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When Working Hard Works Against You

2026 John Michael Lucido, Jose Caballero, Clayton Caldwell
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The guys sit down to unpack the modern obsession with being “always on.” From 4 a.m. wake-ups and Kobe-level discipline, to “finance slop” lunches and the pressure of Slack and Teams messages that never stop coming, the guys break down how work has slowly become more than just something you ...

The guys sit down to unpack the modern obsession with being “always on.” From 4 a.m. wake-ups and Kobe-level discipline, to “finance slop” lunches and the pressure of Slack and Teams messages that never stop coming, the guys break down how work has slowly become more than just something you do—it’s become who you are. But does that actually lead to fulfillment? They explore the tension between busyness and purpose, reacting vs. leading your day, and why so many people feel productive but not actually present. They also dig into the idea of boundaries in a world that rewards constant availability—and why “rest” has become something people either weaponize or completely misunderstand. Plus: inbox zero addicts, Chipotle bowl economies, Cal Newport deep work habits, digital Sabbaths, Blackstone Sunday brunches, and the radical idea that maybe excellence doesn’t require burnout. This is the All-In Podcast.

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