OSGeoLive is a self-contained bootable DVD, USB thumb drive or Virtual Machine based on Lubuntu, that allows you to try a wide variety of open source geospatial software without installing anything. It is composed entirely of free software, allowing it to be freely distributed, duplicated and passed around. It provides pre-configured applications for a range of geospatial use cases, including storage, publishing, viewing, analysis and manipulation of data. It also contains sample datasets and documentation. OSGeoLive is an OSGeo project used in several workshops at FOSS4Gs around the world. The OSGeoLive project has consistently and sustainably been attracting contributions from ~ 50 projects for over a decade. Why has it been successful? What has attracted hundreds of diverse people to contribute to this project? How are technology changes affecting OSGeoLive, and by extension, the greater OSGeo ecosystem? Where is OSGeoLive heading and what are the challenges and opportunities for the future? How is the project steering committee operating? In this presentation we will cover current roadmap, opportunities and challenges, and why people are using OSGeoLive.