I am rich and have no idea what to do

Not being married implies the ability of either to leave whenever it suits them without any financial obligations to the other. She had nothing to fear if the startup failed and left him in debt, and conversely, she doesn't necessarily gain anything if the reverse is true.

I dunno, everyone dunking on him for this feels like a kinda shitty thing to do. It seems like he's self aware enough that he already knows this, and he'll undoubtedly find out later he regrets it when it's too late to fix it.

He also had a moment where he realized how he wanted to look (or be seen) like Elon, and how that's so cringe. Then he goes and works for Elon on the "extremely important" mission of DOGE.

It sounds like what he really wants is a mission where he's learning.

{ "reflections": [ { "text_snippet": "Life has been a haze this last year. After selling my company...", "response": "This reminds me of Joseph Campbell's concept of 'hitting the wasteland' - that disorienting period after achieving what society told you was the ultimate goal. Campbell wrote about this in 'The Hero with a Thousand Faces,' describing how many mythological heroes face their greatest crisis not in battle, but in the emptiness that follows victory. There's a beautiful quote from his lectures: 'If you can see your path laid out in front of you step by step, you know it's not your path. Your own path you make with every step you take.'" }, { "text_snippet": "Everything feels like a side quest, but not in an inspiring way", "response": "This evokes Viktor Frankl's concept of the 'existential vacuum' - the state of emptiness that comes when our primary drive is satisfied but we haven't yet found what he calls our 'will to meaning.' You might find resonance in his lesser-known work 'The Unheard Cry for Meaning' where he writes: 'What man actually needs is not a tensionless state but rather the striving and struggling for a worthwhile goal.'" }, { "text_snippet": "I have infinite freedom, yet I don't know what to do with it", "response": "This reminds me of Kierkegaard's meditation on anxiety and freedom. He saw anxiety not as fear of external threats, but as the dizzying awareness of infinite possibility. In 'The Concept of Anxiety,' he describes it as 'the dizziness of freedom, which emerges when the spirit wants to posit the synthesis and freedom looks down into its own possibility.'" } ], "questions": [ { "personal": "What did you imagine freedom would feel like before you achieved this level of it?", "philosophical": "When you say things feel like 'side quests,' I'm curious - what would a 'main quest' feel like to you now?" } ], "closing_thought": "Your situation reminds me of Hermann Hesse's Siddhartha after he became a wealthy merchant. He had everything, yet felt a profound emptiness that eventually led him to his true path. Sometimes the void itself becomes the doorway to something deeper." }

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Really cool to read the comments in this thread & see the real-life advice of people who have been in these situations too!