Sometimes, getting into a break is an art. Sometimes a voice deep in my head screams at me to go. After 21 years of racing that voice has gotten pretty smart, and when I listen to it, I usually do well. For me, the best time to get into a break is when the race is really hard and you are hurting. If you're hurting, so is everybody else.
After a series of attacks there is sometimes a lull. That lull happens because everybody is hurting and they don't want to go hard anymore. That is exactly why you should pick that time to go. Many times they will all be looking for somebody else to close the gap or chase you down, but nobody will do it themselves.
When I get into a break, I watch everything going on around me. If you get stuck behind somebody who is taking their pulls too hard, skip a pull and get behind somebody who is steadier. Its okay to skip a pull every once in a while if you need to eat or drink.
Think about where the wind is coming from. The person behind is the one who can tell which direction to pull off on. If you think the rotation needs to change, tell the leader to pull off the opposite direction.
In general you probably don't want to work substantially harder than the others in your break. Why make yourself weaker for the finish? But, if you do need to work harder, take longer pulls, not harder pulls. Harder pulls will just break everybody's legs and you'll end up going slower.
In a small group (four or less), don't do a rotating pace line. Use a single file line. Pull until you are done and go to the back. You won't get any rest in a small rotating pace line.
As you get towards the end, you need to know whether you can win this race in a sprint or not. If not, look to see who else is strong. You might want to attack just as the strongest guy finishes his pull. Or if the break is big enough maybe you'll do it when he is near the back and kind of boxed in so that he can't get right on your wheel.
Know Your Competition
Dan: The more you race with the same competition, the better chance you have of identifying the combinations of riders that may work. Sometimes I think it is easier to not go with the moves if the race is really aggressive. Let things play out and conserve energy.
When a move starts looking like it is sticking, then get attentive. Look around and see who missed the move and will be trying to get a rider up there or bring it back. At this point you want to piggy-back on the strategies of the other teams. Now is the time to get in the bridge attempt and use the power you were conserving.
As well as having the power to make or go with a move, you always have to be thinking about what are the motives of the pack. There is no way you can hold off a group of riders if they have reason to bring you back.