The initial interpretation that I came up with, is the idea of "Dreams." All individuals have different dreams and desires, the gateway signifies the pathway of the man's personal dream. While the gatekeepers symbolize the challenges and obstacles that the man has to face to reach his goal. The first gatekeeper says to the Man in the end "since this gate was made only for you, I am now going to shut it." This is because different people have different dreams and this gateway act for the Man's dream. Since he never got past the first step, nor moved away from his challenge, he never achieved his dream. The obstacles created by the gatekeepers can be presented from the people around the Man (society) who are doubting his abilities and telling him that he can't do it. On the other hand, they can represent inner demons related to mental issues such as depression and anxiety. The moral of the interpretation above is that; we all have one life to live and each person must follow their dreams and aspirations. Life is about taking risks and getting out of your comfort zone. Diving into the unknown even if failure is a possibility. As it is better to take the risk of challenging the gatekeepers than to die before the door is sealed and regret it.
Secondly, from a political/social perspective, the parable can viewed as a way of fighting for human rights against an authority such as the government. People should be willing to fight or stand up for their civil rights to achieve justice. It is also similar to the notion of enlightenment as described by Kant. The gatekeepers represent the "guardians", as they aim to control the citizens by imposing their laws and beliefs on them. The man has to the option of disobeying the gatekeeper and moving forward. However, by choosing not to, Kant many argue that the Man is a coward and is lazy as he have remained "minor" all his life. Men like him are incapable of challenging the system. They just wait for change to happen or ask for permission to seek it, instead of standing up and freeing themselves. Even though Laws are made to product people -- if they fail to do so, they should be changed. Sometimes breaking laws is necessary for human civilization to progress.
This parable is a great piece of writing, the interpretations above are just some of my attempts to understand the meaning behind its mystery, people can come up with many different ideas and make sense of them.
I agree with your interpretation that this might be about failing to achieve dreams. It definitely seems like the man doesn't try hard enough to reach his dream and instead waits for the gatekeeper to let him. He expects others to help him with his dream and lets the fear of the next gatekeepers prevent him from taking a step. Then at the end of his life, the gatekeeper tells him that the gate was always there for him but he failed to seize the opportunity.
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