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What Happens When a Gen Xer & a Millennial Talk Shop (LIVE!)

A cross-generational chat with Jonathan Small about writing viral essays & finding your creative niche

Hi Bleeders!

I had an absolute blast hosting my first-ever Substack Live with my pal

earlier today, and I wanted to share the replay with you.

Unfortunately, Substack fumbled the first couple minutes of the video (we have some tech notes), but we covered a lot of ground, including:

  • Jon’s new Substack direction—niching down to all things Gen X over on

    (which even inspired an upcoming podcast rebrand)

  • The Gen X anthem—put your guesses in the comments before you hit play!

  • Lessons about Substack strategy and writing essays that resonate

  • Jon’s advice on topics to explore on my personal Substack,

    Girl Gone Wild, which I recently renamed to support my book launch

  • And of course, we got into my upcoming debut memoir, Girl Gone Wild (it’s such a millennial move to turn your chaotic coming-of-age into a memoir lol)

Our conversation was a big dollop of creative shop talk, a dash of generational debate, and a sprinkle of nostalgia. Basically, it’s what it sounds like when Jon and I go out for margs—minus the mezcal.

Huge thanks to

, , , , , and the 49 total folks who tuned in live! I had so much fun that I’m officially making this a regular thing.

👀 Watch the replay above and join me for the next one in the app. 👇

Get more from Courtney Kocak in the Substack app
Available for iOS and Android

I’m teaching some upcoming workshops you might be interested in:


So… ROLL CALL! 🗣️

What’s the Gen X anthem? Or better yet—what’s your generation’s anthem? I’m still figuring out my pick for Millennials.

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