At the end of my Cure Money Madness talk last month, I had a great opportunity to dissect a common—though complex—money madness situation. On the last day, a 50 year-old man came up to the podium and said, “I’m not sure if I have money madness.” He went on to share that he hadn’t filed a tax return in almost a decade, not only to avoid taxes, but also to avoid the hassle of completing an administrative form.

After we talked about some numbers, he publicly confessed what he already suspected, and what I knew—that he wasn’t actually saving much money by not filing. Then, he blurted out, “I’ve also kept my income low all these years so I’d be below the IRS’ radar – too small a fish for them to fry…But now I’ve spent my small inheritance and am struggling to make ends meet.”

“OK,” I responded, “let’s get clear about what your money madness drives you to do. First, earn less money than you’re capable of earning. Second, reject work that would increase your net worth and refuse to ask for better compensation for the work you’re doing. Third, shirk your legal obligation to pay taxes.”

He agreed that this was a fair assessment, so we explored the money messages on which this behavior was built. Three important messages emerged.
1. The “system” is unfair, and a hassle, to boot.
2. You should get away with something if you can
3.Not paying taxes makes perfect sense, given #1 and #2.

Curing money madness begins with examining the costs of money madness. In this case, money madness locked him into making less than he needed to live, into doing uninteresting work that didn’t capitalize on his genius qualities and into a constant state of stress at the specter of being caught by the IRS.

Then, he had to accept the numbers we’d just looked at, and truly understand that while he might have avoided an end-of-the-year check to the IRS, what he avoided in earnings was far greater than any taxes could ever have been.

Next, he had to make the connection between not paying taxes and his self-confidence.  One consequence of the system he’d concocted was that he lived a smaller, less public, more limited professional life, which no doubt affected his personal life, too. His system both reinforced and created low self-esteem. He had to see that the whole thing was, for him, a way to avoid personal pain, yet a source of the very pain he was trying to avoid.

I recently had a meeting with an unrelated man named Spencer Sherman. He’s 16 years older than me, but we were both born and raised in the same New York City borough, and both moved to California later in life. We share similar values and interests, not to mention a name-very uncommon.

Yes, I was curious about another human being with the same name, but the bigger reason for our meeting was to offer him money for his website and its domain: www.SpencerSherman.com.  I brought up my interest and joked that my business partner was afraid I’d pay him $1 million for the site, and Spencer Sherman stopped, thought and said, “I might consider a million dollars, but just for a moment. Money doesn’t mean much to me and I’m enjoying my website.”

How unusual to find someone who doesn’t equate self-worth with net worth, who isn’t willing to sell his joy for money and who isn’t obedient to the call of money as a well-trained dog to its master.

I recall so many instances when I sold enjoyable, precious private time just to make an extra buck. I believed then that, as long as the price was right, you were supposed to sell your joy for money. I let my money madness override the true value of happiness.

I’ve gotten much better at keeping my money monster from running the show, but it’s still a practice.  With practice, each of us can dissolve the money madness and see the value of life beyond money.  The other Spencer Sherman’s peaceful connection to his own happiness over riches inspired a deeper inquiry into my own money madness, and how I can continue to transcend it. Indeed, sometimes we can see in others exactly what we want to cultivate in ourselves.