Purpose, Reinvented: Leading with Heart, Healing with Work | Bonnie Pomish, CEO of Working Wardrobes

Making Maverick Moves

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A powerful conversation on second chances, purpose, and building dignity through workforce reentry. What does it take to follow in the footsteps of a legendary founder — and make the mission your own? In this inspiring episode, Bonnie Pomish, CEO of Working Wardrobes, shares her bold journey of stepping into leadership with authenticity, compassion, and courage. From empowering veterans and formerly incarcerated individuals to redefining perfectionism and building a values-driven team, Bonnie reveals what it truly means to lead with heart. If you've ever struggled with self-doubt, leadership identity, or finding your purpose — this conversation is for you.

🔗 Donate or get involved with Working Wardrobes: https://www.workingwardrobes.org

Timestamps:

00:00 – Intro: Who is Bonnie Pomish?

02:02 – The mission of Working Wardrobes

04:15 – Serving veterans and translating military skills

06:22 – Parallels between reentry from military & incarceration

07:24 – Succeeding founder Jerry Rosen & "wearing your own shoes"

12:04 – Leading with vulnerability and strengths-based leadership

20:55 – Being a recovering perfectionist & embracing 1% growth

23:06 – Learning through failure and trusting team members

34:16 – What a vulnerable workplace culture looks like

37:54 – Advice for future leaders: be a good human

43:04 – Ways to support Working Wardrobes (time, talent, treasure)

47:25 – Bonnie’s biggest maverick move: moving to CA with no plan