Pretend it’s the first day of school

Today’s edition of Wishful Working is a 3 minute read.

You know in You’ve Got Mail, when Tom Hanks’s character talks about how New York in the fall makes him want to buy school supplies and give Meg Ryan’s character a “bouquet of newly-sharpened pencils”? I may not be in NYC (far from it), but I relate to this sentiment every autumn.

Another quote I always think of in the fall is one from writer Gretchen Rubin:

Although it’s been more than ten years since “back to school” was a rhythm for my life, I can’t help but feel a sense of freshness and energy when September arrives. And while I’m always sad to see summer slip away, I get a little boost of motivation when August ends. 

(A side note: Now that I’m married to a farmer, this time of year has a whole new rhythm — Harvest! Dawson is spending looooong days in the combine, harvesting lentils, wheat, and canola. I am spending looooong days lonely, bored, and waiting for him to come home. 😂)

Transparently, I have another reason to look forward to autumn this year: My summer was a bit crappy, work-wise. I don’t mind a lighter workload and a slower pace in the summer, but I also want to, you know, make a little bit of money. Although my savings and my spouse’s income take some of the sting out, I’m feeling the financial strain of a leaner-than-usual summer. (FYI, last week’s newsletter about self-compassion was basically written for an audience of ME.)

Every new month brings a clean slate, but September is special. Welcoming September motivated me to finally dust and tidy my desk. It makes me want to buy a million notebooks, a stack of sticky notes, and a new pair of shoes. (Is anyone else obsessed with watching back to school hauls on TikTok? Just me?)

I don’t need a new backpack or a million notebooks (maybe just one 😉), but could use a fresh start.

How about you?

On the first day of school, there are no marks in the grade book, no tardies, and no detentions. And once you’re all grown up, you can have a “first day of school” whenever you need one.

Start a new project, try a new routine, break up with a client, send a risky pitch! Sign up for a class or join a new community! Whatever you do, do it without regard to past setbacks or failures.

I’ll leave you with one more quote. This one is from the titular character in Anne of Green Gables, a beloved Canadian classic that I just read for the first time at age 31.

You can substitute “mistakes” with many different words: disappointments, pains, obstacles, conflicts — whatever resonates with you.

Here’s to clean slates and fresh starts and Septembers.

See you next week,

Kara

Wishful Working is inspired by my desire 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.

Who am I? I’m a freelance writer and entrepreneur based in small-town Saskatchewan. I write longform content for B2B clients, and I help founders and independents name their brands and projects through a new venture called Naming. Connect with me by replying to this email or finding me on LinkedIn or Twitter.