A Comparison of Structure and Freedom in This Boy’s Life and The Glass Castle

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The paradox of freedom and structure is an idea that discusses how freedom is most likely to be achieved with specific guidelines, even restrictions. A study found that kids on a playground used the most of their play space when there were fences around them — without the fences, they essentially huddled in the center, afraid to go out too far. Is a certain amount of structure necessary in order for freedom to truly arise? Both Tobias Wolff and Jeannette Walls write on this topic in their memoirs, This Boy’s Life and The Glass Castle (respectively).

Jack’s mother (from This Boy’s Life) suffered from a traumatic childhood with an abusive father. As a result, she’s a ‘freeform parent’ to Jack, meaning “she didn’t have faith in discipline” (Wolff 59). She wants him to be free from limits imposed by many parents, and she “had faith in [him]” (59). She couldn’t even spank Jack if he misbehaved, she “didn’t think [he] needed it anyway” (60).

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Jack becomes a criminal. He “broke windows…[and] streetlights” (61), and he “was a thief (62). The lack of order placed upon him spirals out of control, turning him into a hoodlum. He acts out because he doesn’t know any better. When he gets in trouble with the principal and Rosemary finds out about his escapades from Miriam, she “said nothing” (83), gave him no discipline for his actions. She asks him if he is ok with staying with Dwight, a man he doesn’t like, and he tells her yes, because he “thought [he] had no choice” (84).

Jack’s inability to say no comes from a compulsion to search for structure, seen in his love for boarding school, a “place that [he] secretly and deeply loved” (286). This quality is heavily contrasted by his compulsion to break rules, and the two together show that Jack’s search was one for a structure that he couldn’t break. The final step towards organization was his decision to join the army, which brought him “a sense of relief and homecoming” (286). The army was the perfect home for Wolff: a place he couldn’t get away with bad behavior.

In The Glass Castle, Jeanette’s parents live a very unstructured life. The first taste of structure that she gets is when she’s three and is sent to the hospital for her burns. She says “I wasn’t used to the quiet and order, and I liked it” (Walls 11). She even goes as far as to say she “would have been happy staying in that hospital forever” (12). Life at the hospital was scheduled, and structured, something she doesn’t find at home. It brought a consistency to her life the likes of which she had never experienced before. She loved that she “never had to worry about running out of stuff like food” (12). It’s more than just structure that she likes, it’s stability.

Later in life, she moves to New York City, a giant, ordered grid of buildings, a place Jeanette dreams of for years before finally moving there. She expects to find beauty there, but finds out “about how rude New Yorkers [are]” (246), and that “in New York, you could never see the stars” (247). Life just isn’t as great as Jeanette expected it to be, she even “got jumped a number of times” (248) in her own neighborhood.

The structured life that Jeanette finds is somewhat unpleasant. She went from one extreme to another, unstructured to structured, with no transition, and it was jarring. Jack, on the other hand, slowly brought himself towards structure, and found much more relief in his end result.

Obviously, structure is necessary, as is made clear by the restlessness of both protagonists in their unstructured lives, but as Walls’s memoir suggests, too much structure limits the beauty and freedom of life as well. Both stories show that a lack of order and organization in early childhood leads to compulsion towards heavy structure later in life, in which they may not be entirely free. Much like how Rosemary’s strict upbringing caused her to raise Jack with few rules, the lack of structure in the lives of Jack and Jeanette cause the two to be more inclined towards order later in life, proving the negativity of contrarianism, specifically in parenting. Sure, one may not have worked, but that doesn’t mean that the opposite is guaranteed to as well.

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A Comparison of Structure and Freedom in This Boy’s Life and The Glass Castle. (2022, Dec 24). Retrieved from

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