New York Times columnist Jamelle Bouie joins Ana and Mike to discuss the dismantling of legacy media by billionaire owners and the myth of the “Democratic Joe Rogan”. Jamelle also opens up about the intersection of luck and frugality that allowed him to build financial stability early in his career and how he now balances his work for "the mothership" with his own independent creative outlets.

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Despite writing bestsellers and landing a Reese’s Book Club pick, Xochitl Gonzalez opens up about the lingering shame of precarity, the invisibility of working-class success, and why we need to drag money talk out into the light.

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Jonah Ray joins us to talk about finding joy in creative work after letting go of the version of success he once chased. From DIY punk to rebooting MST3K, Jonah reflects on what happens when you stop waiting for permission and start making the stuff you actually want to see. We get into the fear of going unnoticed, and why it’s still worth it.

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Comedian Devin Field has one of the rarest things in Hollywood: a full-time, year-round job. But even that didn’t protect him from the chaos of the past few years. From presidential threats to network pullouts to a brutal WGA strike, Devin opens up about what it’s like when late-night comedy is under siege—and how he’s learning to navigate the myth of hustle culture.

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Ana Marie Cox and Open Mike Eagle kick off the year with a conversation about survival in a collapsing media economy. They get into dry January, capitalism, self-promotion, YouTube pivots, and what it means to keep showing up even when the numbers don’t add up. Plus: the upside of YouTube thumbnails, the reality of reporting on a shoestring, and why, in a world that wants you to give up, persistence might be the most radical act of all.

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Journalist Karen K. Ho joins us to talk about what it really means to navigate the creative economy as an immigrant, a freelancer, and a former "success story." We talk about the myth of meritocracy, the emotional and financial toll of precarity after grad school, and the difference between community and networking when your visa—and your future—are on the line. Karen shares how ADHD, burnout, and the invisibility of care shaped her path, and why finding the right support system might matter more than any byline.

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Comedian, actor, and writer Baron Vaughn joins us for a deeply personal conversation about what it means to rewrite your story while you’re still living inside it. We talk about growing up with scarcity, the trauma of survival-mode success, the work behind the work, and why healing is harder when the industry expects your pain to be punchlines.

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Comedian and actor Paul F. Tompkins opens up about career insecurity, creative joy, and why the secret to survival in a crumbling industry might just be doing it yourself.

If you want to hear more from today’s conversation with Paul F. Tompkins, including his dumbest money decision ever and the surprisingly smart investment he made that paid off big, join us at ⁠patreon.com/pastdue⁠. You’ll get exclusive extras, extended interviews, and first dibs on upcoming surprises.

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