Reading Siddhartha Across Fifty Years

There are moments in a life when something becomes clear in a way that leaves no room for avoidance. Nothing external has changed. No new information has been introduced. Yet something inside shifts, and what was once easy to overlook suddenly becomes impossible to ignore. What matters is not the moment itself but what follows—whether we turn toward what we see or, once again, find a way to look away.

I recognized something of this while rereading Hermann Hesse’s Siddhartha. It wasn’t the story itself that stayed with me this time. I already knew the arc—the young man who leaves home, who tries to strip himself of desire, who abandons that path and throws himself fully into the world, who becomes a lover, a gambler, a man of appetite, and later a father who can’t hold on to his son.

What stayed with me was something quieter and more unsettling: at each stage, Siddhartha could not understand himself until he had lived through that version of his life in full. The ascetic could not erase the self. The man of the world could not satisfy it. The father could not hold what he loved. Each attempt to resolve himself by escaping into a new identity failed, not because the attempt was misguided but because it was incomplete. Each life had to be lived through to its limit before it could be understood. Nothing could be bypassed. Nothing could be skipped. Each life remained within him, but none could become intelligible until later.

When I first read the book, I was in my late twenties. I was immediately drawn to the young Siddhartha, though I couldn’t have said exactly why. From the outside, my life was moving forward in a coherent way—graduate school, professional training, the early stages of a career that made sense to others. There was structure, direction, and a reasonable sense of purpose. But beneath that, there was a quieter, less articulate awareness that something essential was missing. It wasn’t dramatic. It didn’t interrupt my life or force a decision. Yet it remained, like a question I didn’t yet know how to ask. I didn’t leave my life the way Siddhartha did, but I understood the impulse—to step away from what seemed sufficient to discover whether it actually was. That feeling stayed with me. It didn’t resolve itself, but it shaped how I moved forward, influencing decisions that didn’t follow a predictable path, including the choice my partner, Deborah, and I made a few years later to leave behind what seemed like a sensible life and set out on a long, uncertain journey. At the time, I didn’t connect that decision to anything I had read. Looking back, it feels less accidental.

During that first reading, something happened that I didn’t understand at the time. Deborah and I were living in Vermont, by Lake Dunmore. It was summer. I was sitting on a dock in a beach chair, the lake in front of me, the house behind me on a small rise, surrounded by trees. The air was quiet in a way that let thoughts arrive without effort. I remember lowering the book, keeping my place with a finger, and sitting there without reading for a while. There was no reason for it. Nothing in the story had triggered a specific memory. But something had shifted.

I found myself thinking about someone I hadn’t thought of in years—a man named Ira.

He had lent me five thousand dollars to help me start a small business. The business failed, and I never repaid him. I didn’t decide not to repay him. I didn’t tell myself, “I’m not going to do this.” I avoided it because I could. I let it recede until it no longer demanded my attention. It became something I lived with without examining it too closely, a quiet omission that never quite rose to the level of a problem because I never allowed it to.

At the same time, someone else in my life—a fellow student—owed me two thousand dollars. He had promised to repay it within a month. Months passed, then more time. He never paid me, and I began to think of that money as lost. Sitting on the dock, I saw both things at once. Not as separate events, but as a single, unmistakable recognition. I was waiting for him to act with integrity. I had not done the same. There was no argument, no explanation, no attempt to reinterpret it in a more favorable light. Just clarity that I had avoided something that mattered because I could.

That recognition didn’t feel dramatic. It felt conclusive.

I went inside, found Ira’s number, and called him. I told him who I was and apologized for not handling things responsibly. “I want to make it right, even if it takes time.” He seemed completely at ease. “Whatever works for you,” he said. “I always knew you would pay me back.”

I remember being surprised by that—not by his response, but by my own. The person making that call was not entirely familiar to me. Nothing about my circumstances had changed. I had not gained new information or reached a new intellectual understanding. But I had become able to see something I had previously avoided, and once I saw it, I could no longer leave it alone.

The next day, I went to the mailbox and found an envelope from the student who owed me two thousand dollars. Inside was a check for the full amount. There was no explanation, no note—just the check. I stood there holding it, aware that something had changed, though not in the way I might have described it then. It didn’t feel like a reward. It didn’t feel like coincidence. It felt like a kind of alignment—not of events, but of perception. Something that had been out of balance had come into view, and once it did, my response shifted.

At the time, I thought something unusual had happened. Now, reading Siddhartha, I understand it differently. What changed that day was not the sequence of events. What changed was what I felt, and therefore what I recognized. Like Siddhartha, I could not understand that part of myself until I had lived it. The man who avoided responsibility and the man who made that phone call were not different people. They were the same person, seen at different times and understood differently.

That is what I see more clearly now. We do not leave our earlier selves behind. They remain, whether we recognize them or not. What changes over time is not who we have been, but our capacity to feel, understand, and, at certain moments, respond differently. Those moments don’t announce themselves. They don’t arrive with an explanation. They arrive quietly, often without warning, as a shift in what we can see. When they do, we face a simple but decisive choice: to turn toward what has become visible or to return to the familiar habit of looking away.

I don’t believe those moments are rare. I think they happen more often than we notice. What is rare is the willingness to act on them—to let what we see change what we do.

I’m not done with Siddhartha. Even at almost eighty, there are still parts of myself I do not fully understand. I suspect that when I return to the book, something else will become visible—something that has been there all along, waiting for me to grasp it.