Earlier in the essay, Thoreau says that he can support himself by working six weeks out of the year. Thoreau believed that by living simply, he could have much time to give to things he felt were important--mainly reading, writing, and enjoying nature. In modern terms, he was extremely low maintenance. He made just enough money to support his few needs so that he could spend the bulk of his time doing things he valued.
If Thoreau had worked a regular job all year long, he would have felt imprisoned. That's what he means in this quotation. Making his living by working on a farm every day would feel like a prison to him. He pitied people who worked all the time in order to buy trendy and fashionable things or buy houses too big for their needs because their greed and shallow beliefs caused them to miss out on the richness of friendship and self-improvement.
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