Growing from a shared interest to try something “new,” three teachers at different schools experimented to understand the organic but deliberate aspects of collaboration made possible by technology. Modeling what we were learning about collaboration, students engaged in unexpected conversations across campuses, showcased their learning through multiple media, and inspired critical thinking in all involved, demonstrating the relationship between teaching practices and student habits of mind. Students were empowered to formulate questions for real audiences, to understand through practice the relationship between purpose, audience, and word, and to analyze, create, and synthesize ideas through multiple modes of communication, all on the social space of the internet. We want to share that story – both its successes and false starts. Our conversation also addresses one the largest elephants in the room: what it feels like to take the risk of collaborating with others. Standing in the way of successful collaboration is a tremendous amount of ungrounded fear and anxiety that no one wants to name, and that’s a conversation we’ll be exploring. What did it feel like to collaborate, to yield, to think together? How do we get past our anxieties to connect to collaborative communities of joy?