The "Whizzard 2000" combines voice recognition, tiny cameras to see the paper, a vertically mounted gyroscope that doubles as a fan, tiny attitude jets, on-board microprocessor, and good-old-fashioned ink to amuse your business associates by taking "hand-written" notes for you on paper as you speak (or
scroll, as you prefer).
The pen keeps itself upright and propels itself by puffing air out of the appropriate attitude jets. The air is drawn in by the gyroscope (I'm imagining a vertically mounted Archimedes screw inside the pen spinning at high RPMs, drawing air through a well-concealed opening at the top of the device). There would have to be one or more small cameras around the perimeter of the pen to identify the bounds of the writing surface. It would also have to incorporate accelerometers (and perhaps a combination of Computer Vision technology) to determine its position and orientation. The noise made by the spinning parts would have to be minimized and compensated for by the voice recognition software.
The only "magic" components of this (besides the software) are the power supply and microprocessor that are small and powerful enough. I think we could cheat and outsource these to a wi-fi connected (and more powerful) computer and a clipboard which supplies the pen with power via induction. The microphone could also be built into the clipboard.
[I credit a poorly-remembered fictional Junior Achievement concept from middle school for the inspiration]