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She Took Herself to Italy at 44. What Happened Next Changed Her Life.

She Took Herself to Italy at 44. What Happened Next Changed Her Life.

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What happens when your life falls apart… and you book a one-way ticket to Italy anyway? At 44, with no plan and no art background, Kippi Leonard did exactly that—and everything changed. In this episode, I talk to Kippi about the solo trip that sparked a complete reinvention. From her first emotional moment in front of Michelangelo’s David to selling her paintings for five figures, Kippi’s journey is a powerful reminder that it’s never too late to become who you really are.

We talk about creativity, risk, finding your voice as a woman in midlife, and the realities of building a thriving art business after 40. Kippi shares how she taught herself to draw, built gallery relationships, navigated fear, pricing, and success—and what she’s learned about working hard, setting boundaries, and becoming unshakably herself.

If you're standing at a crossroads, this one’s for you.

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