding down the back side of my post-Yuppie crisis of meaning in life, I've decided that I'm really sick and tired of my fear running my life. This gave me an excellent opportunity to confront that fear head-on. Not only did it accelerate my journey to the poor house, but it also allowed me to confront my irrational fear of doing really stupid things.

In retrospect, I can see now that it's a lot easier to say "yes," and sign a series of checks (representing a large fraction of my life's savings) than it is to actually deal with the consequences. In this respect, I see that I played right into my fear's hand, and so far, it's winning.

So one fine day, while talking on the phone to Georgia, I heard my ex (Robert P.) agree to join the expedition. Something came over me and before I had a chance to engage myself in any rational thought, I heard myself saying "Yeah, me too." Robert later told me that the reason he agreed to go along was that bungee jumping didn't scare him nearly enough, and that this might do the trick. What the hell? It sounded like a stupid enough reason to me. Hell, it sounded like my reason, except that I've never been bungee jumping. I guess that to really enjoy life, I mean really appreciate it for what it is, in the here and now, I have to experience hellish misery first (just to provide contrast), and this seemed like a damn fine way to do that.

I assume that everyone else signed up for more or less the same reasons: Suicidal tendencies, not enough pain in their lives, haven't done anything really stupid in years, or maybe just plain naive. Whatever the reason, since the fee was non-refundable, we all had three choices. We could either just go on the damn trip, or we could forget the money and chicken out at the last minute, or -- my favorite -- we could whine about it a lot.

That left me sitting around the house, less than a week left to go before The Big Trip, with a trunk full of spinnaker, scared out of my mind, and wondering where that mind must have been in the first place for me to have agreed to this.

But, before we get into detailing all the fond memories I have from this trip, let's get to know the parties involved, first. To really appreciate the extent of the stupidity that went into this trip, we really must review the pre-trip planning and meetings. After you've seen how many chances we all had to back out (albeit with the forfeiture of what wasn't that much money after all) will you come to fully appreciate the total absence of rational thought that went into climbing onto those boats.


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