The AJ Jacobs Episode: A Lifetime of Living Curiously
What if the most valuable career skill isn’t expertise, but the courage to experiment?
In Season 2, Episode 2 of The B-Side with Sri, Connico President Sri Kumar speaks with AJ Jacobs, the author of four New York Times bestsellers that are widely acclaimed by numerous top-tier publications. From reading the Encyclopaedia Britannica cover to cover to living by every rule in the Bible and thanking every person behind a single cup of coffee, AJ has built a career by leaning into his curiosity. An editor-at-large at Esquire and frequent media contributor, he brings humor, insight, and humanity to conversations about how we live, work, and make meaning.
What emerges in this conversation is not just a catalog of unconventional projects, but a philosophy for how to stay relevant, creative, and deeply human in a world that moves fast and rewards certainty.
Top 3 takeaways
- Curiosity is a muscle that can be trained. Whether it’s religion, accounting, aviation, or Formula One racing, curiosity fuels AJ’s passion and keeps his mind flexible. The habit of asking “what happens if I try this?” opens doors that rigid planning never will.
- Progress comes from action, not a perfect mindset. AJ emphasizes the power of acting first and letting feelings follow. Instead of waiting to feel ready, he reframes projects as experiments – small, reversible steps that reduce fear and invite learning.
- Failure isn’t the opposite of success; it’s part of the process. Not every experiment becomes a book. Not every idea works. AJ speaks candidly about abandoned projects, uncomfortable moments, and dead ends, reframing them as experience rather than defeat. The willingness to fail publicly, reflect, and pivot is what makes long-term growth possible.
"I do like the idea of faking it until you make it.” - AJ Jacobs
Stay curious, learn how to adapt, and keep evolving
This episode is a reminder that growth rarely comes from staying comfortable or repeating what already works. The most meaningful careers – and lives – are built by experimenting, adapting, and choosing curiosity over certainty.
Love this episode? Listen to other conversations like this with great minds in and outside aviation on The B-Side with Sri.
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