The answer here lies in how we as readers define "hard work" in terms of the context of the story. Literally, readers might be inclined to define hard work as putting much time and effort into doing a job. In this literal sense, Jackson doesn't work hard for the money that he intends to use to buy back his grandmother's regalia. However, a figurative reading of "hard work" yields a better interpretation. Near the end of the story, Jackson says that there are too many good men in the world to count, and included in this count is Jackson himself. During his journey to earn the money, Jackson encounters situations in which he behaves in empathetic, kind, and humane ways towards other people. For example, he uses money to buy people food, he gives a gift to the lottery clerk, and he treats new friends to drinks. Jackson has his share of difficulties, namely those related to his drinking alcohol; however, despite the difficulties, Jackson does good for others. One could argue that as one whose family has been taken advantage of, Jackson would not be so invested in helping out other people. But he does, and it's "hard work" to show kindness to others when one is struggling.
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