Speaker, Authenticity Advocate & Founder of Hurray Kimmay
Kimmay Caldwell
Kimmay Caldwell is a speaker, authenticity advocate, and founder of Hurray Kimmay®, where she helps folks feel more confident and comfortable showing up as their whole selves and in the body they have today. Through her workshops, bra and swimwear education, and TV appearances, Kimmay creates honest, joyful spaces for folks to say hurray inside, outside, and underneath. You may have seen her on Rachael Ray (10x), TODAY (10x), The Drew Barrymore Show (2x), The Marilyn Denis Show, or The Good Stuff with Mary Berg. She’s a trusted voice in the press and is committed to celebrating real bodies, real lives, and the courage to show up unfiltered. From NY, she's currently based in Philadelphia.
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Kimmay's 2026 Weekend Getaway Offerings
CAPACITY CHANGE: ACCEPTING WHAT LIFE IS IN YOUR NEXT CHAPTER - WORKSHOP
Capacity shifts can happen for many reasons and in many seasons. What if it's OK to admit that you can't hold all of the same things you were able to before? In this honest and compassionate workshop, we’ll explore self-forgiveness, acceptance, and celebrating what’s already here, while identifying where a change in expectations or behavior can help us move forward. You’ll leave with a clearer sense of what to release, what to celebrate, and what you’re ready to change. Expect an immersive experience with guided meditation, journaling, sharing, and celebrating.
UNAPOLOGETICALLY YOU: THE COOLNESS OF LEANING INTO THE CRINGE - WORKSHOP
What if the things you worry are “too much,” awkward, silly, or cringe are actually the things that make you most you? In this playful, honest workshop, we’ll explore how to let go of the pressure to be cool, stop overthinking what others might think, and get more comfortable showing up as your authentic self. You’ll leave with permission to take up space, embrace your quirks, and lean into the cringe instead of shrinking yourself to avoid it.
Kimmay's Past Weekend Getaway Offerings
NEVER TOO MUCH (OR NOT ENOUGH) - WORKSHOP
Have you ever felt like you were being too loud, taking up too much space, or had the "who am I to do this?" inner talk? It turns out, feeling like you're too much or not enough are two sides of the same story. Journey through this potent talk and inner exercise with Kimmay to finally feel "full of yourself" in the best, most whole and worthy way so you can take your own step toward standing confidently in who you are, make aligned decisions, and stand up or step down without worry. Hurray!