The only way out is through

Someone I’m close with just started her first year of college. And although my own freshman year was fourteen years ago (omg), talking to her is bringing back memories:

• Moving away from my childhood home and into my dorm room

• Meeting my roommate, Shannon, and realizing that while she was nice enough, we were not going to become BFFs like I imagined

• Being hungry but not wanting to go to the dining hall by yourself

• Feeling crawl-out-of-my-skin awkward around so many new people

As my friend laments that she feels lonely and she misses her dog and she hasn’t met “her people” yet, I almost feel sheepish about my advice.

I tell her that I didn’t meet my lifelong besties right away and that she will definitely find people she clicks with. I tell her that “settling in” will take some time, but it will happen. I tell her she’s doing a great job, because she is. 

I start to realize that I’m of the things I’m saying to her are things I really need to say to myself:

You can’t avoid the discomfort and the struggle. Doubt and fear are part of the process. Some things have no shortcut — they just take the time they take.

I may not be experiencing anything as life-defining as going off to college, but I do feel like I’m in a weird transitional phase or season right now. My friend Alyssa recently wrote about liminal spaces, and I think I’m in one. I’m thinking a lot about my career and my future. I can feel myself moving away from some things and toward others, but I’m in between.

I recently shared my dream of having a career as an artist and novelist. I understand there is a lot of time and unglamorous effort standing between me and that dream — and there’s no guarantee of success. 

The first few weeks of writing my first draft of my first novel have been a slog with a few moments of inspiration and hope sprinkled in. I am not downloading perfect prose directly from my brain to my Google Doc. I catch myself wishing I could fast forward to a tidy final draft with all the loose ends tied up. I daydream about finding a literary agent and landing a life-changing book deal.

But ultimately, I would never want to skip over the striving and struggling phase because it’s more fun and satisfying than I ever imagined. 

When my friend was feeling frustrated with the shallowness of her brand-new friendships at college, she sighed and said, “I could really do with having a lifelong established friend group right now.” And then she laughed because she knows that’s not how it works. She knows that building relationships requires time and patience — and silliness and karaoke pizza parties and sometimes hanging out with people when you’d rather be alone (she’s an introvert, like me).

I’m learning that building something creative also requires time and patience — and silliness and sometimes sitting down at your desk to write when you’d rather watch a movie.

Maybe I should try a karaoke pizza party??

See you next week,

Kara

Out of Office

What I’m doing when I’m not working

• I’m listening to Bird by Bird by Anne Lamott, a book that I’m fairly certain is on every list of recommended books for writers. It is hilarious and relatable and I can’t believe it took me so long to pick it up. (Also, I believe Anne coined the phrase “Shitty First Drafts.” Go Anne!)

• My husband’s family plants a lot of potatoes in the garden every year, and we dug them up yesterday. This picture shows just a fraction of them. 🤯🥔

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.