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:

• 🪐 Pitch Perfect Fall 2026 Waitlist
• ☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 
• 💻 Website
• 🍿Popcorn Club: Monthly meet-up to debrief TV, movies, and the zeitgeist
• 📜 Footnotes newsletter filled with rabbit holes
• 💌 The Art of the Ask Podcast
• 📱 IG: ⁠@chelseariffe⁠
• 🧵 Threads: @chelseariffe

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