In this article I explore, from a cybernetic point-of-view, the associated notions of com-plexity, unmanageability, conversation and trust. Complexity is familiarly presented as a problem of our time. I argue that, when seen through the characterisations of the cyber-netic Law of Requisite Variety, complexity often leads to unmanageability, characterised by a controlling system not having enough variety to control the system it is to control. This leaves two options: to reduce the complexity of the system to be controlled (the option used by dictators controlling peoples), or to admit unmanageability. It is argued that unmanageability can be desirable in offering access to novelty. It is then argued that the primary means by which we can interact (and thus affect the behaviour of another system) should be seen as the conversation rather than encodement. (The alternative, to find another way in which to think of the system displaying complexity is also discussed.) The conditions that support conversation are explored: in particular, the im-plicit obligation to trust other participants in a conversation – and oneself. Trust is considered, and its benefits extolled against a background of experience in a historical context.