In this episode of Self, Made, SAYA co-founder Nathalie D Ramirez sits down with Rachael Wheeler – Creative Director and MD at The Smalls – and Property NXT co-founder Cilla Burgmann to talk about what happens when the lives we’ve built no longer fit who we are. They explore the often-overlooked transitions: the quiet unraveling of identity after a layoff, the tension between creative leadership and commercial responsibility, and the inner conflict of knowing when to stay versus when to walk away. This is a conversation about self-worth beyond job titles, ambition redefined by motherhood, and the courage to admit when the metaphorical shoe just doesn’t fit anymore. Honest, nuanced, and unscripted.