Jail to College: Why Willpower Isn’t the Missing Piece

Send us Fan Mail You can’t “willpower” your way through reentry when the barriers are baked into vision care, literacy, trauma, and the way institutions respond to a record. I’m joined by Denise Richardson and Mildred McKinney, the founders of OpenGate Inc., an Oakland nonprofit that helps people move from incarceration into education, employment, leadership, and a new sense of possibility. Their work started with college readiness classes inside Santa Rita Jail and grew into one of the most practical, humane models I’ve seen for helping returning citizens land on campus and stay there. We talk about how AB 109 reshaped California’s reentry landscape, why the public’s worst fears didn’t come true, and what actually worked: job training, community college pathways, and consistent support. Denise and Mildred also unpack a huge hidden issue in education and workforce development for incarcerated students: undiagnosed learning differences and basic needs like glasses or hearing aids. When you add anxiety and near-universal PTSD to living in constant hypervigilance, “school failure” starts to look a lot like unmet needs. We get specific about DSPS accommodations that change outcomes fast, from extra time to quiet testing rooms to audiobooks and scribes. We also dig into the OG MACs model, where respected formerly incarcerated leaders mentor younger students, hold them accountable, and shift the culture through quiet, credible leadership. You’ll hear why “just get a job” is often disconnected from the reality of literacy, survival grooming, and the grief people carry back into the community, plus what OpenGate is building next with OG MAC Academy. If you care about reentry support, restorative justice, and real public safety solutions, listen through and share it with someone who needs a wider view, or needs support in their reentry. Then subscribe and leave a review on Apple Podcasts so more people can find these stories. https://oaklandliteracycoalition.org/open-gate-inc Resources & Workbooks: Book • Free Starter Guide • Heal What Raised You Workbook • Website © 2026 soulnotskin. All rights reserved.