In my web design class there is a young artist who is building a site for the local art community. He often asks me in depth or difficult questions for things he want his site to be able to do. In the past, this might have worried me as I can't always answer his questions, but today I realised what a joy it is to move beyond the constraints of what can be done easily, and to challenge both his and my learning.
All too often we limit ourselves to the things we are familiar with, instead of taking a step back and asking "what do I really want to achieve, and then trying to achieve it. This is perhaps one of the advantages of not knowing the software. My student has a "surely this is possible" attitude which makes us both try that bit harder to find a way of doing what he wants. Great stuff.