Sunny Side Up with Jessie May – Details, episodes & analysis

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Sunny Side Up with Jessie May

Jessie May Wolfe

Health & Fitness

Frequency: 1 episode/7d. Total Eps: 84

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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Data updated on 14/07/2026

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🇨🇦 Canada - Alternative Health
21/06/2026
#98

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https://sunnysideupsanctuary.substack.com/
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Score global : 58%

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Listening for Alignment: Learning to Trust What Feels True

Season 11 · Episode 84

Sunday, June 14, 2026 • Duration 28:18

What if alignment isn’t something you create, but something you learn to hear?

In today’s episode, we’re exploring the subtle but powerful distinction between effort and force, and what it means to listen for alignment in a world that constantly asks us to push harder. Together, we’ll unpack the difference between the discomfort that accompanies growth and the exhaustion that comes from betraying ourselves, and how cultivating deeper listening can guide us back to what is truly ours to hold.

In this episode, I dive into:

• The difference between aligned effort and forcing

• Why alignment isn’t the same as ease

• How overfunctioning and self-abandonment can masquerade as strength

• The questions that help us discern what is truly ours to carry

• Learning to loosen our grip and partner with life rather than control it

• Why listening may be more important than pushing

What if life isn’t asking you to push harder. Maybe it’s inviting you to listen more deeply.

Come listen in — and if this conversation speaks to you, share it with someone who could use a reminder that not everything meaningful requires force, and that sometimes the deepest wisdom arrives when we soften enough to hear it. ☀️

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Building a Relationship with Discomfort: What Growth Feels Like in Real Time

Season 11 · Episode 83

Sunday, June 7, 2026 • Duration 26:52

What if the unfamiliar isn’t pulling you off course, but inviting you forward?

In today’s episode of Sunny Side Up, we’re exploring our relationship with discomfort and why so many of us mistake unfamiliarity for misalignment. Together, we’ll unpack why growth rarely arrives with certainty, how the nervous system gravitates toward what is familiar, and what becomes possible when we stop treating discomfort as the enemy and begin listening to what it may be trying to teach us.

In this episode, I dive into:

• Why familiar is not always the same as true

• The difference between discomfort and misalignment

• How awareness creates movement and growth

• The space between who you’ve been and who you’re becoming

• Why confidence often follows action, not the other way around

• Building a healthier relationship with uncertainty, change, and expansion

• Reflection prompts to help you navigate your own season of becoming

“The unfamiliar does not automatically mean untrue.”

Come listen in — and if this conversation resonates, share it with someone who may need this message today.

with big warm love,

Jessie May

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Returning to What Matters: A Practice of Remembering

Season 11 · Episode 82

Sunday, May 31, 2026 • Duration 26:30

What if the quality of your life is shaped less by what you achieve and more by what you repeatedly return to?

In this week's episode of Sunny Side Up, I'm exploring the heart of devotion—not as sacrifice or obligation, but as the practice of consciously directing your attention toward what matters most.

In a world designed to pull us in a thousand directions, devotion asks a different question: What is receiving the best of your energy?

Together, we'll explore how our habits, thoughts, relationships, and daily choices quietly shape the lives we're creating—and why attention may be one of the most powerful creative forces we possess.

In this episode, I dive into:

• The connection between attention and devotion
• The hidden habits and patterns that quietly shape our lives
• Why devotion is a practice of remembering and returning
• The difference between force and true alignment
• How to move from distraction toward a more intentional life
• Reflection questions to help you reconnect with what matters most

"We become what we repeatedly attend to."

Come listen in—and if this episode speaks to you, share it with someone who could use this reminder today.

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You Were Never Meant to Be Just One Thing

Season 11 · Episode 81

Sunday, May 24, 2026 • Duration 26:03

We all carry many selves — the roles we step into, the parts we silenced to survive or belong, and the versions of ourselves that emerge in different seasons of life.

But what happens when one of those roles no longer fits? When something in you is ready to evolve, integrate, or simply finally breathe?

So many of us are in a season of becoming. Not performing growth. Not curating healing. But genuinely listening inward and asking: who am I underneath all of this?

In this episode, I dive into:

• Why wholeness is messier — and truer — than perfection

• How we quietly abandon parts of ourselves in order to survive, belong, or be loved

• The difference between adaptation and identity

• What it means to create an inner vessel spacious enough to hold all of who you are

• Why you are allowed to evolve — and to outgrow what no longer fits

• Reflection prompts to help you welcome the parts of you that are ready to come home

“Do I contradict myself? Very well, then, I contradict myself. I am large, I contain multitudes.” — Walt Whitman

Come listen in — and if this speaks to you, share it with someone in their own season of becoming.

Grateful for your presence ☀️

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Reclaiming Your Attention in a Distracted World

Season 11 · Episode 80

Sunday, May 17, 2026 • Duration 23:25

What if the quality of your life is shaped by where your attention goes each day?

In today’s episode, I’m diving into the power of focus in a world constantly pulling us in a hundred different directions. This conversation is an invitation to slow the noise, reclaim your energy, and reconnect with what truly matters — not through hustle or pressure, but through grounded, intentional presence. We explore the emotional side of distraction, the nervous system impact of fragmented attention, and why calm consistency creates far more momentum than chaotic urgency.

In this episode, I dive into:
• Why focus is an energetic practice — not just discipline
• How constant distraction fragments our energy and disconnects us from our rhythm
• The neuroscience behind task switching, overwhelm, and mental fatigue
• Why completing even small tasks builds self-trust and emotional regulation
• The deeper emotional patterns that may be hiding beneath distraction and avoidance
• How protecting your attention can help you create more clarity, momentum, and freedom
• Reflection prompts to help you reconnect with what truly deserves your focus

Where your attention goes, your energy flows.

Come listen in — and if this episode resonates, share it with someone navigating overwhelm, transition, or the feeling of being pulled in too many directions.

Grateful for your presence!

much love,

Jessie May

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The Vessel: Holding More Without Losing Yourself

Season 11 · Episode 79

Sunday, May 10, 2026 • Duration 23:54

What are you filling your vessel with?

This week on Sunny Side Up, I’m exploring the deeper meaning of the vessel — the container holding your life.

Your body.

Your nervous system.

Your relationships.

Your creativity.

Your rhythms.

So often, we focus on what we want to build, heal, create, or call in… but we rarely stop to ask whether the vessel holding it all is actually being tended to.

In a world moving at a relentless pace, this episode is an invitation to slow down, reconnect with yourself, and strengthen the inner container that allows your life to feel sustainable, nourishing, and true.

In this episode, I dive into:

* Emotional capacity and the vessel of relationships

* Nervous system care and overstimulation

* Why strength is not hardness

* Creativity, resilience, and sustainable growth

* The small rhythms and rituals that shape our lives

* What truly nourishes — and what depletes — your vessel

* Reflective journal prompts to help you reconnect with yourself

“Maybe the deeper work isn’t becoming someone entirely different. Maybe it’s learning how to tend to the vessel of who you already are.”

Rebirth & Resilience: When Life Changes You

Season 11 · Episode 78

Sunday, May 3, 2026 • Duration 23:31

What if the moments that shake you… are the ones that bring you closest to what truly matters?

In this deeply personal episode, I share from a week that held both fragility and profound connection—walking alongside loved ones through serious diagnoses, and being reminded in real time of how precious life is. This is a conversation about staying open in the face of uncertainty, honoring the cycles we move through, and allowing life to refine us rather than close us.

In this episode, I dive into:

• The power of presence in life’s most tender moments

• How fragility brings clarity to what truly matters

• Why staying open—rather than shutting down—is a courageous choice

• Recognizing when life is asking you to be more honest

• Rebirth as a subtle shift in how you see, feel, and choose

“You don’t realize how sacred life is until you feel how fragile it can be.”

Come listen in—and if this speaks to you, share it with someone who might need this reminder right now.

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Sensitivity Is Your Superpower: Protecting the Gift

Season 11 · Episode 77

Sunday, April 26, 2026 • Duration 28:06

What if the part of you that feels deeply is actually one of your greatest strengths?

In this week’s Sunny Side Up, we explore why sensitivity is not something to fix — it’s a powerful form of awareness, intuition, and wisdom.

In a world that can feel loud, fast, and emotionally demanding, learning to protect your sensitivity may be one of the most important acts of self-leadership right now.

From nervous system cues to creating soft places to land, this episode is a loving reminder that your tenderness is not weakness — it may be the very compass guiding you home.

In this episode, I dive into:

• Why sensitivity is heightened awareness, not fragility

• How your nervous system communicates through overwhelm, anxiety, and exhaustion

• The importance of protecting your energy in harsh environments

• Creating soft spaces to land, listen, and restore yourself

• How sensitivity deepens love, intuition, creativity, and wise leadership

• Why sensitive souls are especially needed in these times

“You were never too much. You were sensing what others learned to ignore.”

Come listen in — and if this episode meets you, pass it to someone who feels deeply and may need these words today.

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The Wisdom of the In-Between: When Life Feels Uncertain

Season 11 · Episode 76

Sunday, April 19, 2026 • Duration 31:02

What if the uncertainty you’re feeling right now is not something to fear — but an invitation into a new season of growth?

In today’s episode, we explore The Wisdom of the In-Between — those liminal seasons where life feels undefined, shifting, or not yet clear. Through soulful reflections, science, and heart-centered insight, I share how reconnecting to your aliveness can soften fear, deepen trust, and help you meet uncertainty with greater steadiness and grace.

In this episode, I dive into:

• Why trust is a felt sense, not just a mental concept

• How the nervous system shapes our relationship with uncertainty

• Why the in-between can be fertile ground, not empty space

• The power of reconnecting to the life force moving through you

• Reflection prompts to help you navigate change with more ease

“When you trust what feels alive, the path begins to meet you.”

Come listen in — and if it speaks to you, share it with someone moving through an in-between season who could use a little soul fuel today.

Thank you for being here.

Jessie May

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The Power of Trusting Yourself

Season 11 · Episode 75

Sunday, April 12, 2026 • Duration 27:04

What if the very place you keep doubting yourself is where trust is waiting to be built?

Last week, we explored how relationships can mirror what’s happening within us. In today’s episode, I take that conversation deeper and explore what happens next: how to stay with yourself when something gets activated. I share reflections, nervous system wisdom, and practical guidance on how anxiety, doubt, and triggers can become signals guiding you back to clarity, truth, and the relationships where you can truly thrive.

In this episode, I dive into:

Why seeing the reflection is only the beginning
How self-trust is built in the moments you would usually leave yourself
The subtle clues that show you you’ve drifted from your own center
Why anxiety, fear, and doubt can be invitations toward alignment
How trusting yourself changes what you allow, choose, and receive
Building loving boundaries and relationships where you can thrive

“Self-trust is built each time you choose not to leave yourself.”

Come listen in — and if this lands for you, share it with someone learning to trust their own knowing.

Thank you for being here ☀️

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Sunny Side Up with Jessie May – Details, episodes & analysis

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Sunny Side Up with Jessie May – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Substack1

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Substack1