You don't have to go through any of this to put a dropped chain back on! You have to think quickly to do this, but it's second nature to me now. As soon as you feel the chain slip, you put your bike in the big ring and keep pedaling. The chain goes back on by itself. Really.
If you are on a steep hill, this might be hard, but you can carefully shift the chain down to the next lower ring as you keep pedaling once it's back on, but you have to soft pedal. The trick to steep grades is to put your bike in the granny gear (or small ring if you have a double) before you start the climb and put the cogs in a higher gear, so you can shift down as you need to.
You can put a dropped chain back on if you are off of the bike the same way. Put the bike in the big gear, pick it up and rotate the pedals by hand until the chain pops back on.
I do not like those steep climbs with a stop sign at the top, either.
Clipless pedals are not that scary. Make sure you have the tension set at the easiest setting, if you have spd pedals. All this talk of 11 falls is crazy. I never fell and as I said earlier, I am not that coordinated.



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Just as you need to shift before you run out of power, and lighten up on your pedal stroke so you're not putting a lot of torque on the chain when you shift, it's the same with clipping out. Know when you're starting to run out of steam, know the minimum cadence and maximum power where you're no longer able to keep the bike upright (by feel, not necessarily by gadgetry, although those are nice if you have them), and don't be so hung up on getting up the hill without walking that you don't clip out until it's too late.
So I told him - I will ride 4 or 5 times on the pedals - as I mentioned good routes I know and know what to expect. Then I will reassess. If I still can't relax enough and am not enjoying the rides because I'm constantly clipping in and out and scared - then I'll go back to toe cages!
