In this episode of the Impostor Syndrome Files, we explore how to manage self-doubt and recognize opportunities during periods of technological change. My guest this week is Yoli Chisholm, a digital marketing leader who has navigated several major technology transitions throughout her career. Drawing on those experiences, Yoli offers a reassuring perspective on the uncertainty many of us feel about AI.

Yoli shares how building a career without a college degree left her questioning whether she belonged, even as she advanced into senior leadership roles. She reflects on the unexpected doors that opened during times of uncertainty and how learning by doing helped her build confidence. We also discuss how remembering challenges we’ve already navigated can help us approach new ones with greater perspective.

In our conversation, we explore the pressure to keep up with AI and the fear that our experience will become less valuable. Yoli shares what helped her move past her initial resistance and see opportunities for growth. We also discuss practical ways to learn without becoming overwhelmed and recognize the value of what we already know.

About My Guest
Yoli Chisholm is an award-winning Marketing Executive recognized as a “Digital Innovator”. In 20 years as a business professional, she has cultivated a multifaceted career as a Revenue Marketer, Corporate Career Anthropologist, Entrepreneur, and Speaker who writes about these areas including her book on navigating corporations - Crushing Corporate.

Whether she is talking to students or professionals about their career development, small businesses, startups, or seasoned marketers about building their businesses, Yoli fuses a message of proven performance principles and disciplined risk-taking. Playing a leading role in every digital marketing transformation since the commercialization of the internet Yoli has earned a reputation as a very early adopter of new technology. She has a passion for the impact of culture as a lever to optimize business performance and speaks on the topic in her TEDx talk “Are you a strong Tree?” As the Author of Crushing Corporate Vol. 1 & Vol. 2, Yoli brings to her writing a point view on intrapreneurship and entrepreneurship having experienced different corporate cultures at 10+ corporations including Microsoft, Sprinklr, eBay, Lavalife, and consulting with startups globally US, Canada, Switzerland, UAE to working for the Danish Embassy in Africa over a 20-year career span.

A business “backbone builder” with deep B2B marketing innovation roots. Seeking to motivate in ways that deliver measurable transformation to organizations and people striving to excel. Yoli is now the Founder of Borderlessself.com.

~

Connect with Yoli:
LinkedIn: https://www.linkedin.com/in/yolichisholm/
Website: www.Borderlessself.com

~

Connect with Kim and The Impostor Syndrome Files:

Join the free Impostor Syndrome Challenge:
https://www.kimmeninger.com/challenge

Learn more about the Leading Humans discussion group:
https://www.kimmeninger.com/leadinghumansgroup

Join the Slack channel to learn from, connect with and support other professionals: https://forms.gle/Ts4Vg4Nx4HDnTVUC6

Join the Facebook group:
https://www.facebook.com/groups/leadinghumans

Schedule time to speak with Kim Meninger directly about your questions/challenges: https://bookme.name/ExecCareer/strategy-session

Connect on LinkedIn:
https://www.linkedin.com/in/kimmeninger/

Website:
https://www.kimmeninger.com

In this episode of The Impostor Syndrome Files, we talk about what happens when we assume everyone else has it together and we’re the only ones struggling. My guest this week is Teri Pruitt, a Broadway professional who has spent nearly three decades working behind the scenes. Teri shares an honest, funny perspective on comparison, insecurity and the stories we tell ourselves about other people’s lives.

We explore why saying our insecurities out loud to someone we trust can change the power they have over us. Teri shares what she discovered when she opened up to people she’d put on a pedestal and how those conversations changed their relationships. We also talk about the fear of burdening others and what it means to be the person someone trusts with their self-doubt.

And we discuss how to acknowledge the experiences that shaped us and take ownership of what we do next. Teri shares her perspective on giving ourselves grace and continuing to move forward, even on the days when confidence feels out of reach. Lastly, we explore her next chapter, including what the business world can learn from the people who bring Broadway shows to life.

About My Guest
Teri Pruitt is a Broadway professional, speaker, and founder of Open the Aperture, where she brings Theatrical Solutions for Business Problems to organizations and leaders.

With more than 30 years as a working theatrical professional—including 25+ years on Broadway—Teri offers a rare perspective on what it actually takes to build trust, collaborate under pressure, adapt when things go wrong, and deliver consistently at a high level.

Her work draws from the theatrical process and from her Journeywoman’s View: the perspective of someone who has spent a career leading, influencing, problem-solving, and helping complex systems succeed from the middle rather than the top.

Through Open the Aperture, Teri translates lessons from professional theatre into practical conversations about leadership, teamwork, rehearsal, resilience, communication, and sustainable performance. Her central premise is simple: Broadway is the setting. The theatrical process is the framework. The human beings doing the work are the story.

~

Connect with Teri:
Website: https://teripruitt.world
LinkedIn: https://www.linkedin.com/in/teri-pruitt/

~

Connect with Kim and The Impostor Syndrome Files:

Join the free Impostor Syndrome Challenge:
https://www.kimmeninger.com/challenge

Learn more about the Leading Humans discussion group:
https://www.kimmeninger.com/leadinghumansgroup

Join the Slack channel to learn from, connect with and support other professionals: https://forms.gle/Ts4Vg4Nx4HDnTVUC6

Join the Facebook group:
https://www.facebook.com/groups/leadinghumans

Schedule time to speak with Kim Meninger directly about your questions/challenges: https://bookme.name/ExecCareer/strategy-session

Connect on LinkedIn:
https://www.linkedin.com/in/kimmeninger/

Website:
https://www.kimmeninger.com

In this episode of The Impostor Syndrome Files, we talk about the pressure to prove ourselves and how it can keep us working harder without getting where we want to go. My guest this week is Drew Turner, a leadership coach who helps high-achieving women advocate for themselves and pursue the opportunities they want. Drew shares her journey from managing a retail store at 24 to working in leadership development at Tesla and how a layoff forced her to rethink her relationship with work.

We explore the rules many of us learned growing up about being helpful, staying humble and waiting for someone else to recognize our contributions. Drew shares how those rules showed up in her own career, including giving away credit for her wins and questioning whether she deserved to be in the room. We also discuss what happens when we tie our identity to our jobs and how making space for grief, reflection and joy can help us move forward after an unexpected career change.

We also talk about why being busy can feel like proof of our value and how that pressure makes it harder to set boundaries or prioritize ourselves. Drew shares practical ways to reconnect with what matters to us and make more intentional choices about where we put our time and energy. We explore how self-doubt can affect our relationships with other women at work and what becomes possible when we support each other’s success.

About My Guest
Drew Turner is a Jungian-certified leadership coach who helps high-achieving women in leadership who are exhausted from proving their worth be seen for everything they bring to the table, so they can get the opportunities they've earned. Before starting her coaching business, she spent over a decade in retail leadership and L&D roles, including at Tesla, where she experienced firsthand the exhausting cycle of proving her worth no matter how much she accomplished. She now helps women rebuild self-trust from the inside out for lasting change, not tactics that decay.

~

Connect with Drew:
Free 3 Step Reset to Be Seen for Everything You Bring to the Table: www.drewturnercoaching.com/3stepreset

~

Connect with Kim and The Impostor Syndrome Files:

Join the free Impostor Syndrome Challenge:
https://www.kimmeninger.com/challenge

Learn more about the Leading Humans discussion group:
https://www.kimmeninger.com/leadinghumansgroup

Join the Slack channel to learn from, connect with and support other professionals: https://forms.gle/Ts4Vg4Nx4HDnTVUC6

Join the Facebook group:
https://www.facebook.com/groups/leadinghumans

Schedule time to speak with Kim Meninger directly about your questions/challenges: https://bookme.name/ExecCareer/strategy-session

Connect on LinkedIn:
https://www.linkedin.com/in/kimmeninger/

Website:
https://www.kimmeninger.com