Since I'm almost always alone and working on a deadline, I overplan everything so I don't lose time trying to figure out how to get where I'm going or how to get back to my car. I research and write up everything ahead of time: peak/waterfall/hot spring name, elevation, county and quad, distance and elevation gain, route and aspects, trailhead and elevation at the trailhead, driving directions, hiking/climbing directions, and (if a peak) summit views north, northeast, east, southeast, etc. I carry a print-out and update all this information during the hike (which is why I carry a clipboard - yes, I know how stupid it looks).
I also carry a paper map with the route marked, which I make with a Topo program. I create waypoints for the trailhead, summit or other destination, creek crossings, trail junctions, etc., number them and load them into my GPS. I also carry a compass because sometimes a GPS will get out of whack and give you a weird reading. If something doesn't seem right I check my compass and recalibrate the compass on the GPS.
To get the cleanest track possible with my GPS (I have to submit corresponding tracks and waypoints to my publisher for every hike or climb I include in a book) I try to keep my wandering to a minimum. If I have to wander off-route, I leave my GPS clipped to my pack on the trail or route while I'm away, or I manually clean up the track in notepad later on, at home. If my track gets totally screwed up on the way up/out, I get a clean one on the way down/out and then just reverse and save it.
I often carry two cameras (cheap one for beta and better one for photos to use in books, but mostly for backup as I have had cameras die on me) and two headlamps so if the batteries in the first one die I don't have to fumble around in the dark trying to replace them, I just grab the second headlamp. I carry extra sets of batteries for the GPS and the headlamps, too.
This may seem like a lot of preparation, but it's the best way to ensure I don't get lost and hit all my deadlines, and makes the writing, map-making, final track and waypoint creation, etc. very quick and easy when I get home. It's tough to do with other people, though, because most people like to talk when they hike and then I can't think, and I forget to take notes, waypoints, or photos.
A few times in the past I did some non-work-related hikes/peaks and didn't have time to plan at all, but since I was going with other people, I didn't worry about it...big mistake! Don't assume other people know the route. They may be too busy to plan, too, and assume
you know the route
Haha still fun, but lesson learned!
-Susan