Three years with no boss

Freelancing rarely has an official start date, at least not in the same sense as a traditional 9-5 job. Most freelancers I know just pick a day — the day they quit their former full-time job or the day they formed their LLC, for example.

I picked March 30, 2022 — the day I received my first payment (which was actually for work completed almost nine years earlier, but that’s a story I’ve told before).

Which means I just celebrated my THIRD freelance anniversary! 🤯

I wanted to do some reflecting in this week’s newsletter, but I didn’t want to just list lessons I’ve learned 🥱

Instead, let’s do some “how it started vs. how it’s going”

My Workspace

How it started: I worked at the kitchen table or on the couch when I first started. I didn’t have a desk or office.

How it’s going: I have a beautiful workspace that I absolutely love, located in a sort of nook/landing at the top of the stairs in my house. (It’s not usually quite this tidy.)

Lead Sources for Projects

How it started: My first several freelance projects were either from Upwork or people I knew from previous FT jobs.

How it’s going: The vast majority of my work now comes from referrals, prospects finding me on LinkedIn, and ongoing relationships with a few agencies/editors.

Project Rates

How it started: Like many freelancers, I started out writing blog posts for next to nothing. My first few earned me just $50 each.

How it’s going: I now confidently and consistently charge between $500-$1000 per blog post/article, depending on length and complexity. 

Income Variation

How it started:

How it’s going:

This is my first 12 months versus my last 12 months.

Freelance life, amiright? 🎢

Mindset

How it started: Overwhelmed, insecure, major imposter syndrome. No idea what I’m doing. Healing from burnout and toxic hustle culture, trying to unlearn “employee” mindset and become a good boss to myself. 

How it’s going: I still struggle sometimes, of course, but I’m generally much more confident and comfortable. It took a while to find my footing, but I now have a general routine, along with processes and tools in place to handle project management, accounting, client communication, and other tasks.

Work-Life Balance 

How it started: From the very beginning, I’ve been averaging 15-20 hours per week. Early on, a fellow freelancer told me that I’d definitely be working 40+ hours per week once I became “a more established freelancer.” 🙄

How it’s going: I still work 15-20 hours per week, most of the time! Sometimes it’s 25-30 hours, sometimes it’s 5-10. Or even zero.

The main difference is that I no longer feel like a slacker for working fewer hours. In fact, I now feel strongly that no one should have to work 40 hours per week. (Plus, consider the time we spend doing unpaid labor!)

Despite its ups and downs (and I had a long “down” spell in 2024), freelance life is still the life for me! I can’t believe it has already been three years, and I look forward to many more! 

Thank you, readers, for being here with me. 💗 

See you next week,

Kara

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.