Most of us possess physical objects or heirlooms which connect us to our past and which provoke us to think about how we may someday pass on our own treasured objects to those we care about. Increasingly, though, the traces of our lives are made manifest in the digital world. Some collections of digital data we may deliberately amass, but others are simply the result of the digital footprint we inevitably and often inadvertently leave behind us in the online world. The move to the cloud exacerbates this fact, and raises all kinds of profound questions when we begin to think about the digital legacy we are creating not just for ourselves but for future generations. Some of the questions are technical and involve issues such as long term preservation of and access to data. But others are a function of the way our systems are designed, from system architecture to user interface. These include: How can we possess and protect online digital content that is relevant or meaningful to us? How can we confidently relinquish or even delete online digital data we no longer wish to be associated with? How can we manage and control digital content so as to create a meaningful legacy for others? In this talk I will show how exploration of these issues has led us to begin to build technologies that allow us to craft new kinds of materials out of our digital past in ways that we hope will produce long term value in the future.