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My respect for JFK just went up a notch. He was saying that unless people take the risk of exceeding the bounds of everyday behaviour, they are imprisoning themselves by the expectations of the herd. Progress can only be made by people who do (worthwhile) things differently.
Being restrained by a stereotype can forbid you to do something that could possibly bring success and restrict you to learn something new.
Freedom implies individuality. People thinking for themselves and growing from their experiences. Conforming to the beliefs, values and behaviours of everyone else limits your experience. Therefore, it limits your freedom and your ability to grow. This applies to both the individual and society.
People who conform without question become slaves to the group that they are conforming to. They don't think or act for themselves. Therefore, they are imprisoned by their own mind set. Freedom includes having the chance/ability to have new and different thoughts and ideas.
When everyone adheres to established parameters known and accepted by their group, it puts limitations on their own freedom and effectively stops the growth that results from following a different path. Advancements come from the trail blazers among us, not the sheep.
It means that if everyone conforms to the same ideals then no one is truly free because with true freedom you have the right to think and believe whatever you want, no matter who agrees with you. And if you have no freedom in choice, beliefs, and thinking then there is no growth, personally or as a nation.
Basically, it means "think outside the box," and be critical of the notion of "well, that's what everyone thinks, and that's the way things have always been done".
For example, if Galileo Galilee had allowed himself to be "jailed by conformity" as Kennedy would put it, the Catholic Church would still be teaching that the earth is the center of the universe, and that the sun, moon and stars revolve around it.
Sometimes following rules or demands of others allows no room for you to grow as your own person. And to learn as well. Basically it's better to be a leader and not a follower.
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