How Do You Re-Solve a Problem Like Debt?

How do you take a debt and pay it down?

Oh, help.

I remember crying one night, shortly after college graduation, staring out the window of my Murray Hill apartment. There was a lot to be happy about — I had just graduated with my BA from NYU after an exhaustive four years spent in four different cities. I also had a job secured after my internship at a play publishing company became a full-time offer. I even had my first New York apartment which I shared with a friend, and though my room couldn’t fit more than a twin bed and a dresser, it was mine and my share was only $925, rare for a room in Manhattan. By many accounts, things were good.

But despite all these stars aligning—stars that I could not afford to not align and stay in the city—a dark cloud eclipsed them. Even having checked many of the “adulting” boxes, I had to face the music: I still couldn’t afford to quit the part-time job I had at the bookstore I had through my last year and a half of school. I had almost $10,000 in Sallie Mae student loan debt alone and my salary was not enough to cover expenses and payments. All the running back and forth between internships and class and the store would continue on into the indeterminate future when I was finally making “enough.”

I bawled my eyes out that night and then the next day, I went to work.

For almost five years, I worked seven days a week. I put a lot of extra money towards paying off my loans as much and as quickly as I could, though I also maintained a small amount of savings via automatic deductions from my checking account (usually $25–$50), contributed 3 percent to my company 401(k) so I could get the company match, and tried not to skimp on doing social activities. For a whole summer, I would close the bookstore Saturday night, go out to the bar until closing time with my coworkers, and then report back to the store in time for opening.

My philosophy was that if I needed more money, I would just make it. I earned an extra $25 here and there by picking up evening closing shifts at the store, so much so that I was often “on call” if they needed someone to close the place without much notice. It helped that I lived and worked in the city, which was also something that required a lot of money but enabled every other aspect of my lifestyle. I also found freelance jobs: helping typeset study materials for a consulting company for about $5,000, designing the layout for a literary magazine for $1,000, and sometimes doing the odd job for a friend of a friend for $25 an hour. It was completely exhausting, but the momentum I built made adding to my schedule feel normal. What’s one more thing on an already long list?

All my hard work paid off. I paid off my private loans within a few years, though I do still owe my parents a few thousand dollars for school which I think is going to be automatically deducted in tiny chunks from my checking account until I die. I also saved a nice cushion and got a full-time job that paid more. I eventually decided to move into my own studio apartment, which to me represented a great badge of success.

Throughout this, I hung onto my bookstore job but had already slowly begun to phase out my hours when I found myself facing unemployment at my full-time job. During this time, I came to lean heavily on my credit cards and the savings by then were nearly depleted, since I was still recovering from moving expenses. While I was lucky to find a new job rather quickly, by the time all the dust had settled, I found myself in debt again, a little more than I had owed in student loans.

This time around, though, the mantra of working harder wasn’t going to cut it. I had been at the bookstore for seven and a half years at this point and my body was tired. Especially after finally cutting down my working hours so that I would have a day off a week, I needed time to myself and to recharge. I started coming home from what shifts I did work in tears because my body hurt so badly.

So with taking on more shifts at the bookstore no longer an option, I started to implement a few new things to help try to keep my expenses in control:

Stop all frivolous spending

There is a volleyball net somewhere in my boyfriend’s mom’s basement that symbolizes for me the height of my time having disposable income. I had bought it simply because we were going to the beach, and I thought a great beach accessory would be a $25 volleyball net. It never made its way out of the box.

Nowadays, I can’t imagine making a purchase like that, especially for such an uncertain reason. Spending-wise, I focus only on the essentials and try to get the greatest mileage out of whatever I invest in, from clothes to gifts to subscriptions and food.

Focus on getting paid for my work

I had always loved writing, but only a year and a half ago did I decide that I would only write for some kind of pay. While it’s been limiting and I don’t feel like I have as many clips out there as I used to, the challenge of finding paid gigs has pushed me to pitch to media I didn’t necessarily think would want my work — and for a decent paycheck, to boot!

Take on projects that pay more per hour

When I finally quit the bookstore about a year and a half ago, I realized that it would leave a big gap in my income. Therefore, when I started looking for freelance gigs, I decided I wanted to focus on things that would pay more per hour than I was making at the bookstore so that shorter projects, though perhaps not as constant or reliable, would help supplement my income in a substantial way. Luckily, I found a couple of seasonal opportunities that give me a nice financial boost and pay about $15–$25/hr. Plus, I can do them in the comfort of my own home.

Grow my career

While the side hustles are always good, a big part of my decision to leave the bookstore was also so I could focus on my full-time job. I work in an industry and job role that I love, and committing to that job was a step that I wanted to take to grow my career. I’ve worked a few full-time jobs now, but the opportunities for growth were scarce. I’m finally in a position where I can learn and move up, and I want to explore that fully.

The problem with all of these things, however, is that they take time to really make a difference in my finances, much less make a dent in my debt. The process of paying off my debt will be a long one this time around, and while I wish I left my days of crying about finances behind in that Murray Hill apartment, it’s still something I confront every day.

That being said, I feel like the lessons learned this time around will be ones I remember for my whole life. I view money and time differently now — I recognize how finite they are and how important my decisions with them are. Also, I feel like the strategies I’m implementing to help pay off my debt this time around will also have lasting effects. They are attempting to build things that weren’t there before, rather than just serving as a band-aid.

Debt is a problem I will probably have to re-solve repeatedly throughout my lifetime, and I’m learning the hard way that it definitely doesn’t get easier. The good thing, though, is that there’s always more to learn.

Kimberly Lew is a proud writer of plays, articles, and the check when the monthly rent is due.

This story is part of The Billfold’s “Resolve” series.

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