Editor’s Note: It’s been 4 weeks since you last heard from me. This departure from my bi-weekly cadence is with good reason. Over the past month, I’ve been busy marrying off my best friend, sipping poolside cocktails with hurricane Agatha in Cancun (super fun), and eating my way through Mexico City. 

Apart from indulging in weddings and tacos, I’ve been exploring new formats for Stories by Shiv content, starting with the pilot podcast above that I recently recorded with my writer collective Wayfinder. 

I’m excited to share more about my content plans soon, but in the meantime I’ll be sticking with a monthly-ish cadence for this newsletter. If a monthly note in your inbox just ain’t enough “Shiv” for ya, you can follow me on Instagram, Twitter, and TikTok

One of the major topics I write about is openly examining my understanding of “success” and beliefs about productivity. As it turns out, I’m not the only one having an existential crisis every five seconds. (thank God)

When I’ve written posts questioning the typical “rat race” approach to a corporate lifestyle (see: The Comparison Trap, Duality of Self, Give Yourself Some House Money, etc.), I received tons of responses from my readers explaining how much my words have resonated. With this in mind, I expect I’m not the only one who’s — let’s face it — a little sabbaticurious. Sabbatically curiously. Curious about sabbaticals. I’m nervous. Can you tell? 

Sabbaticals are intimidating AF.

My internal dialogue goes something like: How would this impact my career? What would I even do with all that free time? Wait, can I afford this? Nvm, nvm. Better to wait for a promotion before I make any moves…right?

In this podcast you’ll meet my friends Harris, Mark, and Lyle, all of whom have had experience with sabbaticals. I ask them every question under the sun about how some time away from their jobs has impacted them. We chat about themes around productivity, mindset shifts that come with stepping away from a job, and career-identity.

If you’re curious about sabbaticals too, this one’s for you. Give it a watch, and let me know what you think! I hope you enjoy the discussion as much as I did.


Stories by Shiv is part of Wayfinder, a writer collective exploring questions that matter.

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