From Lived Experience to Leadership: The Power of Tech Mentorship for Returning Citizens
Championing Transformation Through Technical Education and Guidance
When I reflect on my journey from incarceration to becoming a technology professional with 30 high-tech certifications and board positions with prestigious organizations like The Petey Greene Program and FICGN, I’m reminded of a fundamental truth: transformation requires both opportunity and guidance. As someone who has walked this path, I’ve committed myself to not only creating educational pathways but also building a robust mentorship framework that supports returning citizens throughout their technology journey.
The Missing Link: Why Mentorship Matters in Tech Reentry
The technology education curriculum I’ve been developing represents a critical infrastructure for change. However, my experience has taught me that curriculum alone—no matter how well-designed—isn’t enough. Returning citizens face unique challenges that extend beyond technical knowledge:
- Navigating industry culture and unwritten rules
- Building professional networks from a disadvantaged starting point
- Managing imposter syndrome amplified by justice system involvement
- Translating technical skills into career readiness
- Developing resilience when facing potential discrimination
This is where targeted mentorship becomes transformative. Over the past several months, alongside curriculum development, I’ve been architecting a comprehensive tech mentorship program specifically designed for formerly incarcerated individuals.
Creating the Mentorship Framework
The mentorship model I’ve developed functions as a complementary support system to the three-tiered technology curriculum. It includes:
1. Mentorship Tiers Aligned with Technical Growth
- Foundation Mentors: Focus on digital literacy, basic professional skills, and initial reentry challenges
- Development Mentors: Guide mentees through intermediate technical skills and project-based learning
- Industry Mentors: Professionals working in target roles who provide advanced guidance and networking
2. Mentor Training Focused on Justice-Impacted Populations
- Cultural competency for working with formerly incarcerated individuals
- Understanding legal and logistical barriers to employment
- Strategies for addressing skills gaps without triggering shame
- Balancing empathy with accountability and high expectations
3. Structured Touchpoints and Milestones
- Weekly technical skill review sessions
- Monthly career development meetings
- Quarterly progress assessments
- Mock interviews and portfolio reviews
- Industry exposure events and networking opportunities
4. Peer Mentorship Component
- Creating opportunities for program participants to mentor newer cohorts
- Developing leadership skills while reinforcing technical knowledge
- Building community and shared accountability
Personal Commitment to Mentorship Excellence
My passion for this mentorship framework stems from my own experience. When I completed the Columbia Business School’s Justice Through Code program, I benefited immensely from targeted mentorship. Those relationships helped me navigate not just technical challenges but also the complex emotional and psychological territory of reinvention.
Now, as I pursue advanced certifications like my recent Microsoft Artificial Intelligence Engineering credential—a rigorous six-month course requiring over 1,000 hours of study—I’m constantly identifying skills and insights that can be translated into mentorship best practices.
Early Results: Mentorship in Action
Though still in development, components of this mentorship model have already been implemented in pilot form. Early feedback has been profoundly encouraging:
“Having a mentor who understands both the tech world and the reentry experience has been game-changing. When I doubt myself, my mentor reminds me that my past doesn’t define my potential in this field.” — Program Participant
“The structured mentorship approach provides accountability without judgment. I’ve never had someone invest in my professional development this way before.” — Program Participant
The most powerful aspect has been witnessing the ripple effect as mentees begin mentoring others, creating a sustainable cycle of support and knowledge transfer.
Scaling Impact: From Individual Transformation to Systemic Change
As the full mentorship program prepares to launch alongside the complete curriculum, I’ve been working with industry partners to expand our mentor pool. The response has been overwhelming, with technology professionals from major companies volunteering their time and expertise.
This collaboration brings multiple benefits:
- Skill Transfer: Direct access to current industry knowledge and practices
- Network Building: Expanding professional connections for participants
- Perception Shifting: Changing how the tech industry views formerly incarcerated talent
- Employment Pathways: Creating direct pipelines to employment opportunities
The Technology Redemption Framework: Education + Mentorship
What’s emerging from this work is what I’ve come to call the “Technology Redemption Framework”—a holistic approach that combines structured education with targeted mentorship to create sustainable transformation for returning citizens.
This framework acknowledges that technical skills alone aren’t enough. Real transformation requires:
- Knowledge (provided through the curriculum)
- Guidance (delivered through mentorship)
- Community (cultivated through peer relationships)
- Opportunity (created through industry partnerships)
By addressing all four dimensions, we create a comprehensive support system that dramatically increases the likelihood of successful reentry and career development.
Personal Reflection: The Mentor I Needed
In developing this mentorship program, I often reflect on what I needed most during my own reentry journey. Beyond technical knowledge, I needed someone who could see my potential when I couldn’t see it myself—someone who understood both the technical landscape and the unique challenges of rebuilding after incarceration.
That dual understanding is what makes this mentorship program unique. Our mentors don’t just understand technology; they understand transformation. Many have lived experience themselves, while others have been extensively trained in the specific challenges faced by justice-impacted individuals.
Join the Movement: Become a Tech Reentry Mentor
As this initiative continues to grow, I invite technology professionals—particularly those with lived experience in the justice system—to consider becoming mentors. Your journey, including both your technical expertise and your personal challenges, represents a powerful resource for those following in your footsteps.
Together, we can build a technology industry that values talent and potential regardless of past mistakes. We can create pathways to not just employment, but meaningful careers that allow returning citizens to rebuild their lives and contribute to their communities.
The code we write creates products and services. The mentorship we provide creates futures.
Joseph DeGregorio holds 30 technical certifications, including recent credentials in Google Advanced Data Analytics and Microsoft Artificial Intelligence Engineering. He serves on the National Board of Advisors for The Petey Greene Program and the FICGN Governance Board. His work focuses on creating comprehensive education and mentorship pathways for formerly incarcerated individuals entering the technology sector.
To learn more about becoming a mentor or supporting this initiative, connect with me on LinkedIn.
