The Inner Life of a Long-Term Investor

New Book Alert: The Long Game

My new book, The Long Game, is available for pre-order now. The book contains reflections from 30 investors who’ve survived decades of market cycles. You’ll learn how to tune out the noise that makes you second-guess yourself, handle the fear and greed that hurt your decisions, and stick to principles that actually compound wealth over time. Shipping starts end of February 2026.

Click Here to Pre-Order Now

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I learned something interesting today.

You know the word “school” comes from the ancient Greek skholē, which meant leisure or free time. It originally meant the unhurried space to wonder, question, and sit with difficult ideas without needing an immediate answer.

For the Greeks, it seems, skholē was the highest form of human activity, because it involved thinking freely without the pressure of any outcome. So, when Plato and his students gathered to debate philosophy under the open sky, that was skholē in action. The place where you did that became a skholē.

But we didn’t need to travel to ancient Athens to find this idea. It was already here. The “gurukul”, where a student lived in the teacher’s home and learned at the pace of understanding rather than the pace of a syllabus was skholē in everything but name. Even the Sanskrit word shiksha, which we loosely translate as education, carries within it the idea of disciplined attention and deep listening, not mere information transfer. Our forests had their own Platos in the form of the rishis who taught with no examinations but only questions and the long silence of reflection that followed them.

And then, somewhere along the way, we built our “schools,” with rigid schedules, bells, homework, compulsory attendance, and continuous grading. We imported the institution and forgot the spirit it was meant to carry.

I don’t say this with any bitterness, but with the clarity that only comes after years of slowly and painfully undoing what those years of formal education had done to me. Because what school gave me, and I suspect it gave most of us the same thing, was certainly not skholē. It gave me a sophisticated ability to absorb information, reproduce it on demand, and seek approval for doing so correctly. It taught me to fear being wrong more than I valued being honest. Also, it taught me that knowing more was the same thing as understanding more. It took me a long time to see that these are not the same thing at all.

I see this loss at a different level today, as my son enters 10th grade, already bombarded with YouTube videos on how to “strategise” for a “guaranteed” 95% in his Board examinations. What is being sold to him, and to millions of children like him, is not education. It is performance. And the tragedy is that he is yet to see the difference clearly, because the entire world around him—his school, his peers, anxious parents at every PTA meeting—is conspiring, with the best of intentions, to make performance feel like the point.

In Education and the Significance of Life, philosopher and teacher J. Krishnamurti wrote:

The purpose of education is not to produce mere scholars, technicians and job hunters, but integrated men and women who are free of fear. Education should not encourage the individual to conform to society or to be negatively harmonious with it, but help him to discover the true values which come with unbiased investigation and self-awareness. When there is no self-knowledge, self-expression becomes self-assertion, with all its aggressive and ambitious conflicts. Education should awaken the capacity to be self-aware and not merely indulge in gratifying self-expression.

When I first encountered JK’s ideas a few years ago while trying to find my own bearings in life, something cracked open in me. Maybe that’s the first time I started believing that I had the permission to question the very frameworks through which I had been seeing the world. And in doing so, he handed me back something school had quietly taken away, which is the capacity to be genuinely uncertain, curious, and free in my thinking.

I have been an investor for 23 years and a teacher of investing for 15 years now, and I have come to believe that these lessons from JK have a very specific consequence in the context of our work.

When I look around, I find most investors suffering not from a lack of information but from unexamined beliefs about information itself. We believe that if we can just know more than others and analyse harder than others, we can achieve outcomes better than others, and with complete certainty. Now, I don’t see these as errors of the intellect. Instead, I see them as emotional identities we’ve built over years, and which have been reinforced by a system that rewarded us for holding them.

I know this because I held all of them. And the undoing—the slow and humbling process of releasing them—has been the most valuable education of my life. More valuable than any course, any textbook, or any financial model.

And what undid them for me was time, the reflection I allowed myself to indulge in, and the reading of philosophers and historians alongside annual reports. What also helped was gradually building relationships with people, both living and dead, who had been playing this game far longer than me. In just sitting with these people, or reading about them in books, I noticed that the best of them were not the most knowledgeable but the most self-aware. They had each, in their own way, gone through their own undoing, and come out the other side with greater inner peace, more patient, and more honest about what they didn’t know.

Over the years, I kept returning to these conversations and questions about the inner life of a long-term investor. I kept asking: How can you stay still when everything around is pushing you to act? How do you tell the difference between conviction and rigidity? How do you know when you are seeing clearly, and when you are merely rationalising?

And the answers I received were always deeply personal. They were rooted in years of observation and honest self-examination and, in the truest sense, the fruits of skholē.

I have been sharing these conversations and lessons by way of my articles, letters, and videos all these years. And slowly, almost without my noticing, they became the education I had always needed but never received.

My new book, The Long Game, has simply grown out of that slow accumulation. I did not set out to write it. I set out, years ago, simply to learn, and The Long Game is what that learning eventually became.

I now offer it to you as a companion for the road. Something to sit with, in whatever unhurried moments you can find, and something that might, if you let it, crack open the same questions in you that it opened in me.

That, I have come to believe, is what the long game actually demands. The willingness to keep learning about yourself, honestly and without end.

That is the only game worth playing for a lifetime.

— Vishal

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