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Second Life

Courtney Smith: Enneagram Coach and Author

Second Life

Who What Wear

Personal Journals, Business, Careers, Arts, Society & Culture, Fashion & Beauty

4.83K Ratings

🗓️ 20 April 2026

⏱️ 56 minutes

🧾️ Download transcript

Summary

Courtney Smith is an enneagram coach, author, and consultant who works with individuals as well as Fortune 500 companies. After receiving a degree in mathematical economics, she graduated from Yale Law School with her JD and intended to start her career in law. She then decided to change course to consulting, where she worked at McKinsey & Company before transitioning to Condé Nast, briefly working for a real estate start-up, and even considering a career as a doctor. She soon joined the board of Planned Parenthood and received her masters in public health, but was forced to pivot due to the start of the pandemic. After this career shift, Smith, who had used the Enneagram personality system herself, began using the tool to help others. This led to where she is today: coaching and consulting high-profile clients such as Brené Brown and co-authoring the book Choosing Wholeness Over Goodness: A Process for Reclaiming Your Full Self.

Transcript

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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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