Jim Eagar joins Tom Anderson and Jeff Battersby for a thoughtful, experience-driven conversation about productivity, tools, and the often-tempting urge to switch apps. Drawing on decades of professional experience—from Air Force chaplain to attorney to productivity writer—Jim shares how his workflows evolved alongside Apple technology, why “shiny new app syndrome” can quietly sabotage real work, and how to evaluate whether switching tools is actually worth the cost.

The discussion digs into intentional productivity, app minimalism, and using frameworks (not rules) to make better decisions about software—especially in an era overflowing with AI tools. Jim also walks through his personal writing and planning stack, explains why he recently switched from ChatGPT to Claude, and shares David Sparks’ advice on limiting major app changes to once per year. The result is a grounded, reassuring episode for anyone feeling overwhelmed by productivity tools—and a reminder that clarity beats novelty every time.

More from Jim:

Original Mac Guy

Retirement Reinvented!

Links from the show:

A Very Nerdy Christmas: Evaluate Your Tech Stack

Why I Quit Paid Apps

MacSparky

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• Show artwork by the great Randall Martin Design

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Transcripts and some images are AI generated and may contain errors and general silliness.