Courtney Smith: Enneagram Coach and Author
Second Life
Who What Wear
4.8 • 3K Ratings
🗓️ 20 April 2026
⏱️ 56 minutes
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| 0:00.0 | Hi, everyone. I'm Hilary Kerr, the co-founder and chief content officer of Who What Where, and this is Second Life, a podcast, spotlighting women who have truly inspiring careers. We're talking about their work journeys, what they've learned from the |
| 0:21.4 | process of setting aside their doubts or fears, and what happens when they embark on their |
| 0:26.6 | second life. Today on the show, I'm speaking with Enneagram coach and author, Courtney Smith. Courtney |
| 0:33.3 | began her career on track to become a lawyer. But after attending Yale Law School, getting her |
| 0:39.0 | JD and passing the bar, she ultimately decided to pivot into management consulting at McKinsey |
| 0:45.2 | instead. Over the next several years, Courtney continued to evolve her career. She helped |
| 0:51.0 | restructure Condé Nast, briefly worked for a real estate startup, and considered becoming a doctor going so far as to doing a post-back pre-health program at Columbia. |
| 1:01.9 | She then joined the board of Planned Parenthood and got her master's in public health, but she quickly had to pivot again when the pandemic hit. |
| 1:10.6 | Courtney had long used the Enneagram personality system to guide her own career journey, |
| 1:15.6 | and she saw an opportunity to begin using the system as a tool to help others. |
| 1:20.6 | Today, Courtney is an acclaimed coach, group facilitator, and consultant |
| 1:26.6 | who works with individuals as well as Fortune 500 companies. |
| 1:31.6 | Courtney is also the co-author of the book Choosing Wholeness Over Goodness, a process for reclaiming your full self. |
| 1:39.1 | I can't wait for you to hear from her. Now, on Second Life, it's Courtney Smith. Courtney, are you ready? |
| 1:48.9 | Let's do it. Okay, great. So we always like to start this podcast at the beginning. So, what did you |
| 1:56.6 | study in school? And much more importantly, what did you think you were going to be when you grew up? |
| 2:01.8 | In my undergrad, I majored in mathematical economics. I have a law degree, and then I also have a |
| 2:08.4 | master's in public health. I've studied a lot of different things. And I think that if you'd asked me |
| 2:14.1 | as a young person what I wanted to be, I think I would have said Supreme Court |
| 2:19.6 | Justice, something like that. Oh, okay. I love that. Talk to me about the mathematical economics. |
| 2:27.5 | What does that actually mean? Yeah. So economics is the study of human behavior with a market mindset, meaning that human behavior is |
| 2:37.5 | influenced by trading, by exchange. And what happens when we trade in exchange? Where do we put our |
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