The design of meaningful graphical objects to represent collection items must balance the following: amount of useful information that can be communicated through the object’s graphical form, meaningful graphical difference between individual items or groups of items, and restraint in form complexity to allow for the simultaneous display of numerous collection items at a small size. How the user interprets difference and sameness and, more importantly, whether the user attaches hierarchical value to the emergent categories, may play a significant role in determining whether that user focusses attention on one set of data over another, on one set of processes over another, and ultimately, on one set of tasks over another. This paper examines the significant consequences for the understanding of the user resulting from representation of data, files, and other objects in a human-computer interface (HCI), and proposes that new approaches may be indicated, given the growing complexity of what is being represented and how what is represented can be used.