Here's how I can do it : My six simple rules on how to relax around money.

Everybody knows how to lose weight. The rules couldn’t be simpler: eat less and exercise more so you burn more calories than you take in. Yet many dieters break the rules, or cheat on them “just a little,” or avoid the rules and then rationalize their avoidance. They go out and buy the latest diet book, hoping for a magic bullet that will let them quite literally have their cake and eat it too. But there’s no such thing, and continuing to insist on one is a somewhat childish response.

   The rules about money are pretty simple, too. And everybody knows them. I’ve distilled them down to a quick half dozen, and I’ll wager that you nod with recognition over each one:

1. Pause, take a breath, think, and look at the numbers before any financial decision.
2. Diversify your investments into different asset classes.
3. Buy low and sell high by rebalancing your portfolio. Get aggressive when the market is down and act warily when the market is up.
4. Keep track of your cash flow and net worth.
5. Spend less than you earn now, not as much as you might earn in the future.
6. Save something and give something—regularly.

Simple, right? Yet from top to bottom, these rules are broken, bent, or circumvented as routinely as the dieter’s rule about skipping dessert or exercising for half an hour every day.

      Which rule is hardest for you to keep?  Can you think of something you can do to play by that rule, just for today?

      When I arrived at SFO for my flight to New York a couple of weeks ago, I used the automated kiosk to check in, and when I got to the screen offering upgrades, I thought I’d just find out how many miles it would cost to sit in first class instead of economy. After all, it was a long flight, and it was the redeye, so comfort suddenly seemed like something I might just be willing to pay extra for. The thought of getting in a few hours sleep without being disturbed by screaming kids was appealing, and as the father of kids who sometimes fit that description, I knew whereof I spoke. As I was mulling over such luxuries, however, I must have touched the touch screen a little too casually, and before I knew it, I was being congratulated for having upgraded to a first class seat!

      I proceeded to the gate, where I decided to take up the issue with a live customer service representative. “Hi,” I said to the young woman behind the counter, “can I get my miles back and return to economy class?”

      The customer service rep looked me up and down. “I wouldn’t if I were you,” she said. Then she added: “Why would you downgrade? It’s just not what people do.”

      Maybe. All I knew was that I was extremely uncomfortable at the idea of sitting in first class. So uncomfortable that although I was sleepy, burdened with carry-on luggage, and would be getting the roomier first-class seat for miles flown—and therefore virtually for free—I couldn’t quite bring myself to do it. What was this about?

      It all had to do with a very recognizable feeling from my childhood. I had grown up in a neighborhood in Queens, New York that was quite literally split down the middle in socio-economic terms. On one side of the wide avenue—our side—were small apartment buildings like the one my family lived in and a number of narrow, two-family houses separated by cement alleys. On the other side of the avenue were “the rich people,” as we thought of them, who lived in sprawling ranch houses and “split levels” with wide, grassy lawns.

      The split was real. The two sides didn’t mix. Nobody ever “crossed” the avenue. I grew up feeling uncomfortable with the whole idea of people who had a lot of money, even though I just about never met any. How could I? Money divided us from one another. My father wouldn’t even set foot in “that neighborhood,” and although nothing was ever spoken directly against rich people, we nevertheless absorbed a sense that they were alien from us—a whole different caste, out of our reach, people we wouldn’t want to be seen with.

      Now here I was in the airport about to become such people. When we boarded the plane, I and the other first-class passengers would go first, marching down a special red carpet meant to announce that there was something special about those whose feet graced the carpet, even though the only thing that set us apart was that we were paying more money for a more comfortable seat. Still, everybody would see me—and would know me to be from the other side of the divide.

      I was on the horns of a dilemma: I wanted to sit in first class, but I didn’t want to be set apart. I wanted the extra foot of legroom, but I didn’t want to be thought of as a rich guy who could afford to pay for that legroom.

      Could there be a clearer example of childhood emotions driving grown-up behavior? My discomfort about first class was born in the distorted perception that money defines who we are. Therefore, if people see that I can afford first class, they’ll lump me with those rich people I found alien as a child—and they’ll be as distrustful and envious of me as I was of the folks on the other side of the avenue.

      I decided it was time to stop being embarrassed to be me, and I kept my first class seat. And for the first time in my life, I wondered what those first-class folks on the other side of the avenue may have felt about those of us on my side—and what they were like as people…