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

EPISODE · May 25, 2026 · 36 MIN

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

from Old Fashioned On Purpose · host Jill Winger

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 & honest conversation about change, humanness, and learning to hold contradictory feelings with grace.Podcast Episode Highlights:My biggest life transition right nowA slow unravelingThe vulnerability & strugglesWhat not to say to someone dealing with a big life transitionHow we project our stories on other peopleContradictory feelingsThe cultural implications in societyBeing cracked open Final ThoughtsResources Mentioned in This Podcast Episode:Find your garden seeds and supplies at True Leaf Market and use the code: homestead15 for 15% off your order.OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:Sign up for weekly musings from my homestead: https://jillwinger.substack.com/Get my free homesteading tutorials & recipes here: www.theprairiehomestead.comJill on Instagram: @jill.wingerJill on Facebook: http://facebook.com/theprairiehomesteadApply to be a guest on the Old-Fashioned on Purpose podcast: https://www.theprairiehomestead.com/podcast-guest-applicationDid you enjoy listening to this episode? Please drop a comment below or leave a review to let us know. This can help other folks learn about this podcast and we also really appreciate the feedback! 

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 ...

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

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How long is this episode of Old Fashioned On Purpose?

This episode is 36 minutes long.

When was this Old Fashioned On Purpose episode published?

This episode was published on May 25, 2026.

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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...

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