S18: E8: What the Hell Happened to Homesteading?

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 businessLesson #1: Solve a problemLesson #2: Respect the history—but also listen to your gutLesson #3: Diversify. Or else.Lesson #4: Don't forget to market to out-of-townersLesson #5: Create an experienceLesson #6: Lean into your liabilitiesLesson #7: Don’t listen to your customers too muchFinal thoughtsResources 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: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! 

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 usWhy 'all or nothing' is ridiculousTool vs. cageFiguring out what drives youFilter #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 outFinal 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=ANnu0O8ySUOTHER 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 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!

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 gardeningWhat happened to me last yearThe issue with obligationThe issue with raised bedsMy plans for the garden this yearHow I'm using my greenhouse this yearFinal thoughtsResources Mentioned in This Podcast Episode:Learn more about Air Doctor here: airdoctorpro.comUse code HOMESTEAD to save up to $300 on your air doctor systemWhere I get my garden soil tested: http://theprairiehomestead.com/soiltestWhere I buy my garden seeds (especially cover crop seeds): http://theprairiehomestead.com/seedsOTHER 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 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!

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 nowMy backstory and why I care about this topicModern homestead beginningsStages of the homestead movementHow the internet influenced homesteadingThe 3 segments of homesteading right nowMy thoughts and reactions to this issueResources 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.comUse the code HOMESTEAD to save 20% on your orderOTHER 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 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!

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 beginningJake, my first horseChoosing my college pathPost-college burnoutKids, business, etc. vs. horsesComing back to myself (and my horse Kate)Deep thoughts on who you were and what you lovedMy horse Tag (and life shifts again)Getting into horsemanship Exploring roping (chasing new dreams)Deep thoughts on fearFinal thoughts about horses and lifeResources 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.comUse code HOMESTEAD to save up to $300 on your air doctor systemOTHER 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 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!

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 belongingMy reactions & feelings about not belongingWhy we shouldn't tone ourselves downInternal and external pressuresWhy not belonging is a giftChoose your own unpaved pathYou're not aloneShifting your mindset about belongingResources 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.comUse the code HOMESTEAD to save 20% on your orderOTHER 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 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!

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 backgroundOur homeschooling routineWhy we went from homeschool to public schoolHomeschooling older kids vs. younger kidsReflecting on our education decisions for our kidsMy grief process and thoughts How it's working for my kidsMy shifting thoughts on public schoolMy concerns about homeschooling todayFinal thoughtsResources Mentioned in This Podcast Episode:My old podcast episodes on school:S15: E10: What I’m Using for Homeschool Curriculum this Year (and a Plea) S7: E2: What We’re Using for Homeschool Curriculum This YearEpisode 153: The Homeschool Curriculum I’m Using This YearHow Being Homeschooled Helped Me Later In Life My Non-Fancy Homeschool Routine What If My Kids Fall Behind?? (And other Homeschooling Questions) The Hardest Thing We’ve Ever Done: The Charter School Tell-AllOTHER 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 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!

I'm now going on five years of owning a restaurant in one of the smallest towns in Wyoming.It’s one of the most gratifying things I’ve ever done. It’s also one of the most exhausting.I’m proud of what we’re building in our little corner of Wyoming. I’m proud of the food. I’m proud of the place. I’m proud that people walk in and feel nostalgia, comfort, a sense of belonging… a remembering.But in this podcast episode, I’m going to say the parts I usually don’t say out loud because, well… I feel like it. And some of it just needs to be said.Podcast Episode Highlights:Backstory of our small-town restaurant Confession #1: The Locals Are Our Lifeblood (And Also… a Lot)Confession #2: I Wish We Could Rate CustomersConfession #3: We’re Not Trying to Make Your Life Hard with Our Limited HoursConfession #4: Staffing Is… ComplicatedConfession #5: I’m Not Getting Rich Off ThisConfession #6: We Care a Lot About What We Serve You Final thoughts...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 Chugwater Soda Fountain here: https://www.chugwatersodafountain.com/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 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!

In the past, I've shared about mainly the homestead part of myself on this podcast. Not because I was hiding the rest of me—but because the rest didn’t really fit the homestead narrative. But lately… it’s been shifting. The homestead part of me is still woven into my days, but it’s not the headline anymore. It’s moved to the background, and other parts of me are finally coming up for air.So this feels like the perfect time for a reintroduction and a closer look at some of my rough edges.Podcast Episode Highlights:Why I'm doing a reintroductionMy deep connection to horses Hot or cold personalityMy beauty routineMy thoughts on pop cultureMove fast, think fast, talk fast, etc.How I talk and how I lookMy clothes preferenceMy intolerance for current Instagram trends about womenMy thoughts on homestead content right nowWhat I love to readMy thoughts on politics and religionFinal thoughts on rough edgesResources 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/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 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!

Folks always ask me how I "do it all" but the truth is, that I don't. Listen in as I talk about I do NOT have a balanced life and what I do instead.Podcast Episode HighlightsMy thoughts on 'balance' in lifeMy summer as an exampleDealing with guilt and the aftermath Learning how to say 'No'Thoughts on using a team for helpDetails on how I use my planner Final thoughtsResources Mentioned in This Podcast Episode:Find my Old-Fashioned on Purpose planner here: http://www.prairieplanner.com/Sign up for my Substack here: https://jillwinger.substack.com/See more details on how I use my planner here: https://www.theprairiehomestead.com/2025/11/my-un-instagrammable-planner-system.htmlOTHER 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 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!