Creating My Own Opportunities : Building a Pathway to Gainful Employment From Inside Prison

By Ivan Kilgore

When people ask me how I prepared for gainful employment after prison, I tell them something many people do not expect to hear : opportunity is not something that only comes once in a lifetime. That is a myth. In my experience, opportunity is something you create. It is something you build intentionally through vision, discipline, relationships, education, and persistence. Even in prison. I entered prison 26 years ago with one major advantage : I already understood entrepreneurship. Before incarceration, I had spent nearly two years studying business administration at community college. During that time, I learned the five primary business models—sole proprietorships, limited liability companies, S-corporations, C-corporations, and nonprofit 501©(3) organizations. I also had years of experience hustling and creating income opportunities in my environment. Entrepreneurship was already a part of how I thought about survival, growth, and independence.

So when I entered the prison system, I did not see prison solely as confinement. I saw it as an environment I would have to navigate strategically. I understood very early that if I depended entirely on the prison system to prepare me for employment, I would likely leave with very few practical pathways toward meaningful economic opportunity. Most prison jobs, in my experience, are menial positions. While they can teach punctuality and basic interpersonal communication, they rarely provide a true pathway to financial independence or entrepreneurial development. That realization forced me to adopt a different mindset. I decided I would use my incarceration to create my own opportunities. Instead of allowing prison to define the limits of my future, I began identifying ways to continue developing myself as an entrepreneur, leader, writer, and organizer.

Ironically, the greatest opportunity came through something I never expected: self-help programming. As with any business endeavor, I first identified the resources I needed and the skills I lacked. I understood that leadership was going to be essential. Communication was
going to be essential. Organizational development was going to be essential. If I wanted to create programs, build organizations, and eventually employ myself after release, then I needed to master those abilities. One of the most transformative opportunities I pursued was participation in Toastmasters International through the prison’s Gavel Club program. Many people think public speaking programs only teach someone how to stand in front of an audience and speak clearly. For me, it became much more than that.

Toastmasters taught me how to organize meetings, coordinate teams, train participants, maintain records, mentor others, and facilitate group dynamics. In many ways, it became my introduction to human resources and organizational leadership. I learned that leadership is not simply about giving instructions ; it is about understanding people. It is about motivating people. It is about conflict resolution, emotional intelligence, patience, accountability, and consistency. Those lessons became invaluable later in my journey. At the same time, I began developing myself as a writer. I immersed myself in creative writing classes, independent study, and disciplined practice. Writing became more than artistic expression. It became leadership development. Teaching creative writing classes inside prison forced me to cultivate patience, empathy, time management, and organizational skills. It also taught me how to work collaboratively with people from diverse backgrounds, personalities, and belief systems.

Prison environments are often emotionally tense and psychologically draining. Learning how to navigate complicated personalities while maintaining professionalism became an education all by itself. In many ways, these experiences sharpened my interpersonal skills more than any formal business seminar could have.

For seven years, I dedicated myself to studying and writing with consistency. That discipline eventually led me to self-publish my first book in 2013, Domestic Genocide. Publishing that book marked a major turning point in my life because it transformed me from someone who consumed information into someone who produced intellectual property.

That process also introduced me to marketing on an entirely different level. After publishing the book, I enrolled in a correspondence college course focused on marketing. I became fascinated with understanding how branding, messaging, audience engagement, and promotion function in the real world. What made the experience unique is that I combined those academic lessons with skills I had learned long before prison through street hustling and guerrilla marketing.

People often underestimate the transferable skills people from marginalized environments possess. Street survival teaches adaptability, negotiation, networking, persuasion, resource management, and strategic thinking. I simply redirected those skills toward legitimate entrepreneurship and organizational development. That journey eventually led to one of the most important accomplishments of my life: becoming the founder and CEO of the United Black Family Scholarship Foundation, commonly known as UBFSF.

Creating UBFSF gave me something prison often attempts to strip away from incarcerated people : purpose. It gave me a mission larger than myself. Instead of focusing only on surviving incarceration, I began focusing on building infrastructure that could create educational opportunities, mentorship, and support systems for others.

In 2017, I made another strategic decision that many people did not initially understand. I enrolled in the prison’s in-person college program, not because I was pursuing another degree, but because I recognized the value of access. I understood that universities are ecosystems filled with resources, talented students, faculty expertise, research opportunities, and professional networks. My goal was to tap into that ecosystem and build an internship pipeline for student volunteers who could work alongside me developing programs, grant proposals, and organizational infrastructure for UBFSF.

The strategy worked.

Together, we successfully built collaborative relationships that expanded the organization’s reach and credibility. Through those efforts, I was able to create opportunities that extended far beyond prison walls. The work opened doors to paid speaking engagements, program development opportunities, grant funding, and professional relationships with people in film, social studies, nonprofit leadership, and other industries.

Most importantly, it proved something I had long believed : incarceration does not eliminate a person’s ability to contribute value to society.
One of the greatest lessons I learned throughout this process was the importance of mentorship. I realized that trying to build anything meaningful without guidance unnecessarily prolongs the learning curve. Finding people who have already accomplished what you hope to achieve can accelerate your growth tremendously.

Mentors taught me how to navigate organizational challenges that books alone cannot teach. They helped me understand the “messiness of people,” leadership accountability, hiring practices, organizational culture, and the importance of effective HR policies and protocols. Leadership is not just about vision ; it is also about managing personalities, expectations, emotions, and conflict while maintaining the integrity of the mission.

Equally important was my commitment to self-education.

Throughout the last 30 years, I have read thousands of books. On average, I keep more than 100 books in my cell at a time. During the 18 years I spent housed in maximum-security prisons, personal libraries became an essential part of our culture. Many of us exchanged books constantly, creating informal educational networks despite the oppressive conditions surrounding us.

Books became our universities. Reading allowed me to study business, psychology, philosophy, leadership, sociology, marketing, organizational behavior, communication, history, and human development. It expanded my perspective far beyond prison walls. Education became both a survival tool and a pathway toward future employment.

That is one of the reasons I often challenge the narrative surrounding prison labor programs. While some prison work assignments can teach discipline and interpersonal communication, most do not provide meaningful economic pathways after release. In many cases, incarcerated people are relegated to repetitive labor with little connection to sustainable careers.

However, even within those limitations, I learned something valuable: every environment contains opportunities for skill development if you approach it intentionally. Even difficult prison jobs forced me to negotiate with authority figures, manage conflict, adapt to toxic personalities, and maintain composure under pressure. Those experiences sharpened my emotional discipline and people-management skills. In many cases, dealing with authoritarian environments taught me how to remain solution-oriented in dysfunctional systems.

Still, I refused to allow prison employment assignments to define my professional future. Instead, I adopted a mindset rooted in ownership and intentional growth. I constantly asked myself: How can I use this time to become more valuable? How can I develop skills that create economic opportunities after release? How can I build infrastructure now that will benefit me later? That mindset changed everything.

What many people fail to understand is that gainful employment is not always about finding a job. Sometimes it is about building yourself into a person capable of creating opportunities for yourself and others. Entrepreneurship taught me that income can come through leadership, consulting, writing, teaching, speaking, organizing, networking, and creating solutions to problems. That understanding helped me transform incarceration from wasted time into preparation time.

Today, when I speak to incarcerated individuals, formerly incarcerated people, students, and community organizations, I emphasize the same principle repeatedly: create your own opportunities. Do not wait for systems to validate your potential. Do not wait for perfect conditions. Do not assume opportunity only arrives through luck or chance.

Opportunity is often hidden inside preparation.

Every class I taught, every speech I delivered, every meeting I organized, every book I read, every relationship I cultivated, and every project I developed became part of building a pathway toward gainful employment and meaningful contribution after prison.

My journey taught me that entrepreneurship is not merely a business model—it is a mindset. It is the ability to identify problems, create value, organize resources, and build possibilities even in restrictive environments.

Prison attempted to limit my physical freedom, but I refused to allow it to limit my vision. And because of that decision, I was able to transform incarceration into a platform for leadership development, nonprofit creation, public speaking, writing, mentorship, and professional networking.

That pathway was never handed to me.

I created it.