HeyJaredSunny Side Up with Jessie May
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.
- Indexed episodes, last 90 days
- 13
- Latest publication
- Sep 27, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 5, 2026
Latest episodes
The More You Trust, the More You See. (opens the original)
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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 avail
The World Changes When You Do (opens the original)
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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 posi
Your Freedom Is Closer Than You Think (opens the original)
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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, ordinar
Simplify: Make Space for What Your Heart Knows (opens the original)
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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
The Imprint of a Life: For Dolly (opens the original)
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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
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