Penny-Wise, Pound-Foolish: Why It’s Almost Always About Winning

Why do people get bent out of shape over pennies and then wastefully blow thousands of dollars? I think it’s because the transactions have become about winning and losing.

I lose when the airline sticks me with another fee I wasn’t expecting. When I pay for a large but get a small instead, I’ve lost. I win when I remember to mail in the rebate coupon (I win triumphantly if said coupon is expired and accepted anyway) or complain to get a free meal because the service was sub-par.

These are easy victories over small prizes, but they help us feel powerful, fragile as we are.

Unfortunately, acting like a fool can feel empowering as well, so we do it. Swiping a plastic card and getting what I want, no questions asked, feels like a win. So does living in a huge house and driving luxury cars and wearing custom suits. Comparison shopping, delayed gratification, life insurance, and a Roth IRA, on the other hand—those don’t offer the same sense of triumph. In fact, saving money by driving an old Honda can kind of make you feel like a loser.

This also applies to health, productivity, business, and a host of other areas with room for improvement. We embrace what makes us feel powerful, not what actually makes us that way.

So the next time someone screws up your order by a couple of bucks, choose to act differently. Be gracious with waiters, vicious with yourself.