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.

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

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