How 5 New York Women Overcame Debt

Photographed by Raven Ishak.
In writing about personal finance, one of the biggest things I’ve learned about my generation is that nearly everyone is in some way touched by student debt. Even people who’ve made it out of their education unscathed often find partners, roommates, or family members whose debt prevents them from living a certain way.

So, now that we've established that one way or another we're all in the same sinking boat here, the question is, how do we do the unthinkable and actually overcome it? To find out, I spoke to six very different New York women about how they managed to get out of debt — and how it changed or influenced their lives — in one of the world's most expensive cities. 

Here's what they had to say.

“I’m one of those stupid Millennials you hear about who spent tons of money on a totally useless degree. I’m often really embarrassed to talk about my experience with debt, because I feel like I fall into such a cliché about my generation: I owed $100,000 for an art history [degree] from a really tiny liberal arts school. In some ways, I don’t regret the experience, because I feel like my school really changed who I am for the better and made me a more compassionate person. But, looking back on the years I spent paying it off, I feel like I can’t even enjoy the things that I did get from my education, because it’s so wrapped up in what it cost me.

"Paying down six figures in ten years is obviously a really big task, so I should clarify a couple things. First and foremost, 40% of my debt was paid at once, when I inherited a small bit of property with my sister from a family member. It sounds like an ideal situation, but it was actually extremely sad; it was a place that meant a lot to us (we spent summers there growing up), and parting with it was something we never would have done if we didn’t need the money. But, we both had a lot of student loans to pay off. And, we knew as soon as it was ours that we needed to sell it, because at the time, we were both making crippling payments every month that were ruining our quality of life. We sold the home and split the profits.

"To pay off the remaining balance — which took about 10 years — I got an evening job. I found a full-time job sort of in my field (it was in advertising, and I got it through non-school connections, so I can’t even thank my degree), where I was earning about $55,000 a year, which is not that much in New York City, but was definitely enough to pay my bills. The hours were, luckily, pretty sane for the industry, so I took on another position two nights a week and one day a weekend. For two years, it was bartending/waiting tables. For the remainder, it was babysitting for wealthy children on the Upper West Side.

"I made a good amount from babysitting (about $400 dollars a week). I did many overnights, and they paid me a really good rate, knowing my situation — and I put every single cent I made from it towards my debt. It was a really tough time, but honestly, I eventually came to love it. They even asked me if I wanted to move in at one point, and though it was tempting, I opted not to (and to pay my debt off more slowly), because it was important for me to maintain my independence. Because of interest, it still took some time, but I was done with it just before I turned 30, which I had a huge party for.

"The funny thing is, I actually still work for that family sometimes. Now, I’m saving up a ton of money, but for a different reason: I’m buying a house!”
— Alison, 31  

“My husband and I both graduated from the same school with similar amounts of debt and not-very-useful degrees. But, since we both knew what we wanted to do in life — which was work with people and our communities — when we found the Public Service Loan Forgiveness program, we knew that it was for us. We are both reaching the end of our time to repay it, and while it’s definitely been a challenge (we both work with underprivileged families, but for different agencies), we are so happy that we have an alternate method for getting rid of the debt we accumulated.

"We had been planning on making huge payments for basically the rest of our lives (between the two of us, it was over $1,400 dollars a month), but the program ended up being a better solution, in a job we both really love. The pay is not great, to be honest, so we might change careers when we're finished, but we definitely want to stay helping people. My husband will occasionally joke that he wants to go back and get an M.A. in psychology. I told him if he takes out any more loans, I’m divorcing him! Just kidding…mostly.” 
— Jessica, 30    
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Photographed by Raven Ishak.
“I emerged from undergrad with various forms of debt, some of which was incurred via the various store credit cards I thought I needed in order to 'dress like a professional.' I dutifully paid those bills for a couple months until my auto-pay somehow shut off, at which point I decided it was someone else's fault and didn't bother following up. Eight years later, I'm still paying for that decision.  

"I also had about $90,000 in student-loan debt — I owed a third of it to the government and the rest to a private bank. For seven years or so, I would pay the government loan when I had the money, and request forbearance when I didn't. Two years before my debt was written off fully, I began making enough money to actually save: I set up my direct deposit so that 10% of my check would automatically deposit into a savings account I don't look at; I put all the singles left in my wallet in a box when I came home at night; and I scheduled my checking account to send $50 to my savings each week. This was a pretty manageable system for me, and when I earned a decent chunk of money in early 2014, I used it to pay off the entire government loan.

"The private loan is more of an epic tale (you can read about it here), but essentially, I defaulted on it almost immediately. The original lender went out of business the year I graduated, so another bank inherited the loan and farmed it out to bill collectors. When they couldn't collect, they returned the loan to the bank, who let the statute of limitations lapse on the debt. They hadn't sued me in time, so my loan was forgiven. I won the clerical-error lottery, more or less. 

"Now that I'm almost completely out of debt, I have an additional 10% coming out of my paycheck that goes directly into a 401K (my company matches this by 3% — hey, free money!), and I use the Acorns app, which essentially collects the spare change from my checking account and invests it (there's been no big returns just yet, but I like the fact that it's another pot of money I don't see when I look at my checking account).  

"Because I got to 'ignore' my private loans, and my government payments were manageable, my debt didn't make me broke. What it did do was ruin my credit — which essentially makes it impossible for me to be self-reliant. I've never been on a lease, and I can't live alone unless someone with good credit takes mercy on me (my boyfriend tried to co-sign for me once, but my apartment application was still rejected). That's probably the biggest sacrifice I didn't know I was making way back when. Sure, my credit is a wreck, and I'm paying approximately all my savings in taxes this year, but I'm grateful lucky as hell to have the opportunity to restart my financial life with way more information than I had when I was 18.” 
— Stephanie Georgopulos, 28    

“A lot of people actually don’t know that I had a lot of debt in the first place, because I didn’t tell them...because I didn’t want to have to tell them how I got rid of it. The people who did know how much debt I had think I still have most of it.

"The truth is, I got a ‘sugar daddy’ my second year post-grad. A lot of people will/would judge that choice, so I chose to only tell my best friend thus far. But, it’s probably one of the best choices I’ve made since college. I found myself at 24 with $76,000 of student debt, working an unpaid internship that would ‘lead to better things,’ while putting in 37 hours a week at a designer store on the Upper West Side. (Just enough not to get benefits, yay!) It was partially working there that motivated me to get a sugar daddy, even though it’s the most un-feminist explanation, ever. 

"I would see rich women come in every day in the middle of the afternoon, with nothing to do except buy hundreds of dollars' worth of clothes. A lot of them would talk to us about their problems — you know, retail therapy — and a lot of them were really open about the fact that they were in pretty loveless, bad marriages. I got to thinking, If it’s okay for these women to basically be 40-year-old sugar babies, why shouldn’t I be one? But, when I went to the site, it was way harder to find someone than I thought it would be. It took me about six months to find the right long-term relationship, and I still see him occasionally, three years later. Over the course of our relationship — where we met one to two times per week — he paid off my student debt, gave me spending money, and bought me tons of gifts (only some of which I sold on eBay).

"[My best friend] asks me if having sex with him is/was gross, and it isn’t. He’s in his late 50s, has all his hair, and has a pretty good body. But, truthfully, I would have done it even if he was less good-looking. My financial freedom is worth a lot to me.” 
— Stacey, 27  

“I got rid of my debt the boring way. I worked a job and put away almost all of my income for a year and a half by living with my parents. My goal was to pay all $40,000 of it within two years, but I didn’t end up making it. It took me a year after the fact, while living on my own, to pay off the last $8,000.     

"I was one of those people who lived at home after college, however, even though I had a good job. And, I will be honest: I definitely felt the sting of the social stigma sometimes. I cringed when I had to tell people I lived at home when we were talking at a bar or whatever. I didn't go to the bars crazy often, because I was working really hard on putting everything I earned into my loans; okay, no one ever puts everything towards their loans, but I did my best to reach that goal. 

"My social life was still really important to me (and, frankly, important to my job), so I made sure to have one to two outings per week. Most of my 'strict saving' came from not buying unnecessary material possessions: I had the same laptop for three years, no new clothes for nearly a year, the same furniture I had growing up, and a first-generation iPhone that all my friends used to make fun of. It wasn't a glamorous life, but it allowed me to have that little 'extra' of still being able to go out and socialize, even though I was in serious saving mode. I can tell you, it takes a lot of pride-swallowing to work a full-time 'real' job for nearly two years and only save $300 of it a month for fun.” 
— Parker, 26 
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