Do you have a cadence sensor? An ideal cadence is somewhere in the ballpark of 90rpm, and in an ideal hill situation you'd be able to spin up it without dropping down to a low (<70) rpm. Sounds like a cadence sensor might help you figure out what gears you 'should' be in.
Keep in mind that 90rpm is just and ideal, and a good starting point for figuring out what cadences work for you in what situations. Once you get used to things, you'll be able to go on feel and won't really need the cadence sensor anymore.
For example, When I'm doing a short hill that I'm attempting to power up, I'll use my cadence sensor to tell me when to shift. I tend to like to spin a bit high, so I try to hit the bottom of the hill at about 100-105rpm, then shift down a gear when I hit about 95rpm and keep doing that until I run out of gears. I actually don't have a cadence sensor on my bike now, although I do kind of miss it (but don't miss the ugly hardware on my bike).
You don't want to immediately shift to an easy gear at the bottom of a hill because you'll end up needing to do a really high cadence, potentially causing you to bounce up and down if you don't control your body movement.
And stop going to your brother for advice if he's just going to be a big meany. Bicycling ain't rocket science and tips and tricks are meant to be shared.



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