“People do some crazy things with money. But no one is crazy.

Here’s the thing: People from different generations, raised by different parents who earned different incomes and held different values, in different parts of the world, born into different economies, experiencing different job markets with different incentives and different degrees of luck, learn very different lessons.

Everyone has their own unique experience with how the world works. And what you’ve experienced is more compelling than what you learn second-hand. So all of us—you, me, everyone—go through life anchored to a set of views about how money works that vary wildly from person to person. What seems crazy to you might make sense to me.”

― Morgan Housel, The Psychology of Money: Timeless lessons on wealth, greed, and happiness

It seems I’m continually working on my relationship with money. 

Issues around finances have often been—tricky. 

Reflecting on my background seems a good way to start in the unraveling of this relationship. I hope in this very personal reflection, there is something helpful to others. I admit, I feel quite vulnerable sharing it. But that’s a huge part of this 100 Day Challenge exercise for me, sharing such intimate reflections. So, here goes…

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In my memory (and emotional truth), money was sometimes a tool of manipulation in my house growing up. Once, as a child, I asked for an advance on my monthly allowance (A sum of two dollars, I believe).  In my emotional memory, ever after that, my father would say, “Didn’t I give you an advance last month?”

I stopped asking for it. The allowance faded away.

Though I looked forward with tongue-dripping anticipation to back-to-school shopping every August, I paid a price, coming home sweaty with guilt every time as my mother said, “Oh, I hope your father won’t be mad. That’s more than we were going to spend.”

Whatever budget they had in mind for this spree wasn’t communicated to me, making it impossible to meet.

I had no formal training in how to manage money that I recall. I was supposed to learn from modeling. But money matters weren’t discussed in front of me much. I categorized us as “upper-middle class,” but knew almost nothing about the family finances. It felt like such talk was deemed inappropriate for me, a girl who was supposed to remain innocent, friendly, cheerful and not ask too many questions. 

I knew my parents had money, but they didn’t like to spend it. There were values implied with spending (rarely stated): education was valued (that was clear; but I had to work to pay half the cost of college living, including some of my rent, as I recall), dinners out were occasional and had to be chosen by my parents if they were going to pay. Though we would have a more expensive meal now and then, Burger King every Friday night was a ritual in the late 1970s and early 1980s. Pizza with my friends—any meal out of my choosing—was my expense. I did service through Job’s Daughters, but I’m not aware of my parents ever giving to charity. They were taught the old “pick yourself up by your bootstraps” mentality.

Though my parents moved us into a country club community for their love of tennis when I was ten, they didn’t spend much on landscape maintenance. The fruit trees in the backyard didn’t survive the first year. They spent only what they had to on home maintenance. There was a florescent light in the indoor garden area that flickered annoyingly for years. The living room remained unfurnished for nearly eight years. They didn’t heat the downstairs area, an open area that included the family room and a billiard room—only used by my brother and me and our friends for the most part—that my father said was too expensive to heat. I generally had to wear a sweater in the house and a couple times was scolded when I snuck to the thermostat and turned it up.

 Though neighbors had Mercedes, my parents seemed proud of their ten-year old Hondas. Rather than become a part of the community—other than their tennis crew—there was an unstated view of the neighborhood as pretentious. 

I was pigeon-holed very early as NOT being good with money. The “old story” was that my brother was good at saving it, and I was good at spending it and giving it away. His Easter basket still contained a few pieces of stale candy the following Easter. Mine was eaten and shared with friends and gone in two weeks. When my mother offered us cookies, according to her, I asked for two. At five years old, I gave away some of my brother’s baseball cards to kids at the bus stop. It was fun. It made people so happy. It was my lesson in possession, that the cards were not mine to give. 

To this day, I just assume that I need more practice and acquaintance with financial systems than my brother in order to be comfortable with them and understand them. Because it feels like I was treated like I didn’t know what to do. And then with head-hanging disappointment came self-fulfilling prophecy. I assumed I was incapable.

It didn’t help that we were brought up in what was then traditional gender roles. My brother was expected to make money. I was to be taken care of. Someday I would marry, and the man would take care of me. But this flew in the face of the hard-work ethic that my dad emphasized. I started working when I was 12 years old—and never stopped. My brother, on the other hand, though very hard-working, had jobs intermittently. Maybe I was always trying to prove my worth. 

My first job—working with my brother—was cleaning chinchilla cages on Saturdays. It was a get-rich-quick scheme of the 70s, and friends of my parents had a huge basement space that was wall-to-wall with the gray, furry rodents in cages. We were paid $12.50 for several hours of work, scrubbing the metal trays under each cage, trying to avoid aggressive females who sprayed their urine when agitated. When my brother had moved on to other things, I continued the work, making $15 a day and was given a breeding pair of chinchillas as pets.

I babysat for multiple families, housecleaned for one neighbor, and ironed clothing for another. I was terrible at the last two! Given the makeup of my country club neighborhood, it made me feel a little like Cinderella. There was some kind of self-pitying romance to the situation.

I didn’t mind working. It was a point of pride. I liked making my own money. But it felt strange in contrast to my peers who generally didn’t work. Many were given cars for their 16th birthday. I spent my savings to buy my dad’s Honda Civic when I was 17. I understood it. My dad wanted to teach us the value of money. That seemed good and reasonable.

But there was a context to it. My parents spent a lot more on their “get-away-from-the-kid” vacations than on family trips. The rules about what they would pay for and what they wouldn’t were rarely stated. We sometimes had to guess. Asking for money often meant receiving some sort of remark or quip. The house was theirs, not ours. And roiling beneath it all—I understand looking back—was a girl constantly looking for approval, for emotional support, and ultimately love, for being who I was.

I worked even more after I turned sixteen, applying for a job as a county in-house caregiver. I kept company with an old woman who had a major stroke and helped her go to the bathroom and get into her bath. Honestly, it creeped me out, but I took the job for the purpose of becoming more accustomed to being around people with such issues. I’m still a little squeamish, but I can overcome it.

I also started working that year after school and weekends at a donut shop in town. The summer after my senior year in high school, I worked four jobs: ushering at a movie theater, delivering singing telegrams, manning the donut shop, and writing a column for a local newspaper about outstanding teenagers. I worked all throughout college, not just summers but when in session. 

When I was graduating from college, and my dad announced, “Okay, you need to be financially independent now.” It came as a shock. That sounds silly, I know. But I didn’t know what to do, it was very sudden, and it was in contrast to my upbringing in many ways. Plus, what I wanted to do was not what I thought they wanted me to do. My mother encouraged me into teaching, which hardly makes a lot of money.

My parents were Depression-era babies. My dad grew up poor in the Bronx. I respected them for being careful with their spending, for saving money, for creating a better life for themselves than their parents had. I never wanted for material things, for food and shelter. Ever. I was lucky. I just wish we had talked about money more, that I had been taught about credit and balancing a checkbook, about investments. I wish I had been empowered more. 

Sometimes I’d still like a parent-figure to sit me down and go over with me how to save, to budget, to enjoy living within my means, and to invest so I’m not only working hard for my money; my money is working for me. I’ve sought that kind of help in adulthood and still do. I know it’s not rocket science. I’ve come a long way with increased earnings, budgets, retirement accounts and a 501K. I guess you could say, I am managing my money much more efficiently and effectively than in the past.

But sometimes it’s still hard. 

There’s still childhood shame wrapped up in it all. I think more than anything else, I need my “inner-parent” to speak up and say, “You are good with money. Don’t be so hard on yourself. You don’t deserve that judgment. You know what to do!” 

Perhaps reading my own words will help that sink in.