I agree that wisdom is intuitive, and is built more by experience and reflection upon it, than by reading or talking about others' experiences. Granted, others' experiences and opinions definitely augment the acquisition of wisdom. But there's no substitute for going out, trying things for yourself, seeing what happens, and then using what happened to guide what you're willing to try later on.
This gets to my problem with 'hip' as an end in and of itself. Being hip essentially means being very, very informed. But just because you're informed doesn't mean you have a good sense of how and when to make use of that information. A hipster who annoys the people he meets by rubbing the obscure facts he knows in their face is being very unwise, I'd argue, by alienating potentially great friends and valuable real-world connections.