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I read it as very self-reflective, but not in a bad way.

His slight self-degrading humour strikes a chord with me as a soon-to-be-30-year-old who is still an utter failure (by "millionaire by 23, billionaire by 28" standards).

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Those are very destructive thought patterns. If you are not already depressed you will be soon if you keep thinking like that, and depression makes achieving your goals near impossible.

I agree I didn't take this as a severely depressed person. Just someone who wants to change. Kudos and good luck I say. Work hard, be good to people and good things will come.

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