This article describes how Web 2.0 technologies may facilitate journaling and related inquiry methods among older adults. Benefits and limitations of journaling are summarized as well as computer skills of older adults. We then describe how Web 2.0 technologies can enhance journaling among older adults by diminishing feelings of isolation, promoting collaboration, establishing learning communities that overcome physical boundaries, and facilitating storage and dissemination of resources. The article concludes by identifying several factors that must be anticipated when using these technologies and provides ideas to overcome privacy, access, and posthumous management. (Contains 1 table.)