In My Non-Expert Opinion

Sabbatical Scene Report: Chicago


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279: Chelsea dishes on her sabbatical starting with Chicago: the extreme sticker shock, the regrets, and the revelations that came with finally not working.

Here's what you didn't see on Instagram:

  • A Hallmark movie moment on the airplane that didn't pan out
  • Nonstop commentary on Chicago prices
  • Why was it so EERILY QUIET?!!?
  • The exhaustion of starting calls at 9 am and going back to back all day
  • What's the point of big cities?
  • Regrets of not leaving the house more
  • The $52 BBQ platter haunting Chelsea to this day

Other tidbits:

  • Breaking down the financials: how TF do you actually budget, save, and prep for two months away? Especially in cities that have about a 5X cost of living than you're used to
  • The emotional rollercoaster: battling productivity guilt and the urge to “earn” your time off.
  • Logistics 101: finding the sweet spot between structured plans and deliciously unscripted days 

The good news is the to-do list will survive without you. The bigger question? Who are you with no to-do list? 👀

P.S. PITCH PERFECT FALL ROUND IS OPEN FOR ENROLLMENT (with a generous 5-part payment plan!!!) Grab your seat here!

Connect with Chelsea:

💻 Website

🪐 Pitch Perfect - next round Spring 2026, get on the waitlist!

🎤 1:1 Podcast Coaching

🎙 Launch your podcast with the ultimate podcast launch course - Mic Drop!

📲 Instagram 📲

✈️ Slight Turbulence Substack


👀 Ready to launch your very own podcast? Grab my FREE cheat sheet right HERE.

☎️ Want to send a voice note to the podcast and have Chelsea answer you on air? Do so ⁠HERE⁠.

🫶 Don't forget to rate, review, and share in the group text. This podcast is free and ratings/reviews and shares are our currency.

🙌🏼 Want to contribute to IMNEO to show your appreciation (and keep us going?) Click HERE

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In My Non-Expert OpinionBy Chelsea Riffe

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