4 years of learning and unlearning

On March 30, I celebrated four years of freelancing!

In some ways, I still feel like a baby freelancer figuring things out, but in most ways, I feel like a seasoned (and sometimes wizened) old pro.

In keeping with tradition, I’ll spend today’s newsletter reflecting on the past four years. Last year, I did a round of “how it started vs. how it’s going,” and two years ago, I reflected on various milestones along my freelancing journey.

This year, I’m sharing four things I’ve learned (or unlearned) about work over the last four years.

My first year of freelancing was all about figuring out how to be a self-employed person — and how that’s very different from being an employee. I learned hard skills like bookkeeping, pitching, invoicing, and self-employment taxes. I learned soft skills like negotiation, networking, and firing clients. I learned many things the hard way.

But most of all, I had to unlearn some deeply held beliefs and habits surrounding work and what working is “supposed” to look like. I felt a ton of guilt and shame about working less than 20 hours/week — even when it was working for me and my clients and I was happy with my income. The employee part of my brain said I was slacking off, lazy, and unproductive.

I also had to rethink how I valued my time. At past jobs, my performance was always measured by hours logged. Once I was working for myself, I could stop trading time for money and start setting flat rates based on well-defined deliverables. Project pricing rewards my expertise and efficiency, but I had to shift my mindset from “employee on the clock” to “expert delivering value.”

I quickly found that the freedom and flexibility of freelancing suited me just fine, and I got lucky with some early success and recurring work in my first year freelancing. Things were pretty great, but I felt I was constantly waiting for the other shoe to drop. The “feast and famine” experience of freelancing was stomach-churning (pardon the pun), and part of me wanted off the freelance income roller coaster.

But the truth is that unpredictability and the push-pull of stability versus freedom isn’t unique to freelancing. In fact, traditional employment is often just as unstable as self-employment — the news is full of headlines about economic upheaval and AI-related job cuts. 

Basically, it’s a choose-your-own-uncertainty type of deal, and realizing that helped me buckle up and embrace the roller coaster. It also made me recognize the privilege and the safety nets that allow me to embrace the risks of freelance work.

I started to dig deeper into the injustices of the modern working world — the insane wealth hoarding of billionaire businessmen, the exploitation of workers at every level, and the systems that keep us too busy and too tired to question any of it. 

This is how Wishful Working came to be. (I’m still really proud of my first-ever newsletter, which landed in precisely 46 inboxes in December 2023.)

Here we are, 104 editions (and hundreds of subscribers!) later! Before I launched this weekly newsletter, I struggled to post one monthly blog on my portfolio website. Isn’t it funny how some things stick and others don’t?

I started to learn that I’m allowed to change my mind. I’m allowed to try something and then turn it into something else — or abandon it entirely! (Sometimes, quitting is a secret superpower.) I consider Wishful Working a success, but I’ve had experiments that flopped hard:

The more things I’ve tried, the more I realized that nothing is really that serious. The stakes are low. And experimentation is absolutely mandatory.

This past year was weird. On one hand, it was my highest earning year yet. On the other hand, I was plagued with existential dread and indecision. 

I’ve long known what I don’t want to do in my career: managing other people, coaching, selling courses, climbing any sort of corporate ladder, etc. But it has taken a while to accept the truth about what I do want, which is to be an author and an artist and to make a living from my own creations.

I started drafting my first novel in September, but progress is frustratingly slow. I’m working on art occasionally, in fits and starts. It’s halting and embarrassing, but I’m determined not to leave these things for “someday.” If I die without having written a novel, my ghost will be very, very upset.

So, I reevaluated my income goals and purposefully scaled them back. I decided to pause on actively seeking more client work because I want time for creativity more than I want money. 

I’m pursuing my own version of success instead of chasing more for the sake of more.

Thanks for walking down memory lane with me.

Here’s to more learning and experimenting and failing and pivoting. 🥂

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.

Why Wishful Working? I want to help people thrive in a world obsessed with work and productivity. Together, we’re expanding the definition of productivity, rediscovering life balance, and exploring the many kinds of work that make life possible.