Every job I’ve ever had

I love a bit of lore, especially when it comes to my professional connections and internet friends. Because we usually talk about work things, casual personal factoids often feel like thrilling lore-bombs. I love it. 

Today, I’m dropping my work lore with a brief rundown of every job I’ve ever had. (With commentary I would never include on a resume.)

Babysitting 🍼

The quintessential first job for a teenager. Looking back, it’s sort of wild that parents would entrust me with their small children when I was essentially just a slightly larger child. 

Little League Concessions 🥨

In high school, I had a brief stint being paid under the table to keep an eye on a hot dog roller and pour cups of bad coffee for grumpy baseball dads. 

Janitorial Services 🚽

In college, I got a (very) part-time job as a janitor for the events buildings. I typically cleaned up after trade shows, which was pretty easy. But once, I helped clean a performance center after an all-day dance recital. So. Much. Glitter.

Grocery Store Clerk 🍷

One summer, I got a job in my local HyVee grocery store’s Wine and Spirits department. To sell alcohol, I had to check IDs and type the customer’s birthdate into the checkout system. “If they’re clearly older, punch in any birthdate,” my trainer said. “Just use your own.” I laughed. I was 19, so that wouldn’t work.

College Library 📚

Though I always dreamed of working at a library, this job was not exactly what I had in mind. I worked in the electronic acquisitions department, manually combing through large spreadsheets to activate digital books. But I also unpacked the brand new boxes of books that arrived in the mailroom each week, cross referencing the invoice to make sure everything was there. Bliss.

Communications Internship 🎧

To complete my advertising degree, I had to do an internship. I found a (paid!) opportunity at a church in Greenville, South Carolina, where I enjoyed a lovely summer working on various creative projects, hanging out with the other interns, and eating good Southern food.

Summer Camp Marketing ☀️

After graduation, I struggled to find a full-time job. I ended up taking a part-time marketing job at a local summer camp, where I got to design t-shirts, event posters, and other promo materials. The work was fun, but I soon realized I needed to get a proper full-time job and move out of my parents’ house.

Volunteer Youth Worker (Gap Year) ✈️

Or, I reasoned, I could have an adventure before facing the world of rent and adult responsibilities. So, at age 22, I took a one-way flight to England and spent a year as a volunteer youth worker in schools and churches. Was this a wise financial decision? Maybe not. But it was truly the experience of a lifetime, and I have zero regrets. I completely fell in love with England and have been back three times since (soon to be four!)

Retail/Nonprofit Marketing 👕

After returning from England, I endured a stint of unemployment before landing a job doing marketing at a regional hub for Goodwill. Yes, the eponymous thrift store. This was my first “real,” full-time job! I really enjoyed the unique blend of retail marketing and mission-driven projects. And yes, I got an employee discount 😉

Marketing Agency 💻

My previous roles were more design-centered, and I wanted my next role to have more of a writing focus. I joined a digital marketing agency with a fun, casual culture — dogs in the office, free drinks in the fridge. Unfortunately, Covid hit just six months in, and we started working remotely, which was decidedly less fun. Still, I learned so much, and I found out I love working with “boring” B2B clients! Seriously, ask me what I know about manhole rehabilitation 🕳️

Freelance Writer ✏️

In October 2021, I married a Canadian farmer and moved to his hometown in rural Saskatchewan, where I live now! After some months off, I started freelancing. It has had its ups and downs, but it’s actually the best job ever. In a few months, I’ll celebrate FOUR YEARS of freelancing! 🤯 Wild! I’ve written lots about my freelance journey in past newsletters, like this one.

Substitute Librarian 📖

My small town library is only open two days per week, and there’s only one branch librarian. She asked if I would be a substitute, so I fill in when she’s traveling or sick. It’s a very part-time, very chill job, and I have loved meeting the readers in my community! I also lead a book club of mostly retired ladies. We have a great time.

What was your first job? Or your favorite job? Tell me an anecdote!

See you next week,

Kara

Out of Office

What I’m doing when I’m not working

• In January, I made a bingo card with goals for the year. Last week, I revisited the card (and filmed it for Instagram) and realized I’m one sewing project away from getting a bingo! 👀 Stay tuned.

• My husband, a farmer and hobby woodworker, discovered a woodworking competition tv show in the vein of The Great British Bake Off. It’s called Good with Wood, and it’s just as cozy and wholesome as GBBO. I only like competition shows where the contestants all help each other and cry when someone gets eliminated, lol.

Kara Detwiller is a writer and creative based in small-town Saskatchewan. She specializes in long-form content writing for enterprise SaaS, cybersecurity, and manufacturing clients. She is also working on her first novel, among other creative pursuits. To connect, reply to this email or find Kara on LinkedIn. To support her work on Wishful Working, share this email with someone or buy her a “coffee.”

Why Wishful Working? I write this newsletter because I want to see more people enjoy a life not centered around work. For some, the path to freedom and flexibility is through self-employment, but we also need to challenge cultural norms and champion healthier working conditions and work/life balance for all types of workers.