I Wanted to Want It, a conversation with Rory Eakin episode artwork

EPISODE · May 13, 2026 · 57 MIN

I Wanted to Want It, a conversation with Rory Eakin

from I'm Here Too · host Ara Tucker

If you've ever chased a career path mostly because it was expected, and felt the gap between what you wanted and what you thought you were supposed to want, this one is for you.Rory Eakin spent a summer in a suit, in an office building, knowing it was wrong. He wanted to want it. He didn't. He said no to the job, went to Cape Town to teach math, and began a series of career deviations that he says got easier with each one.We talk about what it means to grow up with an inherited picture of what success is supposed to look like, and what happens when you start pulling away from it. About burnout and the self-understanding it can unlock. About identity and how hard it is to separate who you are from what you do.And about something that surprised him: a pull toward faith and community after years of describing himself as a confident atheist.About RoryRory Eakin is a co-Founder and Director of CircleUp, a data analytics company founded to help entrepreneurs thrive. Prior to CircleUp, Rory served as Director of Investments at Humanity United, a private foundation. He started his career as a math teacher at the University of Cape Town. Rory received his MBA from Stanford, and a Master’s Degree in International Relations from the University of Cape Town. He grew up in Washington DC, and now lives in San Francisco with his wife and two children, where he enjoys hiking, board games, and Mario Kart.

Episode metadata supplied by the publisher feed · Published May 13, 2026

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I Wanted to Want It, a conversation with Rory Eakin

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