S19: E1: The Biggest & Hardest Transition of My Life

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

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