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jerry@mbp ~/journal % open siddhartha.txt

Siddhartha

Herman Hesse·February 2026

Siddhartha followed a man, borne of the highest caste and a comfortable life, and his winding journey in seeking wisdom. The plot is almost beside the point, but rather what was interesting was the representations of different beliefs and value systems as he went about his life. He sought to become an ascetic at first, abandoning his life of comfort, reflecting a sort of blind veneration for suffering as a proxy for greatness, and promptly realized that blind suffering was not indeed a proxy for enlightenment. He went to listen to the wisdom of the Buddha, but again realized that wisdom cannot be taught, it can only be learned through experience. Thus he began his own life for real, learning what the real world is, learning love for a woman, learning business from a merchant, and learning what it felt to lose himself in childish games of the world. After becoming a rich man, he cast that aside to become a simple ferryman, and finally finding peace with the river and his later-life good friends.

It's almost 3 years in from starting my 2nd company for real. In the middle of his life, Siddhartha grew to be a wealthy merchant, playing so-called games in order to earn money. I often find the deal-making parts of running my company game-like: negotiations not through loud voices but soft leverage and competition, seeing those invisible levers move in real time. Maybe this is taking too lithely a practice, as I'm now negotiating multi-million dollar deals now, but with the right rules, frame of mind, it really does reduce down to simple games of leverage and knowing where it is. I have a pretty clear mind to keep those games as means to a greater ends, and to not let those business deals become too personal, and to keep my goal of serving users/bringing meaning at the end. Maybe that is a bit of a game too, a game for feeling important, but at least the "greater game" I'd call it, I have users who feel the same. I don't envision abandoning everything to chase meaning like Siddhartha did (in fact, it feels almost selfish, like a mid-40s divorcee abandoning everything to 'find themselves', I find that dishonest and more a defense mechanism in therapy terms) since I find plenty of meaning in my work as is, but a definite reminder for me to take games at face value, play them for fun, and put them down once they've served their means.

Since April of 2023, I've been working and fully focused on building my company. I'm always reading and learning, but now the subject matters have changed; books have built my world model but now there's something greater that I can pour my energy in and see it grow.

Alexander must have felt more trepidation, joy, fear, and life when he was crossing the Hellespont than being educated by Aristotle, and so do I now.

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