How Side Hustling Helped Me Pay Off $68,000 In Student Debt

How Side Hustling Helped Me Pay Off $68,000 Of Debt

It was December 2011 and I had just moved to Portland, Oregon from New York City, after graduating from New York University with an M.A. in Performance Studies. I wanted to stay in New York, but after going on job interview after job interview, with nothing concrete lined up, I knew something had to give. The grace period on my student loans was ending and I was to start paying back the $68,000 I still owed. I moved to Portland to cut my expenses in half and to be with my then-partner. I thought I could get a fresh start in Portland but it turned out the job market wasn’t great there either. I found temp work for $10 to $12 per hour but I knew that wasn’t going to cut it. That was barely going to pay my bills. After cutting back as far as I could — sharing a small studio apartment, not having a car, cable or even health insurance — I knew the answer was that I had to earn more. That’s where side hustling came in and changed my life and helped me pay off debt.

Getting started with side hustling

Once I realized that I couldn’t cut back any more and that I hit the end point of frugality, I knew earning more money was what I had to do. I had to find ways to make extra money aside from the temp job I had. So I started searching the Web for opportunities. I ended up finding gigs on Craigslist (it’s not all trash!) and TaskRabbit. My most lucrative side hustle was being a brand ambassador, making between $17 to $25 per hour. A brand ambassador works as an on-site representative of a brand at public events. If you’ve ever been to a concert or sporting event and seen people handing out samples or coupons or free swag, that’s a brand ambassador. It was a fun side hustle as an extrovert and I got to go to a lot of fun events. After doing several events, I signed up for various marketing agencies and had profiles on sites. So, whenever there was a gig in my area, I’d get alerted and apply. Being a brand ambassador is a great side hustle if you like talking to people and need flexibility. Many of the gigs are nights or weekends. On top of that, I worked as a pet sitter. And, one time I even got hired to work an underground rave and sold water bottles to thirsty dancers all night until the break of dawn. One of my TaskRabbit jobs turned into a part-time job. I was hired to work a Passover dinner at  a Jewish congregation and then was hired to work all of their other events. That was a great side hustle too as there was always leftover food that I took home, which helped minimize my food budget. If you can work in catering or events, there may be additional perks like free food and drink! In January 2013, I started my blog to chronicle my journey out of student loan debt. I was depressed and felt so consumed by my debt and wanted a place to write and share my feelings. When I realized that people were leveraging their blogs into other opportunities, I knew I wanted to try something new. So I started pitching other blogs to write for their sites. Quickly, I started writing for other personal finance blogs. Eventually, I started writing for financial institutions and other fintech companies. This side hustle became so lucrative that I became self-employed a year later as a freelance writer!

How side hustling helped me pay off debt

For me, side hustling helped me earn the money I needed to pay off my debt. It also led to learning new skills, trying new things without the pressure of a “real job” and gave me more confidence. I used my income from my day job to pay for my everyday bills and I used my side hustle income to pay off my debt. Originally, I started making an extra $400 per month. That grew to $1,000 then $2,000 and more. Once I started hitting those higher numbers, I became self-employed and grew my income even more, which helped me pay off debt earlier than I had expected to. When it comes to paying off debt, a lot of people say you need to cut back. While that’s a great strategy, it will only take you so far. There is a limit to frugality. In my case, my debt payoff was all about having a low-cost of living, cutting back, and earning more money. Side hustling played a huge role in my debt payoff journey, so if you’re feeling like you hit a plateau or aren’t sure what to do, earning more money might be the fix you need.

How you can start side hustling

If you want to start side hustling, first take an inventory of how much time you can reasonably dedicate to a side hustle. Can you work nights? Weekends? You want to know just how much time you can dedicate to your side hustle. Once you have that figured out, take an inventory of your skills and interests. What are you good at? What do you like doing? I knew I liked animals, writing and being around people, so being a pet sitter, freelance writer and brand ambassador were perfect side hustles for me. When you know what type of gigs you want, it’s time to get out there! You can look on sites like: For many of these gigs, you will be an independent contractor and will need to save for your own taxes. Start by setting aside at least 25 percent for taxes. You may need to save more and you can figure that out with the help of an accountant. Through side hustling, you may just reignite your passion for something, learn a new skill, and make more money to get out of debt faster! Melanie Lockert is a personal finance expert, the blogger behind and author of the book “Dear Debt: A story about breaking up with debt.” Melanie paid off $81,000 of debt and is now on a mission to help others do the same. Feature Illustration: Laura Caseley For The Money Manual