Podcast Summary: Creating Confidence with Heather Monahan

Episode Title: Confidence Classic: Step Into Your Power and Break Free from Self-Imposed Limits with Iman Oubou
Date: October 22, 2025
Host: Heather Monahan
Guest: Iman Oubou

Episode Overview

In this empowering episode, Heather Monahan sits down with friend and multi-hyphenate Iman Oubou—entrepreneur, published scientist, author, and former Miss New York—to talk about redefining your relationship with power, overcoming gendered expectations, breaking self-imposed limitations, and why building supportive communities can be a superpower. Iman shares her multidimensional career journey, the origin of her company Sway Media, her struggles as a young female founder, and the inspiration behind her new book, "The Glass Ledge," which explores self-created barriers to success.

Key Discussion Points & Insights

1. Rethinking Pageants and Female Empowerment

[03:10 – 06:02]

• Stereotypes of beauty pageants: Both Heather and Iman admit to initially viewing pageants as superficial but came to recognize their deeper benefits—namely, that they foster self-improvement and solidarity among women.
• Iman’s transformation:

  "I had never really felt so empowered to be the best version of myself until I competed in my first beauty pageant..." – Iman Oubou [03:38]

• Supportive community: Pageants taught Iman the power of supportive female friendships, which she didn’t experience growing up.

2. Building Women-Focused Community Platforms

[06:55 – 10:40]

• From pageants to entrepreneurship: Winning Miss New York inspired Iman to champion women’s entrepreneurship and empowerment, first via podcasting, then founding Sway Media.
• Dual identity:

  "By day, I am like this nerdy scientist... And then by night, I'm...doing appearances on the red carpet...people look at me like, wait, you're a scientist?...What's the connection here?" – Iman [07:25]

• Need for healthy female communities: She sought to replicate the empowering environment of pageants among women in media and entrepreneurship.

3. Challenges of Launching and Funding Sway

[12:45 – 17:25]

• Fundraising as a young female founder: Iman details the dismissals and inappropriate comments from (mostly male) investors who focused on her appearance or pageant background.
• Impact on self-worth:

  "That became my truth, that became my narrative. I became kind of also defensive and aggressive and just angry. And that's not really my nature." – Iman [15:35]

• Victim mindset: She admits internalizing these attitudes, which hindered her confidence and ability to lead.

4. Origin and Purpose of 'The Glass Ledge'

[17:31 – 20:41]

• Inspired by adversity: At her lowest career point, an agent encouraged her to write about confidence. Iman initially felt unqualified but decided to share her experiences with self-sabotage and rebuilding.
• Self-imposed limits:

  "I was out there trying to break glass ceilings. But I didn’t realize I was also teetering on a glass ledge, which to me is a representation of self-imposed glass ceilings." – Iman [19:43]

5. Lessons from the Book: Understanding Power, Likability, and Balance

[20:41 – 26:46]

• Book structure: Ten themes—e.g., power, likability, appearance, expertise, conflict, authenticity—each explored with personal stories.
• Power dynamics and self-awareness:

  "Instead of...figuring out what went wrong and how I can claim that power back, I just kind of played the victim and realized, okay, there’s nothing I can do…" – Iman [21:29]

• **Not telling readers what to do, but helping them find their own balance and strategies for self-awareness and action.
• On authenticity and adaptation:

  "We all have an authentic self and an adaptive self. And you need to know when to let which one lead and they both need to be in sync." – Iman [25:47]

6. Embracing ‘AND’ Instead of ‘OR’: Multifaceted Identities

[26:53 – 29:09]

• Rejecting false choices: Iman and Heather both refuse to limit themselves to a single identity or skill.
• Iman’s pageant Q&A:

  "If you had to choose between being smart or pretty...which one would it be? ...I never was brought up with this idea that I had to choose..." – Iman [27:31]

• Key lesson: Confidence comes from proving to yourself that you can take on new, uncomfortable challenges and succeed.

7. Letting Go of External Validation and Fear of Failure

[30:33 – 33:55]

• Public failure: Iman admits worrying excessively about what others would think during her career crises.
• Advice from family:

  "You need a champion in your life that can constantly remind you that right now you're thinking about the wrong thing because what you’re thinking has to do with what people think of you." – Iman [32:37]

• Fulfillment over perception: Focus on what truly fulfills you, not what others expect.

8. Book Audience and Message

[34:00 – 34:45]

• Intended for every woman:

  "It's written in a way that it can always serve as some kind of reminder or there’s always lessons there..." – Iman [34:07]

• The book is meant to support women at all stages, across career and life paths—from students to C-suite execs to stay-at-home moms.

Notable Quotes & Memorable Moments

• On support and stereotypes:

  "There was something very different about being part of the pageant world because I think you are also trained to show up as a different version of yourself. One that is secure with herself..." – Iman [04:26]

• Finding your own narrative:

  "I had realized that during my fight for women empowerment, I had actually became disempowered myself. And a lot of that was because of the self-imposed glass ceilings I was putting in place." – Iman [19:49]

• The power of self-awareness:

  "You can’t establish that balance unless you build self-awareness. You need to know what triggers you, why you act the way you do..." – Iman [25:17]

• Heather on identity:

  "In business specifically, until you find that balance of…showing who you really are and that vulnerability coupled with boundaries… it definitely is a dance where many of us can fall." – Heather [23:53]

• On the 'AND' mentality:

  "For people who see Aman and say she had to be a scientist or she could be a beauty queen—no, she was a scientist and a beauty queen." – Heather [26:53]

• On failure:

  "Everybody fails. And that there is a reassurance to tell yourself that, like, and you see people fail publicly much worse than we do. So if they can go through that, then we could easily do it ourselves." – Iman [30:34]

Important Segments & Timestamps

• Introduction & stereotypes of pageantry [03:10 – 06:02]
• Discovering the power of supportive women [06:55 – 10:40]
• Fundraising challenges and internalizing sexism [12:45 – 17:25]
• Writing "The Glass Ledge" and overcoming self-imposed barriers [17:31 – 20:41]
• Key lessons: power, likability, and self-awareness [20:41 – 26:46]
• Embracing ‘and’ not ‘or’ in identity [26:53 – 29:09]
• Letting go of external validation [30:33 – 33:55]
• Who The Glass Ledge is for [34:00 – 34:45]

Tone & Language

The conversation is lively, encouraging, and raw, mixing motivational reflections with personal anecdotes. Both Heather and Iman speak candidly about their vulnerabilities, lessons learned through setbacks, and the ongoing journey of building real confidence.

Takeaways for Listeners

• Don’t judge a book by its cover—stereotypes about women and their choices can hide the hard work, growth, and empowerment happening beneath the surface.
• Building a supportive community, especially among women, can be transformative both personally and professionally.
• Overcoming obstacles is as much about challenging self-imposed limitations as it is about navigating external societal barriers.
• True confidence comes from repeatedly stepping outside your comfort zone, embracing failure, and balancing your different selves.
• The journey to self-assurance is nonlinear and applies to all women, regardless of their path in life.

Further Resources

Iman’s Book: The Glass Ledge (available on Amazon, Barnes & Noble, and major book retailers)
Follow Iman: @imanoubou
Book Info: theglassledge.com (for tours, signings, resources)

This episode is a must-listen for anyone looking to step into their own power, break limiting beliefs, and create an authentic, confident path forward.