Ep #295: Where To START, and Planning to Revolutionize Your Social Life

March 23, 2026

In today’s episode, I answer a question from Nate (a new listener who found me via Cal Newport’s Deep Questions Podcast), who asked where it makes sense to START in terms of implementing all of the planning systems I talk about on the podcast (and in the book). So — how does one begin to build a system – all at once, or piece by piece?

References mentioned:
Airtight Task Management Episode

Annual Planning Episode

Seasonal Planning Episode

Monthly Planning Episode

Weekly Planning Episode (old + newer)!

Daily Planning Episode

Then, I interview September Gerety, an CEO in her empty nest phase who now finds herself with a thriving community and social life — and it all started with planning. She shares her story (as well as a bit about her current systems!). If you have questions for September, you can leave them here and she’ll try to answer!

Episode Sponsors:
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