Achievement of many long-term goals requires sustained practice over long durations. Examples include goals related to areas of high personal and societal benefit, such as physical fitness, which requires a practice of frequent exercise; self-education, which requires a practice of frequent study; or personal productivity, which requires a practice of performing work. Maintaining these practices can be difficult, because even though obvious benefits come with achieving these goals, an individual's willpower may not always be sufficient to sustain the required effort. This dissertation advocates addressing this problem by designing novel interfaces that provide people with new practices that are fun and enjoyable, thereby reducing the need for users to draw upon willpower when pursuing these long-term goals. To draw volitional usage, these practice-oriented interfaces can integrate key characteristics of existing activities, such as music-making and other hobbies, that are already known to draw voluntary participation over long durations. This dissertation makes several key contributions to provide designers with the necessary tools to create practice-oriented interfaces. First, it consolidates and synthesizes key ideas from fields such as activity theory, self-determination theory, HCI design, and serious leisure. It also provides a new conceptual framework consisting of heuristics for designing systems that draw new users, plus heuristics for making systems that will continue drawing usage from existing users over time. These heuristics serve as a collection of useful ideas to consider when analyzing or designing systems, and this dissertation postulates that if designers build these characteristics into their products, the resulting systems will draw more volitional usage. To demonstrate the framework's usefulness as an analytical tool, it is applied as a set of analytical lenses upon three previously-existing experiential media systems. To demonstrate its usefulness as a design tool, the framework is used as a guide in the development of an experiential media system called pdMusic. This system is installed at public events for user studies, and the study results provide qualitative support for many framework heuristics. Lastly, this dissertation makes recommendations to scholars and designers on potential future ways to examine the topic of volitional usage.