What if confidence isn’t something you’re born with, but something you build one decision at a time?
In this episode of Possibilities with Monique de Maio, Monique sits down with Mary Alice Duff, fractional COO, entrepreneur, and portfolio careerist, for a grounded and powerful conversation about confidence, self-trust, and what truly changes when women stop waiting for permission.
This is not a conversation about moving abroad.
It’s a conversation about what makes bold life decisions possible in the first place.
Mary Alice shares her unconventional journey from social work to entrepreneurship, the lessons learned from building and closing a business, and why self-employment became a tool for designing a life that actually feels good. Together, Monique and Mary Alice unpack why high-performing women fear embarrassment more than failure, how perfectionism keeps women stuck, and what “stop waiting” actually looks like in practice.
In this episode, we explore:
This episode is a reminder that confidence does not arrive before action.
Action builds confidence.
If you’ve been feeling stuck, second-guessing yourself, or waiting for the “right moment,” this conversation may be the nudge you need.
00:00 Introduction to Mary Alice Duff and her journey
02:51 An unconventional career path and early leadership experience
05:37 Building and closing a business and lessons from failure
08:14 The factors that made a major life change successful
11:23 How self-employment creates freedom and flexibility
13:55 Supporting small businesses as a fractional COO
16:55 Why self-awareness is critical in leadership
20:49 Micro moments and the compounding effect of confidence
25:01 High performance, fear of failure, and resilience
31:40 Patience and perseverance in entrepreneurship
35:29 Career advice Mary Alice would give her younger self
38:33 Why women must stop waiting for permission and bet on themselves
Mary Alice Duff is a fractional COO, entrepreneur, and portfolio careerist who partners with small business owners to build profitable, sustainable companies without burnout. She works closely with founders of experiential and people-driven businesses, helping them gain clarity across operations, finances, and strategy.
With a background spanning social work, nonprofit leadership, and entrepreneurship, Mary Alice brings a rare blend of operational rigor and human insight to her work. She also coaches experienced professionals who want to transition from traditional employment into confident, sustainable fractional leadership roles.
Mary Alice currently lives in the south of France with her family and writes about the messy, joyful reality of self-employment, leadership, and designing a life that aligns with your values.
Website: https://www.maryaliceduff.com
Mary Alice’s Future Fractional coaching program is currently open for enrollment.
This podcast is part of our mission to amplify women who are redefining work, life, and leadership.
Imagine taking a journey whose destination is confidence—being able to say with certainty that your life serves you, rather than the other way around. Listening to these podcasts can offer you affirmation, inspiration, practical advice, tips, hacks, and a sense of community with like-minded individuals. Join us on this journey!
Clarity doesn’t come from doing more.
It comes from choosing how you want to show up.
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It’s about intention.
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