I was on vacation at my parents’ timeshare in Cabo last week. A gorgeous, luxurious resort with its own beachfront, about 15 minutes outside town. A few days before the vacation started, the sales manager emailed to offer 20% off the all-inclusive add-on package.

I am a person who will pay a premium for convenience. I also love the idea of picking things off the menu without looking at the price. And I love the idea of drinks delivered to me poolside.

With the 20% discount, the numbers almost made sense. That is, if I ate in the resort restaurants three meals a day, and drank seven cocktails a day… for all seven days.

I toyed with the idea for about fifteen seconds before Antoinette said, “Never pre-pay for overindulgence.”

That was the reality check I needed.

There’s nothing wrong with pre-paying for something, and there’s nothing wrong with overindulgence from time to time. But you should never pre-pay for overindulgence.

In this particular case, the all-inclusive option made no sense for us. We don’t drink that much, and we actually enjoy going to the market and making our own meals in the timeshare’s full kitchen. So the all-inclusive wouldn’t have matched our vacationstyle anyway.

Regardless, pre-paying for overindulgence is a bad idea because if I’d already paid for it, I was damn well going to get my money’s worth out of it. Which means I would have eaten and drunk far more than I wanted to, and been tethered to the resort’s offerings.

But the real problem with pre-paying for overindulgence is that when it comes time to redeem what you’ve bought, your choices have already been made for you.

If you pay as you go, you can choose in any given moment whether overindulgence is what you want, and if it’s worth the price.

If you pre-pay, in any given moment your only choice is between overindulge and overpay. There is no other option.

So of course I did not buy the all-inclusive option. There were moments when I watched others ordering food and drinks poolside when I coveted their all-inclusive status, but now that I’m home I’m happy not to have spent all that money and overindulged beyond what I really wanted.

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