When You Should (and Shouldn’t) Switch Productivity Apps with Jim Eagar
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:
Links from the show:
A Very Nerdy Christmas: Evaluate Your Tech Stack
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Intro Music: Psychokinetics - The Chosen
Transcripts and some images are AI generated and may contain errors and general silliness.
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Writer
I'm a long-term Mac user; I bought an original 128K Mac in 1984. I continue to love Apple products for their beautiful design and functionality.
I've had a number of careers. I started out as a minister, then joined the Air Force (medical administration specialist) to use the GI Bill and continue my education. After completing undergraduate and graduate work, I went back into the Air Force as a chaplain.
After getting out of active duty, I attended law school in Oregon. Early on I practiced primarily family law, and later started a practice focusing only on estate planning. I also became a JAG (Judge Advocate) in the Air Force Reserve.
My wife and I retired in 2015 and moved to Arizona. After getting sick of the heat, we moved to Rapid City, SD where we now live.
I've done a number of things since retiring: I've been a patrol shift supervisor for the Sheriff's Posse, written a blog on senior sexuality, and worked as a part-time National Park Service ranger.
I now work part-time to provide administrative support to a well-known creator. I write two blogs: one on healthy productivity and intentional living, and one on retirement. I'm also a Certified Professional Retirement Coach.
