Originally Posted by BackInDaSaddle
I live in a hilly section of Los Angeles. Frequently, these are short up and down dips. I try to shift down (front chain ring big, back little) to get momentum, but may need to do a drastic shift (little ring front, big back) to finish making it up the hill. The gears can really jam around and crunch in the process. I feel like I am doing something wrong. Is riding frequent up/down hills just that way? Or should I not try to gain momentum down and keep the bike in the gearing that will reflect what will get me up and over the hill?
First get the terms right. Otherwise you will confuse yourself and others. Big in front/small in back is a high gear. Shifting into a higher gear is upshifting, not downshifting.
Just to add to the plan ahead and shift front and back seperately. By planning ahead you can shift one or two gears at a time. Shifting more than 2 at a time increases the chances of trouble. Shifting under load increases the chances of trouble. Shifting front and back at the same time increases the chances of trouble. So waiting until you are strugling and then shifting front and back several gears is just asking for trouble.
Also when you shift I would suggest shifting at least a couple of gears in the back first and then shift the front. Ideally be in the middle of the back when you shift the front chainring. You want to avoid being in large/large or small/small. Shifting into either under load can create the problems you describe.