Old Fashioned On Purpose

Jill Winger

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.

  • 29 minutes 25 seconds
    S18: E15: Embarrassment is the Cost of Entry

    Learning to rope at 40 has humbled me in all the best and worst ways, because nothing exposes your ego faster than being a beginner in front of people who’ve been doing something their whole lives. In this episode, I’m talking about a phrase I’ve been repeating to myself in the branding pen: embarrassment is the cost of entry.

    We’ll explore what this phrase means, why so many of us feel threatened by embarrassment, our addictions to competence, the messy stage of growth, and the wonderful rewards that come from stepping out of our comfort zones.

    Podcast Episode Highlights:

    • Thoughts on stepping out of our comfort zone
    • Branding season is coming
    • Embarrassment is the cost of entry (what this means)
    • Why does embarrassment seem so threatening to us?
    • Addiction to competence
    • Growth is so important
    • The reward...
    • Final thoughts

    Resources Mentioned in This Podcast Episode:

    --> Use the code PODCAST for a $15 off discount on Meal Craft

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    20 April 2026, 8:00 am
  • 44 minutes 17 seconds
    S18: E14: If I Were Starting a Business in 2026, This is How I'd Do It

    In this podcast episode, I’m sharing what I’d do if I were starting an online business from scratch in 2026. I'll chat about my own business story, what’s changed in the online world, and the core principles I believe still matter most.

    If you’ve been dreaming about starting an online business of your own, this episode should give you some tips and encouragement as you start your own business adventure.

    Podcast Episode Highlights:

    • Thoughts on making online businesses (and my own)
    • My personal online business story
    • Principle #1: Find a problem to solve or a person to help
    • Principle #2: Show up as yourself
    • Principle #3: Let's talk about AI...
    • Principle #4: You have to commit 
    • Principle #5: Less sophisticated than you think
    • Final thoughts

    Resources Mentioned in This Podcast Episode:

    --> Use the code PODCAST for a $15 off discount on Meal Craft

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    13 April 2026, 8:00 am
  • 28 minutes 23 seconds
    S18: E13: How I'm Cooking These Days

    In this podcast episode, I’m sharing details on how I’m cooking these days. I'll explain why rigid recipes and traditional meal plans just don’t work well for our full, ever-changing family life. We’ll talk about the strategies and principles I lean on instead, including how to make peace with a more flexible approach to food, and why giving yourself permission to experiment can be so freeing.

    I’m also diving into the art of using leftovers creatively, wasting less, and building meals from what you already have on hand. Let's chat about how to start cooking with more confidence, less stress, and a whole lot more real life in mind.

    Podcast Episode Highlights:

    • Life changes but I'm still passionate about food (it's just different now)
    • The meal planning problem 
    • Strategy #1: Ingredient baseline
    • Strategy #2: Not a recipe, but a category
    • Strategy #3: Flexibility and leftovers
    • Strategy #4: Figure out what needs to be used ASAP
    • Principle #1: How to use frameworks
    • Principle #2: Keep the building blocks on hand
    • Principle #3: You can repeat things
    • Principle #4: Make room for imperfect meals
    • Practical example that I recently did
    • Give yourself permission to play and experiment

    Resources Mentioned in This Podcast Episode:

    --> Use the code PODCAST for a $15 off discount on Meal Craft

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    6 April 2026, 8:00 am
  • 34 minutes 48 seconds
    S18: E12: These are the Books I Can't Stop Thinking About

    In this podcast episode, I'm going to share the books that have been most impactful on my life.

    I’ve read a lot of books over the years, but these are the ones that truly changed me. They influenced how I see the world, how I make decisions, and even how I understand myself. 

    Podcast Episode Highlights:

    • These books have been impactful to me (and why)
    • The Devil's Element by Dan Egan
    • 10x Is Easier Than 2x by Benjamin Hardy and Dan Sullivan
    • Braving the Wilderness by Brené Brown
    • Nourishment by Fred Provenza
    • The Omnivore's Dilemma by Michael Pollan
    • The Indifferent Stars Above by Daniel James Brown
    • The Pivot Year by Brianna Wiest
    • The War of Art by Steven Pressfield
    • The Coddling of the American Mind by Greg Lukianoff and Jonathan Haidt
    • The Worst Hard Time by Timothy Egan
    • Untamed by Glennon Doyle
    • Weapons of Mass Instruction by John Taylor Gatto
    • Faith Unraveled by Rachel Held Evans
    • The Woman They Could Not Silence by Kate Moore
    • Final thoughts

    Resources Mentioned in This Podcast Episode:

    Find links to my favorite books here: https://bookshop.org/shop/theprairiehomestead

    Learn more about Meal Craft here: https://mealcraftmethod.com/

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    30 March 2026, 8:00 am
  • 42 minutes 20 seconds
    S18: E11: What I've Learned from Running a Business in a Town of 175

    After reviving the oldest operating soda fountain in the state of Wyoming, I can tell you firsthand that there is something deeply meaningful about bringing an old place back to life. Yet, like most things we romanticize from a distance, it’s usually a whole lot less romantic up close.

    Since buying the soda fountain five years ago, I’ve had a lot of people ask about following in my footsteps. So in this podcast episode, I pulled together a few of the lessons that I feel are the most important when it comes to running a small-town business. Here we go.

    Podcast Episode Highlights:

    • The element of risk in running a small town business
    • Lesson #1: Solve a problem
    • Lesson #2: Respect the history—but also listen to your gut
    • Lesson #3: Diversify. Or else.
    • Lesson #4: Don't forget to market to out-of-towners
    • Lesson #5: Create an experience
    • Lesson #6: Lean into your liabilities
    • Lesson #7: Don’t listen to your customers too much
    • Final thoughts

    Resources Mentioned in This Podcast Episode:

    Find my Old-Fashioned on Purpose planner here: https://www.prairieplanner.com/

    Learn more about Chugwater Soda Fountain events here: https://www.chugwatersodafountain.com/

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    23 March 2026, 8:00 am
  • 36 minutes 43 seconds
    S18: E10: Competence, Not Cosplay: How to Keep What Works, Drop the Rest

    Lately, I’ve been thinking a lot about what old-fashioned living might look like for me in the coming year and beyond. I’ve been considering which skills and rhythms I want to embrace, and which ones I need to release.

    In this podcast episode, I’m sharing that thought process with you. My hope is that it helps you take stock of your own life and figure out which parts of the old-fashioned lifestyle you truly love, and which parts you may be holding onto simply because you think you should.

    Podcast Episode Highlights:

    • Current homesteading issues & how it affects us
    • Why 'all or nothing' is ridiculous
    • Tool vs. cage
    • Figuring out what drives you
    • Filter #1: does this skill give me agency?
    • Filter #2: does this skill give me peace or cost me peace?
    • Filter #3: is this a keystone skill?
    • Filter #4: what season am I in?
    • Filter #5: is this thing rooted in fear or love?
    • Motive #1: does this skill bring me joy?
    • Motive #2: does this feel obligatory?
    • Motive #3: are you doing this out of comparison?
    • The three buckets for figuring things out
    • Final thoughts 

    Resources Mentioned in This Podcast Episode:

    Find my Old-Fashioned on Purpose planner here: https://www.prairieplanner.com/

    Learn more about Azure Standard here: https://www.azurestandard.com/?a_aid=ANnu0O8ySU

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    16 March 2026, 8:00 am
  • 28 minutes 53 seconds
    S18: E9: I'm Not Planting a Garden This Year. Here's Why.

    For the first time in almost 20 years, I'm not planting a garden.

    In this podcast episode, I'm sharing what happened in my garden last year and why I'm taking a break. I'll also share some deep thoughts about obligation and what I'm going to do with my garden space for the upcoming season.

    Podcast Episode Highlights:

    • Quick review of my 20 years of gardening
    • What happened to me last year
    • The issue with obligation
    • The issue with raised beds
    • My plans for the garden this year
    • How I'm using my greenhouse this year
    • Final thoughts

    Resources Mentioned in This Podcast Episode:

    Learn more about Air Doctor here: airdoctorpro.com

    • Use code HOMESTEAD to save up to $300 on your air doctor system

    Where I get my garden soil tested: http://theprairiehomestead.com/soiltest

    Where I buy my garden seeds (especially cover crop seeds): http://theprairiehomestead.com/seeds

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    9 March 2026, 8:00 am
  • 30 minutes 9 seconds
    S18: E8: What the Hell Happened to Homesteading?

    I’ve been wanting to talk about this for a while…but the risk of sounding like a crotchety old gatekeeper, I haven’t…

    In this podcast episode, I'm sharing my thoughts on what happened to the modern homesteading movement and why I've been feeling so turned off by it lately. 

    Podcast Episode Highlights:

    • The problem in the homesteading world right now
    • My backstory and why I care about this topic
    • Modern homestead beginnings
    • Stages of the homestead movement
    • How the internet influenced homesteading
    • The 3 segments of homesteading right now
    • My thoughts and reactions to this issue

    Resources Mentioned in This Podcast Episode:

    Find my Old-Fashioned on Purpose planner here: https://www.prairieplanner.com/

    Sign up for my Substack here: https://jillwinger.substack.com/

    Learn more about Aquatru here: www.aquatru.com

    • Use the code HOMESTEAD to save 20% on your order

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    2 March 2026, 9:00 am
  • 49 minutes 54 seconds
    S18: E7: My Horse Journey (aka Finally Coming Home to Myself)

    If you’ve been listening or following me for a while, then you already know that horses have been a love of mine since childhood. In this podcast episode, listen in as I talk about my horse journey, from childhood to present times. Along the way, I'll sprinkle in lots of deep thoughts on life lessons as well as ALL the details of my horse adventures (and what's coming next).

    Podcast Episode Highlights:

    • Way back at the beginning
    • Jake, my first horse
    • Choosing my college path
    • Post-college burnout
    • Kids, business, etc. vs. horses
    • Coming back to myself (and my horse Kate)
    • Deep thoughts on who you were and what you loved
    • My horse Tag (and life shifts again)
    • Getting into horsemanship 
    • Exploring roping (chasing new dreams)
    • Deep thoughts on fear
    • Final thoughts about horses and life

    Resources Mentioned in This Podcast Episode:

    Find my Old-Fashioned on Purpose planner here: https://www.prairieplanner.com/

    Sign up for my Substack here: https://jillwinger.substack.com/

    Learn more about Air Doctor here: airdoctorpro.com

    • Use code HOMESTEAD to save up to $300 on your air doctor system

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    23 February 2026, 9:00 am
  • 42 minutes 18 seconds
    S18: E6: The Magic of Not Belonging

    I’ve never really belonged. Not in the dramatic, “nobody understands me” way. More in the quiet, lifelong way—like I’ve always been standing half a step outside of whatever circle I’m supposed to slide into.

    But I’ve finally realized something that would have shocked my younger self: Not belonging isn’t a problem. It’s an invitation. Listen in to my podcast episode to learn more about my thoughts on the magic of not belonging.

    Podcast Episode Highlights:

    • My life journey with not belonging
    • My reactions & feelings about not belonging
    • Why we shouldn't tone ourselves down
    • Internal and external pressures
    • Why not belonging is a gift
    • Choose your own unpaved path
    • You're not alone
    • Shifting your mindset about belonging

    Resources Mentioned in This Podcast Episode:

    Find my Old-Fashioned on Purpose planner here: https://www.prairieplanner.com/

    Sign up for my Substack here: https://jillwinger.substack.com/

    Learn more about Aquatru here: www.aquatru.com

    • Use the code HOMESTEAD to save 20% on your order

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    16 February 2026, 9:00 am
  • 44 minutes 10 seconds
    S18: E5: Why I Stopped Homeschooling

    As some of you know by now, I am no longer homeschooling my kids. In this podcast episode, I'm talking all about our homeschool experiences, our journey from homeschool to public school, how I'm handling the change, and some of my deep thoughts and concerns that I have about school and about raising kids. 

    Give it a listen and let me know what you think.

    Podcast Episode Highlights:

    • Homeschooling background
    • Our homeschooling routine
    • Why we went from homeschool to public school
    • Homeschooling older kids vs. younger kids
    • Reflecting on our education decisions for our kids
    • My grief process and thoughts 
    • How it's working for my kids
    • My shifting thoughts on public school
    • My concerns about homeschooling today
    • Final thoughts

    Resources Mentioned in This Podcast Episode:

    My old podcast episodes on school:

    OTHER HELPFUL RESOURCES FOR YOUR HOMESTEAD:


    Did 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! 

    9 February 2026, 9:00 am
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