In the past, one of the orgs I founded was an attempt structurless-ness. In some ways it worked out fine, but in several ways, internally especially, it was always tripping over itself. I burnt out and left for related reasons, but something about the situation has always rubbed me the wrong way.
Why didn’t structureless work? Being a bit of an anarchist, I was pretty sure when I started it, that the do-ocracy system would be better than something with more command and control. It’ only a few years later when reading this article on structurelessness that I realized how non-sense the conceit was to begin with.
TL;DR: Every human group has a structure, it’s inevitable. Specialization, interests, skills, or just I-get-along-with-her-better builds a structure. You can’t have a structureless group.
Once you start there, it’s not far to think through to the conclusion that claims of structurelessness is just denial that there is one for whatever reason. I think most common is naivety or idealism of a group, but sometimes more sinister behavior is at play. Anyone organizing unconferences, or open source development projects should read the post and probably dig into the origional article for a more detailed reading. For the skimmers, I leave you with the following:
A ‘laissez-faire’ group is about as realistic as a ‘laissez-faire’ society; the idea becomes a smokescreen for the strong or the lucky to establish unquestioned hegemony over others. This hegemony can easily be established because the idea of ‘structurelessness’ does not prevent the formation of informal structures, but only formal ones.”