I’ve taught hundreds of songs over the years. Wanting to play the songs we love is a great motivator and it can be extremely gratifying to achieve. However, I see song learning as a side product of my main objective as a teacher. It might seem like we learn music to play songs, but instead, I like to think that we play songs to learn music. The latter perspective allows us to see that by learning one song, and breaking down the elements that shape it, we are in fact learning pieces of thousands (if not millions) of songs at once. If we can understand the structure of where each musical idea in a song comes from, beyond just what notes/strings/fingers/frets it takes to play it, then we are empowering ourselves to see how all songs are coming from the same pool of information. This is the kind of thing that gets me excited!
With this all-songs-are-connected school of thought, being unsure about whether or not a song is within someone’s capabilities is no longer a concern. There is always something to learn from any song, at any level, once you allow yourself to deconstruct it. Being inspired by a song—loving it, being moved by it—is the most important factor in my book (I don’t actually have a book, but I plan on writing one some day 😊 ). This approach can incorporate many phases of learning any one song, slowly working up to playing exactly what’s on a recording, but starting off much simpler while gaining a thorough understanding of what’s going on.