
S19: E1: The Biggest & Hardest Transition of My Life
From Old Fashioned On Purpose by Jill Winger
May 25, 2026 · 37 min · Season 19 · Episode 1
About this episode
Jill Winger shares her experience of navigating a significant life transition, discussing the complex emotions involved and the societal expectations surrounding such changes.
In this deeply personal podcast episode, I’m sharing about walking through the biggest life transition I’ve ever faced. I reflect on how I got here, the vulnerability of being cracked open, and the strange mix of grief, relief, fear, and hope that can all exist at once. I also explore what not to say to someone in a tender season, how we often project our own stories & expectations onto other people’s lives, and why big transitions rarely fit neatly with cultural desires. This is my open ...
People in this episode
Host: Jill Winger
Topics covered
- life transition
- vulnerability
- grief
- relief
- fear
- hope
- cultural expectations
Keywords
- life transition
- vulnerability
- grief
- hope
- cultural expectations
- personal growth
- emotional journey
More episodes of Old Fashioned On Purpose
- S19: E3: How I Unbecame a Homestead Influencer · June 8, 2026 · 39 min
- S19: E2: The Garden I Didn't Plan for: How I'm Starting Over in a New Space · June 1, 2026 · 25 min
- S18: E16: When Good Identities Become Cages (and how to break free) · April 27, 2026 · 29 min
- S18: E15: Embarrassment is the Cost of Entry · April 20, 2026 · 29 min
- S18: E14: If I Were Starting a Business in 2026, This is How I'd Do It · April 13, 2026 · 44 min
- S18: E13: How I'm Cooking These Days · April 6, 2026 · 28 min
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