I tell my kids in school that popularity is a prison.
Now that I think about it, plans can be, too. For a great book on the absurdity of too much planning, read The Men, The Mission, And Me. Military stuff. Part of the theme is that sometimes you just have to go there, see what's happening, and "develop the situation."
Love the stories here a about breaking the chains. Reminds me of the movie "Into The Wild."