This Woman Got A Huge Raise And Paid Off Her Student Loans By Asking The “Over/Under” Question

“Ask your other peers what they make — especially your male ones.”

Do you know that feeling of jumping into a metallic, purple catsuit to express your joy through interpretive dance with two backup dancers costumed in money signs? Probably not, unless you too have experienced the blinding exhilaration of paying off more than $200,000 in student loans. Caitlin Boston knows this feeling — it took her 10 years to get there. And it might have taken longer if she hadn’t asked a simple question of her colleagues.

She uploaded her whirlwind celebration to YouTube.

View this video on YouTube

By the time Boston graduated in 2009, she had a master’s in social psychology and two undergraduate degrees in anthropology and American studies. Altogether, she had $147,602 in student loans.

On Tuesday, Aug. 6 — what would have been her late father’s 72nd birthday — Boston made her final payment on her student loans, which, including interest, added up to $222,817. In her dance video, she explained how she paid off what seemed to be an impossible amount of debt. “I did it all by my single freaking self, as in, no family passing me $$$ at any point,” she wrote in the caption to her video. “It was hard but I did it and I did it alone because I am a f****** boss.”

Hard is an understatement: When she was earning a low hourly wage, “in any given month, I had between $62 and $74 left in my checking account,” she recalled in an interview with BuzzFeed News.

But today, at age 35, she said, “I’m free. I’m freaking free!”

Boston pointed out that she never missed a payment or took off much time from work, even after her father died by suicide. Above all, she said, the most important thing that helped her pay it off: realizing she should be getting paid more by asking her peers if they were making over or under a certain amount. At some point, you can't cut back on your lifestyle any more.

“Ask your other peers what they make — especially your male ones. It might make you feel uncomfortable but it’s the sole reason I started making an additional 41% a year.” For Boston, that was a life-changing amount — tens of thousands of dollars more than she had been making.

Boston dedicated the video — and her final payment — to her father: “I’ve thought about you and this debt every single day since you’ve been gone. So this win, it’s for you too.”

BuzzFeed News spoke to Boston about how she ended up with six-figure student debt, how she managed not to miss a payment, and what led her to start asking people around her — especially men — how much money they made. Here’s what she said:

My family is super working class. My dad was a police officer in Baltimore and my mom was a homemaker. I’m adopted. We never talked about the cost of college. There were periods when I was growing up when there were concerns about money, but my family never really spoke to me about it. We always had money for food, and there were always some new clothes for school. We could afford a house and a car and all these other things. But education — that’s an extraneous cost when you’re living paycheck to paycheck.

I didn’t have a concept of the amount of money that they were taking out for me. I wasn’t even aware of the amount of work that they had to put in until I was going on my third year to study abroad. I had to sign a paper for a loan for $32,000. That was the first time I’d seen a number attached to the debt. And it was for one semester to study abroad in London.

I asked my parents, what is that amount? They didn’t know. They weren’t aware what the total was for all of my loans because it was spread across so many different loans and different types of loans and they were just like, “Well, if you don’t sign this we can’t afford to send you to London.” So they’re sending me stuff to sign and I was signing it. I was just like, “Okay, whatever, I need to do it to get to school.” My parents didn’t have really great money management skills.

I went to grad school, and in my spring of my final year, my parents told me they thought I had six figures in student debt. That’s when I was like, what?

I 100% wish I had learned about money in high school. I wish I understood what debt meant. I didn’t even understand what interest meant. I wish they’d sat me down before any of us signed any papers to just be like, “This is how much money you’ll have to make to pay this off” — at a minimum. Just laid out, in black and white, what the logistics of managing any type of debt looked like so I could make more informed decisions.

That’s how I graduated into the recession in 2009, and that’s the legacy that I have lived through. It was pretty bleak. I was applying for jobs anywhere, and I was very lucky and privileged enough to land a paid internship. When I wasn't working, I was spending the better part of those first six months after graduating just trying to understand how much money I owed, where that money was, who I owed it to, and how to set up payment plans. The total amount that I was expected to pay on that first bill was just over $1,400 — and I was working a paid internship for about minimum wage in Washington, DC.

I was completely beside myself looking at this number. I called my dad and was like, “Can you help me?” And he just said no. He didn’t apologize. It was a very straightforward conversation. He was like, “There’s no way I can help you — you’re going to have to figure this out.” I’ve seen friends of mine being informally coached by people — family friends, other family members — who had already navigated that landscape. But there are folks who have to make it through this wilderness without a map.

I realized I needed another job, so I picked up additional work at a running shoe store and started doing some freelance work doing design research for nonprofits. I lived in a vegan, gluten-free, soy-free, queer community house for $425 in rent. We cooked for each other. That’s why I was able to pay my loans and not accrue credit card debt, because I was living in a community of people that shared expenses and food with each other as a rule for living in the house. And we were rockin’ around with some of the most affordable parts of the food pyramid. I bought a bike because I couldn’t afford a Metro card, but it got stolen and I had to buy another bike.

By the end of any month, with all my bills paid, I had between $62 and $74 left in my checking account.

When you have nothing left to cut, when you’re down to the bone, what can you do? Make more money.

Later, I got a full-time job with a labor union and started making a salary of about $48,000, and I could drop the work at the running shoe store; I kept doing the freelance work. Still, mentally, I just could never get around how I was going to pay off $147,000 in debt.

When you have nothing left to cut, when you’re down to the bone, what can you do? Make more money. I didn’t have a partner or kids, so I moved to New York. I knew that my earning potential would be better there, and my work opportunities would be far greater.

In my next job, I got a pay jump to $72,000 and landed with a roommate in an apartment that, to this day, is very affordable. That’s been my number one strategy wherever I’ve lived — to keep my housing expenses as manageable as possible.

My dad died of suicide in 2013 and had about $50,000 to $60,000 in credit card debt that my mom had to pay off with the life insurance he left her. I have to imagine that the debt was weighing on him — one of the many things, of course, but a significant one, nevertheless. It was terrible watching her navigate the finances of death, much less the bureaucracy. That was the moment I realized, I’m not dying in debt. There’s no more playing around here. I can’t go down like that.

Bit by bit, I had been making progress on my loan, and by that I mean I paid off approximately $15,000 of the principal. I eventually consolidated all my debts with SoFi after running into a guy who worked at SoFi when I went on a boating trip in the Amazon in Brazil after my father died. I realized I hadn’t been able to really get a handle on my loans because so much of my payments had just been going to interest. But I needed to be done with this.

I left the nonprofit world and got a job at a design agency. I ended up loving it. Almost two years into the job, I was making pretty high five figures, so not a small amount of money, but with that level of debt, it’s still not enough to really be making a ton of headway on what I still owed. So I go up for my biannual review and I was like, “Listen, I just helped to bring in a $5 million piece of business, here are all of the other things I’ve done, and I think I deserve a raise.” And my boss just said that I just wasn’t ready for a raise yet.

I went out to dinner that night with three of my coworkers: a South Asian and Middle Eastern woman who had seven years of just banging job experience, a black woman with a PhD in cognitive psych and more than a decade of job experience, and a white woman who was 24 and had been working for like two years. It was review time, and we’d all been told a very similar story when we’d asked for our raises, and we were all very annoyed if not just outright upset. At one point we just started telling each other our salaries as we sat there. Every single one of us was making the same amount of money, including our 24-year-old coworker who only had two years of job experience.

So I was like, “OK, I’m going to give you a number and I want you to tell me if you make over or under that number.”

We had all of the postdoc credentials or all the job experience you could ask for, and we’re still all being paid the same as a 24-year-old white woman. She’s a wonderful, incredibly hardworking, and deserving person, but this is not about who she is; it’s about how three other women of color at that table with more experience, the same work ethic, and ability to deliver at work were all being paid the same thing.

I went to work the next day and decided to talk to one of my white male coworkers. I said, “Hey, so what are you making?” He, being a normal American person, was like, “Oh, I don’t want to talk about money.” So I was like, “OK, I’m going to give you a number and I want you to tell me if you make over or under that number.” And I said a solid six figure number. And he said, “Under.” I went down by $10,000. He was like, “Over.” And that was all I needed. I was, like, well, there you go, I’m making at least $20,000 a year less than you. This coworker had the exact same job background, and the exact same master’s degree, and similar time at the company as me. There was no reason for this kind of pay discrepancy.

So then I just went to LinkedIn and looked up everyone at every company in New York, San Francisco, and LA with my job title and seemingly with my background in terms of education and experience. I blasted dozens — and I’m talking dozens — of people with the same email, saying, “Hey, I’m looking to make a career jump into one of the big tech companies, and I just want to know what you’re making. Can you just tell me, are making over or under X?” I got three responses back.

One guy’s response was: “If you have this amount of years of experience the industry minimum in a major job market is this.” That was pretty much what the other two women who wrote back did as well. They were within 10% of each other, comfortably six figures. Which was crazy.

Coming from a background where your family does not make a ton of money, I couldn’t even fathom asking for that amount of money until I got so angry and I felt entitled to it.

I started interviewing like crazy. I mean, I was on fire. Even though I was super happy in my job, I kept on thinking that if I’m being paid literally tens of thousands of dollars less than what I should be making, and I’m working this hard, I might as well be making the money that men in my industry are. I’m not going to work for a place that doesn’t respect my value.

I got hired by Etsy. I told them what I wanted, and that was what happened. I got a pay jump of about 41%, so tens of thousands of dollars. These are not small numbers.

I am in a really privileged and exceptional position of being able to make a jump into tech. But it wouldn’t have happened if I had not had amazing women coworkers who were willing to have a moment of vulnerability with me at that table, and a couple of dudes willing to be good allies.

The thing is, no one is going to help you figure out how much you need to make. You need to be really proactive and ask how much you’re going to make.

Now I work at another tech company. The only thing that has changed about me making more money is that I see my acupuncturist more regularly. I have a therapist I see weekly. And I buy vitamins. My lifestyle hasn’t changed except for my ability to access health care. I haven’t taken big vacations. I don’t buy a ton of stuff. I don’t go out to a ton of restaurants. I am 35, and this is the first year I am putting more than $50 per month into my 401(k).

This is what privilege is — to have a casual conversation with gatekeepers.

I don’t know if my degrees in and of themselves were worth it or if I could have gotten the same education for a much cheaper price tag. But what I do know is that because of where I went to grad school, I no longer doubt my value or my worth.

I paid off just under 50% of the total loan amount in 2019. When I made my final payment and made the video, I said, I’m going to wear this fucking traditional Korean crown that’s primarily associated with weddings at this point. I can wear it to celebrate myself and my accomplishments. I’m doing this for myself. I wanted the video to be a genuine expression of joy and celebration that reflected that in spite of this debt that has taken so much out of me, spiritually, psychologically, and emotionally.

I still ask the over/under question. I’ve also flat-out told some of my junior teammates what I make. I’m here to tell them what they should be shooting for. There’s a burden that we carry by not sharing what we’re making with each other. It perpetuates this idea that it’s all up to you to figure out how much you should be making, when really you are working for a series of employers who have pay bands, or salary caps, or freelance amounts set by what people are willing to work for. All that the secrecy has done is put the burden — and the shame — on the individual. The only way to circumnavigate that fucking capitalist bullshit, which is built on secrecy, is by having these incredibly uncomfortable conversations.

This is what privilege is — to have a casual conversation with gatekeepers. I was always jealous of friends whose parents were able to set them up for a coffee, an email, or a phone conversation with these people, because it’s those things that give you not only a network, but a spectrum of what you’re worth. That is what I think so many people do not have access to, and that’s one of the reasons why I am vociferous about talking about this.

I didn’t really have that privilege, and I think more people need to be talking about this and be willing to share. But I do have the privilege of rage. ●

This interview has been edited for clarity and length.

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