Five Outcomes After Prison—and Why Preparation Determines Which One You Face
When I walked out of prison after serving more than a quarter century, I expected the transition to be difficult. What surprised me was not the magnitude of the challenges, but the form they took.
Two of the first problems I encountered were simple.
I had to learn how to drive again.
I also had to learn how to eat with silverware.
That may sound strange, but decades inside prison reshape the most ordinary experiences. In prison, a person never moves faster than his legs can carry him. Over time, the body and the senses adapt to that pace.
When I first sat behind the wheel of a car after my release, everything felt overwhelming. Cars approached from every direction. Traffic lights appeared and disappeared before I could process them. Movement happened faster than my eyes were accustomed to seeing. For several months, driving felt like navigating a video game.
Something equally simple felt unfamiliar as well. For 25 years, every meal I ate came on a plastic tray. I used plastic utensils and drank from plastic cups. When I held a glass for the first time after my release, the sensation felt strange because I had not experienced it in decades.
Those were the complications I faced.
I wish every person leaving prison had only those kinds of problems.
Unfortunately, most people returning from prison confront far more serious obstacles. Over the years, I have seen that people who leave prison tend to experience one of five outcomes: unemployment, underemployment, homelessness, new problems with the law, or success.
Preparation during incarceration often determines which of those outcomes becomes reality.
The Challenge of Unemployment
I entered prison at 23 years old. I came home when I was 49. During those years, I spent a great deal of time thinking about the barriers I would face upon release. I believed it was highly likely that I would struggle to find meaningful employment.
That belief was not pessimistic; it was realistic.
Employers invest time and resources when they hire someone. They often hesitate to take risks on people who have spent decades outside the workforce, especially when a felony conviction appears on a background check. Age compounds the problem. Employers sometimes assume that older applicants will bring less long-term value to the organization.
Today, technology and artificial intelligence are transforming the labor market in ways that make the competition even more intense.
Recognizing those realities early in my sentence helped me develop a strategy. I decided that if traditional employment might be difficult, I needed to prepare myself to create opportunities rather than wait for them.
While incarcerated, I earned a bachelor’s degree from Mercer University and a master’s degree from Hofstra University. I wrote books and articles to advocate for reforms that could improve the criminal justice system. Every step I took was part of a deliberate plan to overcome the barriers I expected to face.
Preparation allowed me to leave prison with a foundation rather than uncertainty.
The Trap of Underemployment
Sometimes a person leaving prison does find a job, but the job may lead to another problem: underemployment.
Consider someone who accepts a low-paying position because it is required for halfway house placement or home confinement. Once that person begins earning income, financial obligations quickly follow. Rent must be paid. Utilities must be covered. Basic living expenses accumulate.
Soon the paycheck becomes something that cannot be risked.
Even if the job offers little opportunity for advancement, leaving it feels dangerous. Searching for better work may require time without income, and that possibility feels too risky when financial stability is fragile.
In that situation, the job becomes another form of confinement. It provides survival but limits growth.
Preparing while incarcerated can help people avoid that trap. Skills, education, and a clear strategy create options that make it easier to pursue opportunities with long-term potential.
The Risk of Homelessness
Another outcome many people face after prison is homelessness.
During my time in prison, I met many people who focused their energy on prison politics—arguments about the television room, disputes over seating in the dining hall, or efforts to build status inside the institution.
Those things have no value after release.
When a person returns to society, the structure of prison disappears. There are no guaranteed meals, no assigned bed, and no institution responsible for daily survival. Without a support network or a plan, a person may quickly find himself without housing.
Once homelessness begins, every other challenge becomes harder to overcome. Employment becomes more difficult. Stability becomes fragile. Even maintaining personal dignity requires greater effort.
Preparation during incarceration can help prevent that outcome.
Avoiding New Problems With the Law
Another common outcome is a return to the criminal justice system.
Sometimes this happens because people fall back into substance abuse or reconnect with individuals who remain involved in criminal behavior. In other cases, the pressure of rebuilding life after prison leads to decisions that violate the conditions of supervised release.
Returning to prison does not always require a new crime. Violating supervision rules alone can result in incarceration.
Avoiding those outcomes requires discipline. It requires learning to build new associations, new habits, and new ways of thinking.
Preparation helps a person develop the mindset necessary to navigate those pressures.
Building a Path Toward Success
When I was arrested on August 11, 1987, I spent time in solitary confinement reflecting on the life I hoped to build after prison. During that period I read the Biblical parable of the talents.
The message resonated with me.
Each person receives abilities and opportunities. Our responsibility is to develop those gifts and use them productively. When we invest in what we have been given, we create growth. When we neglect those gifts, we lose even what we already possess.
I had lost my liberty because of poor decisions. But I still had the opportunity to prepare for a better future.
So I began planting seeds.
By the time I completed my sentence, those seeds had grown into tangible results. I had earned two university degrees. I had saved more than $100,000. I had built a support system that included my sisters and the woman who would become my wife. Most important, I had developed a clear plan for how I would contribute to society.
Those preparations made it possible for me to build a career advocating for reform and helping others prepare for success after prison.
That work eventually became Prison Professors.
Become the Architect of Your Future
The lesson from my experience is simple.
Preparation determines outcomes.
Every person leaving prison will face challenges. The question is not whether those challenges exist, but whether you begin preparing early enough to overcome them.
At Prison Professors, we created free courses and tools to help people document the steps they are taking to prepare for success. When you build a profile and record your progress, you demonstrate intrinsic motivation. You show that you are working intentionally to build a better future.
If you do not design your future, others will design it for you.
The results may include unemployment, underemployment, homelessness, or renewed involvement with the criminal justice system.
But if you prepare deliberately—if you plant seeds every day—you can create a pathway toward success.
I believe in that possibility because I lived it.
Self-Directed Reflection
What specific steps are you taking today to prepare for success after prison, and how will you document those actions to show the progress you are making toward a better future?
Write your response and publish it on your profile to demonstrate the plan you are building.