Nude Model, Babysitter, & 32 Other Jobs On My Résumé

EveryjobI'veEverHad_slide1_MaddyIllustrated by Madelyn Somers.
Recently, someone asked me what my very first job was. As I paused to think back to my early years earning a wage, I realized that my work history was quite expansive, indeed. And, pretty interesting to boot! You can't say I was ever afraid to try new things — and get paid for them.
Middle school (1994–1996): babysitter, newspaper reader at the nursing home, piano teacher’s assistant.
I started working the summer I turned 13. Babysitter was an obvious job choice (remember how in the ’90s, 13-year-olds could still be babysitters?), and since my mom is a piano teacher, I got the job of piano teacher’s assistant without even having to interview.
The nursing home job was technically a volunteer position. Twice a week, I read the newspaper aloud to a nursing home resident who was blind. I also read books aloud to her. Um, I totally felt like Jo March.
High school (1996–2000): dishwasher, waitress, piano teacher, choral accompanist, church organist, music transcriptionist, retail worker. My entire family is musical, so it’s not at all surprising that I spent high school working as a piano teacher (ahem, having been promoted from piano teacher’s assistant) as well as a choral accompanist and church organist. I was a good piano teacher, a decent accompanist, and a terrible organist.
Music transcriptionist, in which a family friend gave me her handwritten music scores and I typed them note-by-note into an early music software program, was also a natural use of my talents.
Dishwasher, waitress, and retail worker were, of course, bog-standard teenage jobs of the 1990s. I quit the dishwashing job because it was miserable, and I got bullied. I was still young enough to love waitressing though. I was a reliable retail worker, but I kept accidentally breaking the merchandise.
College (2000–2004): choral accompanist (for two choirs), musical theater accompanist (three different theaters), church organist (two churches), lounge pianist, piano teacher, camp counselor, house-sitter, dog walker, nude model, dinner theater performer — until the owner ran off.
Let’s start with that last one first, since it requires some explanation. I spent exactly one summer in college working as a dinner theater performer. I had to wear the top hat and leotard/vest combo (think the opening to Family Guy). Pay was $50/night, which was a really great deal at the time. Then, the theater owner literally skipped town, ostensibly without paying any of the theater’s bills. However, all of my checks cleared.
I was also still making money off my ability to play (and teach) piano, picking up as many gigs as I could get. In many ways, I was getting my first lessons in how to hustle.
Camp counselor for a fine arts camp was also a logical job choice, and when I needed to spend a summer working on an independent study project, I figured house-sitting/dog- walking would be a good way to make money without doing a lot of work. (I was correct about the house-sitting part.)
And, then there was the time I tried to earn extra cash by nude modeling for an art class. After I got hired and completed my first session, my mom told me she would pay me not to be a nude model. I took her up on the offer.
EveryjobI'veEverHad_slide2_MaddyIllustrated by Madelyn Somers.
The year between college and grad school (2004–2005): telemarketer, house painter, envelope stuffer, receptionist, waitress, booth babe, retail worker, continuing education instructor, assistant children’s theater director, founder and director of Canton Children’s Theater.
I guess I really did know how to hustle. I had, like, a jillion jobs during the year between college and grad school.
Telemarketing was the big job and the first job I considered a “real, grown-up job.” I wrote about that experience in a recent Billfold article.
I also picked up temp work, such as the weekend stint as a booth babe for a trade show. (I was a really, really awful booth babe. I just don’t exude babe-itude.)
And, I founded a children’s theater that year. We got NEA funding, and it ran for three summers. I’m really proud of that, and I don’t get to talk about it often.
Grad school (2005–2008): finance assistant, Country Insurance; assistant company manager, Illinois Shakespeare Festival; assistant to the artistic director, Illinois Shakespeare Festival; visiting instructor, University of Hyderabad.
Now we start getting into the jobs that I put on my résumé. The ones that last longer than a weekend.
I was getting an MFA, and not everyone understood why I was also taking this job at an insurance company instead of, you know, seeking out unpaid internships or exposure opportunities. (In fact, it was pretty clear that, by taking a job unrelated to my MFA studies, I was doing something that was considered Very Bad Form.) On the other hand, I needed the money, and I’m really glad I worked for Country Insurance both for the paycheck and for the actual, real-world office experience.
I also worked for the Illinois Shakespeare Festival for three years, and spent one year teaching Shakespeare in Hyderabad. And, of course, I taught 100-level theater courses for the university.
After grad school (2008–present): executive assistant and project management specialist, Stimson Center; general manager, Hello, The Future!; project management consultant for a bunch of geek bands; freelance copywriter and essayist.
And, here we are at present. I spent four years working as an EA and project manager at a think tank, then I spent about a year as a touring musician (that’s the “failed business” I referred to in my last Billfold piece), and now I’m a freelance writer.
It’s really interesting to see the patterns in my career history. I’ve had administrative office jobs, but I’ve also been hustling and cobbling together my own income, ever since the beginning when I was combining piano teaching, choral accompanying, music transcription, and working as an organist. I’d like to coalesce this into some kind of narrative re: “I’ve always been a freelancer at heart,” but I know that is more confirmation bias than anything else.
It will be very interesting to see what kind of job I have five years from now.

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