Well, I'm no expert. And you didn't give much concrete detail. But what you say reminds me of women who can't be happy with themselves because not as beautiful/

Well, I'm no expert. And you didn't give much concrete detail. But what you say reminds me of women who can't be happy with themselves because not as beautiful/slim as the women in magazines. Which seems like a lot of women. You're happy, with a family, career, health - what more could you want - and still, similarly, feel 'not good enough'. I guess it's common enough on here and in the tech world, the glamour of..well, it's money, isn't it, mega-riches. And I doubt that makes you happy. Like 'everyone' wants to be famous, but that seems like hell on earth. People are worried about their privacy now! Wait till you're rich/famous... Maybe learn to appreciate what you have? It's really not easy to do, easier to forget to do, easier to appreciate what's gone. Don't forget to do what you love doing. Also, maybe 'thinking big' itself will jeopardize your retirement/family's future, who knows, but it seems to happen as often as not. My first instinct was to write "Stop saying you can't!", but after reading all you wrote, I thought this might be more helpful. Good luck!