Obsession, Chess, and the Myth of Mastery | James & Dirk Jan ten Geuzendam on the "New in Chess" Podcast

A Note from James:

So the question is, I really feel that in order to get not good at something, but great at something, you have to be obsessed. You can't just wake up and decide to be obsessed—it has to be deep, almost irrational. Obsession is like addiction. It throws your life off balance, and yet... there’s this insane joy when you enter the subculture of your obsession and get better at it.

I’ve seen this recently in crypto. I saw it in chess in Norway, commenting on what might’ve been the best chess tournament ever. And I felt it again when I sat down with Dirk Jan ten Geuzendam from New In Chess.

We didn’t just talk about chess. We talked about obsession, aging, failing at something you love, and trying to find your place in a subculture that’s moved on without you.

If you care about learning, obsession, or just love chess, you’re going to get something out of this episode. Dirk and I recorded this in Stavanger, Norway. I hope you love this conversation as much as I did being a part of it.

Episode Description:

What does it mean to return to your first love after nearly 30 years away? In this special crossover episode, James Altucher sits down with Dirk Jan ten Geuzendam, editor of New In Chess magazine, to reflect on his lifelong (and recently rekindled) obsession with chess. They explore how obsession shapes mastery, why wisdom sometimes trumps raw skill, and what it’s like to try and reclaim an old identity as an older version of yourself.

James opens up about losing games to kids half his age, obsessively chasing improvement, and why it still might be okay to fail—as long as the journey is honest. From teenage blitz tournaments to dinner with Garry Kasparov, from neuroscience to narrative writing, this episode is as much about how to live as it is about how to play.

What You’ll Learn:

• Why obsession is both a superpower and a danger
• How James approaches relearning chess after a 27-year break
• What changes in the brain as we age—and how to work with it
• The surprising ways chess opens doors in life, business, and writing
• Why storytelling and vulnerability matter more than "success" alone

Timestamped Chapters:

• [00:00] The Power of Obsession
• [01:00] Travel Tales: Norway and Crypto
• [03:00] Chess Commentary and Podcasting with Dirk Jan
• [05:00] Dirk Jan's Intro on James Altucher
• [08:00] James' Curiosity and Love of Learning
• [10:00] Starting Chess at 17 and Becoming Addicted
• [13:00] Losing to Irena Krush and Facing Limits
• [17:00] Chess, Ego, and Real-World Consequences
• [22:00] How Chess Skills Apply to Business Problems
• [26:00] Writing as a Path Through Vulnerability
• [33:00] Returning to Chess: Memory, Aging, and Rediscovery
• [37:00] Eric Rosen, Coaches, and Mental Decline
• [41:00] Pattern Recognition vs. Calculation
• [47:00] What Makes Chess Players Unique
• [50:00] Interviewing Kasparov, Judit Polgar, Hikaru
• [56:00] Obsession and the Myth of Talent
• [58:00] Will the Book Get Written?
• [60:00] The James Altucher Invitational
• [62:00] Reflecting on the Journey

Additional Resources:

• 📘 New In Chess Magazine – The legendary publication covering elite and amateur chess alike
• 🎙️ New In Chess Podcast – Hosted by Dirk Jan ten Geuzendam
• 📚 Choose Yourself by James Altucher
• 📺 Eric Rosen’s YouTube Channel – Where James first relearned modern chess
• 💻 Chess.com – Popular online chess platform
• ♟️ lichess.org – Free, open-source chess platform
• 📘 Game Changer by Matthew Sadler & Natasha Regan – On AlphaZero’s influence on modern chess
• 🧠 Andrew Huberman's Podcast – Neuroscience insights referenced in the episode

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