For me, one of the best parts of making a custom piece of furniture for someone is that you get to work in a way that is somewhat loose. I say somewhat loose because there are always constraints, there have to be. Sometimes they are practical; the piece has to fit somewhere or be used by persons of a certain size. Sometimes they are aesthetic; "Mickey please don't make it look like a wooden electric chair" or "Mickey for goodness sake don't carve it up and down like a cuckoo clock." Sometimes they are simply economic.
Last year I made a piece in which this design process unfolded just about perfectly and wanted to mention it here. The concept began as simply as it could have. My client had a bench in mind and she and I quickly drew some rough sketches until we had some sort of a direction to head in. Once we had pinned the design down a little more, I suggested and procured an appropriate plank of wood... in this case it was an extremely thick piece of cherry from Hearne Hardwoods in Pennsylvania (it was wonderful thank you). There were rough dimensions, material was left oversized and blocky in order that it might be shaped as the piece unfolded. We talked about perhaps a carving somewhere and settled on a simple relief pattern I sketched up. The carving, type of wood and the shape of the base influenced one another to some extent. The piece was always going to be stained dark but just how dark was a decision I left somewhat undetermined until the time came and we explored the possibilities.
In the end the design rationale and the piece itself are probably not perfect; some parts of the process were worried over by me too much while others may not have been deliberated upon enough, but the whole experience, the way in which an idea became an object, could not have been better. It was exciting for me as a craftsman and in the end my client was delighted. I'm sure she was also relieved that it did not end up looking like one of my fanciful aforementioned descriptions.