It's hard. I have, at one time or another, had every class except monk 70 or above, but I've never had any one particularly well-geared. Except DK, but the feel of that class was always a gigantic buzzkill for me, so I never passed outland with one. Leveling is getting tiresome though.
Get going. Get tough. Get angry! Stay hungry! Get mean! Stay lean! Say what you mean and say it mean.