Waking Up With Ryan

What if the monsters we dress up as on Halloween have more to do with us than we realize? Ryan traces the holiday’s origins to the ancient Celtic festival of Samhain, when the boundary between the living and the dead was believed to grow thin. Drawing on Carl Jung’s concept of the shadow, he explores the curious ways we celebrate fear for one night while spending much of the rest of our lives trying to avoid it. Beneath the costumes, haunted houses, and ghost stories lies a surprising invitation: to consider what we’ve hidden away inside ourselves, and what might happen if we finally allowed those parts to be seen.

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Money, relationships, health, work, family — life can feel like an endless series of problems demanding our attention. And just when you finally solve one, another seems to take its place. But what if all those seemingly unrelated struggles have something in common? Ryan shares an idea that fundamentally changed the way he understands life’s challenges: that beneath the countless problems we spend our days trying to solve lies a single, deeply ingrained belief we rarely stop to question. It’s an invitation to step outside the exhausting cycle of fixing, striving, and worrying, and reconsider what might actually be keeping us from peace.

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You’ve spent your entire life building an understanding of who you are. Your name, your history, your personality, your accomplishments, your struggles — all the things that make you, you. But what if the most important discovery you could make about yourself begins with admitting that you don’t actually know who you are? Drawing on a provocative passage from A Course in Miracles, Ryan explores why the mind clings so fiercely to its familiar identity, and how the simple willingness to question everything you think you know about yourself might open the door to something extraordinary.

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There’s something heartbreaking about looking into the eyes of a child and knowing that life will inevitably bring them pain. As Ryan watches his daughter grow, he finds himself wishing he could protect her from the disappointments, heartbreaks, and struggles that shape us all. But alongside that wish is a different kind of prayer — one that reaches far beyond his own family. Continuing yesterday’s reflection on seeing others as they truly are, Ryan explores what it means to love someone without being able to shield them from life, and the extraordinary possibility of wishing something deeper for the people we cherish.

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Every night as Ryan rocks his six-month-old daughter to sleep, he says a prayer that he hopes will shape their relationship for years to come: “Dear God, help me remember who she is.” It’s easy to see the innocence and wonder in a newborn, but what happens as the years pass, disagreements arise, and our ideas about the people we love begin to overshadow who they really are? Ryan reflects on the stories we accumulate about one another, the ways those stories shape our relationships, and the possibility of seeing even the most familiar people through entirely new eyes.

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What if love isn’t something you have to find, earn, or even learn to give, but something you’ve been all along? We spend so much of our lives searching for love outside ourselves, while the noise of our own thoughts can make it difficult to recognize what’s already there. As Ryan concludes a week devoted to building an inner foundation of peace, gratitude, acceptance, and forgiveness, he turns to the one thing that holds them all together. It’s an invitation to question the limits of who you believe yourself to be, and to discover what might change if you moved through the world knowing that love isn’t something you lack, but something you are.

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Why is it so difficult to forgive someone, even when we know that holding onto resentment only hurts us? We all encounter people who disappoint us, frustrate us, or cause us genuine pain. And sometimes, the things they’ve done feel impossible to look past. But what happens when we begin to see people as something more than their worst moments? Continuing this week’s exploration of building a foundation for daily life, Ryan turns to forgiveness — not as a way of excusing someone’s behavior, but as a way of freeing ourselves from the judgments that keep us disconnected from others, and ultimately, from ourselves.

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What happens when the person who encourages you to find peace is struggling to find it himself? Ryan shares something deeply personal about a darkness that visits him from time to time, and the complicated relationship he’s developed with it over the years. It’s a vulnerable conversation about the pressure to be okay, the quiet ways we turn against ourselves when we’re not, and the possibility that even our most difficult seasons have something to offer us. A gentle guided practice follows, inviting you to meet yourself exactly where you are.

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It’s often the moments when life feels most fragile that bring everything else into focus. After a frightening medical emergency, Ryan finds himself confronting questions that are easy to overlook in the rush of everyday life. Have we told the people we love what they mean to us? Do we really see them, or have familiarity and frustration clouded our vision? Through a deeply personal experience, Ryan reflects on the things we take for granted, the love we leave unspoken, and the extraordinary gift of having someone in our lives.

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How do you stay grounded when life seems determined to pull you in every direction? Between the demands of everyday life, unexpected challenges, and the stories our minds tell us, it’s easy to lose touch with the peace we know is possible. Ryan draws on the imagery of a towering tree and the deep roots that keep it standing through a storm to explore what it means to build a foundation within yourself. A gentle guided visualization invites you to discover a place of safety and stillness you can return to, no matter what the day brings.

Tell Ryan about yourself! https://wakingupwithryan.com/hello

Follow on Substack (@WakingUpWithRyan)

You can follow Ryan on Instagram (@wakingupwithryan), YouTube (@wakingupwithryanpod), or visit wakingupwithryan.com.

See omnystudio.com/listener for privacy information.