Episode 304- From DC Spy Dreams To Substack: Amanda Claypool On Media, Money, And Meaning
Sun Feb 01 2026
What if the numbers that dominate headlines tell you less about the economy than the price of your groceries, your rent, and your ability to start a family? We sit with writer and analyst Amanda Claypool to unpack Main Street economics, A.I.’s shock to white-collar work, and why trust in legacy media has frayed. Amanda’s path—from near-CIA ambitions and defense contracting in DC, to cross-country pandemic travels, to building “Tomorrow Today” on Substack—offers a rare, ground-level view of how policy choices ripple through real lives.
We get candid about the post-2008 era, cheap money’s illusions, and the gap between Beltway incentives and the daily reality in deindustrialized towns. Amanda explains why she sees generative A.I. as a Gutenberg-level inflection point: it can upend tasks, compress status ladders, and force a deeper question about what remains uniquely human. That’s where judgment, relationships, and ownership of outcomes come in—and why careers built on brittle prestige need a rethink. We also explore culture and gender debates, how career-first narratives can overshoot, and what resilience looks like when jobs evolve faster than institutions.
Throughout, you’ll hear practical advice for navigating uncertainty: learn the language of economics and accounting, treat A.I. as leverage rather than a threat, and stop hunting only for “a job.” Instead, find work—concrete problems you can solve and get paid for—while investing in community, family, and skills that compound over time. If you’re looking for a grounded, nonpartisan take on media, money, technology, and meaning, this conversation cuts through the noise and gets to what actually matters.
You can further engage with Amanda:
Tomorrow Today on Substack: https://tomorrowtodaynow.substack.com/
YouTube: https://www.youtube.com/@amanda_claypool
My book on Amazon: https://www.amazon.com/dp/B0FZ52SVL3/ref=sr_1_2
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Engage the conversation on Substack at The Common Bridge!
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What if the numbers that dominate headlines tell you less about the economy than the price of your groceries, your rent, and your ability to start a family? We sit with writer and analyst Amanda Claypool to unpack Main Street economics, A.I.’s shock to white-collar work, and why trust in legacy media has frayed. Amanda’s path—from near-CIA ambitions and defense contracting in DC, to cross-country pandemic travels, to building “Tomorrow Today” on Substack—offers a rare, ground-level view of how policy choices ripple through real lives. We get candid about the post-2008 era, cheap money’s illusions, and the gap between Beltway incentives and the daily reality in deindustrialized towns. Amanda explains why she sees generative A.I. as a Gutenberg-level inflection point: it can upend tasks, compress status ladders, and force a deeper question about what remains uniquely human. That’s where judgment, relationships, and ownership of outcomes come in—and why careers built on brittle prestige need a rethink. We also explore culture and gender debates, how career-first narratives can overshoot, and what resilience looks like when jobs evolve faster than institutions. Throughout, you’ll hear practical advice for navigating uncertainty: learn the language of economics and accounting, treat A.I. as leverage rather than a threat, and stop hunting only for “a job.” Instead, find work—concrete problems you can solve and get paid for—while investing in community, family, and skills that compound over time. If you’re looking for a grounded, nonpartisan take on media, money, technology, and meaning, this conversation cuts through the noise and gets to what actually matters. You can further engage with Amanda: Tomorrow Today on Substack: https://tomorrowtodaynow.substack.com/ YouTube: https://www.youtube.com/@amanda_claypool My book on Amazon: https://www.amazon.com/dp/B0FZ52SVL3/ref=sr_1_2 Enjoyed the episode? Subscribe to The Common Bridge, share it with a friend who cares about the future of work, and leave a rating to help others find the show. Support the show Engage the conversation on Substack at The Common Bridge!