I Went on Vacation and Felt Guilty the Whole Time

EPISODE · Mar 3, 2026 · 22 MIN

I Went on Vacation and Felt Guilty the Whole Time

from Rich In Wellness · host Katharine Sawyer

Last week I went on vacation with 12 of my college friends. It was a true vacation that I planned for and was prepared ahead of time with work… but mentally? I struggled.In this episode, I’m sharing the honest tension that comes with being an entrepreneur and trying to unplug. The guilt. The pressure. The “I should be working” thoughts. The identity struggle when you’ve built a business around ambition, drive, and big goals.We’ll talk about timing trips around launches, setting client boundaries, managing your own expectations, and remembering why you chose entrepreneurship in the first place.Because freedom is the goal… but sometimes learning how to actually feel it is the hard part.If you’ve ever gone on vacation and couldn’t fully relax, this one will hit home.

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I Went on Vacation and Felt Guilty the Whole Time

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