The Gilligan Plan: Surviving Your Financial Shipwreck

You don’t have to look very hard to find a lot of fun conspiracy theories about Gilligan’s Island.

One theory is that the whole ordeal was perpetrated by the Howells. Their businesses were collapsing so they decided to create a new world for themselves. They specifically selected certain people to end up on this boat with them in the middle of nowhere. The Professor was essentially MacGyver, with his ability to make anything out of random spare parts. Ginger and Mary Ann were eye candy for Mr. Howell. The Skipper was there for manual labor for Mrs. Howell. And Gilligan is the buffoon who constantly ruins the plans to get off the island, thus solidifying the Howell’s reign forever.

After assembling their dream team, all they had to do was check the weather reports and head out for their boat ride on a day when they knew they were likely to get swept away by a storm.

The best support for this theory is the fact that the Howells are wearing different clothes almost every episode. Why would somebody bring so much luggage for a three-hour tour? Maybe because they knew it was actually going to be 98 episodes instead of just three hours?

Another theory is that this was a drug deal that hit a few snags. Thurston Howell was a dealer to the rich and famous who was on his way to rendezvous with a supplier in the South Pacific. That would explain his suitcase full of cash.

The Professor was there to put his chemistry degree to work. Gotta have somebody to check the quality of the merchandise.

Ginger was a movie star. Obviously one of Howell’s customers. And Mary Ann was either an unsuspecting tourist, or a narc who was hot on Howell’s trail.

Finally, there’s one conspiracy theory that’s actually true…or mostly true. The theory posits that the island is hell, with each of the characters representing the seven deadly sins. Mr. Howell is obviously greed. Mrs. Howell represents gluttony. Ginger is lust. Mary Ann, always jealous of Ginger, represents envy. The Professor, with all of his fancy book learnin’, represents pride. The Skipper is wrath. And Gilligan embodies sloth.

Years after the show went off the air, Sherwood Schwartz, the show’s creator, wrote in his book that this last theory is actually true. Not the part about the island being hell, but the fact that each of the characters was based on one of the seven deadly sins.

None of these theories have anything to do with my main point. From time to time, we like to break down classic TV characters and see what they can teach us about retirement planning (see previous posts about Fred Mertz and Jed Clampett). Today, I really just wanted to talk about Gilligan, but somehow ended up wandering down this conspiracy theory rabbit trail.

In any event, forget about the seven deadly sins. Instead, think about Gilligan the way that most people remember him. He was so lovable. Innocent, naïve, and really had the best of intentions. But at the same time, he also had some really bad luck and an accident-prone way of clumsily stumbling through life.

I recently met somebody who was in the same boat. (Pun intended). He was a real life Gilligan.

Super nice guy. He sees the good in everyone. Even if you’ve only known him for five minutes, he acts like you’ve been best friends for 35 years. He stops to give money to every panhandler he sees and can’t help but pick up the phone to make a donation to the ASPCA when he sees the commercial with the abandoned puppies.

And when it came to his investing life, he was a toxic combination of bad luck and terrible decision-making.

When he got divorced several years ago, and his ex-wife’s legal team ran circles around his attorney. He got taken to the cleaners on that deal.

He’d invested some money in his brother-in-law’s business about a decade ago. That was $50,000 that evaporated almost immediately.

His cat has a rare blood disease that requires a specialized treatment that costs several thousand dollars a year.

After the market crashed in 2008, he decided to get out of stocks altogether, and he never got back in. So he took all of those losses, sold at the very bottom, and then parked himself in cash and hasn’t experienced the growth of the last eight years.

And the crowning blow—he’d had a “financial advisor” who swindled him out of tens of thousands of dollars about 15 years ago. That guy is now in jail, but our real-life Gilligan never got his money back.

The sad thing about Gilligan’s Island was that the show ended with everybody still stuck on the island. When the third season of the show ended, a fourth season was expected. So the last episode of season three ended just like all of the other episodes, with the bubble-headed Gilligan ruining everyone’s chance to get off the island. But then season four was abruptly cancelled, and Gilligan and his buddies were stranded forever.

For our real-life Gilligan, fortunately, there was hope. It took several months of helping him get organized, rectifying some old tax mistakes to pacify the IRS, putting together a plan that had him putting his money into legitimate investments instead of fantastical family businesses or too-good-to-be-true scams.

It certainly wasn’t an overnight fix. After decades of bad decisions that had him financially marooned on a deserted island, we weren’t going to be able to rescue him with the snap of a finger. But with a logical course and a clear destination, he’s in a much better position than he used to be, and improving more every month.

Here’s the point. For some people, once they decide that they’re a financial Gilligan, they just give up and assume they’ll be stuck on this island forever. They assume that they’ll be working until they’re 78, then living in poverty for the rest of their lives after that. But I’ve never actually found a case that’s completely hopeless. A little planning can make up for a lot of past mistakes.

And it’s funny how it usually unfolds. When you take charge of your own situation, instead of just being depressed about your situation, that’s when your ship usually comes in.