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 Advice from Accountant 

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Michael Santos

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Erin is a successful accountant and entrepreneur who overcame considerable hardships at a young age. She began working in her early teens to secure her financial independence and escape abuse at home. Later, she earned a college degree in accounting and eventually became a successful entrepreneur. Erin offers significant lessons in adopting positive personality traits, including self-reliance, self-advocacy, and perseverance to achieve goals.

Objective: Lessons to Prepare People in Prison

  • In this lesson, students will learn why securing financial independence is important for success in society. Students will also learn how bookkeeping offers a viable career option for those without college degrees and those reentering society. Lastly, the video gives critical lessons on the need for a professional demeanor in the workplace and strong critical thinking, math, and communication skills.

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.

Our team at Prison Professors appreciates Erin for sharing her story on becoming a successful accountant and business owner. She overcame several ordeals as a child, including an abusive home environment, and worked several jobs to become financially independent at a young age. After graduating with an accounting degree, Erin gained experience in the corporate world before starting her own business. Throughout her journey, Erin demonstrated a goal-oriented mindset and a fierce work ethic that led her to become a successful entrepreneur.


Erin offers many valuable lessons on the importance of hard work, persistence, and proactiveness. She endured abuse from her father as a child growing up in the U.S. Northeast and lacked mentors in her home. Rather than remaining passive in this situation, Erin began working to earn an income that would enable her to become independent and remove herself from those unfavorable circumstances. Even before she was of legal age to work, she took on informal jobs as a babysitter and pet sitter; to find more work, she publicized her services by preparing and posting her own ads. She also collected positive references from clients, thus becoming more marketable to others seeking domestic services. Later, she worked in several entry-level roles to build her track record as an employee. Often, Erin worked more than one job simultaneously while enrolled in school. She balanced all of these obligations while accumulatingfunds because she remained committed to leaving her toxic home life.

At 17 years old, Erin graduated high school early and relocated to Florida to attend college. She sometimes struggled in school but persevered to earn decent grades and persuade high school administrators to approve her for accelerated graduation. In Florida, Erin found contentment in her new environment because she was free from her father’s mistreatment. In college, Erin took courses in business due to an interest in finances that stemmed from her experiences managing her income from an early age. She had also by then developed a passion for math. Eventually, Erin transferred to another university in Rhode Island where she began studying accounting.

While I was in prison, Erin’s determination to leave a negative home environment and generate income would have inspired me as I coped with my own difficult circumstances. She strove for independence at a very young age as a means of survival. Her diligence reflects many salient lessons from our courses at Prison Professors:

  • People who achieve great things define their own version of success by identifying an objective.
  • They then set incremental goals and maintain a positive attitude.
  • Most importantly, successful people know what they want and remain on course to fulfill their dreams.

Erin identified her mission – to leave her childhood home – and never swayed from that goal. People in prison and jails can learn that committing to a plan and tracking their progress can similarly lead to positive outcomes.

People in abusive relationships, especially young women, can also benefit from these lessons. Tragically, many domestic abuse survivors are in prison and jails today because they were involved with criminogenic partners who led them into unlawful behavior. Often, such individuals are financially beholden to their abusers and thus unable to leave their environment.

Erin offers examples of how people in abusive situations can take proactive steps to become financially independent and escape those circumstances. Likewise, incarcerated people may follow a similar framework to establish their own income after their release and avoid financial dependence on a controlling or abusive partner.


Erin’s story reflects the value of self-reliance and self-advocacy. As a child, she demonstrated her independence by making her own money and developing a strategy to remove herself from her unhappy living situation. Erin advocated for herself by building her work credentials so she would be more marketable for new roles. By proving her merit as a worker, Erin gained credibility as a person capable of taking on more responsibilities. She demonstrated self-advocacy by working hard and earning good grades to convince school administrators to approve her for accelerated graduation. Her approach was more effective than simply bemoaning her circumstances or seeking the pity of others. Rather, she demonstrated mastery of her school’s coursework to bolster her candidacy for early completion of school.

People in prison and jails can similarly become more resilient and better able to represent their interests. Many incarcerated people may seek early release, yet only those who acquire relevant job skills and a positive attitude are likely to succeed in this endeavor. An incarcerated person who works hard, avoids trouble, and actively prepares themselves for a law-abiding life can build a compelling argument for their freedom to caseworkers. Conversely, an incarcerated person who only complains about their situation is far less likely to persuade others of their worthiness for such leniency.

Lastly, people that served time in prison and then transition to the broader community should be willing to accept entry-level positions. Erin used such jobs as steppingstones in establishing her career and securing her independence. Many incarcerated people built lucrative careers and developed strong expertise in their fields before going to prison. However, criminal convictions often involve revocation of licenses and loss of business connections. Successful returning citizens must therefore be more open-minded and pragmatic about their career path upon release.

  • How can you develop more resilience while incarcerated?
  • Describe an instance when you demonstrated resilience in difficult circumstances.
  • How can you become a better self-advocate?
  • What practices and attitudes can you adopt to make a better case for leniency or early release?
  • Why is it important to be open-minded about accepting entry-level jobs after you reenter society?
  • How can entry-level positions serve as steppingstones in your career?
  • Why is establishing your own stream of income important?
  • Why is it essential to be goal-oriented?
  • What attitudes can you adopt to remain focused on your goals in life?

Bookkeeping as a Career

After graduating, Erin began her career in entry-level accounting positions in corporate environments. Eventually, Erin operated her own business at night while working for accounting firms during the day. She acquired transferable skills in math, communications, and critical thinking from these day jobs. At one of these firms, her employer downsized a business, resulting in Erin taking on extra duties that she found undesirable. To take complete control of her career trajectory, Erin left that position and became a full-time entrepreneur. Now she dedicates her time to operating her own firm and working with her own clients.

Accounting is a natural career choice for Erin, given her passion for math and helping others. She uses her math, communications, and critical thinking talents to assist her clients in understanding taxes and avoiding financial losses. She also informs her clients of educational material and other resources to help them better organize their finances and become more acclimated with tax policies.

A bookkeeping career offers copious benefits, including:

  • A high-demand skill,
  • Flexible hours,
  • The ability to work from home, and
  • Reasonable entry-level pay.

Bookkeepers are not required to have a college degree or license, and even someone with minimal experience can earn approximately $25 per hour. Some projects, such as basic tax returns that may take only 15 minutes to complete, can net $250 for the preparer.

There is also a continuous need for bookkeepers, as small business owners depend on such professionals to keep their finances organized.  A business owner without a financial background may find record-keeping to be more tedious or time-consuming than an expert in the field. By outsourcing this task, the business owner has more time to manage their organization’s operations. Thus, the bookkeeper’s pay rate is reflective of their role in offsetting several opportunity costs for business owners.

The bookkeeping industry is well-suited for entrepreneurs, including returning citizens. Erin shares that none of her clients have asked whether she had a criminal history, requested a background check, or otherwise inquired about any interactions with law enforcement. Instead, clients were pragmatic and more concerned about her ability to perform her duties well and resolve their business problems. Bookkeeping is also an optimal career path for caregivers, such as young mothers. Such individuals can benefit from setting their own hours and working from home for an ideal work-life balance.

Erin highlights that entrepreneurs must maintain a positive reputation to retain and acquire clients. Her clients hold her in high esteem and continue doing business with her because she is a consummate professional. Like how people let others know of their positive experiences with doctors or dentists, Erin benefited from word of mouth as her clients spoke highly of her to other business owners. She also leveraged her network to broaden her clientele. When she wanted to expand her business, Erin asked existing patrons to share information about her services with other potential customers. This strategy was successful: Erin found 10-15 new clients within three months due to her outreach


While I served more than 9,500 days in prison, I would have been inspired by Erin’s drive and success in building a career. She developed valuable skills at several jobs and successfully built her own business based on her abilities. More notably, she maintained a strong reputation due to her hard work and solid ties with her network to attract new clients. People in jails and prison should learn that, with time, their potential earnings will be commensurate with their ability to provide value to employees. Returning citizens should focus on saving time and making operations more efficient for their employers to improve their chances of success on the job and  in society. Aspiring business owners should also consider why it is vital to maintain a positive reputation by meeting or surpassing their clients’ expectations.

Erin’s story also reveals how second chances are feasible.  She stated that clients neither asked about interactions with law enforcement nor did they inquire about  a criminal background check.

A recently released person who seeks to become an entrepreneur could learn lessons from  Erin’s message. They could infer that value from skills they develop can open opportunities and lead to success despite past mistakes.

Our team at Prison Professors believes in people. Regardless of what bad decisions we’ve made in the past, we can work toward building a better future. If we can solve business problems, we can find practical opportunities to solve problems for others. If a person prepares to return to society, that person will have more confidence to find clients and business partners that will not discriminate against the past.

People in prisons and jails should consider the advantages of a bookkeeping career. It provides a competitive wage and allows practitioners to gain valuable skills that are applicable at different places of employment or in their own business. Because it offers opportunities for those without college degrees, the industry is a viable option for people with less formal education who are willing to work hard. It also involves a flexible schedule for those with commitments like caregiving.

Basic math and computer skills are vital for this industry. Many bookkeeping roles require mastery of software like Microsoft Excel and Intuit Quickbooks. While incarcerated people may not have access to the programs, they can still develop basic skills in arithmetic and become able to understand these software programs’ concepts and functionalities intuitively. Upon release, a formerly incarcerated person with this skillset will find it easier to master these programs. Incarcerated people generally have access to typewriters; they should use these machines to develop better typing skills to have better odds of finding work that requires computer use.

  • Why is it important to go the extra mile at work?
  • How can meeting or exceeding expectations reflect positively on your reputation?
  • How do you define the concept of “professional network?”
  • Why is it vital to maintain a good professional network after leaving prison?
  • How do you think Erin’s strong work ethic and skillset help solidify her relationships with clients and business partners?
  • Why can entrepreneurship be a good career path for people with criminal convictions?
  • How do you think Erin’s experience working as a child led her to become successful as a business owner?

Communication Beyond Reading and Writing Skills

Erin’s success is rooted in areas beyond her knack for numbers; she also exhibits exceptional communication and presentation skills. During the interview, Erin consistently spoke eloquently and maintained a friendly demeanor. Erin communicates several desirable qualities, such as competence, professionalism, and an affinity for her work by appearing likable to others. Her cadence, speech patterns, and diction are also indicative of her experience in the workplace.

Good communication involves more than having advanced writing and reading abilities. Body language, appearance, hygiene, clothing, and tone of voice also convey unconscious messages in interactions between people. People leaving prison or jail should develop positive habits in these areas to become more appealing candidates for jobs, housing, and social connections.


People in prison or jail often erroneously equate earning respect as instilling fear in others. For this reason, people should consider whether they want to live locked in prison, or succeed in society. To build genuine respect in the business community, a person should extend courtesy to others, and show a positive attitude. A formerly incarcerated person should also refrain from using excessive prison vernacular and profanity, especially in professional settings. Such coarse language will likely repel potential business partners and clients. 

Lastly, returning citizens must develop the right attitude before their release. The video includes an anecdote about a prisoner who wanted a job but still aspired to resume criminal activity after incarceration. Unlike this individual, people who are successful after prison abandon any notion of committing crimes.

  • How do mannerisms, verbal communication, body language, and appearance affect your interactions with others?
  • Why is it important to demonstrate positive body language?
  • How does body language influence other people’s perceptions of you?
  • What does it mean to be likable?
  • What habits can you adopt to become more likable?
  • How can you develop the appropriate mindset for transitioning back into free society?
  • Why is it important to fully desist any intent of committing crimes?
  • How does the meaning of the term “respect” differ in prison in contrast to free society?

The Principles of Success

Throughout her life, Erin demonstrated virtually all of the success principles that Prison Professors teaches in its coursework. As a child, she defined her version of success – to leave her abusive home. Erin also set clear, incremental goals to accomplish her mission, namely earning money and graduating high school early. Throughout her career, she has maintained a positive attitude by focusing on helping customers and remaining committed to her success. Erin always envisioned her future achievements – she saw herself as an entrepreneur and took actions to fulfill that goal. She has also held herself accountable while remaining focused and action-oriented. Erin always delivers for her clients and upholds her reputation as a professional. Lastly, Erin is authentic; she takes pride in her work as an accountant and remains committed to her purpose.

Critical Thinking Questions:

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

  1. How can a bookkeeping career appeal to people leaving incarceration and those without a college education? What facets of the career offer promise to these individuals?
  2. Why does entrepreneurship offer significant potential for the formerly incarcerated?
  3. How do you believe Erin’s handling of adversity as a child led her to become successful as an entrepreneur? What coping skills do you think she developed early in life?
  4. How does your attitude and work ethic affect your ability to self-advocate while incarcerated?
  5. How does Erin’s story reflect the value of setting incremental goals and remaining focused on accomplishing a mission? How can you apply that concept in your present situation?
  6. What resources are at your disposal to help you learn basic math and computer skills? What routines can you adopt now to develop those skills?
  7. How can you maintain a good reputation as a professional? Why is a good reputation necessary to retain and acquire new clients or job opportunities?
  8. How do you impact other people’s perception of you through your body language, appearance, diction, and vocabulary?
  9. How do you earn respect from others? How is earning respect different than provoking fear from others?
  10. How can becoming financially independent by lawful means help you effectively transition into society?

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