The Art of Learning in Investing: Mastering Markets with a Grandmaster’s Mindset

?? Wow—just one week in, and we’ve already got 379 subscribers on this journey with us! I’m genuinely grateful for your interest, engagement, and the thoughtful feedback you’ve shared. The Tai Chi Investor isn’t just a newsletter—it’s a growing community of investors looking to bring mindfulness and mastery into the markets.

And we’re just getting started. I have no doubt that more and more like-minded investors will find their way here, and I’m excited for the road ahead. Now, let’s dive into this edition’s exploration of learning, adaptation, and mastery in investing.

A week ago, I caught an episode of the Huberman Lab podcast featuring Josh Waitzkin. His thoughts on learning, resilience, and high performance really hit home—not just as an investor but as someone who has spent decades navigating the markets. His book, The Art of Learning, had been sitting on my shelf for years, and that interview nudged me to pick it up again.

Reading it with fresh eyes, I saw it for what it truly is—a blueprint for long-term success. Not just in chess or martial arts, where Waitzkin made his mark, but in investing as well. Mastery, whether in sports or financial markets, isn’t about memorizing formulas or chasing the latest trends. It’s about cultivating a mindset that thrives on learning, adaptation, and discipline.

Here’s how Waitzkin’s principles apply to investing and why they resonate so deeply with my approach as a fundamental value investor.

1. Growth Through Adversity – Thriving in Market Volatility

Waitzkin sees setbacks as stepping stones to mastery. In investing, market corrections, drawdowns, and even big mistakes are just part of the game. I’ve lived through multiple crashes—dot-com, 2008, COVID—and while each was painful, they were also invaluable learning experiences. Investors who panic and sell at the bottom often miss the strongest recoveries.

? Takeaway: Don’t fear bear markets. Instead, analyze what went wrong, refine your strategy, and recognize that volatility is the price of long-term returns.

2. Depth Over Breadth – Mastering One Strategy Before Expanding

Early in my career, I jumped at every investment opportunity—growth stocks, momentum trades, macro plays. Over time, I realized that real success comes from getting really good at one thing. For me, that was fundamental value investing. The best investors—Buffett, Klarman, Greenblatt, just to name a few—have focused on mastering a core philosophy.

? Takeaway: Pick an investment style that fits your temperament and strengths. Master it first, then consider adapting it to changing market dynamics.

3. The Soft Zone – Staying Composed Under Pressure

Markets are an emotional battlefield. When stocks are in freefall and the headlines are screaming “crisis,” fear takes over. When everything is soaring, greed clouds judgment. Waitzkin talks about The Soft Zone—a state of calm adaptability under pressure. That’s exactly what separates great investors from the rest.

? Takeaway: Build habits that reinforce emotional discipline—journaling, meditation, or simply stepping away from screens during volatility. A calm mind makes better decisions.

4. Making Smaller Circles – Refining Strategies Over Time

Waitzkin believes mastery isn’t about adding complexity, but about refining the fundamentals. The same applies to investing. The best investors don’t constantly chase new strategies—they focus on making their existing process better. Over the years, I’ve learned that refining my valuation models, risk assessment, and conviction-building process has been far more rewarding than switching approaches.

? Takeaway: Instead of jumping from one strategy to another, focus on incremental improvements—better research, deeper company analysis, and enhanced risk control.

5. Numbers to Feel to Numbers – Developing Market Intuition

When I started investing, I leaned heavily on spreadsheets, models, and ratios. But over time, I began to feel market patterns and investor psychology more intuitively. This is what Waitzkin calls Numbers to Feel to Numbers—where structured learning evolves into instinctive mastery.

? Takeaway: Learn the fundamentals first—P/E ratios, balance sheets, industry cycles—but over time, develop intuition by observing how markets behave beyond the numbers.

6. Psychological Warfare – Understanding Market Sentiment

Investing isn’t just about numbers—it’s about psychology. Markets swing between fear and greed, and those extremes create opportunity. Waitzkin talks about psychological warfare in competition—knowing when an opponent is emotionally off-balance. The same applies to investing: understanding when the market is irrational can help you act decisively.

? Takeaway: Recognize market psychology. When fear dominates, be a buyer. When euphoria takes over, consider de-risking.

7. Recovery & Balance – Avoiding Burnout in Investing

Early in my career, I obsessed over every market move. It took me years to realize that staring at screens all day doesn’t make you a better investor—it often makes you a worse one. Waitzkin emphasizes the importance of recovery and balance in high performance. Some of my best investment decisions have come after stepping away from the markets for a while.

? Takeaway: Investing is a marathon, not a sprint. Step back, clear your mind, and avoid burnout to maintain clarity in decision-making.

Conclusion: The Investor’s Path to Mastery

Re-reading The Art of Learning reminded me why I fell in love with investing in the first place. It’s not just about making money—it’s about the lifelong pursuit of mastery, the ability to adapt, and the discipline to stay rational when others aren’t.

Like chess or martial arts, investing rewards those who refine their craft over decades. It’s a game of patience, resilience, and continuous learning. Whether you’re new to investing or a seasoned professional, the lessons from Waitzkin’s journey can help you navigate markets with greater clarity, discipline, and confidence.

Stay balanced, stay strategic, and invest with wisdom.

?? Follow The Tai Chi Investor for more insights on mindful investing and market mastery.