Poor, Rich, Poor, Millionaire: The Story of a Rebel Girl

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Being a rebel isn’t easy. In fact, it’s downright hard.

I was born with an extreme distaste for anything related to schedules, authority, discipline, cultural institutions, expectations, and most of all, responsibility. I’ve always wanted freedom more than anything else, and I always figured, hey, that’s okay. The world needs every type of person, so I can fill that role. Little did I know what I was up against.

The source of all things

I was born into a seriously wacky family in the early 1970’s. Two hippie parents who did lots of drugs and dressed like Cher and Jim Morrison. My Dad took off when I was 3 because he is afflicted with the same disease that I have: rebel disease (otherwise known as a great fear of responsibility). So, I was raised by and large by my mother’s family. A huge Slavic and Italian Catholic family whose motto seems to be, “If you’re not outdoing the Joneses, you’re doing something wrong.” They’re all very materialistic, and though super successful in their respective fields, they tend to spend way more than they make. Designer everything, big houses and fancy cars.

There’s a strange entitlement to the way they live. So much so, that one aunt has been left homeless for the last year due to her spending. Yet she still gets her hair done in salons and buys Starbucks coffee daily. 90% of them have been addicted to drugs and alcohol at some point in their lives. My mother’s best financial advice to me was, “Marry rich!!!!!”, repeated almost daily. Thanks, mom.

Even though I had these crazy spenders teaching me financial ruin by example, luckily I also have my father’s Jewish side to thank for my natural inclination when it comes to money. Somehow my mind just automatically tracks every dollar coming in and out and I don’t even try! Yay to genetics!

Rebel girl

My rebelliousness started to show when I decided to skip class in middle school. I felt like a trapped animal in school, so I’d just go to the churchyard and look at the grave stones for a period to get some fresh air. My grades were terrible. And since my mom had this ingenious plan that I would “marry rich” someday, she didn’t seem all that bothered by it.

During middle school, I started making art and decided that would be my future. I mean HELLO, it was perfect. Artists didn’t have to go to academic colleges and have jobs. Yuck!

My high school boyfriend encouraged me to audition for the magnet arts school he attended, hoping to score me a future. True to the genetics passed down by my crazy Slavic/Italian family, when I was interested in something, I could excel in that area. So, I got in and worked my butt off. I got scholarships to my dream art school for college and attended.

College was ROUGH. My Dad was supposed to pay for my college education but had only saved for a state school. His exact words were, “I didn’t save for you to go to HARVARD!”. Thanks, Dad. Not that I was going to Harvard, but it was an expensive private school, so I took out loans and was left with very little money to live on. I lived in an unheated basement in a house in Baltimore. I remember being so hungry, I would steal morsels of food from the refrigerator and pray that my roommates wouldn’t notice. I made money by working at the school library, waiting tables, and selling marijuana. But I was still so broke.

Living the high life

After graduating, I was going to be an artist of course, and sell paintings for thousands of dollars and live a bohemian life. It sounded like a great financial plan to me. I hadn’t factored in the general irrelevance of art to American culture at large, and the tiny percentage of artists who actually get noticed by the art world.

I moved to Manhattan, got a job as a cocktail waitress, and started making incredible money. I was strategic about working at the trendy, celebrity filled hotels and clubs. Many nights I would go home with $1,000, all made in one night! I rented a painting studio in Brooklyn.

Then, it happened. I was at work and saw this guy. I remarked to my fellow waitress that I was going to marry him. And I did. He was a rock star. Well, he looked like a rock star anyway. He was dressed in a beautiful Armani suit and his hair was bleached blonde and longish and crazy. It was love at first site.

At 23 I had it all. My partner-in-crime musician husband (who made $10 an hour at a bicycle shop), a 3-bedroom apartment with Jacuzzi bathtub, music and art studio, right by the Empire State building. I was painting on my time off. I was off work and sleeping when all the other suckers in town were going to work bleary eyed. I treated my husband to extravagant meals at the best New York restaurants. We’d dress up and go to the fanciest hotel bars like the King Cole bar at the St. Regis and pretend we were famous. My husband’s band had shows in the best downtown clubs. We were doing tons of drugs. Weed, ecstasy, coke, and my favorite, heroin. I was always careful to “chip” heroin. Basically, that meant to binge once a month to avoid getting addicted. No problem! I had been doing that through college, I was too smart to be a junkie. We were outdoing the Joneses in every way and living my dream rebel life. And I was financing it ALL. Even the $5,000 I had managed to save to buy a house with someday, I lent to my husband for the printing of his first album.

Losing it all

But, as the restaurant business goes, mine was falling out of favor with the celebrities after a few years of glory. My income dropped significantly and we were forced to move way uptown into a much smaller apartment. Then 9/11 happened and we got into a major depressive funk. My husband decided to ignore my rule of not calling the drug dealer when you run out of heroin, and we ended up with a never-ending supply of it in the house. We had both become addicted.

The one lucky part of this time was that I was “discovered” by an art director who worked at one of the biggest magazines in the country. She was a customer at the bike shop and loved the flyers I had designed for my husband’s band. She hired me to be her assistant and taught me the basics of graphic design. I was working in the famous Time & Life building. It was extremely uncomfortable for me to be in a corporate atmosphere. But hey, at least I could feel good knowing that I was a heroin addict and therefore not that uncool! I did very well hiding my addiction. At this point, waiting tables was no longer an option. I had a full-scale panic attack when I returned to my nightclub job after September 11th. I just couldn’t do it anymore.

Soon we were in dire financial straights. I was paying for food with a credit card and cash for heroin. We were running out of money and something had to give. I made my husband see a doctor who gave us withdrawal medication and we kicked our heroin habit and moved up to the country to a sad looking house that we could actually afford.

My husband continued to spend just as my mom’s family does. Eventually, I got tired of being destitute and kicked him out. During that time I borrowed a down-payment on a house from my parents and purchased a home in the Hudson Valley. After a year, my ex-husband was promoted to manager of the bike shop and was making good money, so stupidly, I took him back. But within a few months he filled our garage with motorcycles and leased an Audi without my consent. He also became an abusive alcoholic which is why I finally left him for good.

My life was in financial shambles at that point. I was over $20,000 in debt. I had rented out my house and moved to yet another basement in a house that was very sad. I continued to work as a graphic designer and took a full time job at a huge newsstand title as an art director, so I was digging my way out slowly.

My self-esteem was so down in the dumps that I dated one loser after another and they all treated me like crap and used me. I started drinking heavily and would find myself on many occasions alone in my house on the bathroom floor crying over the fact that I was near 40 and alone and basically broke. One too many of these situations and I had hit a rock bottom of sorts and realized that I’d better get it together and start making smart decisions.

Finding my way back

Cue my old friend from college who contacted me on LinkedIn and started talking to me. This guy was the exact opposite of me. He was “normal”. He had a good, steady job straight out of an Ivy League university and had money saved! He was nice to me. He was more than nice to me, he cared about me.

To my mom’s great glee, during this time I was dating a multi-millionaire hedge fund guy. I mean MULTI, like close to billionaire, and he was somewhat famous in New York. But after a couple of dates it was clear that he was just like all the other guys I had dated and was waving all kinds of red flags that I recognized all too well.

Also during this time, I was about to have surgery to have my gallbladder removed. I emailed 3 guys: my ex-husband, the multi-millionaire and the old college friend, to let them all know about my surgery. From my ex-husband: basically nothing. From the multi-millionaire: “call me when you’re feeling better”, from the college friend: “I googled this and it looks like it isn’t too bad of a procedure, will someone be there with you?”.

I was in love. I dumped the multi-millionaire and ended up marrying the college friend. This was the first non-rebel decision of my life and probably the best one ever.

We married and moved to Paris for his job. He helped me pay my parents back all the money I owed for my house. We rented my house out and traveled the world. Even though we both made good money (I had started a graphic design business from home), we weren’t rolling in it. But because we had no expenses due to our expat status, we saved an incredible amount of money. We’ve traveled the world and stayed in the most amazing 5 star hotels and lived in the most beautiful homes paid for by his company. It’s almost the rock star life, but without the drama!

So this is the happy ending, right??? No.

Looking over the cliff again

The rebel girl returned and now in the form of an alcoholic. I hid it really well. I had very few consequences and drank often in the middle of the night so my husband wouldn’t see me drunk. When he’d go away on trips, I would be drinking from morning until night. When I drank around my husband I became nasty.

I realized that I had to do the next right thing and quit drinking. I had to sit my rebel side down and have a long talk with her. Look, I said, we can’t go on like this. We must find moderation or we are going to end up broke and alone, again. So she agreed to go to AA. We have managed to find a balance by working at home and on our own schedule and terms, but also making each day totally different from the last to keep us happy and feeling free. I’ve learned that no is a complete sentence and that acceptance is the key to happiness, not wanting what you don’t have.

The next right thing

I now have a hefty retirement fund (what?!) and we have a second home and invest in the stock market (whaaaaat?!). We are technically millionaires (not like that other guy, but technically). We’ve done it by saving, saving, saving and budgeting and always spending less than we make. I’ve learned all of this from my current husband. I drive a 6 year old used Volkswagen (that I love) and we have a modest house in a nice part of our city. It’s exhilarating knowing that I will be okay for retirement and can live within my means and still have wealth.

I suppose the point of my story is that even a rebel can find financial stability by realizing that balance and moderation are key. It applies to everyone and everything. As I’ve learned in AA, doing “the next right thing” takes you to great places, always. And being a “rock star” isn’t all that it’s cracked up to be.


Kate Jett is a pen name for a creative professional living a new life in the northeast. The stories are real. The names have been changed.

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