Every Side Hustle I’ve Ever Had: Playwright, Professional Desk Cleaner, Transcriptionist

Photo credit: Lara604, CC BY 2.0.

My first eight years living in New York, I was always working multiple jobs. Most of those eight years were spent at a full-time office job while working nights and weekends in a bookstore. Because I am that much extra, I ended up also seeking out any other money-making hustle I could in hopes of building up my savings and paying down debt. Here is a list of pretty much every side hustle I’ve had in the past ten years:

Writing plays

One of my favorite parts of working full time at a play publishing company was that my coworkers were also writers an incredibly creative. One of the founders wrote some of the most popular one acts in the country, and it is with their encouragement that I published two one act comedies with the company. Both were based on life experiences—one was about studying abroad and the other was about working in retail.

Since publication, those plays have picked up productions around the country in middle and high school drama programs. While I’m no Arthur Miller (or even Jon Rand, the ever-prolific co-founder of our publishing company), I have gotten around $25/performance, a welcome passive source of income, in addition to the honor of knowing my work is being performed in parts of the country I have never even been to.

Writing articles

When the play publishing company I worked for started publishing musicals, I was especially excited. In college, I had fallen down a rabbit hole of watching YouTube videos of concerts of songs by up-and-coming musical composers, and I viewed this as an opportunity to help give exposure to these artists I had fallen in love with. To help champion the artists I loved, I started a blog that featured their work, and I maintained that blog for 5 years (I even had a theme song, procured by supporting the Kickstarter of one of the writing duos I featured).

Because of the musical blog, I got the chance to be a regular guest blogger for Crazytown, a blog started by one of the composers I really admired, Ryan Scott Oliver. Though writing for Crazytown, like my musical blog, was unpaid, I got to write alongside a big group of writers who I adored and worked in all kinds of sectors of the arts community.

After doing this for a few years, I realized how time-consuming writing for free was. Feeling emboldened by my years of writing experience for free, I decided to turn my attention to trying to pitch venues that paid per article. This has led to credits on HelloGiggles, Extra Crispy, The Toast, and the Washington Post. And, of course, The Billfold, which is a forever favorite.


While working at the play publishing company, a big part of my job was typesetting/formatting the play manuscripts for them to be printed into books. I had already had some experience with Adobe InDesign from my days as Editor-in-Chief of my high school’s literary magazine (yes, sometimes the things you learn in high school can help your entire career), but when the company moved over to that program for its layout needs, they brought in someone to train us over the course of a couple days. I took to it immediately, loving creating templates and finding ways of streamlining our design process.

A coworker, who was taking design courses, told me that one of her classmates worked for a financial company that needed help creating test prep materials out of slides. She put me in touch, and I was contracted to work on designing the page layouts for a few books. I made a few thousand dollars and even negotiated a higher fee for some of the books based on the length of the project. Upon reflection, I think getting this job was the main reason I was able to pay off my government student loans only a few years out of school.

Years later, while working at a publishing consulting company, my coworker was serving as Editor-in-Chief of a literary magazine and was stressed because she was having trouble finding someone to lay out the issue she was working on.

“Let me know if you have a recommendation for someone,” she told me one day.

“Um… me?” I asked.

I earned $1,000 for the entire job, paid in installments as I worked on it. It was nice to feel like my experience in doing layouts came full circle as I worked on a literary magazine, years after finding a passion for publishing working on the literary magazine in high school.

Marketing for LGBTQ theater festival

I was starting to think about my next career move and knew I wanted to focus on something in marketing. I had written copy for conferences, done social media and website managing, and even was named an honorary member of the marketing department at the play publishing company, but I didn’t have work experience that explicitly had the word marketing in my title. So when I saw a listing for an LGBTQ theater festival looking for a freelance marketer, it seemed like a good opportunity. I could make some money working in a theater position on the side and the gig was temporary, since the festival would conclude only a few months after I started.

I found the board of the festival to be incredibly welcoming and the participants’ passion and enthusiasm inspiring. I was happy to be advocating for a cause I believed in, and I liked giving the artists involved a more visible platform for their work.

That being said, taking on a very involved role in a theater festival, along with my other two jobs, was incredibly stressful at times. Outreach and managing goals and expectations from lots of different personalities was very time-consuming, and working remotely sometimes only complicated communication.

In the end, ticket sales were higher than they had been in the past, and I was thankful that the organization appreciated my work. They asked me to stay on, but with the amount of time I had put in for the festival, I had calculated that the amount of money I made from the stipend only came to pennies for each of the many hours I put in. Realizing I needed to focus on my other jobs, since they were my bigger sources of income, I turned them down.

Freelancing for a digital marketing agency

When another publishing consulting company that worked often with the one I was working for decided to start a digital marketing agency, my colleague who worked there offered to add me to their stable of freelancers. She gave me an extensive training session in how to do digital audits, looking at book titles in publishers’ backlist catalogs and see how to improve their SEO and metadata. It was an eye-opening crash course in how online profiles are constructed and ways of improving discoverability online. I was paid $17/hr to put together research reports with recommendations, and I valued everything I learned from the few assignments I got from them.

While this was not my most lucrative hustle, it was one of the most valuable learning experiences. When I started working for a publishing house, I already had a lot of tools for marketing and metadata that set me apart from the rest. I can thank this job for that.

Cleaning a lawyer’s desk

After finding a new job after being laid off, I was living particularly lean. Luckily, a friend recommended me for a gig helping organize a lawyer’s office. Once every couple of weeks, I would come in and just tackle the mountains of paper that would build up on his desk. I was paid a very nice $25/hr in the form of a check at the end of the night, but sometimes the job would feel brutal. I was sifting through papers that were just stacked with no order and were mixed in with trash. I found lids from lunch salads, soda cans, and receipts and napkins mixed in with stray mail. I once found a dried lemon wedge stuck to the back of a court document.

To be fair, I also don’t think I was necessarily doing a good job. It was hard to figure out how to best organize things when I had no context or order for the documents in front of me. After coming in a few times, the lawyer stopped asking me to come in, and I didn’t follow up.

Taking surveys for money

I had seen a YouTube personality mention taking surveys for money—she sold me on it by saying I could do it anywhere, passively. Just take them while you watch TV! she had said.

While taking surveys is a pretty brainless job, it’s not entirely so. You need to pay attention so that your answers are truthful and consistent. It also requires reading and, in some cases, watching video or listening to audio. The pay was terrible. I literally made $0.50-2.50 a survey, and I couldn’t get paid out until I had accrued over $10. Almost every survey also had a pre-survey to see if I qualified, which meant I did a lot of question-answering for free, checking boxes on to be told after the fact that I didn’t qualify.

I finally decided to stop taking the surveys altogether when I was taking a rather long (though more lucrative) survey and got cut off near the end because of a technical glitch. The survey would be considered incomplete and I would not be compensated, despite putting in a good amount of time. This was also not the first time this happened. Realizing my time and attention was more valuable than a dollar or two, I stopped logging in.

Judging students’ writing

Every year, I get an email asking for people to serve as judges of a writing award for students. In exchange for critiquing a packet of pieces, usually across 3 genres of your preference, judges are awarded an honorarium that has ranged $60-85.

This is always a nice gig to participate in because it’s fun to see what you writers are submitting and it can be done remotely. The biggest drawback is only that payment often comes a few months after completing the judging, but the work itself is interesting and it’s all for a good cause.

Doing transcription

I had seen transcription jobs being listed on Craigslist before when I was in college, but I think I had tried to do a sample once and my typing was so slow that I was convinced that I wouldn’t be able to do it fast enough to make any real money. However, someone in a Facebook group I was in asked one afternoon if anyone would mind taking over a job she didn’t have time to finish, and I was strapped for cash.

After immersing myself in it, I eventually got the hang of transcribing, in this case for a documentary television show about different environmental concerns in different parts of the country. The contact I made at the show started sending me my own assignments, and I found myself transcribing interviews for a few different episodes every year. My favorite part of doing these jobs is that I always learn so much from every tape I transcribe, whether the video is about flood regions or hiking trails or quail.

Kimberly Lew has had many side hustles—some that she almost did but did not do for various reasons include: doing the overnight shift writing product placement quizzes for television surveys, working as a retail associate for an all-frozen-food grocery store, and becoming a Task Rabbit. www.kimberlylew.com

This story is part of The Billfold’s Career History series.

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