The problem, of course, lies in the difference between language and feelings. Feelings are a raw physical reaction that is hardwired into our earthly being. Words, on the other hand, are an abstraction of reality. Language (at least in the human sense) is a layer of formalized associations created through common experience. The self-aware and introspective nature of our consciousness allows infinitely deep abstraction to be applied to existing ideas. The thought process can affect our feelings and mask them behind numerous memes, but it does not generate feelings in and of itself, it only allows us to perceive them more fully.

The degree to which language is an effective communicator is directly related to the similarity of experience between people. The fact that language works as well as it does is due to the fact that humans generally share the same set of senses, live on the same planet, and have similar emotions (we presume).

Common feelings are easy to describe. Everyone on the planet knows the basic feelings of joy, sorrow, guilt, envy, etc. Even two indigenous people from opposite sides of the world share many experiences intrinsic to being human. The kinds of feelings that are hard to describe are the result of a more specific set of circumstances. Particularly the feelings that have many direct tie-ins to important life events of an individual. This is why kids can't be made to understand many of their parents' actions; they simply don't have the experiences on which to base those feelings.

At the risk of over-simplification, I would say communicating complex feelings effectively is based on breaking down a feeling into progressively more basic influences until you have a list of simple motivations and emotions anyone can understand. Then (and this is the hard part) communicating the entirety of the feeling based on common associations to the simple, universal ideas. Although the reader may not have the experience to really understand a given feeling, through clever suggestion and a little imagination, they will be able to gain some insight into the feeling, however crude.

Incidentally, I also imagine someone could become quite deft at playing the piano with a baseball bat (or even two).