I Wanted to Want It, a conversation with Rory Eakin
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“I sort of wanted to want them, if that makes sense.”
Rory Eakin spent a summer in a suit, in an office building, knowing it wasn't right. 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.
In this conversation, he talks about growing up with an inherited picture of what success was supposed to look like, and what happens when you start pulling away from it. About burnout and the self-understanding it can unlock. About how hard it is to separate identity from the work you do.
And about an unexpected turn: a pull toward faith and community after years of describing himself as a confident atheist.
About Rory
Rory 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.