What are three challenges Ray faces on his journey in Shoeless Joe?

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Two of Ray's challenges are closely related: becoming a more responsible, practical person and creating financial stability for his family. A different type of challenge is also related to the first: to heal and ease the way of other people. He surmounts these challenges by staying true to his nature through some fantastic means as well as more conventional ones. Ray has to follow his dreams to find his path on solid ground, literally and metaphorically, through building the baseball field.

Ray is a devoted husband and father who is involved in pursuing one big dream: owning and operating a farm. Unfortunately, from combined factors including his lack of skill, the farm is operating at a severe deficit. Ultimately, through the hard work of building the field, he learns how to follow through on a project and matures considerably so that the dreamer and doer sides of his personality are more balanced.

The field also becomes the vehicle to help solve Ray's financial problems. Again a combination of dreaming—that he needs to ease J. D. Salinger's pain—and following through, when Salinger goes to the game and then comes home with him, lead to overcoming this challenge. Charging admission to the field will generate regular income and reduce his debt.

When Ray hears the message "ease his pain," he believes it refers to Salinger and decides that baseball will do that for him as it so often does for Ray. Along the way he learns that the pain is felt by his father, who is deceased, and his brother, who is very much alive. In the end, he does help Salinger, and by doing so, sets in motion the reconciliations among his father, his brother, and himself. Through becoming a more practical provider, he also helps his beloved wife and daughter, greatly easing their way in life. His short-term dream of helping the author and long-term dream of unifying his family are achieved.

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