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

Old Fashioned On Purpose

Have you felt it? Something is rippling through humanity at this moment. It's a stirring... a longing... a remembering. A sense that we are more capable than we’ve been led to believe. We want to feel alive, not sedated.. but we've lost our way. We've traded a life intertwined with nature for asphalt and artificial lights. We've swapped natural movement for a sedentary existence. We've given up food from the earth in favor of food from the factory. We've sacrificed our traditional skillsets for apps and gadgets. But while our overdose on modernity may have made us sick, there is an antidote. Join best-selling author and mentor, Jill Winger, each week as she digs into a different facet of the old-fashioned on purpose lifestyle.

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Old Fashioned On Purpose

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

May 25, 2026 • Jill Winger • Season 19 • Episode 1

0:00 | 36:54

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 now
A slow unraveling
The vulnerability & struggles
What not to say to someone dealing with a big life transition
How we project our stories on other people
Contradictory feelings
The cultural implications in society
Being cracked open
Final Thoughts

Resources 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.com
Jill on Instagram: @jill.winger
Jill on Facebook: http://facebook.com/theprairiehomestead
Apply to be a guest on the Old-Fashioned on Purpose podcast: https://www.theprairiehomestead.com/podcast-guest-application

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