Just don't assume that what you would find encouraging is the right thing for someone else.
I think that there are two issues,
1) Newbie's and Old Timers
2) Personally dealing with losing something that you love
The first one's easier. Invariably it's been a newbie who comes out with this kind of thing. They're trying to be nice but really, once you've been up that hill a few thousand times you sort of know where the top is. It's kind of like you go to your favorite restaurant and you spill some water out of your water glass. So you mop up the water, you pick up your glass, move it towards your mouth and some newbie at the next table looks at you and says, good job, you're almost there.
No **** Sherlock.
And maybe I would just have felt like laughing about it, if it wasn't for thing #2.
Maybe my friend isn't going to make it back. Maybe my friend has lost one of the things that she dearly loves.
It's not a matter of lack of training. She's been a athlete her whole life.
It's not a matter of lack of will. Stanford has a great Sports Medicine program and they've got great Neurologists. And those nice people say there is no cure. They say take drugs that twist your neural transmitters into knots and stop riding. Maybe the pain will be manageable. But she says, I want to ride.
And then there are the injuries that Sports Med folks say aren't repairable.
And then there's tomorrow's MRI. Maybe the thing that knocked the legs out from under her mother, and that's doing the same to some of her sisters, is about to do it to her.
Maybe it's not just riding that's not going to be an option.
Sometimes you just want to get on your bike and ride. You want to feel that freedom of motion. You want to feel alive and well. And you don't want someone who doesn't know a damned thing about you telling you "you're going to make it". Because the truth is, maybe you're not.
Don't assume that when you see someone struggling on a climb that they need your encouragement. That climb may be a act of courage that a relatively healthy person can barely imagine.
Sure, be friendly, smile, say hello. But I can tell you, as someone who's been in a similar postion. As someone who was damned sure that he was going to make it that day but didn't know if he'd be around a few months later; I can tell you, that the last thing I wanted to hear was "you're going to make it".
Sometimes you need the option to enjoy what you can of what life you have left; and to detach from what you're losing. And you don't want to be pulled back into the reality. You just want to finish your ride on your own terms.
When you get to the top, maybe you'll want to talk about the weather, or the view, or maybe you'll just want to say, yeah, I'm not feeling my best today.
Just don't assume that what you would find encouraging is the right thing for someone else.