When I was a wee girl in the Ozarks, I would often crawl onto my papa’s lap and ask him when his next gig was. My grandpa picked and grinned in a bluegrass band, and I loved accompanying him so I could dance (a jig, probably) for the folks he entertained with his renditions of bluegrass standards. When the show concluded, I would often run up to him and ask for his autograph, something that delighted him as much as it did me.

Playing these gigs was one way my grandpa kept himself busy in retirement, and it even paid on occasion. Most of the time he just played for fun or at the bequest of an assisted living home. My grandpa certainly did not make his primary income off of music (he owned a gas station and later in life became a car salesman), but that’s exactly what his son does. His son/my uncle teaches piano and also travels to play music for assisted living homes where he brightens the residents’ days by playing any tune they want. Tonight he’s playing accordion in an Oktoberfest in Kansas City. Occasionally he books performances in other states. These are paying gigs. They don’t all pay him a lot, but my uncle keeps track of his mileage and writes it off his taxes. He also keeps track of the upgrades (new piano, entryway rug, etc.) he has to provide to keep his home studio attractive and welcoming for students and parents alike. He’s been self-employed for as long as I can remember and delights in discovering a new self-employed cost he can deduct. I always thought this was him being cheap and a little shady, but now that I’m partially self-employed, I understand how necessary and legitimate these deductions are.

Remote work seems like a dream to the lowly highway flying adjunct, speeding up and down the interstate between 3-5 colleges and universities each semester. It was enchanting to me after losing my most recent job mid-semester. If nothing else, it seemed like a simple way to make some supplemental income between teaching jobs. What I failed to realize before I jumped in head-first was that if I’m an independent contractor, I’m not paying taxes year-round like I did as an adjunct. And that means I might owe the government money instead of getting a fat refund come April. I’ve never made much money (I repeat, adjunct), so I have sincerely counted on this influx of cash in April to help me pay down debts, upgrade my laptop, or finance a well-earned vacation. The idea of not only losing my return, but OWING money has kept me up at night.

When I first started tutoring online, my teaching colleagues told me horror stories of tutoring for some side cash and then owing 1/3 of what they earned to Uncle Sam. Of course, that money earned tutoring is long spent on the school supplies, coffee, and pricey work clothes necessary to keep our day jobs as teachers (precarious as they may be). So what can we do? There has to be a better way, right? There must be a way to actually make money off of your side-hustle and not just borrow against the government May-March. Yes, I know we can pay quarterly taxes, but that doesn’t work when your gigs are short-term and unpredictable. My side-hustle income varies so much from month-to-month that I’m too nervous to count on it, budget as if it doesn’t exist, and perpetually search for more gigs.

So I started reading about deductions and how to make your taxes a little less cruel. One awesome discovery I made was that all of those expenses K-12 teachers think of as necessary evils that are often just paid out of pocket [pencils for students, kleenexes, hand sanitizer (SO MUCH HAND SANITIZER), conference registration and travel, research tomes to inform the presentations we give at those conferences] all fall under the Educator Deduction (up to $250). Of course, I’m not a K-12 teacher. I’m an adjunct at colleges and universities, make waaaaaaaaay less than a K-12 teacher, get laid off at a moment’s notice, and buy all of the aforementioned things, yet I cannot take advantage of that deduction.

This is where my self-employment becomes an asset instead of a detriment. I tutor ELLs online for TakeLessons.com, rate essays for ETS*, and am currently designing a course about ELLs for mainstream K-12 teachers with CE Credits Online. I also spend a chunk of each day hunting down more gigs on Freelancer (where I have had no luck at all), Upwork (where I got my gig with CE Credits Online), and FlexJobs (which requires a monthly fee, but is outrageously worth it for the curated, easily searchable, not at all spammy array of jobs it provides). These consistent gigs (TakeLessons.com since March and ETS March-September) classify me as an independent contractor.

I complete these gigs at home and for the online tutoring job (where I video chat with language learners across the country), I have to maintain a presentable home office in order to build ethos with my client base. This is where things get good. My internet costs are a requirement for both gigs, so beginning in March, I can deduct the cost of my internet service up to the percentage that is used for business ($600 * .3 = $180, in my case). I use the internet at home ALL DAY (and some nights) for work, but Clint and I both also use the internet for entertainment, which is unfortunately not tax deductible, so I have to be realistic about what percentage overall has been used for business. To my surprise, the cost of my health insurance, which as an adjunct I was not offered from my employer, becomes deductible in full as an independent contractor.

I attended a conference this spring that enabled me to get the job I currently have doing online course design. That cost me $1,350, which I can deduct. I pay for this domain in order to increase traffic to my site and drum up business (to the tune of $99/year) which I will absolutely deduct. I maintain memberships to many online tools that help me with my tutees (total $500 per year deducted). These are all costs that I’ve been eating in the name of my career as a teacher, but as an independent contractor, I can re-envision them as what they really are: the costs necessary to maintain my own business. Indeed, an actual brick-and-mortar business gets to write-off the overheads that would otherwise negate their profits. Independent contractors get to do the same.

I plan to write more posts about adjuncting + freelancing (for many of us, a necessary combination for self-sufficiency). Let me know your story in the comments! I would love to hear about other people’s experiences with freelance academia as I continue to explore it myself and write about the topic here.

*As of Friday September 29th, the California State University system no longer administers the English Placement Test, so this job no longer exists, sadly.

NB: I love reading tax code. I don’t know why, but it’s extremely rewarding for me. It probably isn’t for you. We should probably both hire an accountant anyway.