Unplanned encounters or casual collisions between colleagues have long been recognized as catalysts for creativity and innovation. The absence of such encounters has been a negative side effect of COVID-enforced remote work. However, there have also been positive side effects such as less time lost to commutes, lower carbon footprints, and improved work-life balance. This vision paper explores how serendipity for remote workers can be created by leveraging IoT technologies, edge computing, high-resolution video, network protocols for live interaction, and video/audio denaturing. We reflect on the privacy issues that technology-mediated serendipity raises and sketch a path towards honoring diverse privacy preferences.