46.The Dream That Took 13 Years

46.The Dream That Took 13 Years

What happens when the dream you've held onto for years is the very thing holding you back? In this heartfelt episode of Caraline's Adventure, Caraline sits down with Jon Hill—a two-time Emmy Award-winning sports producer, filmmaker, and director of the award-winning independent film Above the Clouds. What unfolds is an honest conversation about grief, perseverance, identity, and discovering that sometimes the path to your greatest dream begins with letting it go. After losing his father, Jon experienced a chance encounter in a coffee shop that would change his life forever. He knew the story needed to become a film—but bringing it to life would take 13 years. Along the way, he battled self-doubt, imposter syndrome, creative burnout, and the pressure of chasing a dream that seemed just out of reach. Ironically, it wasn't until he stepped away from that dream and fully embraced the opportunities in front of him that everything began to fall into place. Together, Caraline and Jon explore what it really means to redefine success, trust life's timing, and embrace the discipline required to pursue something meaningful. Jon shares the deeply personal story behind Above the Clouds, how creating the film became a powerful part of his healing journey after losing his father, and why telling authentic stories has the power to help others heal too. From covering the Super Bowl and World Cup for Fox Sports to directing an award-winning feature film inspired by his own life, Jon's journey is a reminder that success is rarely a straight line—and that our greatest setbacks often prepare us for our greatest purpose. AbovetheCloudsFilm.com JonHillDirects.com Rent the film on Amazon: https://www.amazon.com/gp/video/detail/B0DYMFPWV5/ref=atv_dp_share_cu_r Find more episodes at: https://www.youtube.com/@CaralinesAdventureOfficial [https://www.youtube.com/@CaralinesAdventureOfficial] Or www.CaralinesAdventure.com Credits: Technology support - John Hickman Graphic Design - Sterling Rose Creates

48. When the Mountain Calls

In this episode of Caroline's Adventure, Caroline sits down with leadership coach, keynote speaker, and bestselling author James Robbins to explore what it truly means to answer life's "call to climb." Drawing from his latest book, The Call to Climb, James shares how learning to listen to our inner voice can help us find purpose, embrace uncertainty, and navigate life's biggest transitions. Together, they discuss why growth often begins in discomfort, how nature and quiet reflection can help us hear ourselves more clearly, and why authenticity is one of the greatest gifts we can offer the people around us. Through stories of career changes, personal struggles, and unexpected lessons, this conversation is filled with practical wisdom for anyone feeling stuck or searching for their next step. If you've ever wondered whether you're on the right path, struggled with fear of the unknown, or needed encouragement to trust yourself, this episode will remind you that the greatest adventures often begin when we choose to keep climbing. Website: https://www.jamesrobbins.com Book site: https://iwillclimb.com YouTube: https://www.youtube.com/@james.r.robbins Facebook: https://www.facebook.com/jamesrobbins97 TikTok: https://www.tiktok.com/@james.r.robbins Book (Nine Minutes on Monday): https://www.amazon.com/s?k=nine+minutes+on+monday Find more episodes at: https://www.youtube.com/@CaralinesAdventureOfficial [https://www.youtube.com/@CaralinesAdventureOfficial] Or www.CaralinesAdventure.com Credits: Technology support - John Hickman Graphic Design - Sterling Rose Creates

47. The Courage to Keep Climbing

What does it take to build real confidence? In this inspiring episode, Caraline sits down with international speaker, bestselling author, and TEDx speaker Simone Knego to explore the journey from self-doubt to unshakable confidence. From climbing Mount Kilimanjaro to raising six children and launching a successful career, Simone shares how embracing failure, letting go of comparison, and taking one courageous step at a time transformed her life. Together, Caraline and Simone dive into the lessons that come from life's hardest moments—including parenting, personal trauma, imposter syndrome, and learning to stop hiding behind perfection. Through honest stories and practical wisdom, they reveal why confidence isn't something you're born with—it's something you build through resilience, authenticity, and a willingness to keep growing. If you've ever questioned your worth, struggled to believe in yourself, or wondered if you're capable of more, this conversation is a reminder that your greatest setbacks can become your greatest strengths. You don't need to change who you are—you simply need to change the way you see yourself. https://simoneknego.com FB- https://www.facebook.com/SpeakerSimoneKnego IG- https://www.instagram.com/simoneknego/ LI- https://www.linkedin.com/in/simoneknego Amazon - https://geni.us/ExtraordinaryYou https://www.youtube.com/@her_unshakeable_confidence https://podcasts.apple.com/us/podcast/her-unshakeable-confidence-podcast/id1667058474 https://www.ted.com/talks/simone_knego_t_a_l_k_ing_to_kids_about_bias https://www.ted.com/talks/simone_knego_how_to_find_your_kilimanjaro https://realconfidencebook.com/ Find more episodes at: https://www.youtube.com/@CaralinesAdventureOfficial [https://www.youtube.com/@CaralinesAdventureOfficial] Or www.CaralinesAdventure.com Credits: Technology support - John Hickman Graphic Design - Sterling Rose Creates

45. Finding Hope After a Lifetime of Survival

What happens when a child is forced to become the adult long before they're ready? In this unforgettable episode of Caroline's Adventure, Caroline sits down with Shelly Grimm—financial consultant, author, founder of The Perpetual Caregiver, and a woman whose life has been defined by extraordinary resilience. Shelly's story begins with becoming the lifelong caregiver for her chronically ill mother, one of the first women diagnosed with Crohn's disease in the United States. By just 13 years old, Shelly was legally emancipated, managing adult responsibilities that most people never face. At 17, her life took another shocking turn when a hit was put out on her, forcing her to flee her hometown with the help of a police officer. But this conversation isn't just about surviving unimaginable circumstances. It's about what happens afterward. Shelly shares how trauma shaped her relationships, why resilience is a muscle that must be exercised, and how grief isn't something we "get over"—it's something we learn to carry. Together, she and Caroline dive into caregiving, childhood trauma, financial preparedness, emotional healing, and the surprising role that humor can play in surviving life's darkest seasons. Today, Shelly has transformed decades of hardship into a mission of helping families prepare for life's unexpected challenges through financial planning, caregiving advocacy, and her upcoming memoir, Some Asses Just Need Wiping. This episode is a powerful reminder that while we can't always choose what happens to us, we can choose what we build from the broken pieces. https://www.theperpetualcaregiver.com/ https://www.linkedin.com/in/shellygrimm/ Find more episodes at: https://www.youtube.com/@CaralinesAdventureOfficial [https://www.youtube.com/@CaralinesAdventureOfficial] Or www.CaralinesAdventure.com Credits: Technology support - John Hickman Graphic Design - Sterling Rose Creates

44. Rock Bottom to Remarkable: How Ken Miller Rebuilt His Life

How do you rebuild a life after losing everything? In this episode of Caroline's Adventure, I sit down with Ken Miller to explore one of the most remarkable stories of resilience I've ever heard. Ken's journey took him from an Ivy League education to addiction, homelessness, prison, and rock bottom. Today, he's a successful entrepreneur, bestselling author, speaker, and mentor helping thousands of people transform their own lives. But this conversation isn't just about overcoming addiction. It's about learning to face painful truths, healing childhood trauma, finding purpose after unimaginable loss, and discovering that your greatest setbacks can become the foundation for your greatest strengths. Together, we dive into the mindset shifts that changed everything, why courage isn't the absence of fear, how shame keeps us stuck, and what it really takes to create lasting transformation. Whether you're navigating your own challenges or simply looking for a reminder that hope is never out of reach, this episode will leave you believing that no matter how far you've fallen, your story isn't over. Learn more about Ken:  Website: www.kenmillerspeaks.com [http://www.kenmillerspeaks.com/]   Book: Becoming Ken: One Black Man's Journey from Ivy League to Prison and Back Again   Instagram: @thekenmillerspeaks   LinkedIn: www.linkedin.com/in/kenmiller84 [http://www.linkedin.com/in/kenmiller84]   X (Twitter): @kenmillerspeaks   Facebook: Ken Miller Speaks Find more episodes at: https://www.youtube.com/@CaralinesAdventureOfficial [https://www.youtube.com/@CaralinesAdventureOfficial] Or www.CaralinesAdventure.com Credits: Technology support - John Hickman Graphic Design - Sterling Rose Creates