If its just me and the weather looks good, then I use Astroplanner + Notepad to write up a planned list of Messier (or Glen C Messier-like) objects to image or view that will be visible, starting with most northerly and then westerly visible objects for time of year (then moving back through RA to the E as objects rise during the night).
Notepad is great for jotting down a roughly planned list for different times which you can tweak or put down detailed notes as you go if need be. I usually take at least some images, so the notepad file gets thrown in that directory as a diary record. I also try and put some detail into Astroplanner if time allows, but at the very least make note of having seen something so I don't keep revisiting the same objects. Use defined columns in Astroplanner are a big help in noting which objects I've decided to have a go at and at what time for a particular planned session (or just for noting something I'd like to try for at the next dark sky site).
Once I've "done" Glen Couzen's All Sky Messier catalogue, I think I'll move on to a list of the brighter NGC objects. Mind you the more you learn about imaging, the longer you want to spend on each decent object, slowing the rate you "discover" new things.
I suspect lots of people will have changed how they explore and plan over the long period this thread has been running!
p.s. If friends or family with me, I'll often fire up EQTour part of EQMOD and use that to find objects once I've exhausted those I know myself.