Lesson: Continued Career Success


Casey started a roofing company that grew within five years to operate with more than $28 million in revenue. He began his career in his family’s roofing business and worked his way through the ranks by demonstrating strong personality traits, including perseverance, self-reliance, and accountability. Roofing offers a good career option to the formerly incarcerated as the industry often has positions open to those with criminal convictions. 


In this lesson, participants will learn how the roofing industry offers promise to those leaving prison and jail. In addition, participants will understand why it is important to learn a basic skill set in math, communication, and critical thinking. Upon completing this lesson, students should understand how roofing offers a viable career path and why it is important to master skills in those three areas. 

Lesson Requirements:

  • Watch the video that accompanies the lesson
  • Write a definition of each word highlighted in bold and written in italics
  • Use ten of the vocabulary words in a sentence
  • Respond to a minimum of three open-ended questions by following instructions at the end of the lesson.

Lesson Outcome:

  • Participants will increase their vocabulary by at least ten words.
  • Participants will improve writing skills and their ability to contemplate how their responses to open-ended questions relate to their prospects for success upon release.
  • Participants will add to their journal, demonstrating a self-directed, self-improvement pathway to prepare for success upon release.

How People in Prison can Prepare for Roofing Careers

Continued Career Success

Casey always found his career gratifying because the results were tangible and visually apparent: he took pride in his role in constructing large buildings in what was once empty space. He also enjoyed positively impacting others. He vividly recalls a sense of fulfillment when he helped other crew members become more adept at their jobs and when he ensured that customers were satisfied with a project’s results. 

Casey learned to become more tolerant from his interaction with people from different backgrounds. At first, he faced communication barriers and social misunderstandings once he began working with Spanish-speaking crew members. Casey overcame that challenge by learning the language, an act that earned him colleagues’ respect and a position as foreman.

Through his persistence and work ethic, Casey rose through the organizational hierarchy and assumed managerial roles. These senior positions required Casey to take responsibility for his team’s performance and persevere through adversity. When he accepted a superintendent role at a construction project in Tennessee, several contractors defected from the team as higher-paying positions were available elsewhere. Rather than focus on the negative, Casey quickly located, hired, and trained substitute workers. His efforts paid off: the project in Tennessee, the largest in the country at the time, was successfully completed.

While incarcerated, I would have resonated with Casey’s lesson on tolerance. At a federal prison in Fort Dix, New Jersey, I was incarcerated alongside prisoners from 91 different countries. In that environment, the prisoners most eager to show tolerance were the most likely to succeed. Casey’s willingness to learn Spanish would have also impressed me as proof of his respect for others and open mindedness.  

In addition, I would have admired Casey’s continued persistence, hard work, and desire to perform well. The personality traits that he acquired as a child enabled him to advance in his professional life. He also distinguishes himself through his pride in his work – he appreciates seeing his team succeed by meeting or exceeding the customers’ requirements. 


In prison or jail, it is important to maintain a good attitude, perform well on the job, and treat people of all backgrounds with respect. Though it may be difficult to maintain a good attitude behind prison walls, complaining will only make the situation worse. Successful people focus on what they can control and make incremental progress towards better outcomes.

  • What does it mean to have pride in your work? How can you go “the extra mile” in your everyday life? 
  • Why is tolerating people of different cultures, faiths, and language backgrounds important? 
  • How will tolerance help you succeed in prison and upon your release? 
  • How do you deal with adversity? Why is coping with adversity a vital trait for leaders?
  • What personality traits can you adopt to win the respect of others? 

Critical Thinking Questions:

Write at least three paragraphs, with a minimum of three sentences each, for each of the following questions

  1. Why does a career in roofing appeal to many formerly incarcerated people? What skills could you learn from a job in this industry?
  2. How did Casey’s early start in the workforce influence his success later in life? What character traits did he develop because by starting to work as an adolescent?
  3. How can you demonstrate self-discipline, self-resilience, and accountability? Why are these traits important when working with others?
  4. Has prison led you to interact with people from different backgrounds? Has this led you to become more tolerant? 
  5. Casey demonstrated resilience to overcome adversity. How have you demonstrated resilience? Why is resilience an important trait in leaders?
  6. What skills can you develop now in the areas of communication, critical thinking, and math to help you advance on the job?
  7. Education goes beyond earning a degree. How can you demonstrate proficiency in communication, critical thinking, and math? How will this proficiency help you perform a job well?
  8. In your opinion, what characteristics of Casey’s leadership enabled his business to grow so rapidly? 
  9. What role do essential communication skills, such as persuasion and negotiation, play in your life? How will these skills help you after prison?
  10. How does Casey’s story inspire you to live a law-abiding life after prison? 

Our team at Prison Professors thanks Casey for sharing his story on how he started as a tradesperson early in life and later became a successful entrepreneur. Although he never earned a college degree, Casey founded his own roofing company with minimal capital. Within five years, his business substantially grew and now operates with more than $28 million in revenue.

Many facets of Casey’s story should inspire people in prison or jail. A career in roofing offers promise to returning citizens, as many positions are often open to those with a criminal background. The industry also helps novices obtain a valuable skill set in roles that have significant growth potential. Casey’s story also proves that people without a college education can still enjoy a lucrative career so long as they demonstrate persistence, self-reliance, and a willingness to learn.