Every day for about 6 years I would take a hill on my "going home" route that is 500 feet up in 1.2 miles. My cycle friends call it "The Speed Bump."
I started with an avg of about 10mph (at 255 lbs). After six years I could do about 16mph (195 lbs). Still, it never seemed easier.
After 10 years of avoiding hills I now have bike that is way comfortable so I just started pounding big hills again. Now I'm doing about 700 feet in 1.2 miles. Dang it's hard. I know I'll get faster but It will always seem hard.