This Boy's Life by Tobias Wolff is a painful examination of what happens to a young man who is left to navigate life by himself. The adults in Toby's life are too preoccupied with their own lives to pay attention to him. His mother is self-centered and childish and never really indicates that she wants Toby around. His wealthy father lives with his other son on the east coast and doesn't pursue any relationship with Toby.

Toby is left to fend for himself, which has a negative impact on his personal development. His mother moves from city to city, whenever the wind isn't blowing her way, which is often. Since Toby has no role model and frequently doesn't stay in one place long enough to form lasting relationships, he clings to anyone who will pay attention to him. As a result, he ends up befriending troublemakers.

Toby's mother sends Toby to live with Dwight, a man who she is considering marrying. Toby doesn't necessarily like the man, but the prospect of a normal family life is attractive to him. Dwight is cruel and immediately lets it be known that he has no intention of treating Toby like a family member. In fact, he treats Toby like a slave until Toby's mother finally decides to move in with them.

Dwight is abusive toward Toby, but Toby doesn't do anything about it for years. He understands that Dwight and his family are the closest thing to a family he will probably ever have. He also holds on to some hope that Dwight will come around.

Toby is constantly seeking acceptance. He doesn't get it at home, so he looks for it at school. Toby wants to be a good kid, but he has no one to show him how to act so he is awkward around other children. He makes a reputation for himself as a tough guy, using physical violence to deal with his emotional pain.

When Toby's in high school, he cuts off a part of his finger in shop class. After this incident, Toby starts complaining about everything. All of the pent up anger and frustration of being a second-class citizen finally boils up inside of him. Once this happens, the course of Toby's life changes. He separates himself from Dwight and gets into serious trouble. It's at this point that Toby starts to lose his humanity.

Luckily, two positive male role models enter Toby's life at this critical time. They give him a hand up by offering him guidance. His older brother gives him companionship, and Mr. Hill gives him the opportunity to get a good education. Though these two influences don't entirely save Toby from himself, they offer enough hope that Toby decides not to throw his life away. They show Toby enough that he makes a critical decision that gets his life back on track.