Journeying East

September 16, 2026

When I first read The Journey to the East, it was the fourth Hermann Hesse novel I was reading within a year. In fact, I had read Demian twice, the second time over the course of a few months as I composed a far too lengthy explication of its motifs and themes. I was Hessed out. As I sped through the novel, I noted only the familiar elements: the allusions to old German poets, musicians, and classic novelists; the clash between intellectualism and down-to-earth saintliness; the “psychological journey” toward the “Good Life;” the rejection of Protestantism in favour of a syncretic, universal mysticism. All of this is in Demian, Steppenwolf, Glass Bead Game, and to a greater or lesser extent Siddhartha (which eschews a few of these motifs in order to focus more specifically on others.) I saw all this and I thought: we’ve been through this already, Hermann!

But I don’t trust first impressions, and I don’t even trust my opinion after an initial read. In many ways, reading through a book once is merely preparation for tackling it again later. It takes time for certain things to sink in, to develop a familiarity with the characters, style, and themes of a work, and to be able to fit all of this into a coherent structure. While reading a book for the first time, you are an  initiate, taking your first steps into its world. It is not a time for judgment.

So while my initial impression was negative, I kept the book on my shelf. Hesse and I have shared too many good times for me to cast aside one of his works so quickly. A few years later, the book popped into my head for reasons that remain unclear, and I felt the inclination to read it again. And it is during this second reading that I saw beyond my initial weariness and into the true nature of the novel.1  (1 I had this exact same experience when I first read Demian.)

Journey to the West is a Chinese “novel” by Wu Cheng’en, written in the 16th century and very loosely based on historical record (in a similar fashion to Romance of the Three Kingdoms.) In it, a Buddhist monk, accompanied by a few strange companions, travels to India in order to collect sutras and bring them back to China. In a certain sense, you could describe Hesse’s career as a metaphorical attempt to make the same journey from the opposite direction. While he is not searching for any particular religious knowledge, his dissatisfaction with the philosophical world he’s born into led him to wander in search of what we might call additional context. So when you see the title of this novel, it makes perfect sense that Hesse would write a novel called that, and it’s only fitting that the journey eastward in this novel is itself a re-imagining of his own career. 

In Journey to the East, the main character, H.H. (for some reason, he never tells us what this stands for…) wants to tell us about a journey he took as a young man, a “journey the like of which had not been attempted since the days of Hugo and mad Roland.” This was just after the first World War, and Europe is in disarray. As a member of The League, a secret society akin to the Freemasons or Rosicrucians, he was allowed to participate in this Journey to the East, a free-form sort of endeavour in which each participant pursues his own particular goal, free to wander in groups or alone, to join or split up as they like, and generally make their own way. While you might expect such a journey to tend eastward, all the specific locations mentioned in connection to this journey are in Central Europe, located within a few degrees of longitude. Its not stated where they started from, but no matter how you slice it, their path was decidedly more north-south than it ever was east-west. This is all beside the point, however; we are told early on that this journey is hardly geographical at all; as Rod Serling would later put it, it is “not only of space, but of time.” They “boldly crossed half Europe and a portion of the Middle Ages;” they “roamed through Italy and Switzerland, but at times […] also spent the night in the 10th century and dwelt with the patriarchs or the fairies.” We should note that H.H.’s personal goal was to meet the Princess Fatima and “if possible, win her love.”

All this confusion and vagueness is perhaps why the narrator struggles so much to tell of this journey in any kind of straightforward way — this combined with the fact that the Journey fell apart after a short time, leaving the narrator unsure of The League’s continued existence. This collapse was occasioned by the disappearance of the servant Leo, who, despite being a servant, seemed the most clear-minded and astute of the bunch. After Leo’s disappearance, the members of H.H.’s cadre start to question the very nature and basis of the Journey. They start to misplace items, and the items they misplace, regardless of how trivial they seemed before, start to take on a massive importance as soon as they are gone. One of these misplaced items is a League document — while its contents are never stated clearly, it is implied to be some sort of original charter. Yet, nobody within H.H.’s group can agree as to whether it was the original, a copy, or a translation, or even whether the document had been in their possession in the first place. This points to a fundamental loss of grounding for their Journey: they can no longer tell what their purpose is, which leads them to appeal to authority, only to realize that this authority is nowhere to be found. 

Leo represents the humble, down-to-earth wisdom of the saint, as opposed to the book-learning and sophistication of the other members. He seeks wisdom and enlightenment in life rather than in thought. When it is later revealed that he is the President of the League, it’s hardly a surprise. Hesse is making a clear value judgment here that is representative of his work as a whole. To his mind, philosophy is not merely an intellectual pursuit, to be written and talked and reasoned about ad nauseam. It is a means to an end, and its end is the Good Life. A solid philosophy is not compiled in a book but lived. When Leo leaves the expedition, this balance is lost, and since nobody seemed to have heeded his example, the Journey becomes disenchanted. 

While H.H. moves on from the Journey, becomes a “respectable” person, and lives through this disenchantment, he can’t help but hold on to the ideals of his youth, refusing to disregard the Journey as youthful folly. The goals of the Journey, which to others seem immature and idealistic, to him still seem as important as ever. We find in life that many consider it only rational and reasonable to give up on philosophical inquiry after college and tend to the practical matters of the “real world,” while others never get over the idea that these big questions are perhaps the most pertinent of all. H.H., like Hermann Hesse himself, never stops wondering about these big questions, and only accepts disenchantment ruefully, not as a fact of the world but as a sort of failure of imagination. 

What H.H. is disillusioned with is not life as a whole, but a certain sliver of life. The Journey represents the life of the free intellect, not bound by space and time but free to wander and wonder. Its connection to the League provides it with a sense of tradition, of following in the footsteps of the great artists and thinkers of previous generations. It involves pursuits that are unreal and impossible. 

The Journey’s participants include both real and imagined characters, and at one point H.H. wonders why the fictional people “were more animated, more beautiful, happier, and certainly finer and more real than the poets and creators themselves,” who seem only “half-alive.” One of the examples cited is the Gothic novelist E.T.A. Hoffman, but another is the unnamed creator of “Pablo” from Steppenwolf — Hermann Hesse himself. And if we look closely at the locations visited in the journey — Brandensee, Swabia, Italy, the Morbio Inferiore in Switzerland — we find that they are all significant locations in Hesse’s own life. So, of course, we have to start factoring in the autobiographical nature of this work. 

Taking this into account, what is the nature of H.H.’s Journey to the East? It is a voyage into a world that synthesizes history, intellect, and emotion — that is to say, the world of art. H.H.’s goal of winning the love of Princess Fatima is an aesthetic goal: the desire to capture beauty, as also seen in Emil Sinclair’s passion for Beatrice in Demian. Art is a means of connecting with history, through carrying on a tradition established over centuries. It is a means of expressing thoughts and ideas. And it is a means of conveying and understanding one’s emotions, in an attempt to find the correct path: the Good Life. These three aspects are equally important; when you lose one, you lose access to this world; hence why the departure of Leo, the emotional core of the Journey, abruptly throws H.H. and his compatriots out of their reverie. 

Hermann Hesse’s life, like those of most people who feel deeply and concern themselves with questions larger than their capacity, was tumultuous. One needs no biography to see this: it’s all there in the novels. His protagonists are always confused, always wandering; always self-incriminating, questioning, and plagued with doubt. No two novel ends with the same answers, proving that these answers are mere hopes rather than discoveries. “Perhaps,” Hesse is saying, “this is the way to the Good Life!” Several years later, he returns to say, “Well, no, that wasn’t quite it…” 

This is why the Journey to the East is perpetual. Years later, while struggling to compose his chronicle, H.H. runs into Leo. Surprised to find him alive and well, and still seemingly connected with the League he believed to be disbanded, H.H. is frantic to retrieve what he had lost so long ago. But he finds out that it wasn’t something material that had been lost, but something inside himself. The League carried on, the Journey kept on happening, but without him. He had lost access due to his own folly, due to not understanding the basic tenets of what the whole endeavour was about. 

At the same time, we must ask ourselves: is it possible for H.H., or Hesse himself, to understand what this endeavour is all about? At the end of the novel, we find that H.H. and Leo are two sides of the same figure: that is to say, that Leo is that very aspect of himself that H.H. has lost. If we consider what was said before about creators and their creations, we find the key to understanding what Hesse is saying here. Hermann Hesse, the man, cannot answer any of the questions that burn deep within him. He can not, in the real world, live The Good Life. It is only when we see Hesse not as a man, but as a synthesis of man and art, of creator and creation, that we find a figure capable of revealing to us the mysteries that plague our existence. An artist can not live his art — for if that were the case, there would be no need for art at all. He must construct it as something outside of himself, something that will only be a part of “him” in posterity. For us, reading Hesse in the 21st century, Hesse is his work. He is a man-book hybrid. And it is only as this strange chimera that he can invite us on his Journey.