Confidence Classic: Step Into Your Power and Break Free from Self-Imposed Limits with Iman Oubou
In this episode of Creating Confidence, Iman Oubou discusses her path from beauty pageant skeptic to founder of Sway Media, a platform focused on female thought leadership. She explains how participating in pageants changed her perspective on female-centric communities and led her to create spaces where women can support and empower each other.
The conversation explores the challenges Oubou faced while raising capital as a female founder, including gender bias from male investors who focused more on her appearance than her business capabilities. She shares how she overcame these obstacles by rebuilding her confidence through new experiences and developing resilience that doesn't depend on external validation.
This is a preview of the Shortform summary of the Oct 22, 2025 episode of the Creating Confidence with Heather Monahan
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1-Page Summary
Iman Oubou's Growth Through Pageants and Entrepreneurship
Iman Oubou's journey from beauty pageant skeptic to founder of a women's empowerment platform demonstrates how pageantry can serve as a catalyst for personal and professional growth. After participating in her first pageant in Colorado in 2013, Oubou discovered that pageants weren't merely about beauty but fostered a supportive community for women.
Iman's Focus on Community and Empowering Women
Before entering pageants, Oubou struggled with insecurities around ambitious women and avoided female-centric groups. Her pageant experience marked a turning point, introducing her to an unexpectedly supportive culture among contestants. This transformation inspired her to create Sway Media, a publishing platform that recognizes female thought leadership and provides the same supportive environment she found in pageants.
Iman's Challenges as a Female Founder and Solutions
While raising capital for her startup, Oubou faced significant challenges. Male investors often focused on her looks and pageant background rather than her business acumen, leading to inappropriate comments and bias. These experiences initially led to self-doubt and a victim mentality, but Oubou overcame these obstacles through intentional self-work. She rebuilt her confidence by taking on new roles without prior experience and developed a resilience independent of external validation. Through her book, Oubou shares guidance on reclaiming power and self-worth while facing industry biases.
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Actionables
- You can explore personal growth opportunities by participating in local community events that focus on skill development and networking. For instance, join a public speaking club or a local entrepreneur meetup to refine your communication skills and meet like-minded individuals who can offer support and insight into your personal and professional endeavors.
- Start a peer mentorship group with friends or colleagues to foster a supportive environment similar to what pageant communities offer. This could involve regular meetings where each person shares their goals, challenges, and progress, providing mutual encouragement and advice.
- Reflect on and journal about your own biases and self-doubt to build resilience and self-worth. Set aside time each week to write down instances where you felt undermined or doubted yourself, then list the strengths and achievements that counter those feelings. This practice can help you develop a more empowered mindset over time.
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Iman Oubou's Growth Through Pageants and Entrepreneurship
Iman Oubou's trajectory transformed from initial skepticism about beauty pageants to leveraging her experiences as Miss New York to create a platform dedicated to women empowerment and entrepreneurship.
Iman's Perspective on Pageants Changed
First Pageant Empowers Iman, Fosters Supportive Women's Community
Iman Oubou was empowered by her participation in her first pageant in Colorado in 2013, which shifted her view of pageants as shallow to important platforms that foster a supportive community for women. Competing in the pageant, she felt inspired to be her best self for the first time and was part of an uplifting environment, where even as competitors, women championed one another.
Iman's Success Inspired Her to Create a Platform to Uplift Women
Iman Created Sway for a Supportive Community For Women, Like the Pageant World Provided Her
Winning Miss New York in 2015 was a defining moment for Iman, compelling her to focus on women's empowerment and entrepreneurship. The pageant world showed her that she could be both smart and beautiful and didn't have to settle into a singular identity. The pageants were not just about beauty, but also about the confidence built through embracing various challenges, such as presenting oneself on sta ...
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Iman Oubou's Growth Through Pageants and Entrepreneurship
Additional Materials
Counterarguments
- While pageants can be empowering for some, they may perpetuate certain beauty standards that can be harmful or exclusionary to women who do not fit those standards.
- The idea that pageants are necessary to demonstrate that women can be both smart and beautiful could be seen as reinforcing the notion that beauty and intelligence are linked, which is a stereotype that many seek to dismantle.
- The supportive community found in pageants might not be universally experienced; some participants may feel that pageants foster competition over camaraderie.
- The effectiveness of pageants as a platform for women's empowerment could be questioned when considering the broader societal impact and whether they contribute to systemic change.
- Sway Media's aim to emulate the pageant community might not ...
Actionables
- You can redefine personal success by creating a vision board that includes both intellectual achievements and personal beauty goals. Start by gathering images and quotes that represent your academic, professional, and aesthetic aspirations. Place them on a board where you'll see it daily to remind yourself that you can pursue both brains and beauty simultaneously.
- Start a blog or social media account dedicated to highlighting women who embody the dual pursuit of intellectual rigor and personal style. Share stories, interviews, and content that showcase how women can excel in their careers and personal lives, breaking the stereotype that you have to choose one over the other.
- Volunteer ...
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Iman's Focus on Community and Empowering Women
Iman's journey from isolation to community has fueled her desire to create an environment that celebrates and supports women.
Iman Lacked Support Before Her Pageant Experience
Iman's pre-pageant experiences were marked by a lack of support and an avoidance of female-centric groups like sororities due to feelings of intimidation. She felt insecure being around other women who were ambitious, and she struggled to build healthy friendships with women because of these insecurities.
Iman Felt Insecure Around Ambitious Women
Before participating in pageants, Iman's insecurities made her feel threatened by "beautiful, competitive and smart women." As a result, she often felt intimidated and did not have a solid support system of women friends.
Iman's Pageant Journey Highlighted Women's Support
Iman's involvement in pageantry proved to be a turning point, which not only helped her confront and overcome her insecurities but also introduced her to the camaraderie among contestants.
Iman Was Inspired by the Camaraderie and Non-competitiveness Among Contestants to Create a Similar Environment
Inside the pageant community, Iman discovered a supportive culture that was contrary to her prior exper ...
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Iman's Focus on Community and Empowering Women
Additional Materials
Actionables
- Start a small book club focusing on women's empowerment literature to foster a sense of community and support among women. By selecting books that highlight women's achievements and struggles, you can create a safe space for discussion and mutual encouragement, similar to the nurturing atmosphere Iman experienced. For example, you could choose memoirs of women leaders or novels with strong female protagonists to spark conversations about personal growth and empowerment.
- Initiate a "compliment exchange" with friends or colleagues to build confidence and a supportive culture. Make it a habit to give genuine compliments to the women around you, focusing on their strengths and accomplishments. This practice can help overcome insecurities by recognizing the value in others and yourself, much like the camaraderie Iman found in pageantry. You might start with a simple message or note of appreciation that acknowledges something specific they've done well. ...
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Iman's Challenges as a Female Founder and Solutions
Iman Oubou, a female founder, bravely shares the difficulties she faced while raising capital for her startup and how she overcame the ensuing self-doubt and victim mentality.
Iman Encountered Bias and Inappropriate Comments From Male Investors During Fundraising
Raising a seed round for her startup proved challenging for Iman. Despite having initial investment from women and support from her company’s community, she faced bias from male investors, who were often older. They focused on her looks and her background as a beauty pageant contestant rather than her business merits. Iman tried to tone down her appearance, but inappropriate comments and a lack of serious regard for her business acumen persisted.
Investors Focused On Iman's Looks and Pageant Background Over Her Business Merits
Due to Iman's pageant success and how she presented herself, these male investors would pass remarks on her appearance, or imply that her pageant background was a hurdle in being taken seriously as a businesswoman. As a result of such encounters, Iman found herself trying to change her appearance in hopes of being seen for her business potential rather than her looks.
Iman Internalized These Experiences, Leading To Self-Doubt and a "Victim" Mentality
Iman internalized the negative feedback from these interactions, and it began to shape her self-perception and narrative. She became defensive, aggressive, and overwhelmed by a fear of power imbalances. These factors led to an unwarranted sense of insufficiency and serious doubts about her prospects as a founder.
Iman Rebuilt Confidence and Resilience Through Self-Work
Realizing the need for self-work and acc ...
Here’s what you’ll find in our full summary
Iman's Challenges as a Female Founder and Solutions
Additional Materials
Actionables
- You can start a reflective journal to track instances of bias and your responses to them, helping you identify patterns and develop strategies for empowerment. Begin by writing down any moments where you felt undermined or unfairly judged, noting your immediate emotional response and the actions you took following the incident. Over time, this can help you recognize triggers and build a repertoire of assertive responses.
- Create a personal "confidence portfolio" that includes your achievements, positive feedback, and moments of resilience. Whenever you face self-doubt or a setback, review this portfolio to remind yourself of your capabilities and worth. This can be a digital folder on your computer or a physical binder with printed emails, certificates, and notes of appreciation.
- Engage in role-playing exercises with a trusted friend or mentor to practice ...
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