This article deploys the anarchist notion of self-management to critically investigate the global organic farming network WorldWide Opportunities on Organic Farms (WWOOF) as an initiative that offers insights into the possibilities and challenges of encounter. WWOOF facilitates the giving of food, accommodation, and hands-on learning experiences for volunteers, in exchange for their labor on organic farms. It operates as a moneyless sharing economy, designed as a site of mutual learning and cultural exchange. Literatures on encounter divide between brief tourist encounters of difference and everyday encounters in diverse, usually urban, communities. In linking these two bodies of work, I argue that the principle of self-management, as conceived by anarchist thinkers, can help develop a unified, critical framework for making sense of encounter event-spaces. This adds important nuance to theorizations of encounter by recognizing the entwinement of the intimate and the structural, while foregrounding the capacity of people to autonomously create shared spaces of interdependence. The case study indicates that structural contradictions and inequalities in voluntary relationships within statist-capitalist modes systems can seriously undermine otherwise promising interpersonal encounters. By articulating self-management as a tool for both analyzing and producing spaces of encounter, this essay offers new possibilities for a more holistic and unified analytical framework.