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
☄️SUPERNOVA doors open - starting Feb 2026
🪐 Pitch Perfect - next round Spring 2026, get on the waitlist!
📲 Instagram 📲
☎️ Want to send a voice note to the podcast and have Chelsea answer you on air? Do so HERE.
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