The Master Plan Major and Minor Quotes

“I wanted a different life, but I didn’t want to do the work.” (Part 1: The Cave – The House Becomes the Cave)

—Chris Wilson

Analysis: When Chris Wilson’s son Darico is born, Wilson’s life is changed. He suddenly wants to be a better person—to be a real father to his son. His own father had failed to be present in his life. Wilson gets off drugs and takes custody of his son, gets a job, and thinks about getting his GED. But this brief span of time proves to be a false start. Looking back as he’s writing about it, Wilson says that the desire was there but not the willingness to put in the amount of work it really takes to turn one’s life around. By the time he wrote this book, of course, Wilson had learned the importance of doing the work and had also learned how to do the work.

Wilson learns how necessary hard work is for success in prison. His Master Plan isn’t only about setting goals or dreaming about the future. It is about the daily actions and attitudes needed to achieve goals and dreams. Wilson imposes on himself a strict schedule and rules for behavior, right down to keeping himself neatly dressed and not making crude jokes. And in the end, his intense self-discipline pays off. It’s this perspective that allows him to see that his 16-year-old self didn’t yet have what it took to change his life.

“[T]hey called me by my number, 265–975. But I was Chris Wilson.” (Part 2: The Middle Passage – Decisions)

—Chris Wilson

Analysis: In The Master Plan, Chris Wilson describes the dehumanizing conditions in prison, including humiliation by the guards, being referred to as “property” of the state, and being called “inmate” or by an ID number. In this quote, he acknowledges this harsh reality but also resists the loss of identity it would imply. By naming himself, he holds fast to the idea of selfhood and asserts his worth as a human person. He also links his name to his sense of purpose; he wants his name to mean something, and this provides motivation for self-improvement.

For a Black man in the United States, naming has even deeper resonance, which Wilson evokes by naming this section “The Middle Passage.” During the transatlantic trade in enslaved humans, the Middle Passage was the journey from Africa to the Americas. Captured Africans were stripped of their names and considered property, not people. By alluding to the Middle Passage, Wilson draws a parallel between enslavement and imprisonment. In this context, retaining one’s name is symbolic of retaining a measure of freedom and personhood.

“Every path starts with a step.” (Part 3: The Master Plan – Giving Water)

—Chris Wilson

Analysis: This metaphor compares a person’s quest for self-improvement and purpose to a path, emphasizing its linear nature: each action or change leads to the next, which leads to the next, and each step takes you closer to the goal. Chris Wilson’s path toward a meaningful life is long and difficult because he is starting from a life sentence in prison. But his advice holds true for anyone who has a goal for the future. This advice is to take one step—the easiest one, the one right in front of you. You can take another step after that and then another. In his own Master Plan, getting his GED is the first step.

The use of a path or road to symbolize life’s journey is a common one; it is appealing because it balances the importance of the goal with the importance of the process for achieving it. If your goal is to live a life of purpose, as Wilson’s is, each step makes your life that much more purposeful. In addition, the path metaphor suggests the possibility of straying from the path, and it is clear that this is where having a Master Plan comes in. The Master Plan keeps Wilson on his path; it clearly identifies each step so that he remains focused on steps that will move him forward, not backward or off the path entirely. 

“I had taken charge of my life. And I had a plan.” (Part 3: The Master Plan – Giving Water)

—Chris Wilson

Analysis: Throughout The Master Plan, there is a tension between what happens to Chris Wilson and what he causes to happen. His childhood is traumatic, through no fault of his own. Systemic racism exists and has a detrimental effect on his life, and this, too, is not something he caused or can change. In many ways, even his crime seems to have been caused by traumas he endured. The beginning of his transformation into a person of purpose and worth is the moment he takes charge of his life by setting goals and making a plan.

This assertion of agency in his own life, while in prison facing a life sentence, is a dramatic moment in the narrative. It is a turning point, and it is empowering. Empowerment and agency are hard to come by in prison since the system is designed to take away a person’s power over their own life. But Wilson’s life shows that even in such circumstances, a person still has some power, and he sets an example of leveraging a minimal amount of agency into a small change and then building on that change incrementally over time. Taking control over your own life can be a grind, as he points out often, but each successful step in the plan builds momentum for the next. 

“It’s being the artist, not just admiring the view.” (Part 3: The Master Plan – Positive Delusions)

—Chris Wilson  

Analysis: For motivation to stay on track with his Master Plan, Chris Wilson creates a collage of “Positive Delusions.” These Positive Delusions are the rewards he envisions he will be able to obtain by following his Master Plan—a nice car, vacations at the beach, and other things any young man might want. At first, he just cut out pictures of the Positive Delusions, but then he began pasting them into collages that became works of abstract art. He eventually comes to realize he loves creating artwork, not just looking at the pictures.

There are a few things going on here. One is that the creation of art becomes another metaphor for what he’s trying to achieve in his life. He’s pulling all the items in his Master Plan together to fashion a whole and beautiful life, but as he goes along he realizes that the process of creating this life is itself purposeful. “Yes, the picture was the dream,” he says, “but making the picture was the dream, too.” The second thing that happens to Wilson is that, as he finds joy in creating art, he’s able to tap into an aspect of childhood that had become overshadowed by trauma. He recalls loving to draw when he was a kid, and he’s able to recapture some of that childhood joy again through art. There is healing in art, as well as a lesson about life.

“But society created the cave.” (Part 3: The Master Plan – Ethics)

—Chris Wilson

Analysis: One of the main allusions in Chris Wilson’s memoir is to Plato’s “The Allegory of the Cave.” In this story, Plato describes a cave in which people see only the shadows of reality. They believe the shadows are reality. But then a man goes outside, and he sees “real” reality. Throughout the memoir, Wilson refers back to this story, identifying sometimes as the man who goes outside and other times describing the different caves people get trapped in.

In this section of the book, Wilson describes how he learned about the systemic racism that created the “cave” of Black poverty. Enslavement, lynchings, segregation, voter suppression, and discrimination are aspects of society that trapped Black people in a cave of poverty and violence so that these became the only reality people living in impoverished, violent Black neighborhoods believed in. For Wilson, having this knowledge is both terrible and motivating—terrible because of its nature and motivating because it helps him understand the real problem and potential solutions.

“You were a number now, and the only important rule was this: numbers stay inside.” (Part 4: The Middle Passage, Part 2 – The System)

—Chris Wilson

Analysis: In describing how difficult it was to get out of the prison system, Chris Wilson points to an attitude among prison administrators that, once inside, the inmates—often just called by their ID numbers—should stay there. Not only is being identified as a number rather than a name dehumanizing, but the sense that a kind of transformation—from human to number—takes place when a person enters the prison system does great harm. It makes prison administrators more interested in keeping people inside than in helping them make changes to better themselves. It suggests that people who do bad things are simply bad people and that nothing can change them. It takes away the incentive for prisons to have educational programs like the ones Wilson uses to improve himself. And it also removes the motivation for prisoners to improve themselves because there’s nothing tangible to be gained from trying to be a better person.

Wilson doesn’t spend a lot of time calling for structural change in his memoir—focusing instead on what individuals can do to create a beautiful life no matter what cards life may have dealt them. But he laments the lack of support for incarcerated people who genuinely want to change and become a constructive presence in the world.

“We don’t believe in redemption.” (Part 5: From Plan to Action – Get Out of Prison)

—Chris Wilson

Analysis: One of Chris Wilson’s main criticisms of the criminal justice system—and of US society in general—is that it is focused almost exclusively on punishment, with little effort to rehabilitate offenders. This is because even though people may be allowed the chance at freedom once they’ve served time—and there are programs for releasing prisoners who seem to have changed—the system also seriously undermines the lives of “returning citizens,” as he calls those released from prison. They leave prison with almost no money and few possessions. They don’t have jobs or homes and can’t easily get these things due to their criminal record. They must pay fees to be on parole. As a result, many quickly get into trouble and end up back behind bars.

Yet he sees himself as an example of what can happen when there’s an effort to help inmates become better people, but he notes that his experience is very rare. The youth program he’s in, which allows him to gain the education needed for self-improvement and success, is the only one in the state at the time. And even as he goes through the system, he can see that most people think it isn’t worthwhile because they believe incarcerated people are never going to change.

“[T]he world is complicated, and knowledge opens doors.” (Part 5: From Plan to Action – Become Financially Independent)

—Chris Wilson  

Analysis: Chris Wilson’s attitude toward education is that it is worthwhile and will help you reach your goals in ways you can’t imagine. Not only is the world complicated, but it also presents surprising opportunities, and having knowledge of nearly any type will help you take advantage of those opportunities. His memoir is full of examples. The most obvious is that he learns Italian in prison because he has the chance, even though it doesn’t have a huge practical effect on his life at the time. But once he gets out of prison, he ends up having a job interview, and the interviewer is Italian. Because he knows the language, they are able to make small talk in Italian—which of course presents him in a positive light and helps secure him the job.

But there are other examples. He learns woodworking and later takes joy in restoring old furniture and gets involved in a furniture business. He learns about business and entrepreneurship and uses this knowledge to run successful businesses. Because of the ways the knowledge he gains opens up opportunities, he is able to navigate the complicated world effectively and gracefully. And he advises others—both in his daily life and in the pages of The Master Plan—not to pass up any chance to learn.

“What’s your endgame?” (Part 5: From Plan to Action – Start a Business)

—Chris Wilson

Analysis: The first question a person has to answer when considering their future, according to Chris Wilson, is “What’s your endgame?” That is, what is your ultimate goal in life? What do you want people to remember about you after you’re gone? Wilson asks himself this question as he begins to have dreams and hopes for the future. Once he identifies his “endgame,” he’s able to create his Master Plan, which is a list of goals he needs to achieve along the way to his ultimate goal: to matter.

Furthermore, Wilson says people need to ask this question continually throughout their lives. This is partly a way to remind yourself of your path so you stay committed to it. But it’s also an acknowledgment that your endgame can take on new dimensions and layers as you go. While the general sense of purpose Wilson has as a teenager in prison remains with him, he also learns more about what it means to matter, to leave a legacy, and to have a purpose. As the epilogue concludes, he says his endgame is to help others make something beautiful of their lives. Then he invites readers to take the first step to a life of purpose by asking themselves, “What’s my endgame?”