It began with the decision about when to go: summer, fall, winter or spring? Winter. Which led to where should we go: cruise ship or sandy resort? Sand. Domestic or international? International.  Mexico or the Caribbean? Mexico. Cabo or Cancun? Cancun. All-inclusive or pay-as-you-go? All-inclusive. Which resort? Sandals, Sliver Sands, Sand in Your Eyes, or Sand in Your Shorts? Silver Sands.

Pretty simple, right? Of course not! It took us no less than 14 months of frustration and roughly 73 thousand emails to make these decisions. Once we finally reached an uneasy consensus, our well-meaning travel agent, Helpy Helperton, kindly called to remind us that the resort we selected "has kind of a small beach." Little did she know that her "insider tip" had reopened Pandora's box for another two months. By the time we decided to stick with our first choice, the price had gone up by $200 per person.

Why We Spoil Our Own Fun  

I wish I could say that our vacation planning debacle was an isolated event, and that it was not a representative sampling of holiday parties, family reunions, weddings, and virtually any other event involving two or more of my relatives. I also wish I could say that my family was an anomaly. But I would be lying if I said either of those things.

At the root of the problem are three fundamental myths about decision-making. 

Myth #1: With enough deliberation, we can guarantee that our choices will maximize our pleasure. 

This very commonly held belief is a sure-fire recipe for disappointment. First, there are far too many pleasure-impacting variables for you to control (flights get delayed; people slip into bad moods; the sun sneaks behind clouds; the room is too hot/cold, etc.). Secondly, psychologists like Daniel Gilbert at Harvard University and Timothy Wilson at the University of Virginia have proven overwhelmingly that people are incredibly poor at predicting what will make them happy or sad. That means even if you could control all of those chance events, you still stand a very good chance of creating a monstrous event. (Think: Bridezilla.)   

Once my loved ones and I decided on Cancun, we continued endlessly dissecting the features of all 10 resorts. One had a smaller beach, but nicer rooms. Another was less expensive, but didn't provide transportation to the airport. The fact is that this was new to us. We have no idea whether the ride to and from the airport would be a hassle or a piece of cake. We have no idea whether we'll end up wanting to spend time at the beach or the pool. It's new. It's unpredictable by definition. So, why are we obsessing about it?   

Myth #2: The amount of fun we have is directly proportional to the amount of research we do. 

Actually, the relationship is not direct or linear. It is more of an inverted-U. A little research can increase our enjoyment, but at a certain point the returns on research start to diminish. Beyond that point more research will only waste time, raise expectations and ultimately reduce our enjoyment. Once we had the key factors for our vacation covered—sunny climate, comfortable rooms, more than one restaurant option, and good customer reviews—more research did nothing but complicate, confuse and irritate us.

Myth #3: Somewhere over the rainbow, the perfect venue/date/price/amenities is just waiting for us to find it.  

Back in the 1940's a young social scientist name Herbert Simon called this decision approach maximizing. Maximizing is where we do whatever it takes to find the absolute best option. (Sure, these jeans fit well and the price is right, but how do I know that the perfect pair of jeans isn't waiting for me on some other rack in some other store?) Due to our limited processing power and time, psychologist Barry Schwartz at Swarthmore College, and the author of Paradox of Choice argued that habitual maximizing is not only inefficient, but also harmful to our well-being.   

Dr. Schwartz recommends that we employ a satisficing strategy. Satisficing means selecting the first option that is simply "good enough" on the important criteria. (Do they fit well enough? Are they in my price range? Great, I'll take these and you spend four more weeks hunting for Denim Utopia.)

 As you enter the holiday blitz this season, do yourself and your family a favor and remember this: When it comes to special family events, good enough is almost always better than best.  

Find out how much indecision is affecting you and your family by taking this quick quiz and passing it on to your nearest and dearest.