Jeff and I had become good friends at work. He was a few years older and had put in more time at the brokerage house where I was just starting out, so in some ways, he was a mentor. But this was a real friendship, not just a “professional association” like so many relationships with work colleagues. I felt we were soul-mates under the skin, with everything important in common.

So it stunned me when, one day over lunch in Jeff’s office, he suddenly asked: “By the way, where did you summer?”

I grew up in middle-class Queens, a generation removed from the immigrant experience, and had never heard the word “summer” used as a verb. But I got it. Instantly. It was unmistakably a class code, and it was a shock to my system. In that single moment, I went from feeling intensely close to Jeff to feeling absolutely separated from him, as if a brick wall had just shot up between us. Soulmates under the skin? What was I thinking? I said to myself, when clearly, as a single word had revealed, we were as different as two people could be.

I am not the first person to feel the jarring sensation of class distinction. But my emotional reaction to this experience was something more intense-it was money madness.  In that moment, I fell prey to defining my self-worth in material terms. My money madness told me that a summer spent at the public pool in our Queens neighborhood was inferior in every way to the kind of summer experienced by people who “summered” in the Hamptons, or on Cape Cod, or along the coast of Maine. And if my summer was inferior, surely my whole year was; and if my year was, surely my whole life was; and if my life was, so was I. My money madness also insisted that money was identity, maintaining that Jeff’s identity and mine could not possibly form and keep a friendship.

It was too bad. The truth is that my boyhood summers at the municipal pool had been wonderful, and if I had not been the slave of my money monster, I might have been able to say to Jeff: “I summered in the neighborhood.”  I might have created space for us to learn more about each other. Instead, money madness ruled my behavior, insisting that Jeff and I should not be friends. It was painful.

But money madness will do this every time. It will make you uneasy with your identity, or unclear about what your identity is. And it will dictate how you connect with people. There’s a great story about two women who’d been close friends for 20 years. They knew everything there was to know about one another, had been there for one another’s joys and sorrows, could virtually finish one another’s sentences. Then one of the women confessed to the other that she didn’t exactly work at the Museum-that is, in the sense of having a job there. It was rather that she visited there often because she donated so much money to the Museum out of her enormous trust fund.

That was the end of that friendship, as the woman who received this information wondered what else had been held back or fudged or lied about over the past 20 years. We can only marvel at the trust-funder’s 20-year discomfort with her own money situation, even as we pity her for letting that discomfort break faith with a friend.

The irony is that there is also financial danger in letting your money madness rule your relationships. In that first brokerage job, I saw myself as less worthy because I had grown up middle class and had never “summered,” and it led to behavior that influenced others’ perceptions of me. When my colleagues headed for the nearest watering-hole after work or went out for a boisterous lunch together, I hung back. I saw myself as different, and I believed the difference made me less. It affected my performance on the job. After all, how could I look to new money associations when I was still hung up on past money associations? I was the kid who summered in the municipal pool in the neighborhood. How could I possibly make the kind of money the Jeffs of this world make? How could I even be comfortable around people like that? There’s also irony in the fact that, most likely, I wasn’t the only person in the firm for whom summer meant the municipal pool, not Martha’s Vineyard.  Not only was my sense of otherness damaging and dysfunctional, it was probably inaccurate.

A friendship sundered, a job gone sour and my self-esteem thrashed. I was 25, and the score was Money Madness 3, Spencer 0.

More on money in the workplace :

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…

Some interesting blogs on the first class topic :

I am drawn to make others take a step back and think outside the box – especially with money.

Have you heard the latest money joke?

No?

That’s probably because there isn’t one. ( Ok, I did find the jokes about money listed at the end of this blog  – but in general, it’s not a huge humor topic! )

Money is serious. Say the word, and people’s posture improves. It’s as if they were hearing a parent’s voice telling them to mind their manners and tuck in their shirt. I’ve seen playful looks freeze into masks of solemnity when the subject of money comes up, with worry lines around the mouth and anxiety wrinkles around the eyes. Money is stressful; as my father used to say, it’s “no laughing matter.”

Well, it should be. All this gravitas around money is actually an obstacle to money success. It keeps us from thinking clearly about money, from looking at it realistically and making wise decisions about it. We feel weighed down by the ponderous complexity we assume surrounds the issue of money. The bulk of all that information hurled at us by the media displaces our common sense. And the freight of a culture that equates financial worth with self-worth produces the kind of stress that makes us react to events when we ought to be responding with objectivity and common sense.

That’s why one of the things I always try to do in my workshops is to get folks to lighten up about money. So when I found myself staring at a money boa in a San Francisco novelty store one day, I bought it instantly.

What’s a money boa? It’s about a hundred folded up hundred-dollar bills—fake ones, of course—strung together like a scarf. The fakes are pretty authentic-looking, so at a glance, I really do appear to be “wearing” $10,000 around my neck.

I first wore the money boa at a curing money madness workshop I did in New York for 500 people. I knew, because it’s always the case, that a lot of the workshop participants were feeling stressed, hopeless, and frustrated about their money situation. Yet even as I approached the podium, boa flapping as I moved, I could hear a few embarrassed titters. Then some chuckles. And by the time I was center stage, the place was downright mirthful. The point was made. A weight had been lifted, and in this more buoyant environment, it was a lot easier to help participants cure their money madness.

A few days after the workshop, I had to fly east on business. To my dismay, I found that I couldn’t really pack the boa; the hundred-dollar bills could not be refolded. So I simply wore the boa, and the reactions this provoked were pretty astonishing.

As I made my way through San Francisco Airport to board my plane, kids ran up to touch the boa and to ask for money. Adults smiled at me and shouted out questions; I just responded that I wanted all of us to lighten up about money, and every one of them agreed and thanked me for the reminder. A security guard asked if the money were real, and once I boarded, my fellow passengers were quick to start chatting; all by itself, the money boa broke the ice.

Then I arrived in New York. Cold, distant, unfriendly New York, as legend has it, money capital of the world. In fact, despite the fact that it was May, New York was chilly and windy—at least, until I walked its streets wearing my boa.

People laughed. They waved. Cops directing traffic at the world’s busiest intersections blew their whistles. New Yorkers wisecracked one-liners at me. Yes, there was a man living on the street in Times Square who tried, somewhat aggressively, to rip some “money” off the boa, and there were a number of people who simply didn’t notice at all, but for the most part, the reaction was: that’s funny.

All of this says to me that there is an untapped reservoir of lightness about money that has been pushed down inside us by a lifetime of stressful conditioning. The conditioning affects different people in different ways: some are obsessed by money, some are determinedly oblivious to it, some find it a distasteful necessity. But it seems to me that if we can access that reservoir of lightness, going back to a time before the conditioning planted distorted childhood money messages in us, we might clear the way for curing our money madness and making better, more successful money decisions.

How to do that? Remember back when you were seven or eight years old and were given a five-dollar bill to spend as you liked? If you could recapture the sense of wonder and excitement those five bucks incited in you, you’d be halfway there. So here are three suggestions for putting the fun back in money:

1. Save in a shoebox. Literally. Identify something you want to save for, find a shoebox (or piggy bank, or similar), and start putting in loose change on a regular basis. Even better, save with a friend: maybe plan a vacation together, and determine that every time you get together, you will each put ten bucks into the vacation kitty. Watch your savings grow, just as you would if you were seven or eight—with a sense of wonder and delight—and have fun spending it.

2. Consider the path your money travels next time you pay for something. The dollar that bought you today’s newspaper, for example: it helps pay the bills of the newsstand vendor, the salary of the driver whose truck delivered the papers, the reporters and photographers who covered the stories you’re reading, the editors, production team, and so on. Money works; it has a function. But it travels light; money is not leaden.

3. Come up with three reasons why you are overpaid for your work. Maybe it’s the lunchtime use of the office computer to do your shopping. Or the skybox at the stadium you get invited to regularly. Or the secret fact that you would do this work for nothing. Think about it, come up with your three, and write them down. No, this is not a joke.

Jere are the jokes about money i could actually find!

I often face conflict with myself and scheduling.

Often I arrive just in time for performances—out of breath, heart racing, adrenalin flowing—and then relish my sense of victory…we made it! No matter how mediocre the play or show or concert, I’ll remember crossing the finish line before an usher might say, “I’m sorry, but I’ll have to seat you after intermission.”

But recently, I’ve been noticing the connection between this behavior and my old style of accumulating money: for years, I was so focused on achieving a million dollar net worth that I never noticed my energy was all about striving and adrenalin, not about what I’d actually do with the money once I had it.

Flash forward to a recent Saturday.

I was commanding my minivan, filled with three adults and five kids, en route to Cirque du Soleil, and I had vowed to allow plenty of time to arrive at a sold-out event as expensive as this one.

The show began at 4pm, and just as planned, we arrived at 3pm with plenty of time to find parking. That’s when my money monster spoke up: Hey—if you have enough time to avoid the overpriced, designated parking and find off-site parking, why not go for it? Plus, you’ll avoid the crowd of exiting cars when the show is over…

I steered the minivan out of the designated Cirque parking and toward a city garage. The first garage we pulled into wasn’t open to the public, and the attendant directed us further down the street. We entered the next garage, got our ticket and parked. The eight of us walked down to the ground floor—only to discover a chain link fence blocking the entrance. After unsuccessfully trying different floors and wondering why the cashier’s office was closed, we saw the sign: Garage open Monday-Friday only.

A wave of panic flooded us adults, and then the kids got it – we’re trapped. We called the posted emergency phone number and were told to exit through an emergency pedestrian door. They would send someone out after the show to open the gate—the charge for this service was $100.00.

We raced to the theater and arrived at 3:55.

During the show, all I could think about was finding away to not pay their $100 retrieval fee. Then I noticed that the fear and anger around this fee were absorbing my attention much more than the performance I paid so much to attend.

So I did the opposite of my habitual reaction; instead of ignoring my feelings, I opened to the anger and fear. And what do you know, they were all familiar! I know this variety of anger and fear very well, because it’s been with me since I was five years old. I did a few money breaths, and my first insight occurred: I don’t know what will happen with the car after the show, but right now, I’m at the show, and I need to just watch it. I instantly felt my heartburn dissolve. My second insight was this: my anger and fear have nothing to do with the actual garage and everything to do with berating myself for being someone who parked in a closed garaged.

Then I had yet another insight: maybe the machine malfunctioned and should never have let me in. In other words, maybe it wasn’t my fault, or anybody else’s fault, either.

And just like that, I was suddenly free to enjoy the show. I still had the possibility of losing $100, but I felt full of life. When the show ended, I was determined to find someone leaving the garage, and I did, so I even got to park for free.

Later, I called the garage owner again and told her I got out. She said, “I’m glad, because the machine malfunctioned. It never should have let you in.”

Learn more about Cirque :