Why You Should Side Hustle to Pay Down Your Student Loan Debt

As I’m currently on vacation in the Pacific Northwest, I have another guest post to fill the void. I have Jacob from Dollar Diligence with us today. He took over the site this year and he’s using it to document his journey to financial freedom, one step at a time.

Without further ado, here’s Jacob:

Side hustles are one of my favorite things because they have allowed me to become financially free from the debt that was holding me down. Prior to my side hustles, I made a small, modest teacher’s salary and this was in no way, shape, or form going to make the payments needed to pay off my student loans.

I knew I did not want to make payments for the next 14 years and I definitely did not want to pay as much as I was going to be in interest alone. So, I decided that I needed more money.

But, how was I going to get more money when I already worked a full-time, demanding job?

I needed something that was flexible and would allow me to still work in my traditional role. I chose to pick up some side hustles and I will talk more about them in this article.

Freelance Writing

Freelance writing was my first side hustle. Prior to writing for money, I did like to write, but never really did it. I decided to put my skills to use and start to work with clients who needed help creating pages for their websites and blogs through the freelancing site Upwork.

One of the things that I did to set myself apart from all of the other freelancers was I specialized in an area of writing and then I honed in on my skills and expertise and chose a specific niche.

I decided to write sales copy and do some side copywriting jobs. I did not want to mess around in the smaller articles section because it would take me days to make any type of substantial money and that was just not going to cut it. I needed money, a good amount of it, and it had to be made on the weekend.

Once I got into the grind of things, I was able to take on quite a bit of work on the weekends and I was easily making a couple to few hundred dollars. In addition to the money, I enjoyed the flexibility of the schedule, as I was able to stay home and work when I wanted. I was never chained to my chair.


While I did like to write, I wanted to use my free time as wisely as possible and I did not want to become burnt out from writing because it helped me make extra money. I decided I needed a second side hustle and I chose photography. I had taken photography classes in high school and I figured I might be able to use my skills to make some extra cash.

My plan was justified when one day a friend asked me to take a picture of his wife and himself. They loved my work so much and told me I should be charging for my services. They then proceeded to refer some people to me. I liked the idea. Who wouldn’t?

I knew I could always use the money from it, so I decided I needed to build up my portfolio, so I charged less than normal to get some clients that would allow me to use their photos to showcase my work.

Once I had enough of these photos, I was able to charge fair prices and take on clients. Since I did work as a teacher, my times were limited, so I chose to offer my services throughout the summer and then during the school year, I offered services on the weekend. This held me over and made me a nice chunk of change, especially throughout the summer time when teachers are off. I was good at capturing precious moments on film and my clients really enjoyed my work while I really enjoyed the extra income. It worked out nicely for everyone.

If you have a camera and decent photography skills – or even the willingness to learn more about photography – you, too, can make some easy cash for pushing a few buttons and some basic editing. Here are some great tips to get you started that helped me out too.

Make Bigger Payments

Now that you know about my side hustles, it is time to talk about something else…making bigger payments. I used all of the money I received from my side hustles to pay down my student loan debt. In fact, I can honestly say that I never once touched that money for my own personal gain. It ALL went straight to my student loan provider.

You see, like most college graduates (Editor’s note: these numbers are scary!) these days, I was saddled with debt and couldn’t stand the anxiety it gave me. This is why I chose to freelance in the first place, and it really helped me make a huge dent in my debt in a short amount of time (on top of being extremely frugal and diligent with my money).

One of the things you should keep in mind is that when you make additional payment above the minimum amount due, you will pay down your principal balance quickly and you will not be charged as much in interest, as the interest charge is based on the principal amount.

Final Thoughts to Consider

Now that you know what I did for my side hustles, the wheels in your head should be turning. You do not have to choose the same side hustles I did and there are plenty out there from dog walking to mowing lawns and much more.

The best piece of advice I can offer, that worked for me, was to set small, realistic goals and then work towards them. Each time you reach those goals, you will feel accomplished and it will push you to meet the next goal.

* * *

Jacob is a personal finance blogger over at Dollar Diligence. Follow him for more advice on making and saving money @DollarDiligence .