Digital media operates on a curious boundary between storage and loss. While each new storage format promises a permanent solution to our exponentially expanding media libraries, they inevitably fail or otherwise become unusable. This paper reflects on a long-term design process that attempts to bring a different paradigm to the experience of personal digital media: destruction. We present an annotated portfolio of a set of sound listening devices, critically unpacking the particular temporal, perceptual, and experiential qualities that emerge when designing for the loss of personal media. These annotations show how destruction comes to matter in designing against the traditional bias towards growth and accumulation in HCI.