Today I received my first set of waterstones, a kit of Norton combination stones (220/1000, 4000/8000 and the flatening stone). The kit came with an instructional video featuring Joel Moskowitz teaching a freehand method.
I gave his approach a try on 1 5/8" iron out of Stanley 120 block plane. I must be doing something wrong, because Joel somehow managed to hone his chissel in the video without wearing the tip of his index finger raw and bleeding all over the chissel he sharpened in the demo.
In the end, I had some level of success; now I just need to work on my technique.