This article explores the different understandings of intentionality as applied to the San Francisco cable car transportation employees. We argue that part of doing work requires a person to act and choose, meaning foreclosing on some possibilities while attending to others as an intentional expression of freedom. We draw a parallel between cable car operators and public administrators and suggest that each has to do more than just learn a set of skills traditionally depicted as knowledge acquisition. They must also become skillful by developing a feel for the work and a greater appreciation for the meaning of their craft.