IMO Narcissus and Goldmund and Steppenwolf are his best.
Instead it seemed like a was harrowingly long weird sci fi fanfic over some vaguely defined but stupidly complex future society imagined in the lamest and most naive almost pubescent mind. Simple in the sense that everyone from the politician to the ascetic guru seemed like complete one dimensional stereotypes.
Also you don't stop reading because of esoteric complexity you might "get" later when you know more of the western cosmology like in fellow complex works like Ulysses (funfact both books are among the top 10 most abandoned), - you stop because it's boring imagined political history. There really doesn't seem to be a whole lot under the surface, and the schisms between "academic life" or a "life of devotion" versus "a mercantile city life", or "life of politics" was incredibly naive with no mythological, historical or even poetic context mirroring our world.
I guess i must have missed something?
I would add, in my opinion, start with Steppenwolf and then read Siddhartha. It blows my absolute mind that these books were written a hundred years ago.
They're still so relevant to life. It's really, genuinely astounding.
The more you read history, and the actual written words or written speeches of intellectuals and politicians, you'll continue to be amazed. Much of their language is poetic, and their prose seems more coherent than today's, but that's probably because they wrote a lot more letters to one another.
Why are so many old houses built so well? It's not just because craftsmanship was better. It's because the ones not built so well didn't get old. (I owned a house built in 1884 for a few years. Most of it was excellent craftsmanship. Some ... not so much. Previous owners had been lucky the dining room floor had never been stressed too much.)
Another book I'd recommend (in a very different category) is Godel, Escher, and Bach, by Douglas Hofstadter.
Maybe I've completely misunderstood the book, but my key take away is that : true enlightenment (and by enlightenment you can say, true knowledge), only comes from life experience.
And that takes quite some human understanding, specially when we've grown to value information and theory, to the point where we build a perceived complete understanding of matters, only to later realize it's an illusion.
Things like talking about the concept of Love, Grief, Hate and any other complex emotions, end up falling short no matter how you read about them, either from a technical point of view, or simply from a character from a short story. You can't truly empathize until you've lived it.
Like it's not your knowledge to own unless you've experienced it, no matter what shape or form, and maybe that deserves some sort of respect.
Maybe that reflects on our lack of appreciation for a lot of things we take for granted.
Is it wrong that he wrote it through the lens of a intellectualized male character that didn't give enough focus on women? I don't know. It's his narrative after all.
Here's a quote from the New Yorker:
"Many young men, in particular, see a glamorous reflection of themselves in the typical Hesse hero—a sensitive, brooding man who cannot find a place for himself in ordinary society. This figure might live in India in the age of the Buddha, like Siddhartha, or in Germany in the Jazz Age, like Harry Haller, or in the Middle Ages, like Goldmund in “Narcissus and Goldmund.” Whatever the setting, his path will generally feature the same landmarks. He will be plucked out of his childhood surroundings and sent to an élite school, where he will suffer deeply. He will rebel against conventional ideas of success and refuse to pursue any kind of career, combining downward mobility with spiritual striving."
Siddhartha, while an enjoyable read, confuses/"borrows" eastern religious concepts to turn it into "follow the beat of your own drum, man!".
This has real world consequences: Hesse justified his taking the "middle ground" between Nazism vs its opponents by his "politics of detachment".. you know, because he is above society, quoting from JewisPress.com:
"Hesse’s failure to publicly condemn the Nazi Party and the fascist regime was due, in large part, to his “politics of detachment” – his policy of viewing the war fever infecting Germany from a distance and his general aloofness to the deadly struggle during the 1930s and 40s as he publicly sought to occupy the “middle ground” between the Nazis and exiled German writers.
Early in the war, Hesse published an essay in which he clearly applied his “middle ground” standard, expressing and anticipating German victory but also insisting that humane values be protected. Even this bland caveat earned him everlasting hostility from the German public."
I am not claiming Hesse was a Nazi, and privately he was more anti-Nazi than anything else. His wife was Jewish.
Hesse's heroes are more Ubermensch that view regular society as cattle, than harmless Hippies.
I also tend to think the US Hippie movement of the 60s as a philosophy of selfishness..(yes, I'm aware of anti-war origins etc.) so perhaps there's more to our disagreement. My politics lean left fwiw.. social democrat.
Why are you even trying?
Not mind bending. No Twists. No roller coasters. Just a calm conversation with the author and yourself.
And yet, it had a profound impact on me.
One poem I revisit every once in a while: https://www.lieder.net/lieder/get_text.html?TextId=119749
If you understand German, I do believe it needs to be read in its original tongue. The translations I found thus far were not entirely convincing.