Welcome to Second Life, a podcast spotlighting successful women who’ve made major career changes—and fearlessly mastered the pivot. Hosted by Hillary Kerr, cofounder and chief content officer at Who What Wear, each episode gives you a direct line to women who are game changers in their fields. Subscribe to Second Life on Apple Podcasts, Spotify, or anywhere you get your podcasts to stay tuned.
Courtney Smith is the ultimate multi-hyphenate, as her career path reads like a masterclass in reinvention. As a Yale Law School graduate who earned her JD and passed the bar, Smith initially seemed destined for a traditional legal career. But shortly after, she pivoted to management consulting at the prestigious firm McKinsey & Company. Over the following years, her professional trajectory continued to shift dramatically: She played a role in restructuring Condé Nast, contributed to a real estate start-up, and even explored a career in medicine by completing a post-baccalaureate pre-health program at Columbia University.
Smith’s curiosity and drive for impact then led her to join the board of Planned Parenthood and pursue a master’s degree in public health. But when the COVID-19 pandemic struck, she was forced to adapt once again. Throughout these transitions, one constant remained: the Enneagram personality system. If you aren’t familiar, the Enneagram personality system is a powerful framework that identifies nine core personality types, helping people gain deep self-awareness, understand their motivations, and navigate personal growth and relationships.
Article continues belowSmith had long used the Enneagram for self-awareness and guidance in her own career shifts. Recognizing its potential to help others, she transformed her personal practice into a professional calling. Today, she is an esteemed Enneagram coach, group facilitator, and consultant. She works with individuals seeking clarity and purpose, as well as with Fortune 500 companies looking to strengthen team dynamics, leadership, and organizational culture through the lens of the Enneagram.
In addition to her coaching practice, Smith is the co-author of the book Choosing Wholeness Over Goodness: A Process for Reclaiming Your Full Self, offering readers a practical framework for moving beyond the pressure to appear “good” and instead embracing their complete, authentic selves.
Listen to the latest episode of Second Life to hear how Smith has truly mastered the art of reinvention when it comes to career paths, and helping others do the same.
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