Might quit my job to focus on summer

I keep seeing variations of this joke floating around the internet:

It’s one of life’s great tragedies that most of us can’t just quit working during the summer. Even teachers, the targets of corporate worker envy every time the school year ends, often work summer jobs to make up for inadequate teacher pay (ugh).

But if you work for yourself, you control your schedule. When I became a freelancer, I threw the traditional 9-5 schedule out in favor of slow mornings, afternoon naps, and running errands in the middle of the day. I can take a day off without asking anyone for permission.

Becoming a freelancer also meant getting on the freelance income roller coaster. This ride has tall hills and low dips. A record-high revenue month can quickly come crashing down into a goose egg month. This means I’m more financially comfortable when my schedule is quite full, so I try to keep it that way… often to the point of overwhelm.

Fellow freelancers will be well acquainted with these feelings. You spiral about having too much work, soon followed by a spiral about not having enough work. I’ve gotten used to the roller coaster, and I’ve learned it’s a feature of freelancing, not a bug.

But I’ve also started experimenting with another option: getting off the roller coaster. Not permanently — I don’t want to quit freelancing, and I don’t want a full-time, 9-5 job. Perhaps a better metaphor would be getting off the 70mph VelociCoaster (IYKYK) at Universal Studios and boarding the little train that circles Walt Disney World at 10 mph. (Can you tell I’m a theme park fan?)

My first intentional-slow-down experiment was in 2023, when I decided to wrap up client work by the end of November and take the entire month of December off, save for a bit of admin work and planning for the new year.

Reader, I hated it.

While it was nice to have a break from client work, I floundered in the unstructured free time. I wasn’t intentional about it because I didn’t have a plan. Instead of a month full of rest and hobbies and leisure, I ended up with a month of boredom and anxiety. 

One of the biggest problems? December in Saskatchewan isn’t particularly nice. It’s cold and dreary. I learned I’d rather work through December or take a vacation, but I don’t want to lie around my house doing nothing.

But summer in Saskatchewan is a different story. Summer in Saskatchewan is glorious. The weather is lovely and warm but not nearly as hot and muggy as my summers in Iowa. The fields get lush and green. The canola blooms bright yellow. The meadowlarks are literally calling to me. In the summer, I like to spend as much time as possible doing nothing, preferably outdoors in a hammock or lawn chair or kayak.

So when my super busy spring started slipping into an equally busy summer, I decided to do something about it:

• I told a smaller client that I needed to pause our monthly recurring project until September.

• I declined a meeting with a potential new client because my plate was already full.

• I told another client that I wanted fewer assignments due to summer travel and leisure plans.

To be honest, doing this felt bad. It felt insane. As a freelancer, you learn to take work when you can get it because you never know if it’s going to dry up. And if I’d had a slow spring, I might not feel comfortable purposefully turning off the tap like this. (It’s not completely off, to be clear. I do have a few projects on the go.) 

If things don’t pick up again in the autumn, I might have major regrets. I might curse Past Kara for her imprudence.

But I doubt it. 

Because I’ve already logged more hammock hours than I can count, and it’s only mid-July. When this email hits your inbox, I’ll be in Iowa visiting my family for the second time this summer. I’m taking a lake vacation with some of my besties in August. And I’m enjoying it all with less stress and fewer deadlines breathing down my neck. 

What’s the point of freedom if you don’t take advantage of it?

See you next week,

Kara

Out of Office

What I’m doing when I’m not working

• I scheduled this post in advance because I’m currently in Iowa visiting my family and friends! I’ll have more to share in next week’s email, I’m sure. 😎

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. 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.