Freelancing can't be the only path to freedom

A few weeks ago, my workspace was featured in one of my favorite newsletters — Workspaces.

If you subscribed after seeing my desk in Workspaces, welcome! I’m so glad you’re here! If you missed it, check out my workspace tour (and subscribe to Workspaces!)

Sharing these desk pics got me feeling reflective about freelancing and working from home.

Like many, my first experience working from home started in March 2020. In the early days of the pandemic, my employer sent us home with our company-issued laptops, spare monitors, keyboards, and mice. 

I worked from home for the rest of 2020 and most of 2021.

The circumstances sucked, but working from home was kind of awesome. I’m an introvert, so I didn’t mind the solitude (plus I had an awesome roommate at the time). I was happy to have my commute shortened to the distance from my bed to my desk. I made eggs for breakfast. I napped during my lunch hour. I worked with my cat on my lap. 

I returned to the office in July 2021, and I left my job, got married, and moved to Canada a few months later. From November 2021 to March 2022, I took a much needed break from working. 

While we did some major renovations on our house, I recovered from burnout and planned my next career move. We live in a very rural area, so I knew I would probably work from home.

I considered looking for a full-time remote job but eventually decided to try freelancing (again).

I sat at my kitchen table with my old laptop that died within 3 minutes if it wasn’t plugged in, scrolling Upwork for hours and Googling things like “how to make an invoice.”

I wrote many blog posts for $50 and bought a new laptop way before I had earned enough to pay for it. 

After a few months, I moved from the kitchen table to my current office “nook” upstairs. I found more clients. I sent a well-time pitch that led to projects that pay upwards of $500 instead of $50. 

I adjusted to rural living and working from home in an area with no coworking spaces and no coffee shops. If I need a change of scenery, I can take my laptop out to my in-laws’ farm yard and sit on the porch or at a picnic table, farm cats winding around my legs.

In my first year freelancing, I matched my previous full-time income while working an average of 14 hours per week.

Personally, it’s hard to imagine going into an office every day. It’s hard to imagine working 8-hour days and 40-hour weeks. 

And it’s hard to stomach the injustice of corporate hierarchies where executives make billions while workers juggle multiple jobs just to survive. It’s hard to stomach the mass extraction of wealth from the global south.

As my personal working conditions have improved, I’ve grown increasingly uneasy with the answer to the question, “Why can’t it be this way for more people?”

Greed. Corruption. Capitalism doing what capitalism does.

Honestly, the scale and scope of the problem is so overwhelming that I don’t know what to do. I started this newsletter as a tiny way to shed light on problems with work and imagine a better future for all workers. I want to do more with my time, privilege, talent, and knowledge. I’m not sure what that looks like yet.

Coincidentally, traveling and time with loved ones are two things that always bring clarity for me, and I’m heading to Iowa to visit my family. I’ll be back in your inbox on June 26!

Again, I’m so glad you’re here.

See you later,

Kara

Out of Office

What I’m doing when I’m not working

• I enjoyed the fourth season of Clarkson’s Farm, a hilarious documentary-style show about Jeremy Clarkson running a farm in the Cotswolds in England. My farmer husband provides insightful commentary, and I contribute comments like, “That’s a Claas combine, right?”

• In addition to freelancing, I’m a substitute librarian in my small town, and I’m also on the library board. We just had a quarterly meeting, where we discussed things like new shelves, fundraiser ideas, and the exorbitant prices publishers charge libraries for ebook licenses.

• We planted four Parkland Pillar Birch trees in a row in our backyard. After they grow and fill out, they’ll form a sort of privacy screen. Yay trees!

P.S. Got a question about self-employment, anti-hustle culture, business books, or something else?

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 or Bluesky. 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.