Thanks for all the good advice. You guys have really rejuvenated my spirits and cracked me up.

I should have originally posted that equipment-wise I am fine. Thanks to previous posts here I have a touring bike with toe clips that I modified with an even smaller chainring and skinnier tires. Before that I was doing the walk of shame before I even got halfway up the hill.

I have to agree with those of you that have said that it’s mostly a mental thing. I thought that by now the hill would be a piece of cake but since it hasn’t I thought something was wrong. I now realize that I’m not riding up the hill like I was at the beginning. I’m usually in a higher gear and don’t have to resort to the granny gear near as often.

So here’s my new game plan. On days when I feel full of energy: charge up it like a bat out of hell. On days where I don’t have as much gumption: take my time, rest before I head up, rest halfway up, drink lots of water…and oh, yeah do that think about perky breasts thing

After all it would be a real shame for me to bail out on this hill. How many other people get to ride through two golf courses, past two waterfalls, up to a canyon rim trail with spectacular views of a winding river 550 feet below you, and finally underneath a bridge where more-often-than-not I get to watch base jumpers fling themselves into the air?