Sunny Side Up with Jessie May

What happens when the life you’re living no longer fits the story you’ve been telling about who you are?

Coming off 100 episodes and into a season of extraordinary change, I’ve been reflecting on the identities we inhabit — the capable one, the independent one, the achiever, the caretaker, the one who holds it all together. The familiar versions of ourselves that have served us beautifully, but may no longer tell the whole story.

Between my own unexpected season of healing, learning to receive in entirely new ways, and witnessing profound shifts in the lives of my clients and communities, one thing keeps revealing itself: Sometimes our lives change faster than our identities can catch up.

And perhaps the invitation isn’t to shed who we’ve been, but to expand our capacity to hold more of who we are.

In this episode, I dive into:

• Why the identities that once supported us can quietly become the very things that limit us
• The psychology of self-concept, confirmation bias, and why familiar patterns can be so difficult to change
• How we can be living a new life while still making choices from an old identity
• The paradox of wanting change while clinging to the roles and stories that keep us where we are
• What becomes possible when strength makes room for softness, independence for intimacy, and ambition for ease
• A powerful identity inventory with reflections to help you recognize what’s ready to expand.

Our history is part of who we are, but it does not have to be what limits us.

This is a conversation about honoring everything that has brought us here without becoming confined by it. About allowing ourselves to surprise ourselves, stretch beyond what’s familiar, and give more of who we are the space to breathe, bloom, and become.

Come listen in, my loves. And if this one resonates, pass it along to someone who’s finding their way into a new expression of themselves.

What if your calling isn’t something you have to find—but something that has been calling you all along?

In this very special 100th episode of Sunny Side Up, I’m coming to you raw, unproduced, a little under the weather, and with a heart fuller than it’s been in a very long time.

After a season of heartbreak, healing, unexpected love, synchronicity, surrender, and profound transformation, I’m reflecting on what 100 consecutive weeks of showing up have taught me about listening to what keeps calling—and becoming available to receive what life is trying to bring toward us.

In this episode, I dive into:

• Why our calling may be less about becoming and more about remembering who we’ve always been
• How the threads that keep returning can reveal what wants our attention
• Why calling isn’t only about purpose or work—it can lead us toward love, people, places, and entirely new ways of being
• The relationship between devotion and receiving, and why both are essential
• How disruption can quiet the noise enough for us to hear what life is actually asking of us
• What 100 weeks of Sunny Side Up have taught me about trusting the unfolding

We don’t always have to know what we’re making space for. Sometimes we’re simply being asked to create the space.

Thank you for 100 beautiful weeks on the Sunny Side. Come listen in—and if this one speaks to your heart, share it with someone whose presence has touched your life in a meaningful way. 🌞

With big warm love,

Jessie May

What if life is speaking to you in ways you’ve been too busy to notice?

Those uncanny moments of timing. The person who appears just as you were thinking of them. The conversation that unlocks something you’ve been sitting with. The unexpected door that opens while you’re still staring at the one that closed.

This week on the Sunny Side, Jessie May explores synchronicity—and what becomes possible when we loosen our grip, surrender the need to know exactly how things will unfold, and become available to notice how life is already meeting us.

From Carl Jung’s concept of meaningful coincidence to the science of selective attention, we explore why synchronicity can feel heightened during seasons of transition, how our inner world shapes what we’re available to see, and why noticing the breadcrumb is only the beginning.

Because synchronicity may open the door—but we still get to walk through it.

✨ What keeps repeating?
✨ What feels alive?
✨ What unexpected door opened while you were focused on the one that closed?
✨ What thread keeps appearing in your life that you haven’t followed yet?

You don’t need the whole map. Trust the next breadcrumb.

Your presence is your power. 💛

Thank you for being here.

Jessie May

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.

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☀️

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.

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. ✨

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.

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.

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.