Summary: Part 5: From Plan to Action

In “Get Out of Prison,” Chris Wilson describes what happened after his release. Released prisoners have a criminal record, a parole officer, and sometimes monthly fees that must be paid, he says. But they have no job and no place to live and are not allowed to contact anyone still in prison—which cuts them off from their friends and mentors. It’s nearly impossible for them to get an apartment with a criminal record, and sometimes they can’t move in with family because public assistance housing doesn’t permit felons. He points out that this situation sets people up to fail. How did he manage to make it? First, he moved in with Erick Wright. He avoided people and places that got him into trouble before. He started mowing lawns for people to make money. He used the internet to find out how to get food stamps and made a little cash helping people make resumes. He was allowed to have contact with Steve, who was still inside, and Steve’s parents helped him, too.

“Remain Out in Society” describes the next steps Wilson took to put his Master Plan into action. He applied for financial aid for college. He went to interviews. He kept up the calls with Steve. His son Darico had been sent to prison for five years, and he wanted to be able to be there for him when he got out.

In “Become Financially Independent,” Wilson explains how he got a job. One of his professors put him in touch with a nonprofit that had a job opening. They did work in impoverished neighborhoods to raise the quality of life there. The interviewer had grown up in Italy, and they made small talk before the formal interview—in Italian. He got the job as a workforce outreach coordinator in a poor Baltimore neighborhood called Barclay. He began going out into the community, meeting the people. He visited homes, shops, and churches. He talked to the drug dealers, the homeless, and the unemployed. He created a new program to help people find jobs and got a promotion and a raise. He found an apartment.

In “Start a Business,” Wilson’s job was going well, and he was able to help people find jobs often by providing practical support like appropriate clothing and childcare during interviews. He contacted people’s grandmothers to get their help making sure their grandchildren showed up to job interviews. He found that many people didn’t understand basic things about getting a job, such as the fact that an interview is a one-time event and that if you miss it you don’t get the job. Then he started a weekly program to help entrepreneurs in the neighborhood. He was able to start an upholstery business with Warren Savage, another former inmate who had gained upholstery skills in prison. He also leased his first car.

In “Remain a Lifelong Learner,” Wilson switched to business school at college. He won business competitions. After a reception for one of the competitions, though, he and a friend were out driving, enjoying the evening, when they were pulled over. They were in a white neighborhood. The cops took their licenses, saying they were fake and demanded that the trunk be opened. Wilson called a friend of his who was a cop, who arrived to help out. After searching the trunk, the cops said they were impounding the car because the two were driving without licenses (which they had taken but refused to admit). Wilson’s cop friend drove them home. But the incident reminded him that being Black in Baltimore was risky.

In “Figure Out How to Afford to Be a Lifelong Learner,” Wilson found more ways to fund his education. He reached out to nonprofits and had the opportunity to meet a woman named Jane Brown, who gave him some funding. He also talked the dean of the business school into giving him a full scholarship. The university also had him talk to incoming students, alumni, and potential donors. One donor gave the university a seven-figure donation after hearing his story.

“Focus on Continual Self-Improvement” describes the effect on Wilson after a man was shot to death near his apartment and Wilson watched him die. At the time, gang violence was ramping up in the neighborhood. Wilson decided to be part of the solution and keep trying to help the neighborhood, but he also decided to move out of the neighborhood. He targeted Bolton Hill, a neighborhood that had been wealthy in the 1800s but then had declined due to redlining before it began to recover in the late 1900s. After some difficulty due to his past, he rents an apartment owned by a young white couple with a couple of kids.

In the chapter “Start My Own Business That Makes a Difference in People’s Lives,” Wilson took his entrepreneurship to the next level. He was admitted to the University of Baltimore’s Entrepreneurship Fellows Program, and he also bought into a business that hired a lot of recently released people for construction and cleaning jobs. While he liked the idea of the company, he didn’t agree with how they managed their money, so he left to start his own, similar company, which would hire workers from Barclay—especially those recently released from prison. With help from Jane Brown, he started the Barclay Investment Corporation (BIC). By the third month, he had two crews of workers employed full-time and was making a profit.

In “A Stoop Story,” Wilson continues to describe his outreach to and for the Barclay neighborhood. He saw each speaking engagement as a chance to tell a story tailored to the audience. He used humor, sometimes, to get across hard truths, such as the fact that in Baltimore in 2015, 52% of Black men in their 20s were either locked up or on parole or probation. But he didn’t always bring up his crime or his prison time for fear of people’s reactions. Then someone at work suggested he try out for “Stoop Stories,” an NPR show where people tell real stories about their lives. He debated with himself and talked to Steve about it and then decided to go for it. He told his story honestly, and he got a standing ovation. Furthermore, it got a positive reaction from the community.

“Positive Delusion” describes Wilson’s experience of fulfilling one lifelong dream: getting a black Corvette. It felt very, very good.

In “A Blessing,” Wilson was asked to give a talk at the University of Baltimore. He told a story about how once Mr. Edwards told him and Steve he’d had a vision from God, who had promised both young men would get out of prison one day. He’d believed it. But Steve wasn’t out of prison yet. The state was still fighting to keep him behind bars, even though many of the others Wilson had been in prison with were out. He’d even given some of them jobs. Eventually, Steve got a sentence reduction hearing and was given his freedom. Wilson picked him up from prison in the Corvette.

“Be an Active Member of My Community” continues to describe what happened after Steve got out of prison. Wilson was busy with school and his businesses. Steve was working on building a career in computer programming. The two had dinners together and talked as before, but they had different dreams and goals. Wilson also saw an increase in crime, and in over-policing Black people, due to the beginning of the opioid crisis. But he kept working hard to make a difference for his employees and for Baltimore. One day he ran into his old caseworker and remembered that he’d said his revenge would be his success.

In “Make (Another) Difference in People’s Lives,” crime and overdose deaths were spiking in Baltimore. Steve decided to move to Washington, D.C., and Wilson was disappointed, but he recognized that the two friends had different paths to follow. Wilson also found some family relationships difficult. His brother resented him for his success. His grandmother didn’t recognize how he’d changed. He did go back to visit Patuxent, talk to some of the inmates, and encourage them to have a Master Plan and work hard.

“The Uprising” describes what happened when Freddie Gray died after being treated violently by police. People protested, fueled not only by Gray’s death but by the deaths of other Black people: Trayvon Martin, Michael Brown, Eric Gardner, and Tamir Rice. Tensions rose, and widespread chaos swept through the city for a number of weeks. Wilson says, even though it was a rough time, he’s proud of Baltimore for standing up for the lives of Black people. 

Wilson says in “Burning the Boats” that the uprising changed the atmosphere of the city. People in power began to listen to the voices of people who had been pleading for change for years without being heard. The mayor implemented some changes to try to fix the problems in the police force. Many city leaders asked for Wilson’s opinion on what was causing the problems, and he told them the truth: “guns, poverty, policing, racial stratification, over-incarceration, and lack of opportunity.” There’s no quick fix, he notes, because these issues were 200 years in the making. We need to ask ourselves, “What’s our endgame?” and then make a Master Plan to achieve it.

Despite all the energy about making real change in Baltimore, not a lot of real change actually happened. Wilson decided to make a few changes, though. He gave up his Corvette because he’d been pulled over 26 times in two years—cops thought he must be up to no good—and it just wasn’t worth living under that stress. He felt like giving up the car to stay in Baltimore safely was like conquistadores burning their own boats when they reached the Americas: no going back now.

In “Be a Father,” Darico got out of prison, and Wilson gave him a job and a home. As he got to know his son, Wilson learned what he’d been through and how he’d gotten mixed up with a gang. And Darico turned out to be a natural crew leader, which made Wilson proud and hopeful. But then, Darico punched his girlfriend, and she called the police. Darico ran away to hide from the law in D.C., and Wilson had to cut ties with him or endanger his own freedom since he was still on parole.

In “The White House,” Wilson was awarded the President’s Volunteer Service Award by President Obama and went to the White House to receive it. Even there, his record almost made it impossible for him to enter the premises—he had to wait hours to get cleared to go in. He also gave two talks while he was in D.C. and came away feeling down about the continued violence in his old neighborhood and about his own son’s worsening situation; he’d learned that there’d been a murder and retaliation among people his son was hanging out with.

In “Open Arms,” Wilson discusses his deepening depression after his son ran away to D.C. It became overwhelming to him how many people the Black community was losing each year to violence, drugs, and prison. He let his business slip. He was tired, physically and emotionally. He started hanging out with some new friends in New York and worked on refinishing furniture as a kind of therapy. Then an artist friend gave him painting lessons, and he started painting scenes from his life in prison. But his son kept having trouble—he spent more time in prison, then was badly injured from a gunshot, and had trouble making a break from his old life. Wilson gave him space, even though it hurt, and determined he would be there, with “open arms,” whenever his son needed him.

Analysis: Part 5: From Plan to Action

As he implements the parts of his Master Plan that guide his actions post-imprisonment, Chris Wilson shows that staying out of prison is nearly as difficult—and as much work—as getting out of prison. Wilson had to “grind” to better himself and get his sentence cut, and he still has to grind after he’s released. The aspects of his character that helped him inside also help him outside: he’s ambitious, intelligent, hardworking, and outgoing. Despite these huge advantages, the obstacles he has to overcome are daunting, and it is very clear that it takes Wilson’s almost superhuman self-discipline not to get caught by one of the many traps meant to put people straight back in prison. Even then, he has to rely on the help of others, like Erick Wright, to get on his feet.

While the main message of the book is the need for individuals to have an endgame, make a plan, and do the work, the need for reform in the system is another idea woven into the fabric of this memoir. It is especially reflected in Wilson’s account of the “uprising,” in which the people of Baltimore bubble over with anger in the wake of Freddie Gray’s death—and the deaths of Trayvon Martin, Michael Brown, Eric Gardner, and Tamir Rice. But even so, Wilson quickly returns to the idea that each person can make a difference; when the city’s efforts for reform after Freddie Gray’s death fizzle, Wilson counters this inaction with his own action. In general, though the memoir does touch on the need for systemic reform, Wilson is clearly more invested in the idea that even when life seems stacked against you, you still have some control and agency in your life, and it is important to take it. In yet another allusion, he refers to himself as a conquistador—the conqueror, perhaps, of his own life—burning the boats he sailed on and therefore forcing himself to walk into the new world of his own future.