My gig, my taxes, and my first car

ccheshire Blogger

cchesire.jpgThe author with the results of her hard work

As a college student, I’m always looking for ways to maximize my income. From working sunrise shifts at my school gym, to desperately applying for the few paid internships available, finding new ways to earn a few bucks is something I strive for.


Like many others in their pursuit of supplemental income, the gig economy is a great way to make a living while being able to control both my hours and environment. My gig of choice is freelance writing because it allows me to work from wherever I am. I regularly write for a college baseball scouting and scour Twitter for publications looking for some fresh content from eager writers like me.


However convenient, the gig economy comes with its own fair share of challenges. The first is the sometimes painful process of being discovered. For me, that means writing tons of content and sharing it with anyone and everyone who will listen, without any promise of being compensated for my work. Unlike me, not everyone is a college student who’s in the “resume-building” stage of life and can afford not to be paid, even if that means gaining the small satisfaction of not having to pay taxes on that work.


Which brings me to the next notable drawback of the gig economy. It is surprisingly difficult to navigate how to report income on your taxes. A common misconception of freelance workers is that we pay fewer taxes because we are our own boss and business, or maybe that our income is all “under the table”. Unfortunately, that is just not the case.


For contrast, the website I write for regularly pays the employer tax portion of Social Security and Medicare and I only have to pay the employee tax portion. However, the income I generate from websites that I only write for once as a freelancer, I have to pay both the employee and employer taxes. This may be the biggest downfall of being my own boss. Unlike someone who regularly drives for Uber or rents out their home on Airbnb every weekend, I won’t even make enough with my writing gig to reach the self-employment tax threshold, but I will still have to pay income tax like everyone else.


However, the complicated nature of freelancing and taxes won’t stop me from using it as a way to expand my horizons and my income. Without freelancing I wouldn’t have been able to invest in things that enhance my quality of life like buying my very first car. I won’t give you all the details, but the amount I stand to make freelancing this year adds up to just about the same as my car payment per year. This means I can devote my other funds to things like putting money into my savings account, feeding myself well, and going out to the movies instead of eating popcorn at home for every meal while I stare at my laptop screen with Netflix on.


Figuring out how the gig economy can work for me gives me the flexibility to plan for my financial future by helping me build a cushion that I wouldn’t otherwise have while allowing me to focus on my long-term goals, like owning a car, rather than on my day-to-day expenses. I’m glad to be living in a time where I can find side hustles on Twitter… even if I still have to pay taxes on them.


Catie Cheshire is a Creative Marketing intern with Transamerica this summer. Though she’s just learning how to “adult” she hopes her insights will get you thinking. Posts and blogs created by Catie on the Wealth Meet Health community are for informational purposes only and are not meant to take the place of your relationship with a health professional. For personal health considerations, please consult a health professional directly.



When I was at college, I had a few side gigs in addition to my bartending job.


When Ikea opened in my town, a friend and I took out an ad in the local newspaper offering to assemble furniture for a fixed rate. If it took us 5 minutes to assemble a chair, that would be the same price it would cost to assemble a wardrobe.


My favorite side gig was selling stuff on eBay. I would visit antique shops and second-hand clothing stores for items that I thought were underpriced or needed a little TLC and then fix them for sale. I got burned a couple of times and lost money but it was fun.


Reporting the taxes on these was incredibly frustrating but luckily a friend's father was able to assist. So I feel your pain. 


None of these are on my résumé, but I still love to assemble furniture and go antiquing!


Hi @ccheshire - I think it is wonderful that you take so much pride in being independent while learning full time. I worked as a receptionist part time while going to University and never had to think twice about taxes. You are inspirational. 


I wondered about two things based on your post:

1) Why not advertise your skills on UpWork? It is a wonderful place to find freelance work engagements and might help you keep your income a bit more organized.

2) Why have you chosen freelance writing over the "traditional" gig economy opportunities like driving for Uber or Lyft?


Thanks for sharing.