Simple Farmhouse Life
314. Raising Hardworking, Humble Kids in an Entitled World | Casey & Jason Cashell
04 Nov 2025
What if the best way to raise capable kids is to let them work and create beside you? Casey and Jason Cashell share how restoring their 1859 Virginia estate has shaped their family through hands-on learning, hard work, and entrepreneurship. They talk about giving kids real responsibility, letting them learn through mistakes, and helping them turn their skills into small businesses. Their story offers practical encouragement for parents who want to raise hardworking kids and homes full of purpose and partnership. In this episode, we cover: - How Jason and Casey found and restored an 1859 Victorian home and 37-acre estate to serve as a hub for family, business, ministry, homeschool, and hospitality all under one historic roof - How their kids have been hands-on in every home renovation since toddlerhood and what they’ve learned from real responsibility - Why kids often rise to higher expectations when given meaningful work and trust - Practical ways to raise capable, competent kids even if you don’t have a homestead by simply inviting them into what you are already doing - The heart behind raising “humble leaders” instead of entitled adults in an over-psychologized culture - Why letting children experience struggle and failure leads to humility and long-term success - The difference between confidence built on praise versus confidence built on true competence - Restoring old-fashioned trades and hands-on creativity as an antidote to modern tech dependency - Encouragement for parents who feel unequipped to teach skills– how learning with your kids is often the best approach - Practical examples of entrepreneurship in childhood and how the Cashell kids have turned their skills into online classes - What restoring this historic Virginia estate has meant to their family: living among the birthplaces of America’s founders and making history come alive View full show notes on the blog + watch this episode on YouTube. Thank you for supporting the sponsors that make this show possible! RESOURCES MENTIONED Check out the Cashells’ Mayhurst Estate B&B here Explore the Cashells' hands-on workshops offered at the Artisan Kids Hub Join my FREE masterclass to learn my 4-step framework for making money on YouTube Master the rhythm of sourdough with confidence in my Simple Sourdough course Gain the sewing knowledge and skills every homemaker needs in my Simple Sewing series Turn your content creation dreams into a profitable business with my YouTube Success Academy Keep all my favorite sourdough recipes at your fingertips in my Daily Sourdough cookbook CONNECT Casey & Jason Cashell | Website | Instagram | Facebook | YouTube Lisa Bass of Farmhouse on Boone | Blog | YouTube | Instagram | TikTok | Facebook | Pinterest Do you have a question you’d like me to answer on the podcast? A guest you’d like me to interview? Submit your questions and ideas here: bit.ly/SFLquestions.
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