Folks, I believe this may very well be the “first worldiest” of first world problems. You see, for some reason, I have three times been the lucky, totally random winner of a $100 gift card at my company holiday party. No complaints. But, each year, what follows is a tale of true indecision so egregious, it would leave even the wishy-washiest waffler screaming “make up your damn mind already, you hand-wringing nelly!”  I admittedly sat on the first of these free money treats for so long that the funds EXPIRED. Yes, expired. I lost it.  (Though, clearly, I lost it long before then.) What is wrong with me? What could possibly hold me up to the point of losing out on $100? Panic, paralysis, and abject fear of failure to make the “correct” decision. To help you understand, below is the typical internal dialogue I permit to ensue after each win:

“So, this is a significant enough amount of money that you don’t just casually toss it around like chump change, but it’s also not enough to, say, help lower the balance on your 30-year mortgage loan. You’ve got to think about this. Because it was free money, a blessing, a gift, a welcomed burden reducer, you have to spend it on something that you really need and that you were inevitably going to have to pay for (diapers, gas, the cable bill, etc.). This will save you those funds and reduce your expenditures. Good. You should just spend it on something useful, necessary and smart. It’s the mature thing to do.”

But then… the pessimistic, embattled loser in me claws her way to the top with “But nothing good ever happens to you!” followed then by the idealistic ex-cheerleader with “This is awesome!  Free money. You need to treat yourself. You deserve this. You were going to spend money on diapers anyway. … It’s sunk cost. This is BONUS cash! For the stuff or things you’d never buy yourself with your hard-earned dollars. Be spontaneous! Be cool!  This is the kind of stuff gift cards were made for… Gifts!”

Oh God, then more paralysis.

“So, needed or wanted? Necessary or indulgent? Save what you would have spent, or get something you’ve secretly wanted without actually having to pay for it and burdening your pocketbook?”

Then I get real crazy… (what a rebel I am!)  I opt to splurge! Yes, I will not be dull or practical! I will be fun and spontaneous. I will buy something that isn’t a necessary household item like a case of dish detergent and do something just for me that is enjoyable.

Layer two of panic sets in.

“Now that you’ve decided to spend it on something indulgent and totally not necessary (you wild and crazy gal, you!), you have to decide what that something will be. Here we go again… I mean, do you go and blow it all on a concert? A massage at La Pomponnee? What about a gorgeous meal at Stagioni or Casbah? This would mean you could get more than one cocktail? It would mean that you finally permit yourself to eat dessert at the restaurant instead of getting the check and pulling into the drive-thru at Wendy’s for a conciliatory Frosty while still wearing your fancy heels!”

“Or, should you spend this free money on something that will LAST? Not something that will vanish into thin air (like that other gift card that expired, you nimrod!) and be over in less than an hour. A meal is a meal, and at the end of it, you’ll likely have nothing to show for it other than a melted butter stain on your neckline or a pound of additional bingo-arm content. The gift card will have served its purpose and completed its transaction dutifully, but without really getting to make a difference in this world. Wouldn’t his little plastic soul rest more soundly if he were to know you’d spent him on something that will last and last, and that every time you looked at it, you’d think of him and his ample time until expiration date? Like leather boots, a legitimate full-sized Shutterfly album, eyelash tint (whee!), or that handsome copper French press at Williams Sonoma?”

And on and on it goes until, before I know it, I’m coming dangerously close to a repeat performance of “The great lack of spending tragedy of the millennia.” Time is running out! The card rides with me for days in my purse in anticipation of his big moment, as eager to see what I do with him as I am. And then, at about 10 minutes to closing time at the mall on the final day of his viability, he gets handed over to a cashier, rather unceremoniously, as I realize I’ve spent all that time building up to an ironic purchase of a new, moderately priced little black dress for the next company holiday party, ‘cuz the year before, when I was excited to learn I’d won yet another gift card, I spilled wine on my other dress. It’s a wash, really.

What would you do in this situation? Are you pragmatic or indulgent? Would love to see your comments.