I was a trained draftsman in a previous life so I tend to plan most
projects to a certain extent. When I say "draftsman" I was trained
at a drafting table using drafting instruments of the day. I did get
some CAD training in later years but moved into some writing and
management jobs before I got a chance to use the CAD tools much.
Planning includes some sort of graphic representation of the project
and a list of materials. I currently keep some of my old drafting
tools near a small drafting table in the basement; and some of the
tools are in my workshop. Smaller projects are planned on a clipboard
in the shop. As projects become more complex, I resort to the
drafting equipment. Instead of vellum or mylar drawings I usually do
a scaled and fairly detailed layout or "shop sketch" on a sheet of 24"
or 30" poster board which is cheap and durable when I hang it on the
wall of the shop. I am artistic by nature but art and drafting are
two different disciplines. I sometimes say I do a half-a**'ed job at
both. When a board drawn shop sketch gets to the shop I refer to it
often, and modify it as needed. Sometimes the modifications reflect
my artistic side; sometimes I'm fixing screw-ups.
Had I come along a few years later, I would probably be using Sketch
Up or a CAD tool of some kind. While I consider CAD pretty
interesting, I would rather be using my time building, not learning
software. Contrary to some people's belief, a trained board draftsman
can put lines on paper (and move them) pretty fast. In my earlier
life we made a lot of design changes on a change order pad while
working with an aircraft technician in the hangar. Also, I would say
that about 50-70% of my projects get planned on the clipboard.
To summarize: planning to some level is essential to successful
projects. But don't let the planning methods override your
woodworking creativity. Visualize, think, sketch, make sawdust