Self-organizing isn't hard at all. As a species, humans automatically self-organize in any group great than about 4 or 5 people.

The problem is that people self-organize to optimize some instinctual pattern, not to optimize towards business goals. The moment you start organizing towards some other goal than what we naturally do, you are no longer "self-organizing", period.

Holacracy and other mumbo jumbo choose to ignore this simple fact, and pretend like anybody can do anybody else's job and you'll find that once you start to map out how "self-organizing" organizations always work, they aren't in fact self-organized at all.

It's actually quite maddening.