5 Questions with A.J. Jacobs

5 Questions with A.J. Jacobs

Author: Paul Ollinger June 10, 2026 Duration: 32:17

✍️ Follow Paul Ollinger on Substack by clicking here ✍️

A.J. Jacobs is a journalist, bestselling author, self-described “human guinea pig,” and one of the most interesting people I know. He was a great choice to be my second guest on my 5 Questions series of Substack livestreams.

Over the past two decades, A.J. has built a remarkable career by asking questions most of us would never think to ask—and then answering them by turning himself into the experiment.

He’s read the entire Encyclopedia Britannica, lived according to the Bible as literally as possible, pursued bodily perfection, traced his family tree to millions of relatives, thanked every person involved in making his morning cup of coffee, explored the world of puzzles, and most recently spent a year trying to live according to the original meaning of the U.S. Constitution.

The result has been a string of New York Times bestsellers, including The Know-It-All, The Year of Living Biblically, Drop Dead Healthy, Thanks a Thousand, The Puzzler, and The Year of Living Constitutionally. Along the way, he’s become one of America’s most entertaining guides to the intersection of happiness, curiosity, gratitude, self-improvement, and human connection.

What I love about A.J.’s work is that beneath all the humor and outrageous experiments is a serious question: How should we live? And instead of lecturing, he goes out and tests ideas on himself—often with hilarious consequences.

We talk about:

* The United States’ 250th Birthday

* Geeking out on compound anniversary words like “semiquincentennial”

* What I should keep in mind while I help my kids search for colleges

* Summer blockbuster movies

Subscribe to A.J.’s Substack, A.J. Jacobs



Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 50

Reasonably Happy with Paul Ollinger
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