Tip #28: Switch rings before climbing
2008
There’s nothing more frustrating than dropping your chain at a pivotal moment of a race. Being behind someone who’s dropped their chain at a pivotal moment is a close second, and I have experience with both.
Most chain drops are avoidable. They happen when you are climbing with full tension on the chain and attempt to switch to the small chainring. Your front derailleur will send your chain past the small ring, where it will come to rest on your bottom bracket, sad and useless.
Here’s the easy way to avoid this scenario: Shift to the small ring before you start climbing. The small-ring climbs around here shouldn’t catch us by surprise. Take the Baraboo climb, please: You’ll see it from a mile away. As you approach, go small ring, small cog while you’re still in the flat and there’s slack on the chain. Then as you start to climb, progress up your cogs as needed.
Just be on the lookout for the dude who didn’t read this tip. He’ll be the one dismounting his bike and swearing.

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May 1
2008
10:03 am
samoots
another tip would be to spend the $20 and install a “dog fang” type chain guide.
http://www.competitivecyclist.com/road-bikes/product-components/2008-deda-elementi-dog-fang-chain-guide-4180_23_TRUE.html
i haven’t dropped a chain since i installed it (knock on wood)