Quote Originally Posted by Allie1DukeFn

He also has me confused about shifting on the hills. He originally told me that I should start shifting down when it started getting hard to pedal because you shouldn't shift on the hill because you can damage your bike. After this ride he told me that I'm killing myself because I slow down to shift and I lose my momentum going up the hill - and I can shift going up the hill I just have to back off the pressure when I pedal.

I wish I could get a trainer! Taking direction from your DH isn't the easiest thing in the world!
Downshift when you can no longer maintain your desired cadence, but not so early that you lose momentum before you need to. You can shift on a hill, but you can't shift with lots of pressure on the pedals. So, keep up your momentum but soft pedal (back off the pressure) for a revolution as you shift. Sometimes you need a couple extra-hard pedal strokes just before the shift to maintain momentum. It might take some practice. The slower your pedal speed before the shift, the trickier it becomes. So try not to let your cadence fall below about 70-80.