Sunny Side Up with Jessie May

Jessie May Wolfe
  • 5.0 (1)
  • Alternative Health
  • Updated Weekly

Welcome to the Sunny Side ~ I'm Jessie May, your heartful guide. Sunny Side Up is your weekly space to reboot your radiance on the regular. Each episode invites you to slow down, tune in, reflect and reconnect. To reclaim your power and remember who you are, before the world told you to be. Through heartfelt stories, conversation, meditation and reflective insights, we’ll explore themes of courage, connection and living life on purpose. May this be your sanctuary to come home to every Sunday. So come cozy on up and let's recharge that sunshine from within.

  1. 2d ago

    The Rhythm of Renewal

    What if life isn’t asking you to begin again, but to meet what’s already here with new eyes? In this episode, I’m exploring the rhythm of renewal — the ways life is continually reorganizing, revealing, rooting, and inviting us to pay closer attention. From my own unexpected season of healing to the re-emergence of HeartRise in a new form, this is a conversation about trusting our timing, honoring what’s happening beneath the surface, and becoming present enough to recognize what life is already showing us. This week’s episode, we dive into:
• Why renewal can begin before the hard part is over
• Trusting the wisdom of your own timing rather than forcing what comes next
• How old ideas, callings, and parts of ourselves can return with entirely new meaning
• The power of thresholds — from Lion’s Gate to the meaningful moments we create for ourselves
• Following the winks, patterns, synchronicities, and recurring threads asking for our attention Renewal is not a destination. It is a rhythm. Come listen in — and become a loving witness to your own life. Notice what’s returning, what feels complete, what wants more space, and what may have been speaking to you all along.

  2. Aug 2

    Your Heart Speaks In Layers: Learning the Language of Your Heart

    What if your heart speaks a language you’ve never been taught to understand? In this episode, I’m shining a light on HeartRise—the heart-centered methodology that has shaped my life, my work, and the way I’ve supported thousands of people over the past two decades. Together, we’ll explore why emotional fluency matters more than ever, how our hearts hold multiple truths at once, and why changing our relationship with our emotions can transform the way we move through life. In this episode, I dive into: ​ Why the heart speaks in layers, not labels​ The difference between emotional intelligence and emotional fluency​ The neuroscience of naming our emotions and how it helps regulate the nervous system​ The four HeartRise steps: See • Feel • Free • Flow​ How curiosity can replace certainty and deepen our compassion—for ourselves and one another You don’t need fewer feelings. You need a deeper relationship with the ones already here. This conversation is an invitation to stop simplifying your experience and start honoring its beautiful complexity. Your heart has been speaking all along. Maybe all that’s changed is your willingness to listen. If this episode speaks to you, share it with someone who might need to hear it, too. ✨

  3. Jul 26

    The Deeper Your Surrender, the Deeper Your Capacity to Receive

    What if the very thing that’s asking you to slow down is actually making space for something far more beautiful than you could have planned? This week, I’m coming to you live from the California coast with a raw, unfiltered reflection on one of the biggest lessons this season has offered me. Through my “Golden Break,” unexpected detours, beautiful conversations, and the countless reminders that life has brought this week, I’m exploring what becomes possible when we loosen our grip, trust a little more deeply, and make room for life to surprise us. In this episode, I dive into: * Why the deeper the surrender, the more expansive the potential * The miracles often hidden inside delays, detours, and disappointment * How trust creates space for what control never could * Reflection prompts to help you soften, receive, and notice what’s already unfolding Surrender doesn’t shrink our lives—it expands our capacity to receive them. Come listen in from the beach with me. And if this episode speaks to your heart, I’d love for you to share it with someone who could use this reminder today. with big warm love, Jessie May

  4. Jul 19

    Changing the Way We Relate Changes Everything

    What if the quality of your life is shaped not by what happens to you, but by the way you relate to it? Fresh from leading HeartRise & Shine at Illume Festival, this raw and heartfelt episode explores a realization that has been quietly transforming the way I see healing, growth, and our shared human experience: everything is relationship. Together, we’ll explore how the way we relate—to ourselves, our bodies, our emotions, uncertainty, and one another—shapes not only our perspective, but the very experience of being alive. In this episode, I dive into: * Why we experience life through relationship, not just circumstance * How every challenge invites a new way of relating * The neuroscience of how we create meaning from our experiences * Reflection prompts to deepen your relationship with yourself and with life * How changing the way you relate can change everything Love is not something we find. Love is how we learn to relate. Come listen in—and if this conversation speaks to your heart, share it with someone you love. Because sometimes the smallest shift isn’t in our circumstances… it’s in the way we choose to relate to them.

  5. Jul 12

    What Is This Here To Teach Me?

    What if the question that changes everything isn’t “Why is this happening?” but “What is this here to teach me?” This week on Sunny Side Up, I’m sharing a deeply personal reflection inspired by a milestone I had been eagerly anticipating—having my cast removed after breaking my wrist. What I thought would feel like the finish line became a beautiful reminder that healing isn’t an event… it’s a relationship. Together, we’ll explore what happens when we stop rushing toward arrival and begin meeting life with curiosity instead of control. Because whether you’re navigating change, uncertainty, grief, growth, or standing on the edge of a new beginning, there is wisdom waiting for us when we’re willing to stay open. In this episode, I dive into: • Why we so often postpone living while waiting to “arrive” • The transformative question: What is this here to teach me? • How curiosity creates space where judgment cannot survive • The neuroscience of growth and our brain’s remarkable capacity to keep evolving • Why your “brace” may look different than mine—and how to meet it with greater compassion • Learning to surf life’s waves instead of trying to control the ocean Maybe life isn’t asking us to get everything right. Maybe it’s simply asking us to stay teachable. Come listen in, and if this conversation meets you where you are, I’d love for you to share it with someone who might need this reminder today. 🌞

  6. Jul 5

    Life is Always Speaking: Are We Available Enough to Listen

    The most meaningful moments of our lives rarely announce themselves. More often, they arrive quietly, waiting for us to notice. In this week’s episode of Sunny Side Up, I’m reflecting on an unexpected season of slowing down after fracturing my wrist—and the profound gifts that have emerged in the pause. Together, we’ll explore The Sacred Ordinary: the practice of noticing, the quiet power of wonder, and how life begins to feel richer when we become fully available to the moment we’re already living. In this episode, I dive into: • Why our lives become what we practice noticing • How slowing down can deepen healing, trust, and presence • The neuroscience of attention, awe, and why wonder transforms us • Why witnessing is one of the purest expressions of love • Finding the sacred in the beautifully ordinary moments we so often overlook Nothing becomes sacred because it’s extraordinary. It becomes sacred because we finally give it our full attention. Come listen in—and if this conversation inspires you to pause, look up, and notice the beauty that’s already here, I’d love for you to share it with someone who could use this reminder today. With big warm love, Jessie May 🌞

  7. Jun 28

    Uncovering the Cost of What You Value

    Some words don’t just describe our lives—they determine them. Value is one of those words. This week, I’m unpacking the hidden systems of valuation that influence where our attention goes, how we make decisions, and what we come to believe is worthy of our time, energy, and love. Inspired by an unexpected season of slowing down, this conversation is an invitation to reconsider the inherited beliefs that may no longer belong to you. In this episode, I dive into: • How the brain continually assigns value to our experiences. • The beliefs we inherit about worth, productivity, and success. • Three layers of value that influence the way we live. • Why attention may be our most precious currency. • Reflection questions to help you reevaluate what truly matters. “The unexamined values quietly become the unexamined life.” If this episode speaks to you, I’d love for you to share it with someone who might be in a season of reevaluating what matters most. And if you’re enjoying Sunny Side Up, a rating or review helps this conversation reach more hearts

  8. Jun 21

    Finding Grace in the Unexpected: A Personal Reflection

    This week’s episode is a little different. Following an unexpected wrist fracture that brought my upcoming travels, events, and carefully arranged calendar to a sudden halt, I found myself being called into a much deeper surrender. What began as an unwelcome interruption became an invitation to trust more fully and open to the grace, support, and unexpected angels that have appeared along the way. In this deeply personal reflection, shared from the midst of this unexpected season, I explore what happens when life asks us to relate to time in a different way. Drawing on the ancient distinction between Chronos—the world of schedules and timelines—and Kairos—the sacred space where grace, synchronicity, and deeper wisdom can emerge—I share some of the insights, tenderness, and miracles that have found me in the pause. As we stand on the threshold of a new season, perhaps we are being invited to soften our grip, listen more deeply, and remember that life isn’t a race to be won, but a mystery to be lived. After all, as Montreal’s own Leonard Cohen so beautifully reminded us, “There is a crack in everything. That’s how the light gets in.” Maybe what feels like an interruption is actually an invitation. And maybe something beautiful is waiting to emerge. With big warm love, Jessie May

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About

Welcome to the Sunny Side ~ I'm Jessie May, your heartful guide. Sunny Side Up is your weekly space to reboot your radiance on the regular. Each episode invites you to slow down, tune in, reflect and reconnect. To reclaim your power and remember who you are, before the world told you to be. Through heartfelt stories, conversation, meditation and reflective insights, we’ll explore themes of courage, connection and living life on purpose. May this be your sanctuary to come home to every Sunday. So come cozy on up and let's recharge that sunshine from within.

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