After revisiting one of my favorite books (The Anthropocene Reviewed by John Green) earlier this year, I decided to borrow his format to review the world of work. So far, I’ve mostly reviewed office-related things, like performance reviews, sad desk lunch, office gossip, and the “magic table.”
Today, I’m going to tell you how I really feel about self-employment:
Working in sweatpants
I’m not going to beat around the bush: I love this. I did it today. In fact, it has only recently started being cold enough here to wear sweatpants instead of shorts. A few days ago, I took my puppy outside for a morning potty break while wearing my summer uniform (shorts and a t-shirt) and found the air had a bit of a bite to it! I looked at the weather app, and it was 41 degrees. Anyway.
As much as I value comfort, I’ll admit that working in sweatpants does occasionally make me feel a bit… frumpy. But alas, I have yet to crack the code on a WFH wardrobe that is fun, comfy, and me. The closest I’ve come is probably this fleece jumpsuit I sewed a while back:

(Intentionally cropped image, #nofreefeetpics) - This is the Clyde Jumpsuit by Elizabeth Suzann, btw. I can fit my 13-inch laptop in the pocket lol
I think the sweet spot might be to find some stretchy pants that are slightly more elevated than sweatpants. Cute joggers maybe? I’m not a big fan of leggings. I should at least replace my current favorite sweats because they are full of tiny holes from baby Sammy’s needle puppy teeth. In any case, I give working in sweatpants 4 stars. ⭐⭐⭐⭐
The revenue roller coaster
I’ve written about the freelance revenue roller coaster before — I called it the “income roller coaster” then, which is much less jaunty. If I tell you that I don’t actually mind the unpredictability of self-employment income, I wouldn’t be lying. But it would be my privilege speaking. And my safety net in the form of a spouse who also has a job, and whose income pays the majority of our bills. If I have a lean month (or a $0 month, which has happened), it’s not great, but it’s not a disaster.
And the peak months? Way more money than I ever made in a month at my previous job(s). Ideally, the good months create a buffer for the less-good months. Plus, I’m a budgeting nerd, so I figure out how to make it work. The ride is actually pretty thrilling. I give the revenue roller coaster 3 stars. ⭐⭐⭐
Taking random weekdays off
There are a lot of ways to take advantage of the flexibility and freedom that self-employment offers, but having random weekdays away from my desk is a special one. Whenever we need more than basic groceries, we have to drive to “the city.” For us, that means a 90-minute drive (3 hours total), so we tend to make a day of it: Costco, thrift shopping, pet store, farm errands, oil change, Facebook Marketplace pickup. We’ll pack everything in.
It would be hard to do that if I had to clock in for regular hours every weekday. Also, my husband is a farmer, which means he’s very, very busy during certain times of the year (i.e., now, during harvest) and very unbusy during other times (i.e., winter). I like having the flexibility to work in a way that lets me spend more time with him! And that lets us travel. Last year, I got to spend an entire week crossing the Atlantic Ocean on a boat (boat may be underselling it a bit) and an entire month traveling around the UK at Christmastime.
I give taking random weekdays off 5 stars. ⭐⭐⭐⭐⭐
Making freelance friends
I feel extremely lucky to have stumbled my way into an incredible community of freelancers very soon after I started freelancing in March 2022. This particular group was on Twitter (RIP #FreelanceChat), and I’m still connected with many of them! I’ve also met lovely people on LinkedIn and through other freelancer communities (RIP Pollen 💔) I’ve even had IRL coffee chats with two Canadian pals who made it a point to reach out to me when they were visiting Saskatchewan.
Freelancing can be lonely. I do, at times, miss in-person collaboration. But after nearly five years doing this freelance thing (omg), I find myself surrounded by a lovely little network of folks all over the world. And whether they call themselves freelancers, fractionals, consultants, solopreneurs, or founders, they all have something in common: they’re sharp, scrappy, generous, and kind. I give making freelance friends 1 million stars. ⭐♾️
See you next week,
Kara
Out of Office
What I do when I’m not at my desk
Reading: The book club I lead through my local library is back after a summer hiatus! We’re reading Homegoing by Yaa Gyasi.
Watching: Now that my husband is almost done with harvest (hallelujah!), we’re getting back into TV and movies. We just started the current season of The Traitors (Canada edition), and we’re SO HYPED for The Celebrity Traitors (UK). I am not into many reality shows, but my British friends got me hooked on The Traitors last year.
Doing: Idk, rethinking my entire life??? Something about back to school/autumn makes me want to mix things up and start something new, or maybe end something??? That sounds ominous. Stay tuned 👀
Kara Detwiller is a writer and artist 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.
