Stephen Dubner, host of Freakonomics Radio, has done more than change the way we think about economics — I consider him a spiritual guide of our time. But for all his success, he’s got a laundry list of careers he’s left behind, from rising-star musician to New York Times writer. We debate the merits of expecting the worst versus hoping for the best and discuss how to trade nuance for novelty as we get older. It’s never too late to keep learning — or, according to him, to start a podcast.

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