Evolve Your Path
Filling Bigger Shoes, Leadership Growth, and Unapologetic Confidence with Amy Beaulieu, LCSW
Megan Flanagan talks with Amy Beaulieu, licensed clinical social worker and founder of Three Shoes, about the winding path from therapy to leadership development. Amy explains how her “shoes” framework helps people recognize when they’ve outgrown their current role, step into bigger responsibilities, and lead with more confidence and self-awareness.They also discuss what makes leaders thrive in the first 90 days, why human behavior in workplaces changes less than people think, and how women can stop apologizing for taking up space and asking questions. Key topics: In this episode, Amy shares how Three Shoes came to her in a dream and became a metaphor for career growth, coaching, and leadership transitions. Megan and Amy discuss the difference between “big shoes” moments like promotions, parenting, marriage, retirement, and role changes versus “small shoes” situations that feel stifling. Amy explains that the universal signal you’ve outgrown a role is discomfort, often showing up as Sunday dread, feeling underused, or feeling forced into skills that don’t fit. Amy traces her career from social work to EAP work to JetBlue and eventually entrepreneurship, showing how her desire to help people thrive has stayed constant. Amy shares how clinical social work shaped her whole-person approach to coaching, emphasizing the impact of community, school, family, work, and environment on behavior. The conversation explores why leaders and organizations invest in training, and how open-minded cultures often see benefits like retention, productivity, innovation, and easier change management. Amy reflects on the realities of running a business, including contracts, bookkeeping, networking, marketing, websites, and social media, which she underestimated at first. Megan asks about women in leadership, and Amy argues that the biggest barrier is often self-esteem, mindset, and comparison to polished, picture-perfect appearances. Amy introduces her emerging concept of “unapologetic leadership,” centered on candor, conviction, confidence, and bringing your humanness to work. In the bonus clip, Amy explains what thriving leaders do in their first 90 days: build relationships, lead with humility and curiosity, and take work seriously without taking themselves too seriously. Three Shoes - A metaphor for career and life transitions Unapologetic Leadership - Amy’s developing framework built on Chapters: 00:00 - Megan introduces Amy Beaulieu and the Three Shoes concept01:04 - How Three Shoes began in a dream02:37 - The winding career path from social work to leadership development06:06 - How to know when you’ve outgrown your current role08:26 - Why social work still shapes Amy’s coaching style10:30 - How leaders decide whether to invest in training12:32 - The business side of entrepreneurship no one warns you about16:15 - What has changed in workplaces since Amy started in 199420:48 - Why self-esteem and mindset hold people back23:01 - What Amy took away from Mic Drop Live24:25 - How to find an audience for your story25:37 - Surprises about running a business26:56 - What keeps Amy energized in her work28:03 - Leadership as being followed, not just being in charge29:48 - The growth edge of learning to think like a business owner31:25 - Amy’s unapologetic leadership framework33:06 - Why Amy challenges women who start questions with “sorry”34:32 - What unapologetic leadership looks like in practice00:00 - Bonus clip: What thriving leaders do in their first 90 days00:19 - Humility, curiosity, and being human in a new roleKey frameworks Notable quotes: “Everybody needs a coach, everybody needs training.” “Leadership is about being able to be followed.” Connect with Amy: LinkedIn
