I swore I’d never be a freelancer

Today’s edition of Wishful Working is a 4 minute read.

Once upon a time, I swore I’d never be a freelancer.

The year was 2014. I was a fresh college graduate. 

With my advertising degree in hand, I hunted for a role in advertising, marketing, or design. I dutifully scrolled through job boards, filled out applications, sent cover letters, and heard crickets. 

In the meantime, a lady from my church reached out and asked if I would be interested in helping her with a logo design for her small business. “Hell yeah,” I thought, and offered to design her logo for $125. I came up with a design based on her notes, worked through edits, sent the files and my invoice.

And heard crickets.

I followed up five times in the next six months, and then I gave up. Although it was one bad experience with one client, it left a bad taste in my mouth about freelancing. Between that failed freelance gig and the never ending job search, the wind went out of my 21-year-old, recent-grad sails.

A few years later, during a different but equally endless job search, I cautiously, cynically, dipped my toes into freelancing again — this time with moderate success. I used Upwork this time, and I wrote product descriptions for contact lenses and Halloween costumes for pennies per word. It was fine as a way to earn a bit of cash while unemployed and living at home with my parents, but I couldn’t imagine making a career out of it.

Eventually, that endless job search did end, and I put Upwork and the whole thought of freelancing behind me once again.

Until 2021, when I married a Canadian grain farmer and moved to his small town in rural Saskatchewan. As a brand-new Canadian resident, I didn’t have a work permit yet. If I wanted to work, I would have to find a remote role with a US-based company.

Or.

I could try freelancing. Again. 💀

Given my past experiences, the idea did not appeal to me at all. But I was super burned out from my last job, so jumping into a full-time, remote role also didn’t appeal to me. 

Ultimately, freelancing was the lesser of two evils.

As I researched freelancing, worked on my personal website, and did a lot of soul-searching about myself and my career, I discovered an unexpected barrier in my mind — a ghost from my past, if you will. A hatchet that needed burying.

So I sent one more follow-up about my ignored invoice from 2014 — almost nine years later. Was it a bit petty? Yes, absolutely. Was it cathartic? 1000%. Did I get paid?

Kind of.

Turns out, the “small business” I designed a logo for was actually a sketchy MLM smoothie shop. It tanked years ago, and the church lady’s business partnership with two others had not ended amicably. She agreed to pay “her share” (⅓) of the invoice total — $41.66. To her credit, she paid me this amount, promptly, via Apple Pay.

And so the first payment I received as an official, “full-time” freelancer was actually payment for my first freelance project ever. 

I wish 21-year-old Kara could see me now.

I don’t work with clients who ghost me. I don’t use Upwork. And my invoices are for quite a lot more than $125. Now, I’m more likely to swear I’ll never be an employee again!

Funny how that happens.

See you next week,

Kara

Kara Detwiller is a writer 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.