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Home > Oh My Pod! with Chelsea Riffe > Sabbatical Scene Report: Chicago
Podcast: Oh My Pod! with Chelsea Riffe
Episode:

Sabbatical Scene Report: Chicago
Category: Business
Duration: 00:45:56
Publish Date: 2025-08-14 10:00:00
Description:

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?

Total Play: 0