My Debt Story

Revisiting the big life lesson that turned out to be a pretty good investment.

This time last year (tax season🤓) I shared a story here tracing a piece of my life that brought me immense shame—getting into debt and also the hairy business of getting out of it. It wasn't easy, but it's only now 20+ years later that I continuously think about how much those four years of rebuilding taught me. Not just about money and wealth, but the endurance it took to shift my relationship with my own sense of worthiness for both.

So, here it is again, "My Debt Story," available today to all free subscribers to ATA, so feel free to share it. Along with another one of my earlier pieces, this essay really seems to resonate with so many. Probably because we don't talk about money enough. Probably because of the ancestral ties to money we spend our lives understanding…or severing. Wealth and abundance mean different things to all of us. I know what it means to me after living this time of my life and writing it down. And I hope, after reading it, you come a little closer to knowing what yours means, too. xxCb

Doing my taxes recently (like most of us) got me to thinking about money, the history and arc of It. And, in particular, when I was about 26 years-old, and I got into an unspeakable amount of debt. Or, more accurately, I was getting into it for several years leading up to that and just chose not to notice it. When my NYC roommate and best friend from college decided to go to law school and move back home upstate while she prepared for the bar exam, I had a choice to either find another roommate or…something else entirely. So, like the good procrastinator that I am, I delayed making any kind of real decision by moving down the block to sleep on the pull-out couch of another friend, who invited me to stay with her while I figured out what to do next.

I hadn’t told anyone about my debt. I was one of those people whose whole body would clench and contort when I opened up the mailbox or got an ominous American Express-related missive. My credit card actually got turned off a few times and my bank account practically echoed as my teeny paycheck vanished virtually moments after it appeared. And yet, I continued to go out with friends, shop, and fritter away whatever money briefly passed through my fingers. Until the day when my friend told me that her brother wanted to sell the apartment where she was living…where we were living. And we both had to leave. I had been sleeping there on that pull-out couch in the living room for two months, and my lower back ached from the stiff metal bar that supported the mattress. Every day, the pain worsened, causing my hips to spasm and occasionally making it hard to walk. Real physical, self-induced pain, all reminding me of what was coming, what I had to face. But still didn’t want to. I mean, I would rather hobble in denial up and down subway steps than actually deal with the truth.

And then, one evening, I came home from work (my friend wasn’t home), and when I sat down at her kitchen table, I saw that she’d left some papers open. I’m not a nosy person (not really), but as I picked them up to move them out of the way, I caught a glimpse of a number on the page. I gasped. Could that possibly be how much money she had? Did people actually have that much money? It was one of those moments when everything was suddenly different, and there was no going back. I felt so ashamed because I looked and shouldn’t have. But like giant church bells clanging in my head, I also knew it was finally time. To do the one thing I’d been pretending I’d never have to.

The next day, I called my parents. At the time, they still lived on the South Shore of Long Island, about a two-hour door-to-door commute from where I sat with a phone against my ear that very moment. I told them the truth, about the debt, about everything. Since I had taken a pay cut when I moved from an executive assistant role to become an editorial assistant a few years earlier, I’d never really faced the fact that a lot less money was available to me. I never budgeted or re-budgeted. Instead, I kept living the same, spending the same, and my one credit card helped me to keep up the ruse. Until it didn’t. And now that I couldn’t even afford to pay the monthly interest rate, and my credit rating was on the verge of ruin, I was fucked.

And I’m 100% sure they knew it.

I grew up in a small two-bedroom house, where they still lived. But one of its handiest features was that it had a tiny apartment upstairs, originally occupied by my grandparents when they were living. My older sister briefly lived there before she found her own house a few towns over. And since then, it was mostly empty if not for the occasional Costco overflow. On the phone with my parents, I told them what I hoped would happen: I would move back home, commute back and forth every day to my editorial job in the city, I would pay them something for rent every month and live there until I could both pay off my debt and (hopefully) save what, at the time, I thought was an extraordinary amount of money: $10,000. By my calculations, this would take about a year to two years. I could do it. With their help…I could absolutely do it. And months before my 30th birthday, which already felt like a looming deadline for getting my shit together. I thought, if I could pull this off in just a few years, I would be living in my own sun-drenched apartment in SoHo, with more money in the bank than I could have ever hoped for…and zero debt.

The dream…

So, here’s what really happened: I moved home and began commuting to work…two hours each way. I woke at 5 a.m. every day and most evenings came home after 8. The cost of commuting even then wasn’t cheap, and thankfully my parents, knowing I was in a terrible spot (and also probably knowing my calculations were completely absurd), didn’t charge me rent. I contributed to groceries and other household incidentals and paid for the gas in the 1987 Plymouth Duster I still had from college. It was a stick shift with a cassette player and no air-conditioning, and I drove it back and forth to the train station as well as to my favorite thrift store in Babylon every Saturday morning. On most Friday nights, I would drive from the train station to my aunt’s house a few towns away from my parents for dinner. And since we were close, we would often talk at length about life, along with my predicament and how ashamed I was, something I had a really hard time sharing with anyone. I was nearing 30. I had no money. I was struggling in a job that was going nowhere. And I was living in the house I grew up in…with my parents. I didn’t date anyone for the entire time I was back home. Mostly because I was exhausted by the grueling schedule of my life, waking so early and going to bed most nights at 11. And also, more accurately, because I couldn’t bear the idea of telling someone I might meet at a bar or out with friends that I had to move back in with my parents. Even imagining it, meeting someone I might actually like, was enough to keep me from going anywhere with anyone.

I remember one Friday night, sitting on my aunt’s living-room floor, worn out, depressed, and angry at myself for being what I thought was such a fuck-up. And my aunt said something I’ve never forgotten: “Sometimes, you have to choose to be happy. You can’t just wait for it…you have to choose it.”

And so, in the absence of any social life, I focused on other things…or chose them. I painted the upstairs apartment and helped my mother get rid of my grandmother’s ancient belongings, keeping just a few special ones. I bought a new bed and started arranging and using some of the treasures I found thrifting, like a set of four vintage Thonet chairs for about $100 (I still have them) and a signed/numbered Allan D’Arcangelo serigraph from 1965 ($10). Some days my mom would come thrifting with me, and she was there when I found a beautiful perfect Pucci bag with its tiny change purse still inside. For $5.

Slowly, steadily, I was making progress at paying down my debt. Every month when my statement would arrive and I would see the balance shrink a little bit more, I would celebrate by drinking some wine from one of my grandmother’s fancy crystal glasses. I cooked for my parents, trying out recipes from stories I was working on, something I had never done before. It was weird, but I’d never really had grown-up meals with my parents. And, during these new evenings, I got to know them and enjoy them. And love them a little more for what they were instead of resenting them for what they weren’t. Or, more accurately, what I wasn’t. I know, too, that that unexpected time to get to know my father a little bit better was so much more than just us sharing a beer on their back porch, looking up at stars. I healed something with him, something I can only know now that he’s gone.

There were other strange gifts, too. I read and re-read so many books on those long train commutes, mostly classics like A Moveable Feast or The Secret History, which I scribbled a million notes inside because I wanted to understand how it worked. A few times, on very late nights, I took advantage of the company’s overtime policy—employees who worked past 8 p.m. were permitted to buy themselves dinner and take a car service home. Even if most nights I was driving home in the dark from the train and falling into bed, only to wake up at 5 a.m. to do it all over again, those rare nights in the back of a car with music and a takeout Cobb Salad from the Waldorf Astoria (across the street from my office), felt like the most profound luxury.

It took four and half years to pay off all my debt. And to save $6,000. Even though I had become obsessed with reaching the $10k mark, and had zoomed right past my own two-year deadline, I knew it was time to move back and find my own place. I knew I was beginning to hide out, afraid the same thing would happen again. Afraid I would never be able to afford an apartment on my own, or fall in love, with a person or a job. Afraid I would never make enough money to have a real life. When I was a kid I don’t remember dreaming much about babies or wedding dresses. But I daydreamed a lot about someday living an independent, creative life. I didn’t know what it looked like exactly or how it would play out, but I could feel it…and I trusted it. Like a friend that was always close by.

One winter night, getting off the train and walking down the platform, I looked out over the parking lot to where my car was parked, and could see that the glass of the hatchback had been shattered—a giant gaping hole in the middle of it. Someone had thrown bricks through the windows of a few of the cars, and mine was one of them. I drove back to my parents with the freezing cold air blasting through the car, the brick still in my back seat. And while I can’t remember exactly what was going through my head, it was so late and I was so cold, I remember smiling…almost with relief.

I knew the brick was a sign—it was time. I was 30. I got the lesson. xxCb

Photographs by Jen Steele