A New Mental Operating System: 7 Lessons From ‘Siddhartha’ by Hermann Hesse

Siddhartha by Hermann Hesse was a new operating system for my mind. Despite the book’s age (100 years) and brevity (152 pages), it was one of these rare cases of literature that combined philosophical ideas with deep sentiments. It radically redefined how I see and navigate my life.

Bold claims, I know. But if there’s one book where I feel confident making them, it’s got to be Siddhartha.

For one thing, I’ve lost count of how many times I’ve read the book. Generally, re-reading books bores me, but since first devouring Siddhartha, I couldn’t help but return to its world, language, and ideas — again and again. Heck, I practically wrote a book about the reflections I’ve had during my lengthy reading process.

For another, Siddhartha has chiseled a mark into my biography. I’d even say that I can divide my life into a pre- and post-Siddhartha period. The pre-Siddhartha period is dominated by worry, regret, and existential dread. The post-Siddhartha period is also dominated by worry, regret, and existential dread — let’s not fool ourselves. However, what I’ve discovered through Siddhartha is that there’s space surrounding these struggles. I’ve watched how my discomfort became shrouded by airiness.

A sense of militant okayness emerged.

But what fascinates me most about Siddhartha is that I can flip open almost any page and extract a lesson. The book feels like an endless well of wisdom. Over the past year, I’ve been pondering seven lessons in particular. These are the lessons I keep returning to, even after many months of excessively reading and writing about Siddhartha.

It’s them I want to turn to now.


Prologue: The Paradox of Seeking Contentment

I have had to experience so much stupidity, so many vices, so much error, so much nausea, disillusionment and sorrow, just in order to become a child again and begin anew.

 — Hermann Hesse, Siddhartha

What’s Siddhartha about? Essentially, it’s a novella that explores the self-discovery process of a young man during the time of the historical Buddha. This young man’s name is, well, Siddhartha. (And I might add that Siddhartha and the Buddha are not the same person in this book. It took me a while to realize this.)

Now, what is it that makes Siddhartha so special? After all, there are thousands of books catering to the theme of self-discovery.

The genius behind Siddhartha, I think, is that the plot is built on a paradox. Call it the paradox of seeking contentment. Siddhartha’s central goal throughout the book is to end his suffering, be contented, and attain peace of mind. To achieve this goal, he goes to great lengths: He abandons his career as a priest, leaves his family, joins an ascetic cult, rejects the Buddha’s teachings, becomes a capitalist, leads a pleasure-driven life, gets depressed, lives a simple life, and much more. 

The trouble is, none of these lifestyles satisfy him. Whatever he does, whatever he tries, he never truly arrives. That’s the paradox. It’s only at the very end that Siddhartha begins to awaken to the possibility that, all along, contentment has been available. Siddhartha realizes that seeking contentment (or anything else, really) means “having a goal.” Finding, on the other hand, means “being free, being open, having no goal.”

It’s much like Alan Watts once said:

To pursue … [the future] is to pursue a constantly retreating phantom, and the faster you chase it, the faster it runs ahead … To understand music, you must listen to it. But so long as you are thinking, “I am listening to this music,” you are not listening.

The hint is in the protagonist’s name. “Siddhartha” can be translated as “he who has attained his goal.” And yet, paradoxically, Siddhartha only reached his goal when he abandoned his goal. Siddhartha went on a very long journey to find answers, only to conclude that the most crucial answers have always lingered inside him.

Let’s unpack what these answers are all about.


1. The Seeds of Discontent

Everyone loved Siddhartha in the same way. To everyone he brought joy. To himself, though, Siddhartha did not bring joy.

 — Hermann Hesse, Siddhartha

Siddhartha’s story begins as he grows up in fairly privileged circumstances. He has friends and family. He’s intelligent and good-looking. And he’s headed toward becoming a Brahmin priest — the ancient equivalent of, say, an influencer or a rock star. In short, Siddhartha seems to have the perfect conditions for flourishing. There’s just one problem.

Siddhartha is deeply unhappy.

“A joy to all,” Hesse writes, “there was yet no joy in his own heart.” What’s happening here? I think Siddhartha’s struggle represents a hauntingly familiar conundrum: external validation can’t quench internal problems — at least not for a long time.

From the outside, it looks like Siddhartha is living The Good Life™, but from the inside, Siddhartha is stuck in a nightmare. He feels out of place, restless, and unfulfilled. In one English translation of Siddhartha, this predicament is wonderfully worded as “the seeds of discontent.”

When I first read about the seeds of discontent, I felt catapulted back into early adulthood. At the time, I was walking down the secure path of an engineering career. I had garnered respectable work experience, had just started a master’s program, and lived in a wonderful apartment with close friends nearby.

From the outside, I flourished.
From the inside, my soul withered.

Much like Siddhartha, I felt my seeds of discontent growing rampant. I couldn’t quite pinpoint who or what had planted these seeds. All I knew was that tendrils were snaring me, thorns piercing me.

I felt the urge to change, escape, and cut myself loose from my past life. But with that urge for change, I also faced an overwhelmingly puzzling question. It’s the same question that Siddhartha faces at the beginning of his long journey: If this doesn’t make me happy, what else will? In other words, What the hell should I do with my life?

Luckily, Siddhartha has a few ideas.


2. Wherever You Go, There You Are

And Siddhartha said softly, as if speaking to himself: ‘What is meditation? … It is a flight from the Self, it is a temporary escape from the torment of Self. It is a temporary palliative against the pain and folly of life.

 — Hermann Hesse, Siddhartha

Siddhartha takes the spiritual path. After leaving his hometown with his best friend, Govinda, he joins the Samanas, a religious group whose practices consist of fasting, begging, and emptying the mind.

Surprisingly, this works. Siddhartha masters the art of meditating, abandoning his desires, and forsaking his sense of self. And yet, deep from within this void, Siddhartha must come to an awkward realization: Becoming empty — letting the Self die — is just another distraction. Siddhartha may have trimmed the weeds of his discontent. But the sprouting seeds remain rooted inside his soul.

I know it all too well — this sense of chasing solutions but circling back to the initial problem. When I felt stuck in my engineering career, I escaped to Portugal. I tried to become a full-time writer. And yet, once I was there, I faced avalanches of problems. I got constantly sick. I was deeply lonely. I felt utterly lost. It seems some cliches are true, and “Wherever you go, there you are” belongs to that category. 

So, perhaps the lesson here is that we should stop trying to lose ourselves, let alone adopt a different self. A more fruitful, sustainable approach might be to navigate the immediate reality of our unfathomably complex current self.

But how can we possibly do that? How can we orient ourselves when we’re lost in a dark, scary forest?

Siddhartha’s answer is simple.


3. The Blind Art of Taking the Next Step

Siddhartha suggests an operating mode I’ve come to call “the blind art of taking the next step.” It goes like this: Upon feeling lost or clueless, simply take a stab at the next-best option. While doing so, know that the decision is flawed. Be aware that the results are imperfect and simply trust that the path will grant a valuable experience.

Three years after joining the Samanas, Siddhartha and his friend Govinda hear about an enlightened person wandering the lands. It is claimed to be no other person than the Buddha himself. This puts Siddhartha and Govinda in a tricky spot. To seek out the Buddha, they must abandon the Samanas — the community where they’ve spent the last three years of their lives. (Hello, sunk cost fallacy.) So, how could they possibly know this is the right move?

Here are the wise words that Siddhartha tells Govinda:

Let us enjoy this fruit and await further ones, Govinda. This fruit, for which we are already indebted to the Gotama [the Buddha], consists in the fact that he has enticed us away from the Samanas. Whether there are still other and better fruits, let us patiently await and see.

Let us enjoy this fruit and await further ones. These words reminded me of a quote by the novelist E. L. Doctorow: “Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way.” Of course, this metaphor applies not just to writing but to life in general.

The bitter truth is, we can never gather complete data about what lies ahead of us. It’s all just an extrapolation based on present and past experiences. But at the very least, we can get a rough idea of our immediate surroundings. We can see the small area that our headlights illuminate, even on the foggiest night. We can work with what’s here, what’s now. 

Even if the present moment seems unworkable, that’s also valuable information. For instance, it might imply a radical change in scenery or — to paraphrase Siddhartha — the patience to wait for other and better fruits.

For Siddhartha and Govinda, their next blind step is to abandon the Samanas. This much they know. They feel magnetized by the Buddha’s message and can’t help but go. Whether the Buddha’s teachings are actually valuable is beside the point. The point is, only by going there can they get further directions. Only then can they take the next step.

And the next. And the next.

Now, if you’re anything like me (a chronic, self-doubting overthinker), you might encounter a challenge with this approach. Perhaps you might believe that the next step must be the right one. That you mustn’t stumble. That missteps will be punished. However, what I’ve learned from Siddhartha is that there’s no right or wrong when it comes to taking the next step. What counts is taking the step in the first place.

After abandoning my engineering career, I lived in Portugal for seven months. It was one of the most insightful periods of my life, and yet, one day, I ran into a cul-de-sac. I lay in bed with a high fever for two weeks. When I finally decided to go to the hospital, I waited nine hours in a soulless waiting room. I never got called. At that point, an unexpected thought entered my mind. What am I doing here? I’m in a foreign country with no friends or family. I’m constantly getting sick.

And so, I decided to leave.

My next blind step — though it felt like a small defeat — was to move back in with my parents. Whether this was the best available choice, I didn’t know. I’ll never know. Even so, I’m convinced it was a good enough choice. It was sufficiently insightful, for once I returned home, the foggy area before me illuminated. I could see the ground once again and take the next step.

And the next. And the next.


4. The Value of Wasted Time

I learned through my body and soul that it was necessary for me to sin, that I needed lust, that I had to strive for property and experience nausea and the depths of despair in order to learn not to resist them, in order to learn to love the world, and no longer compare it with some kind of desired imaginary world, some imaginary vision of perfection, but to leave it as it is, to love it and be glad to belong to it.

 — Hermann Hesse, Siddhartha

What happens next in Siddhartha’s life is one big fever dream. After hearing the Buddha’s sermon, he decides to go his own way. And sure enough, he strides through the lands with lightness, feeling a sense of enlightenment.

But not much later, his life turns upside down again.

One day, Siddhartha enters a city governed by lust, greed, and pleasure. Thus far, Siddhartha’s life has been shaped by the desire to become empty. But now, suddenly, it’s dictated by the desire to become full. Siddhartha falls in love, becomes a merchant, earns money, takes up gambling, wastes money, wastes time. He eats, drinks, has sex, and does it all over again.

How many years does Siddhartha spend in this senseless cycle? Ten years? Twenty years? We don’t really know. But we do know the cycle takes its toll on him. Eventually, Siddhartha feels deeply lonely, worthless, aimless, and “like a shipwrecked man on the shore.” Depressed, Siddhartha leaves the city and gets very close to taking his life.

When we zoom out and glance at this portion of Siddhartha’s life, it seems full of stupidities, setbacks, and absurdities. After all, he went from being enlightened to feeling utterly miserable. This seemingly negative transformation would fill a person like me with regret, shame, and self-loathing.  How could I’ve been so stupid? I would probably tell myself. I’m good for nothing. Why even try when I always end up failing, going back to the start?

Siddhartha has these thoughts, too, to some degree. Yet, he manages to employ a powerful perspective shift that turns these self-defeating thoughts upside down — and ultimately saves his life. The perspective shift is that every experience is necessary. In Hesse’s words:

This emotion, this pain, these follies, also had to be experienced.

To be sure, the point here is not to sugarcoat trauma, abuse, violence, war, or other crises. Much rather, the point is to embrace one’s life as it is today, and that includes — by definition — a fair share of regret, sorrow, and setbacks.

After leaving the city, Siddhartha finds shelter at a ferryman’s hut. The ferryman, a sage named Vasudeva, teaches Siddhartha to listen, flow with the constant flux of change, and adopt a non-judgmental quality of mind.

As Siddhartha spends more and more time by the river, he begins to realize that his life hasn’t been so bad. He didn’t waste a single moment. Quite the opposite. Everything was worth experiencing. Siddhartha accepts that he needed to fail, needed to indulge in stupidities, needed to experience setbacks. It was only thanks to these negative experiences that Siddhartha could finally appreciate his life for what it had always been: a series of valuable lessons.

Another way to put this is that Siddhartha attained contentment not in spite of adversity but because of adversity. Siddhartha gained peace of mind not in spite of wasting time but because of wasting time. I’d even go as far as saying that wasted time is a fallacy. Follies must be experienced. 

Wasting time is the prerequisite to spending time well.


5. Start Again 

As we’ve seen, Siddhartha’s life constantly changes throughout the book. In the end, he lives as a sage by the river, but he gets there by living many lives — the lives of a Brahmin’s son, Samana, wanderer, lover, merchant, gambler, ferryman, friend. He’s continually born again.

What all this boils down to, I think, is best encapsulated in a quote by Alan Watts:

You’re under no obligation to be the same person you were five minutes ago.

Funnily enough, it’s unclear if it was actually Alan Watts who said these words. But if you ask me, this confusion adds even more depth to the idea. It’s as if the quote itself was under no obligation to be authored by the same person who uttered it five minutes ago.

The Stoic philosopher Seneca once said something related:

Begin at once to live, and count each separate day as a separate life.

These two quotes are perfectly united with some thoughts by Siddhartha himself:

I have indeed awakened and have only been born today … he, who was in fact like one who had awakened or was newly born, must begin his life completely afresh.

Perhaps this sounds overly dramatic, but one of the evident truths of life is that we are at no point the person we thought we were. All the labels we use to structure our lives — names, job titles, relationship statuses, etc. — don’t really exist. They’re constructs. And for that reason, we can always tear down this fickle scaffolding and begin again. Each day, each hour, each second, we can start fresh.

Siddhartha is a master at discarding old labels and stories, like a snake shedding its skin. We could even argue that Siddhartha eventually sheds the label of having no label. What remains for Siddhartha is that he merely invites everything that is appearing.

The idea of starting again doesn’t imply that we should all suddenly abandon our old lives, move countries, leave people, and change jobs. Not necessarily. What it aims at, I think, is becoming aware of the storylines and narratives we’re telling ourselves and realizing that they’re just that — stories.

If Siddhartha had clung to his identity as a priest, ascetic, or merchant, he could’ve never moved on from his past and found peace by the river. That’s why overly engaging with our past can keep us stuck. We regurgitate the same stories and labels rather than inviting what’s here, now. As the psychotherapist Bruce Tift says:

There’s a potential problem with looking to the past as a way of better understanding the present: we may start to think that an improved present is dependent on clearing up the past.

Starting again — returning one’s attention to the present — short circuits this problem. Of course, the past will inevitably affect us in some ways. But ultimately, the only relevant consequences of the past are the ones happening in the present.

The meditation teacher and psychotherapist Loch Kelly offers a powerful question to shift the focus — ever so slightly — from the past to the present: “What is here now if there’s no problem to solve?” Using this question, we might adopt a quality of mind that’s similar to Siddhartha’s after he found peace and contentment. It’s best encapsulated by one thought that Siddhartha has while studying the river:

He saw that the water continually flowed and flowed and yet it was always there; it was always the same and yet every moment it was new.


6. How to Become Wise

Wisdom is not communicable. The wisdom which a wise man tries to communicate always sounds foolish.

 — Hermann Hesse, Siddhartha

Perhaps the most cardinal lesson from Siddhartha is that wisdom cannot be taught. It can only be learned by experience. No philosophical theory will ever be able to explain the whole truth. The moment one tries to capture experience or wisdom in words is the same moment that wisdom evaporates.

This is not to say that words, teachings, and theories are useless. They’re quite helpful. They’re like the railings and cobblestones that guide our path. But we mustn’t confuse them with the path itself. The path is our lived experience. The path is our missteps, our mistakes, our despair.

One can only become smart by words, but one cannot become wise by words. The only holistic teacher is experience. For instance, when Siddhartha was still a young man, he rationally knew that wealth and superficial pleasures weren’t the answer. But it was only after experiencing these pleasures that he could internalize this insight:

It is a good thing to experience everything oneself, he thought. As a child I learned that pleasures of the world and riches were not good. I have known it for a long time, but I have only just experienced it. Now I know it not only with my intellect, but with my eyes, with my heart, with my stomach. It is a good thing that I know this.

I cringe at saying this, but I’m increasingly convinced that the best remedy for life’s struggles is aging. Which is to say, getting older. Which is to say, gathering experience. For instance, people feel happier as they age. Studies found that, as we get older, we become more resilient to criticism and negative moods. We also become better at regulating our own emotions. Why? Because of lived experience. That’s part of the reason why Siddhartha emerges as such a wise person in the end. He’s been through some shit.

The secret to wisdom, then, is simple but not easy. Becoming wise is not about knowing that life has many flavors; it’s about having experienced these flavors.


7. The Meaning of Life

Before reading Siddhartha, I’d been stuck in existential crises for years. Questions about life’s meaning raced through my brain like the race cars of a never-ending Formula One championship. There was no answer I found satisfying. It wasn’t until I read the following passage in Siddhartha that I could finally adopt an answer that felt meaningful to me:

When anyone reads anything which he wishes to study, he does not despise the letters and punctuation marks, and call them illusion, chance and worthless shells, but he reads them, he studies and loves them, letter by letter. But I, who wished to read the book of the world and the book of my own nature, did presume to despise the letters and signs. I called the world of appearances, illusion. I called my eyes and tongue, chance. Now it is over; I have awakened.

In other words, the meaning of life is a fake problem. It only arises when you detach from the immediacy of life. Siddhartha provides the perfect metaphor: Asking about the meaning of life is like questioning the formatting of a book. “Why did they put a comma here?” one might ask. Or: “Why did they use the word perilous rather than dangerous?”

But when you immerse yourself in the book of life, when you start reading, all these doubts crumble away, naturally.

Fernando Pessoa, one of the most fascinating authors of the 20th century, echoes this idea in one of his poems:

I believe in the world as in a daisy,
Because I see it. But I don’t think about it,
Because to think is to not understand.
The world wasn’t made for us to think about it
(To think is to have eyes that aren’t well)
But to look at it and to be in agreement.

The world wasn’t made for us to think about it. That pretty much encapsulates how I think about the meaning of life.

“One cannot love words,” says Siddhartha. When you try to come up with an explanation for the meaning of life, you use words — that is, fickle representations of the world. But to find meaning in the world — if there is such a thing — words can only get you so far. What counts is the real thing. This moment. This experience.

This, this, this.


Epilogue: Seeing Life Through Siddhartha’s Lens

It’s funny. When I started writing about Siddhartha, I started developing complex literary theories. (There’s a lot to unpack, after all!) And so, I drafted sophisticated subheadings:

  • The Meaning of Water in Siddhartha: Depth, Reflection, and Flow
  • The Circular Structure of Siddhartha: How to End up Where One Started
  • The Three Realms of Siddhartha: Spirituality, Sensuality, Wisdom

But ultimately, the book speaks for itself. No further interpretation is needed. All I’ve ever tried to do when writing about Siddhartha was to express my experience and insights that unfolded while reading.

What made Siddhartha such a life-changing book for me wasn’t just the lessons I learned. Much rather, it was the long (and sometimes boring!) process of seeing my life through a different lens, Siddhartha’s lens. That’s why, although I’d initially devoured Siddhartha in two days, I needed more than a year to digest its many lessons.

To drive home a larger point, a book becomes life-changing not just because of its content but because of its context. Siddhartha redefined my life because I stumbled upon it when I needed it most — and even more so because I kept spending so much time with the story. Some people might call it a waste of time to hyper-fixate on such a small book. My response, as you can imagine, is the opposite.

I’ve found every second valuable. Each moment was necessary.


Want to Get More Out of the Next Book You Read?

If I learned one thing from studying philosophy and devouring hundreds of books, it’s this: reading books in a community supercharges your ability to extract their wisdom. That’s why I started The Bibliosopher’s Club, a book club where we explore what it means to live a good life – one book at a time.

Enter your email below to join hundreds of avid readers on our quest to read and live better.