S18: E14: If I Were Starting a Business in 2026, This is How I'd Do It

Today, I’m exploring the power of identity and how it shapes us, anchors us, and sometimes quietly begins to confine us. Even the identities that are good and meaningful can become cages when we cling to them too tightly or start to outgrow the version of ourselves they were built around.In this episode, I unpack how to recognize when an identity is supporting you versus trapping you, the questions worth asking when everything starts to feel different, and the very real grief that can come with letting an old version of yourself go.Podcast Episode Highlights:Everything feels differentMy huge identity shifts over timeIdentities can be good AND bad (aka in the grey)Identities can become cages BECAUSE they are goodQuestions to ask yourself to see if your identity is helping you or notHow to know when your identity is trapping youThe grief connected to losing your identityFinal thoughts on releasing identitiesResources Mentioned in This Podcast Episode:Learn more about Meal Craft here: https://mealcraftmethod.com/--> Use the code PODCAST for a $15 off discount on Meal CraftEarlier podcast episode I mentioned today: Season 18: Episode 6: The Magic of Not BelongingOTHER 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! 

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 zoneBranding season is comingEmbarrassment is the cost of entry (what this means)Why does embarrassment seem so threatening to us?Addiction to competenceGrowth is so importantThe reward...Final thoughtsResources Mentioned in This Podcast Episode:Follow me on substack here: https://jillwinger.substack.com/Learn more about Meal Craft here: https://mealcraftmethod.com/--> Use the code PODCAST for a $15 off discount on Meal CraftOTHER 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 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 storyPrinciple #1: Find a problem to solve or a person to helpPrinciple #2: Show up as yourselfPrinciple #3: Let's talk about AI...Principle #4: You have to commit Principle #5: Less sophisticated than you thinkFinal thoughtsResources Mentioned in This Podcast Episode:Learn more about Meal Craft here: https://mealcraftmethod.com/--> Use the code PODCAST for a $15 off discount on Meal CraftInterested in having some personalized coaching from me? Email me at: [email protected] and we'll talk detailsGet the 5 Minute Dinner Decision (free download)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 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 baselineStrategy #2: Not a recipe, but a categoryStrategy #3: Flexibility and leftoversStrategy #4: Figure out what needs to be used ASAPPrinciple #1: How to use frameworksPrinciple #2: Keep the building blocks on handPrinciple #3: You can repeat thingsPrinciple #4: Make room for imperfect mealsPractical example that I recently didGive yourself permission to play and experimentResources Mentioned in This Podcast Episode:Learn more about Meal Craft here: https://mealcraftmethod.com/--> Use the code PODCAST for a $15 off discount on Meal CraftLearn more about Azure Standard here: https://www.azurestandard.com/?a_aid=ANnu0O8ySUHelpful blog posts on building up your pantry: https://www.theprairiehomestead.com/2021/10/how-to-store-and-use-bulk-pantry-goods.html and https://www.theprairiehomestead.com/2021/09/how-to-store-a-years-worth-of-food-for-your-family-without-waste-and-overwhelm.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.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 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 Egan10x Is Easier Than 2x by Benjamin Hardy and Dan SullivanBraving the Wilderness by Brené BrownNourishment by Fred ProvenzaThe Omnivore's Dilemma by Michael PollanThe Indifferent Stars Above by Daniel James BrownThe Pivot Year by Brianna WiestThe War of Art by Steven PressfieldThe Coddling of the American Mind by Greg Lukianoff and Jonathan HaidtThe Worst Hard Time by Timothy EganUntamed by Glennon DoyleWeapons of Mass Instruction by John Taylor GattoFaith Unraveled by Rachel Held EvansThe Woman They Could Not Silence by Kate MooreFinal thoughtsResources Mentioned in This Podcast Episode:Find links to my favorite books here: https://bookshop.org/shop/theprairiehomesteadLearn more about Meal Craft here: https://mealcraftmethod.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! 

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.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! 

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.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! 

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.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! 

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.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!