If the clutch hub nut becomes loose, more times than not the o-ring between the clutch hub and transmission mainshaft bearing is damaged, along with the clutch hub shim if present. If the o-ring is damaged, the clutch hub nut will work itself loose again. This o-ring MUST be removed and discarded. Do not put another o-ring in, leave it out. Some of the early warning signs are difficulty shifting, excessive play in in the clutch hand lever that wasn't there after the last clutch adjustment, or the bike tries to pull at a stop when in gear. Adjusting the clutch only prolongs it, until that day you are miles from home and it leaves you stranded. Then you could be looking at the very least a new clutch assembly, and most likely transmission bearings and mainshaft. Not to freak everyone out, but this can become a serious issue and can be easily prevented. Follow the instructions posted earlier, and it will be fine. Another important note is that while you are in there, check the mainshaft bearing by moving the mainshaft up and down and side to side. If there is any movement at all, then the transmission bearings need replaced.