Today we’d like to introduce you to Jessica Roberts.
Jessica, we appreciate you taking the time to share your story with us today. Where does your story begin?
My life changed the moment I realized my past did not disqualify me from purpose—it prepared me for it. What once felt like my greatest setback ultimately became the foundation for my calling, leadership, and voice.
I am the author of Triumphant: One Woman’s Journey from Prison to Purpose, a memoir that reflects my personal transformation and the lessons gained through adversity. That experience reshaped how I see people, systems, and second chances, and ignited a lifelong commitment to re-entry advocacy and community restoration.
In 2011, I became a board member of Empowering Men and Women on the Move for Re-Entry Inc. In this role, I conducted meetings with potential partners and was directly responsible for creating official organizational documents, professional correspondence, marketing materials, and coordinating event planning and outreach efforts. I also received clearance to accompany the organization’s CEO into local Atlanta prisons, transitional centers, and halfway houses. There, the CEO and I conducted post-release interviews, facilitated life-skills and re-entry classes, and led outreach initiatives such as feeding the incarcerated during Thanksgiving, Father’s Day, and Self-Love Valentine’s Day events.
In 2012, I transitioned from board member to Board Chair, helping guide organizational strategy, partnerships, and program growth. In 2025, I became Director, leading supportive housing, accountability-based programming, and re-entry initiatives rooted in dignity, structure, and second chances. Empowering Men and Women on the Move for Re-Entry Inc. provides supportive housing and wraparound re-entry services for justice-impacted individuals and those experiencing homelessness, helping them rebuild stability, accountability, and purpose after incarceration.
Today, my work is driven by a simple truth: people are more than their past, and with the right support, purpose can rise from even the most difficult chapters.
“When you turn pain into purpose, your story stops being a sentence and becomes a service.”
We all face challenges, but looking back would you describe it as a relatively smooth road?
No, the road has not been smooth—and that honesty is important. Rebuilding life after incarceration comes with challenges that don’t disappear once your sentence ends. There were barriers related to stigma, trust, and access—being judged by my past while trying to build something rooted in purpose and integrity. Balancing motherhood, personal healing, and professional growth required resilience, discipline, and faith.
Professionally, leading within the re-entry space meant navigating limited resources, burnout, and the emotional weight of advocating for individuals who are often overlooked or misunderstood. There were moments of doubt, setbacks in partnerships, and times when progress felt slow. Internally, I also had to unlearn shame and consistently choose confidence, accountability, and perseverance.
However, every struggle strengthened my leadership. The challenges taught me how to build systems, advocate effectively, and lead with empathy and structure. The road was not smooth—but it was meaningful. Those obstacles are what allow me to lead authentically today, with compassion, clarity, and a deep understanding of the communities we serve.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
As a professional, my work sits at the intersection of lived experience, leadership, and systems-building. I am the Director of Empowering Men and Women on the Move for Re-Entry Inc., where I specialize in supportive housing, accountability-based programming, and re-entry support for justice-impacted individuals and those experiencing homelessness. My work focuses on helping people rebuild stability, restore dignity, and create sustainable pathways forward after incarceration.
I am known for building structure where there is often chaos—developing policies, programs, and partnerships that balance compassion with accountability. I lead with both empathy and expectation, understanding firsthand what it takes to rebuild a life while also recognizing the importance of responsibility, consistency, and community standards.
What I am most proud of is creating environments where people feel seen, supported, and challenged to grow. From leading supportive housing initiatives to developing programs rooted in second chances, my greatest accomplishment is helping individuals move from survival to stability.
What sets me apart is that I don’t lead from theory—I lead from lived experience. I understand the systems because I’ve navigated them, and I use that understanding to create solutions that are practical, humane, and effective. My work is grounded in the belief that transformation is possible when people are given both opportunity and accountability.
Any advice for finding a mentor or networking in general?
My advice for finding a mentor or building meaningful networks is to focus on alignment, not access. Look for people whose values, work ethic, and integrity reflect where you want to grow—not just where you want to go. A true mentor doesn’t just open doors; they challenge you, hold you accountable, and help you see blind spots you may not recognize on your own.
What has worked well for me is leading with service before asking for support. I built relationships by showing up consistently, doing the work, and adding value wherever I could—whether through volunteering, collaborating, or simply being reliable. Over time, those relationships evolved into mentorship, partnership, and trust.
I’ve also learned the importance of discernment. Not every connection is meant to be long-term, and not every mentor will walk the full journey with you. Be open to learning in seasons, stay teachable, and don’t be afraid to outgrow spaces that no longer align with your purpose.
Most importantly, be authentic. When you lead with honesty and integrity, the right mentors and connections will naturally align with your path.
Pricing:
- 18.20
Contact Info:
- Facebook: https://www.facebook.com/share/1Ah78U2B6e/
- Other: https://www.amazon.com/Triumphant-Womans-Journey-Prison-Purpose/dp/1947656996
