Excellent writing, thanks Ong Kar Jin! I came thru Occupy, got super inspired by the Valve Company Handbook, and helped build some “flat” organisations. It has been a long journey to finally understand the Tyranny of Structurelessness! It is so common to see orgs try to decentralise, and then go thru the kind of toxic chaos you described at Valve. I hope that there is a way to shorten this learning process, because it is so wasteful for people to have to go through it over and over.
You might enjoy this piece I wrote which makes a similar argument about the perils of “non hierarchy”, and adds some practical guidance about how to do things differently.