I feel that raising your child like so (having fewer rules) in fact parallels doing well later in life. The measure of success, especially here on hacker news, feels heavily skewed towards making money, success in the Silicon Valley, etc. But while some creative lifestyles may not make enough money (poets, writers, artists) I would argue that they would end up living more fulfilling lives, following their intrinsic motivations rather than any socially constructed notion of success.