The Cost of Doing What Made Me Happy

Growing Up Working Class In Country Club Land Shaped My Choices — And I’m Still Dealing With The Consequences

I grew up in a working class family in an upper-middle class town in Connecticut. It was country club land and I was always someone’s guest. When I was in kindergarten my parents moved my brother and me out of the city and into an affluent suburb 20 minutes away. We didn’t live extravagantly but we definitely lived above our pay grade.

My dad operated a printing press in a factory that manufactured labels for consumer health products. He’d bring home rolls of holiday stickers and labels for cassette tapes. When we were young they were traded and used as currency among friends. Though he did his best to scrub his hands clean, they always looked dirty. But they weren’t, the ink had permanently stained them. He wore his wedding ring on a gold chain around his neck because jewelry was an occupational hazard. If his ring got caught in a machine, he could lose his finger.

My mom was a birth to three special education teacher. She spent her days traveling from one home appointment to the next, evaluating toddler’s readiness to enter mainstream school. Her car was her office and the backseat was where she stored her teaching tools, clear bins filled with beads, and sand, shoestrings and teddy bears. It was as if we were constantly getting ready for a garage sale that never happened. To an untrained eye it might have looked like garbage, but it wasn’t. Each item was a carefully chosen tool for testing fine motor skills or cognitive functioning.

In some ways, I was raised very differently from my friends. For one, most of my friend’s moms did not work. And when their dads came home they all had ties on, some of even wore bow ties. The walls of their computer rooms were lined with degrees from their alma maters. My dad never went to college. He got drafted into Vietnam soon after graduating high school. When he returned, he had a few manual labor jobs, always working with his hands, until finally landing a job at the printing press where he stayed, standing on the factory floor for 30 years.

My friends traveled often and to exotic destinations. In high school, one of my best friends brought me with her on a spring break trip to the Bahamas. It was amazing. We got our hair regrettably corn-rowed and one day at the resort pool we sat on chaise lounges next to Gloria Gatti and her sons. It was everything I imagined wealth to be like.

A week was the longest I had ever been someone’s guest and by the end I began to feel like a member of the family. My mom later told me my friend’s dad paid for my plane ticket. He refused to take any money from my mom. Until that moment I had not thought about how I was able to afford the same life as my rich friends. My parents did a good job of making me feel like I belonged.

From a very early age, my parents instilled in me the importance of doing what makes you happy. Growing up, one of my favorite books my mom read to me was about a girl whose life’s mission is to make the world more beautiful. She does this by spreading Lupine seeds all over her town so that in spring the town is covered in blooms. I too wanted to do something with my life that inspired joy.

The arts made me happy. The fact that it’s not an industry known for its practical, moneymaking application did not bother me. I found something I loved early in life and I felt lucky. I was encouraged to explore all aspects including creative writing, oil painting, piano, and cartooning. I was too timid to ever be good at gymnastics but my parent’s still supported me through 10 years of tumbling. I attended a field hockey sleep away summer camp for two years until giving up the stick and ball for track and field. The lessons, classes, private tutoring, sketchbooks, paints, mouth guards, shin guards, leotards, track shoes and cost of gas to shuttle me across the state, were all paid for, magically, by my parents.

I asked for braces and got them. I attended all my overnight school trips and with only a handful of gift-wrap sales. Every other Friday in 5th grade I attended a birthday party and bought each girl the same Bath & Bodyworks gift basket for $19.99. My parents paid for me to wear 3 prom dresses my junior and senior year.

On paper, it didn’t add up, but I never thought about the details; I was a kid. I knew I was lucky but I didn’t think about how I was actually able to do the things I was doing. I worked a few busy-work jobs in high school but only to earn enough money to buy a CD or a movie ticket. I didn’t have any concept of saving. I lived in the moment and was happy, like my parents wanted.

In my town everyone went to college. It was never a choice. So I applied for college at 17 with no idea what I wanted to do. I wasn’t even sure how college would help me figure that out, but it’s what everyone did so I thought they couldn’t all be wrong.

I was an average student so I wasn’t setting my sights on the big-budget schools. I got accepted into a nearby state university and figured, even if the whole college thing didn’t pan out, I wouldn’t lose much. It was a state school and those, I thought, are cheap. I knew my parents didn’t have the money to put towards tuition but I still thought it was a problem I could handle. Whatever money I owed after graduation, I’d start paying off immediately with the job I got.

I attended four years at a public state school entirely on loans and graduated with $70,000 in loan debt. While in school, I lived modestly. I stayed in the 1970s-era prison cell dorms my freshman year; I bought my textbooks used; I worked at the school bookstore. I thought that would cover things. I worked with my mom each year to fill out the loan application paperwork.

I never thought about how much money I was borrowing. Ever. My primary job at college was to figure out where my passions lay. I did really well at that job. I fell in love with writing: poetry at first, then short stories, then personal essays. When I graduated in May of 2009, I was more sure than ever: I wanted to be a writer.

The other thing I was sure of upon graduation: I needed to move to Chicago. I studied at the Second City Theater for a semester while I was in college and was blown away by the city. Chicago, compared to New York or Los Angeles, feels livable, which means it feels affordable. You don’t have to buy a car, and rent, at least when I moved in 2009, was moderate. When I told my parents I was moving, they were sad but supportive. If that was where I needed to live to realize my dreams and make it as a writer, then that was what I needed to do.

They did not want to get in the way of my happiness — but they also made it clear they did not have the money to support me financially.

In August of 2009, I drove from Connecticut to Chicago with my boyfriend in a tiny rental car we packed with whatever we could fit. I had some money saved from my summer job, enough to split rent until the end of the year. I had an internship at a non-profit literacy center that I was certain would turn into a full-time job right at the end of the year, when conveniently I would needed to re-up my funds.

That did not happen because, as it turns out, five-person non-profits rarely hire new staff. At the start of 2010 I was unemployed and answering the first of many debt collector calls. I needed to start paying my loans back, and I had no money to do that.

I graduated college in 2009, ready to begin my life as an adult. The #1 way I could do that would be to start a career and save money. Instead, from 2009-2012, I had many jobs that paid little money and I saved absolutely nothing.

First I worked at a family-run daycare where teacher’s paychecks regularly bounced. Then I worked a series of part-time gigs in after-school programs funded by government grants. I was an administrative assistant to a bar owner for 3 months until he realized I couldn’t do math and was too uptight to laugh at his misogynistic jokes. I worked for free for years for a startup I believed in and hoped would get funded; I wrote tweets for a dog walking business, and coupon blurbs for a deals website. All the while, any money I made I put into rent and paying my monthly loans. I lived in constant fear of over-drafting. I tried to start a savings account but I constantly had to dip into to it to keep my checking from going in the red.

In 2012, a student loan rep told me over the phone that I had run out of deferment options on one of my loans. I had to start making the $330 monthly payment. Combined with my $80 loan, I’d be paying over $400 in loan payments a month. I was making $20,000 a year. It was an unfathomable request. I started crying, not caring who she was or what she could do, but needing her to feel my desperation.

I continued to be a burden on my family for another couple of months until, in 2013, I finally landed my first full-time, salaried position. No benefits, but a small salary. It was a stability I had not known in many years. I still lived paycheck to paycheck, but I was able to pay my monthly student loan and be a contributing member of my household. Around that time I started saying aloud the amount of student loan debt I incurred. I was tired of being ashamed of it. I needed to start owning it. It was an ugly part of me but it was a part I couldn’t deny.

At the end of 2014, I got my first full-time, salaried position, with benefits, doing something that makes me happy. I was able to take a deep breath. This year, I decided to be more intentional about my finances. I could now float, but I wanted to do more; I needed to take full ownership.

So I met with a financial coach and I told this stranger all about the guilt and shame I carried, for most of my twenties, over my inability to provide for myself while at the same time carrying around this mountain of secretive debt. And I wanted to vomit, but I didn’t. He told me I was not alone and that we would work on a plan. I am now in the process of building that plan. Though it’s scary, I see a positive future, which is not something I ever thought I’d say about my relationship to money.

Ali Kelley is a writer living in Chicago. She hosts and produces the long-running storytelling show, Story Club Chicago. She writes about ’90s pop culture, teen angst and riding the train on her blog, Sleepoverz.


Support The Billfold on Patreon

The Billfold continues to exist thanks to support from our readers. Help us continue to do our work by supporting us on Patreon.

Become a Patron!

Comments