☕Not All Pivots Are Permanent
A guest post by Kara Detwiller of Wishful Working
Kara was one of my first freelance friends from back in the Twitter days. Today, she’s taking over the Over Coffee post to share about her experience with pivots throughout her freelance career!
I started freelancing in March 2022. At first, I felt quite lonely and isolated, but soon, I started meeting amazing freelance friends through Twitter — specifically the #FreelanceChat community. Stephanie was one of my first freelance friends! I love the story of her freelancing journey, and I admire her drive and tenacity. We’ve been cheering each other on for well over two years now
I miss old Twitter. I loved connecting with other self-employed folks, and I was slowly but steadily building a following there. Because I was all in on Twitter, I clung to it a while longer than many of my fellow freelancers, who jumped ship as soon as it started going down the toilet (thanks, Elon).
I don’t regret leaving, but I’d be lying if I said I haven’t struggled to find community since. I tried to get into BlueSky and Threads, but they don’t feel the same. I joined a paid freelancing community, but then it closed down. I tried a virtual coworking app but didn’t stick with it. I’ve basically cobbled together a sense of community through LinkedIn and a few other groups (like Lex Roman’s Legends!)
Leaving Twitter and finding a new freelance community is just one example of a pivot I’ve made in my freelance journey, and there have been many:
After an early bad experience with a freelance project after college, I swore I’d never be a full-time freelancer.
When I first started freelancing, I offered a ton of different services, including graphic design. I quickly learned that, while I enjoy designing for myself, I hate doing it for clients.
I once said I didn’t want to freelance for agencies, and now the majority of my income comes through agency partnerships.
I once launched a productized service that got exactly one customer.
I tend to feel sheepish about these pivots, thinking of them in terms of failure and giving up. But that’s both unfair and untrue. Freelancing is all about experimentation! Some pursuits don’t pan out, and that’s okay. Some projects do pan out, but then we realize they’re not taking us in a direction we want to go. Sometimes there’s no real problems, but it’s simply time to move on to a new experiment.
The beauty of freelancing is that you’re in control. The horror of freelancing is also that you’re in control. No one is telling you what to do (in a bad way), but no one is telling you what to do (in a good way).
Don’t let decision paralysis or fear of the future stop you from pivoting or trying something new. Trust yourself and know that you’re allowed to change your mind.
📖Reading
I finished two books in October: Bird by Bird by Anne Lamott and Last Days of Summer by Steve Kluger. Bird by Bird is one I’ve seen on just about every list of “books about writing,” and it is also a memoir. I love Anne Lamott’s voice, and I definitely want to read more of her books. Last Days of Summer is a book I first read more than ten years ago — it was my gateway drug to epistolary fiction. If you like coming-of-age stories and unique novel formats, this one is for you. I’m currently reading Nora Goes Off Script by Annabel Monaghan, one of my new favorite romcom authors.
🎧Listening
I’ve been listening to the audio version of The Secret History by Donna Tartt. (I know, this is also technically “reading,” but it deserves its own time to shine.) The dark academia atmosphere is so immersive, and the plot is absolutely enthralling. Also, Donna Tartt’s writing and narration are excellent — she really makes her characters feel like real people. I don’t read a ton of literary fiction or thrillers, but I’m having such a great time. (FYI: The chilly descent into winter is the perfect time to read this book.)
🤍Loving
Last year, my husband became obsessed with wool and started buying secondhand wool sweaters for every occasion. I guess the obsession is contagious because I’ve been on a bit of a Poshmark binge lately. I love wearing clothing made from natural materials like cotton, linen, and wool, but they can get expensive. Poshmark, ThredUp, and eBay are full of awesome (and affordable!) secondhand and vintage options.
🧠 Thinking
I’m trying to wrap up all of my freelance work for the year by November 30 because I’ll be traveling in December. That means November is going to be busy, but it’s going to be worth it! I’m also thinking about travel plans because I don’t have everything booked quite yet.
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Kara Detwiller is a writer and creative based in small-town Saskatchewan. She publishes Wishful Working, a weekly newsletter exploring self-employment, anti-hustle culture, and the future of work. She also writes long-form content for enterprise SaaS, cybersecurity, and manufacturing clients. She is also working on her first novel, among other creative pursuits. Connect with Kara on LinkedIn.