HeyJaredSweeter After Difficulty
🎙️ Sweeter After Difficulty is a podcast about the beauty that can only emerge through struggle. Hosted by Randy Highsmith, this series features intimate conversations with people who have endured pain, faced fear, and discovered peace—not despite their challenges, but…
- Indexed episodes, last 90 days
- 6
- Latest publication
- Sep 6, 2026
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- Earliest in this view
- Jul 5, 2026
Latest episodes
S2 EP65 Jason Bussey - What Would You Want If Nobody Was Watching? (opens the original)
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What would you want if nobody was watching? In this episode of Sweeter After Difficulty , Randy sits down with therapist, coach, consultant and Ironman Jason Bussey for a wide-ranging conversation about what happens when we stop building a life around what we're supposed to want and start asking what actually matters to us. Jason shares the unlikely path that took him from business consulting to psychotherapy, why making more money didn't necessarily make life better, and how a difficult relatio
S2 EP64 How We Got Here | Sweeter After Difficulty × Winning Twice (opens the original)
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In this special crossover episode of Sweeter After Difficulty and Winning Twice , Randy Highsmith and Austin Cheviron trade sides of the microphone for a conversation about friendship, curiosity, communication, business, difficulty, and what it actually means to build a life worth living. They go back to their first meeting at an eXp event in 2019—when Austin showed up with a seemingly endless list of questions and Randy was building the systems that would eventually help connect thousands of pe
Sometimes The Options Still Suck (opens the original)
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What happens when new information changes the choices you can see? In this solo episode, I think out loud about a back injury that shaped nearly twenty years of my life, what Jiu Jitsu taught me about awareness, why more options aren't always better options, and the boundary where nobody else gets to choose for us. Sometimes awareness opens a door. Sometimes the options still suck. But I think there's something worth fighting for in being able to see them. 🎙️ Sweeter After Difficulty is a podcas
S2 EP62 Have You Ever Had a Conversation That Changed Your Life? (opens the original)
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What if we don’t need more answers? What if what we really need are better questions? In this episode of Sweeter After Difficulty , Randy Highsmith steps back from the usual interview format to explore the idea behind his newest project: Honest Conversations, Better Lives. After a year of conversations with people from all walks of life, Randy has become increasingly convinced that we are not suffering from a lack of information—we’re suffering from a lack of space to slow down, listen, question
S2 EP61 Linda Chavez - Faith, Failure, and Finding Your Calling (opens the original)
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In this episode, Randy sits down with Linda Chavez for a conversation about resilience, reinvention, and discovering purpose through life's hardest seasons. Linda shares her remarkable journey from working behind the bar to building a thriving business, losing nearly everything during the 2008 financial crisis, and finding the courage to start over from scratch. Along the way, she reflects on the mentors who shaped her, the lessons failure taught her about leadership, and how Brazilian Jiu-Jitsu
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