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Hi Reader,

I know it’s a bit random to get freelance advice from a comedy podcast, but stay with me.

A few weeks ago, I was listening to So True, a podcast by comedian Caleb Hearon (I’m a big fan). He said something that’s been stuck in my brain ever since.

He was talking about live shows and how he never skips the opener. Even when it’d be easier to stay at dinner a little longer or show up right before the headliner. Because sometimes the opener ends up being the best part.

He said:

“There’s value in inconvenience. Even when the opener sucks, it’s still worth experiencing something unexpected.”

There’s so much advice for solopreneurs on how to avoid inconvenience. Automate this. Delegate that.

And while I’m all for efficiency and structure—I mean, it’s basically the theme of this newsletter (lol)—some of the best things in my business and life started as tiny, inconvenient detours.


Like the time I said yes to a poetry night with someone I’d just met, and gained a biz bestie.

Or when I started going on long, unstructured morning walks during the pandemic and had to pause constantly to jot down all the ideas that started flowing.

Or how The Reach came to be during a season when I’d cut almost all weekly meetings from my calendar… and then realized I missed human connection.

The lesson? Optimization can make your business more sustainable.

But surprise, inspiration, connection—the good stuff—often show up when you leave a little room for what’s not on the agenda.

So here’s your gentle nudge to let a little inconvenience in.

You never know what might come of it.

‘Til next time!

Big (virtual) hugs,

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Jasmine Williams Media is a company that was founded and primarily operates within the ancestral, traditional and unceded territories of many nations, including the Mississaugas of the Credit, the Anishnabeg, the Chippewa, the Haudenosaunee and the Wendat peoples, also known as Toronto, Canada. This land is now home to many diverse First Nations, Inuit and Métis peoples.