That is a good question you are asking coberst. I like how you weave the work into the sequence of gradually increasing cages.
Your story could be continued, you know. The worker can become a foreman, then a manager, then start his own business. This is a dead end. This is a story of a financial freedom. It can be achieved. I did it in my early twenties. But it leads you nowhere. There are other kinds of freedoms out there as well. Spiritual, freedom of self-expression and so on. They also can be achieved to an extent.
But the greatest freedom of all is not there. Self-actualization is only a step on a ladder. It leads to purpose, to the life mission. Once upon a time you reach that point. It is not that difficult. You are standing there, one with the universe, shrouded in eternal warmth and light and kindness. At this moment it is possible to die with no regrets. You don't need anything anymore. Pure ecstasy. Pure happiness. Pure delight. Pure freedom. The only question that is left and hangs on the periphery of your mind is "Why come back?"
And the answer is surprising. Once you are completely free, the greatest freedom left is the choice to surrender this freedom and begin living co-dependently with the world. Co-dependently with other people, with work that has to be done for money or not. Co-dependently with you family - your parents, your spouse, your children. Freedom is worthless, it is the way you spend this freedom that matters.
Once you are free, you find out that it's better be needed than free.
Which, in my opinion is the telos of the quest for freedom.
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