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. 4d ago

    The World Changes When You Do

    There is always more happening than the story we’ve decided is true. This week, I’m continuing our conversation about freedom by exploring what becomes possible when we widen the lens through which we see our lives. I’m sharing from a deeply personal season—one holding physical pain, disappointment, and circumstances I never would have chosen, alongside extraordinary kindness, unexpected connection, love, laughter, and some of the most magical moments I could have imagined. This isn’t about positive thinking or pretending the difficult things aren’t happening. It’s about becoming available to the whole picture—and recognizing how profoundly our inner landscape shapes what we notice, what we expect, and ultimately what we experience. In this episode, I dive into: • How our brains filter reality through expectations, past experiences, and attentional bias
• Why what we look for, we become increasingly good at finding
• How old stories can quietly become the evidence we keep searching for
• The heart’s capacity to hold pain and possibility at the same time
• A simple practice for widening the frame: “What else is here?” Something can be deeply wrong, and something else can be profoundly right. We may not get to choose everything that happens, but we do have agency over the world we cultivate within us—and what we become available to see, receive, and contribute. This week, pay loving attention to what you’re looking for. The darkness may be real, but it doesn’t get to convince us it’s all there is.

  2. Sep 13

    Your Freedom Is Closer Than You Think

    What if you don’t need to know what happens next to trust yourself now? After a summer of healing — and months of wanting my arm to move when it simply wouldn’t — I’ve been thinking a lot about freedom. The obvious kind, yes: opening my palm, reaching, sleeping comfortably, putting my hands together in prayer. But also the quieter freedom we can lose when we become convinced that something out there needs to change before something in here can. This week, I could clap again. Such a tiny, ordinary movement — and it cracked something wide open for me. Because freedom can return in millimeters. In this episode, I dive into: ​What happens when an outer limitation becomes an inner constriction• The science of why stress narrows our perception — and why possibility becomes harder to see when we feel trapped• The ways we outsource our deepest knowing when we’re desperate for certainty• Why surrender isn’t giving up — and how it can become the bridge between acceptance and change• The relationship between freedom, spaciousness, intuition and self-trust• The small freedoms still available when the whole door hasn’t opened yet Freedom isn’t knowing exactly how everything will work out. It’s trusting yourself enough to know you’ll meet what comes. This one is personal, embodied, and very much being lived in real time — an exploration of the freedom that remains available even when life feels limiting, and the knowing that returns when we create enough space to hear ourselves again. Come listen in — and if it meets you somewhere you’ve been feeling stuck, share it with someone who might need a little more spaciousness, possibility, and freedom today. Thank you for being here, Jessie May☀️

  3. Sep 6

    Simplify: Make Space for What Your Heart Knows

    What if the way forward becomes clearer when you stop trying to hold everything—and everyone? In today’s raw, unproduced episode, I’m coming to you fresh from the field to explore how quickly life becomes crowded—with other people’s needs, competing possibilities, responsibilities that may not be ours, and all the thinking we use to try to find certainty. This is a conversation about simplicity as a return to what is true—and the courage to listen when your heart is asking you to choose. In this episode, I dive into: • Why complexity can become a way of postponing our truth
• How people pleasing and overfunctioning leave us overwhelmed and disconnected from our own knowing
• What may actually be living beneath “I don’t know”
• The courage to choose what deserves our full devotion
• Why focus gives us the freedom to be fully present When everything is treated as equally important, we lose sight of what actually is. Come listen in—and give yourself permission to put down what isn’t yours, stay close to what is, and choose the truest next thing.

  4. Aug 30

    The Imprint of a Life: For Dolly

    What kind of imprint do you want your life to leave? In today’s raw episode, I’m honoring the legendary Dolly Parton — not only for the songs, the sparkle, the wit, and the extraordinary life she built, but for the way she lived. This is a reflection on what she embodied so beautifully: knowing who you are, keeping your heart open, turning hardship into deeper roots, and using your gifts in service of something larger than yourself. In this episode, I dive into:• The courage to know who you are and live it on purpose• The deeper wisdom of Coat of Many Colors and redefining what makes us rich• How to let life deepen your roots without hardening your heart• The difference between success and significance• Why our light was never meant to stop with us• The imprint we leave through generosity, presence, courage, and love “Being a star just means that you find your own special place, and that you shine where you are.” — Dolly Parton This episode is part tribute, part reflection, and part prayer — an invitation to honor Dolly not only by remembering her, but by carrying forward the love, generosity, and radiant spirit she showed us so beautifully. Come listen in — and if it speaks to you, share it with someone who could use a little Dolly wisdom and soul fuel today. ✨

  5. Aug 23

    What Are You No Longer Available For? Changing the Agreements You’ve Outgrown

    What are you no longer available for—not because you’ve become harder, but because something in you has become clear? There comes a point when the patterns, agreements, and ways of relating that once served us simply no longer do. This conversation is an invitation to listen to what your body, heart, and life already know—and to discover the power that comes from honoring what is no longer yours to carry. In this episode, I dive into:
• The invisible agreements we make without realizing it
• Why your body often knows before your mind catches up
• The difference between discomfort that asks you to grow and discomfort that says enough
• Reclaiming your “no” as an expression of self-trust
• What becomes possible when you stop negotiating with what you already know You don’t need to make anyone wrong in order to decide something is no longer right for you. Come listen in—and ask yourself: What am I no longer available for, and what does that make me more available for now? And if you’re craving a space to take these conversations deeper, join us in Sanctuary, our monthly Sunny Side Up community circle.

  6. Aug 16

    Tender is the WAY

    What if the way through isn’t asking you to push harder, but to tend more deeply to the truth of what is here? In this week’s episode, I’m exploring tenderness as a way of meeting our lives with greater presence, honesty, and loving care — especially in the places that ask us to slow down enough to really listen. Whether it’s our bodies, relationships, work, emotions, or the deeper transitions shaping us, tenderness invites us to stop rushing toward resolution and become more available to what is actually needed. In this episode, I dive into: • Why another layer doesn’t mean you’ve gone backward • Tenderness as deep listening, discernment, and care • The pressure to fix, force, and rush what needs more time • How to meet challenge without hardening your heart • Tending to yourself so you can show up more fully for your life and others Tenderness is not about choosing the easiest response. It is about becoming present enough to recognize the most loving one. Come listen in — and if it meets you somewhere tender, share it with someone who may need a little more loving care today.

  7. Aug 9

    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.

  8. 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. ✨

See All (98)

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.

Information