How To Be Unhappy But Successful

“Are you measuring yourself in the gap or the gain?”

No, this isn’t a question pitting retail clothing against laundry detergent. It’s a question posed by Greg McKeown, the author of the essential book Essentialism, in his recent 1-Minute Wednesday newsletter.

Your answer matters, both in the way you approach money and life—but especially money.

“Gap thinking means looking at the distance between where we are and where we want to be (or comparing ourselves to what other people have achieved),” said McKeown. “Gain thinking means looking at the progress we have already made.”

For example, I had breakfast Friday morning with two friends, both of whom have experienced degrees of success in their professional lives that I could argue dwarf my own. That’s where my head would be if I was a gap thinker, anyway.

If I was a gain thinker, however, I might relish the fact that these dudes thought highly enough of me to give me a seat at the table…or at least that I was in good company for a free breakfast at a great restaurant!

As a financial advisor for a couple decades, I can tell you that the #1 question I’ve been asked by clients is some version of, “So, how am I doing…you know…relative to your other clients in similar situations?”

It’s not because these people are overly insecure or emotionally needy. But money—and, in many ways, financial planning—breeds gap thinking. Dollars, cents, credits and debits make it so easy to create a seemingly tangible success scorecard.

Perhaps you’re familiar with Lee Eisenberg’s book from several years back, The Number: A Completely Different Way To Think About The Rest Of Your Life. He recalls a regular-rotation TV commercial at the time (that may still be running in some form today) for a big financial institution where you see people walking down a busy street, each with a dollar number hovering over them.

This is the type of image that the very nature of money makes it hard to avoid.

It’s not an entirely unhelpful notion to quantify our financial security in the form of a single number, despite the risk of oversimplification. But such thinking leads us very quickly to comparison, which many years ago Teddy Roosevelt accurately declared to be “the thief of joy.”