Award-winning author Mary Robinette Kowal joins us to talk about building a creative ecosystem that actually fits your brain. From viral cat videos to Patreon-powered writing sessions, she shares exactly how she budgets, hires, monetizes, and prioritizes joy across multiple income streams, and how being honest about what you don’t want might be the key to building the career you do want.

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Healthcare analyst and ACA expert Charles Gaba joins us to explain what freelancers, artists, and anyone with unpredictable income really need to know about this year’s open enrollment. We cover rising premiums, the danger of auto-renewals, and how to avoid surprise tax bills or lost subsidies. Whether you're switching plans or signing up for the first time, this episode breaks down what the ACA does—and doesn’t—offer the creative class.

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Bestselling sci-fi author John Scalzi joins us for a conversation about creative longevity, pragmatic optimism, and why the goal isn’t to stay hot, it’s to keep going. We talk about building a sustainable career with your partner, the myth of the one big break, and how generosity, structure, and a little chaos can power a life in the arts. Plus: what journalism teaches you about rejection and why it’s okay to not be the next big thing.

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Journalist and 404 Media co-founder Jason Koebler joins us to talk about what it takes to build an independent newsroom. From the cost of defamation insurance to the weight of mailing your own merch, we get into the invisible math of staying scrappy without burning out—and the true cost of reader-supported journalism.

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Broadcaster and podcast pioneer Jesse Thorn joins us to talk about building something sustainable without selling out. From his early days of mailing CD-Rs to NPR stations to running Maximum Fun as a listener-supported network, Jesse shares the emotional and economic math behind 20 years of independent success. We get into what it means to build trust with an audience, how community gets harder in a platform-driven world, and why “working for the people” still feels like the best job he’s ever had.

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Wrestler and podcaster Colt Cabana joins Ana and Mike to talk about building a life in wrestling. From getting fired by WWE to becoming a blueprint for sustainable DIY success, Colt breaks down the real economics of creative work—merch tables, mattress money, and all—and why betting on yourself might be the best decision you ever make.

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Comedian and podcaster Babs Gray joins us to talk about staying creative in the long middle—the part where the dream hasn’t died, but it hasn’t fully arrived either. We get into the quiet power of community, the joy of weird little projects, and why success isn’t always loud. From survival jobs to self-trust, Babs reminds us that showing up for your work, even when no one’s watching, might be one of the most important things you can do.

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Comedian and actor Will Hines joins Ana and Mike to talk about trading a salary for freedom, and why time might be the only currency that really matters. From leaving a corporate job at 33 to building an improv school from the ground up, we get into the real economics of creative work: how to manage taxes, protect your energy, and figure out what’s worth outsourcing (and what’s not).

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