Illustration by Carly Jean Andrews

Into the Black: I Paid Off $48K in Student Loan Debt in One Year

Determined to pay off his loans, Ryan started driving for Uber, walking dogs and more

This is the latest installment in our series Into the Black, where we hear from people who escaped the burden of unpaid bills and loans through sacrifice and ingenuity. This week we talk to Ryan*, who worked four jobs to pay off his student debt.

Ryan, 29, Quincy, Massachusetts

Past debt: $60,000
Source: Student loans
Past job: Magazine reporter, Yesterday’s Island, Nantucket
Past salary: $18 an hour
Current job: Marketing manager at an accounting firm, part-time Uber driver, security guard and dog-walker
Current salary: $70,000
Current net worth: $25,000

I graduated from Assumption College in 2010 with an English degree and $60,000 in debt. All my fellow English-major friends were freaking out about life and jobs, but I was relatively calm. You know what you’re getting into when you become an English major.

I had lined up a summer job writing for a magazine in Nantucket, Massachusetts, and knew it would take me through the summer. It was a fun summer. I was 22, newly single and going out a ton.

But I was burning through money. The reporting job paid only $18 an hour, and I bounced at a roadhouse bar five nights a week for $10 an hour. I spent all my money on bars and going to the beach. I had no idea what budgeting was then, and wasn’t paying down my loans. I had just gotten out of a rough breakup, and was enjoying not having the structure I did when I was a college athlete. I ran track, so it was nice to not have to run 10 miles every day. I just wanted to have fun, not worry about my debt.

When I finally did take stock of my finances, it was a rude awakening. I was expecting my student loan debt to be $30,000, but it was actually twice as much, $60,000, because my tuition increased from $35,000 to $50,000 from my freshman to senior year. I felt overwhelmed. Looking back, my time in Nantucket was probably me trying to avoid the stress of my debt.

The job was set to to end in October, so in September I got serious about finding a full-time job. My loan payments were going to begin soon, so I needed a steady paycheck. I applied to about 20 random job listings I found on Craigslist.

I ended up getting a job through my alumni center, which emailed me a listing for a marketing job at a trade association. They were looking for someone with a writing background to handle their blog and social media feeds, and I was always intrigued by ad copywriting.

They hired me at $34,000. I thought it was low, but the job had full benefits and a lot of my friends didn’t even have jobs yet. I figured I’d try it for a few months and get another job.

Instead, I ended up working there for five years. The job was low-stress. I only worked eight-hour days and got a full hour for lunch. After a year, they raised my salary to $38,000 per year. I liked the people a lot, especially my boss, and I enjoyed the business trips they sent me on.

But I was still drowning in debt. I was living with four other people in a five-bedroom apartment in the Mission Hill neighborhood in Boston, paying $625 a month in rent. I started working at a bar on Friday nights to make some extra money and to avoid going out and spending. But I had only $400 per month in spending money after rent and my minimum loan payment ($670 per month). Whenever I had money left over, I’d throw it at my loan. But I felt panicked, trapped by my debt.

After five years into my job, my career was stagnant. Every day felt the same, like Groundhog Day. It felt like time to leave, but other companies wouldn’t hire me because I didn’t have enough digital marketing experience. So I started a 10-week digital marketing course at General Assembly during my free time. It cost $3,500, but I left with vital digital marketing skills such as search engine marketing and Google AdWords, and a portfolio to prove it.

This is about the time I started to get serious about my finances. I saw my former classmates buying houses and I felt left behind. I moved out of the city and into an apartment with my girlfriend in Quincy, Massachusetts, where rent was cheaper.

I started working for Rover, a dog-sitting service, making up to $90 a night, to pay for the class. My friend was a coordinator for a security company and would get me shifts working security at Apple Store. Usually, the job paid $15 an hour, but I could make $25 an hour if I did the overnight shift. I would stay in the Apple Store all night watching Netflix or studying for my course. People would walk by shitfaced at 3 a.m. and bang on the glass screaming, “What are you doing in there?!”

And I landed a new job that paid significantly better. One of my co-workers at the trade group told me there was an opening for a marketing manager at a local accounting firm, so I applied. I knew the accounting industry really well by this point and I had nearly completed my web marketing course.

They offered me the job for $65,000 per year, but I negotiated the salary to $70,000. I knew the industry average for the position was $90,000, so I fought hard for that extra $5,000.

You Have to Negotiate Your Salary

Despite the raise, I still didn’t feel like I was making enough progress on my financial situation. Sometimes, I would drunkenly joke with my friends: “I’d like to work really hard for one year and just pay off all my debt.”

And then I decided to do it. I had $48,000 left in loans when I started my new job in spring 2016, and I was determined to pay it all off within a year.

I had starting reading people’s personal finance success stories on Reddit during this time, and I realized two things: I needed to make more payments to my loans, and needed more revenue streams to do it.

My old job paid out my four weeks of unused paid time off and I put all that toward my loans. I kept working Rover and the occasional security gig, but the real difference-maker was driving Uber.

You know in movies about drugs — like, say, Blow or Scarface — all have that one montage scene where you see the characters selling tons of cocaine and piling up huge stacks of money while some song from the ’80s plays in the background? That’s what driving Uber was like for me (only legal, and on a much smaller scale).

I made more than $540 my first week driving Uber. I made $240 in surge charges alone on a Friday night. I was soon consistently making $500 a week for 25 hours of driving. Between Uber, security and my full-time job, I was putting anywhere between $3,500 and $5,000 toward my loans each month.

In July, I put $7,000 toward my loans, but that’s when I started to burn out. After a full week of work, I would drive Uber from 6 p.m. on Friday to 3 in the morning, and do it again Saturday night. One weekend, I worked 36 hours of security at the Apple Store. I did the overnight shift on Friday, went home and slept for a few hours, then went back for the day shift on Saturday and did another day shift on Sunday.

Some weekends I wouldn’t work at all, though, because I could feel my girlfriend getting pissed off that I was working all the time and never home. My friends were supportive of my plan, but they told me to slow it down so I wouldn’t exhaust myself.

My last debt payment was on December 2, months ahead of my one-year goal. When I was driving Uber, living off beef jerky and Red Bull from 7–11, I had all these fantasies about telling Sallie Mae to fuck off. But by the time I actually made the payment, I was over it.

My big takeaway from the experience is that if you’re in debt, it’s all on you to pay it off. You have to formulate a plan and go after it.

You can’t give up. Before, I was stuck in a job, making shit pay, wondering if I would ever pay off my debt and having panic attacks over it. And within a year, I got a new job, got paid more, moved in with my girlfriend and paid off my debt.

I can finally go out with friends and not feel guilty about it. I feel free.

*Name has been changed.