From System-Involved to System-Changer | by Helen "Skip" Skipper

I often say I have a PhD in lived experience. I earned that degree on rooftops, park benches, and places I never want to return to. My journey has taken me through battles with addiction, brushes with the justice system, and long stretches of feeling lost in the very institutions that were supposed to help. Through it all, I discovered a resilience within me, and a hunger to challenge systems that weren’t built with people like me in mind. Today, I’m proud to be on the board of the organization that helped me see my future in higher education: College and Community Fellowship. 

I wasn’t always certain I wanted a traditional college education. In fact, the idea of those letters after my name—bachelor’s, master’s—never resonated much at first. I used to say, “I’ve got my master’s from a park bench and a PhD in lived experience.” Sitting behind a desk reading textbooks hardly seemed to compare with the lessons you learn navigating the streets. But after years of working in peer support, I noticed something: my lived experience wasn’t always taken seriously in professional settings. My insights and ideas were dismissed, and I was repeatedly shut down.

I found myself questioning whether my contributions mattered at all in those circles. It got to a point where I was ready to walk away from peer support completely. I kept asking: What do I need to do so that I’m not just occupying space, but really influencing outcomes? Eventually, I realized I did need formal education credentials, if only to ensure my expertise wouldn’t be so easily overlooked.

A Chance Encounter That Changed Everything

Around that time, I was giving a presentation, sharing my story of addiction, incarceration, and mental health challenges. Afterward, a CCF counselor named Anna approached me. She said, “You mentioned wanting to go back to school. I can help you. Here’s my card.”

Anna guided me through complicated paperwork and processes I knew nothing about. At the same time, I’d also started taking a class at the Prisoner Reentry Institute (now called the Institute for Justice and Opportunity) at John Jay College. That course gave me a taste of what being in a college community could feel like. I walked those halls, sat in lecture rooms, and thought: I can do this. I want to do this.

Then came a bureaucratic roadblock—my old SAT scores (or lack thereof) meant I needed to enter a community college first. That felt disheartening. When I was younger, community college had been a hangout spot for me. I barely attended classes. I’d grown so much since then and wanted to jump right into a four-year program.

As if by fate, a friend told me about St. Francis College and its Justice Initiative Scholarship. It was a private four-year college that offered an opportunity for formerly incarcerated students to attend tuition-free. I was ecstatic—until I discovered an ancient hold on my transcripts from 1986! The community college I had briefly attended decades ago refused to release my transcripts unless I returned a library book … from the Reagan era. It was comical and heartbreaking all at once.

Anna and CCF never gave up. She mediated phone calls. She navigated the paperwork. Ultimately, the school agreed to waive all overdue fees if I simply paid for the missing book. That was one of the best payments I’ve ever made.

And so began my journey as an undergraduate. It wasn’t always easy: I was a non-traditional student with a full-time job in peer support, juggling family obligations, rent, and homework deadlines. But CCF stayed with me every step of the way, offering scholarships and guidance. After four years, I earned my bachelor’s degree. Then, without hesitation, I went straight into a master’s program in criminology, again with CCF’s support.

The Realities of Reentry and Education

Being a formerly incarcerated student is often misunderstood. The resources that make college possible—like technology support, transportation, stable housing, or even a hot meal—are barriers that can derail an education. Many people who pursue college after incarceration have spent years behind bars; technology has raced forward while they’ve been away. If you don’t know how to use Outlook or navigate a laptop, how will you turn in assignments on time? Some folks only have a phone to do all their coursework, and that’s not sustainable. Others live in shelters or face food insecurity, making studying nearly impossible.

I’ve seen too many people walk away from education because these basic needs were never addressed. In my own cohort of around ten formerly incarcerated students, only two of us reached graduation day. We lost bright, passionate people along the way—people who had the talent to succeed but not the support structures.

At many institutions, help stops once you get a foot in the door. “We got you into college, didn’t we?” they’ll say. But that’s just the first step. You need supplies, mentorship, tutoring, mental health support, and sometimes simple things like a granola bar to get you through a late-night study session. I’ve seen providers say they “don’t have the budget” for these extras, even though that extra support is often the difference between success and attrition.

Why I Joined the CCF Board

I decided to join CCF’s board for three main reasons. First, I believe deeply in the organization’s mission: to expand educational opportunities for justice-involved women. Second, I recognize that my lived experiences are invaluable to guiding policy and programming. And third, I saw firsthand where programs excel and where they fall short. Being on the board allows me to speak up about those gaps and work toward closing them.

CCF is special because it focuses on women, who are currently the fastest-growing segment of the incarcerated population. Our pathways back to society often look different than men’s, and we need programs specifically tailored to our experiences. That could mean providing resources for childcare, facilitating family reunification, or addressing trauma histories unique to women.

I told CCF early on during my board tenure: “You’ve carved out a niche, but there’s still more you can do. Higher education is evolving, and we need to evolve, too.” College might not be every person’s path. Some may choose vocational training or coding boot camps that lead to well-paying jobs without a traditional four-year degree. We want to be ready to support all of those journeys. Because at the end of the day, what matters is creating economic empowerment and sustainable independence.

A Holistic View of Success

Every time I see a justice-involved person falter because of a preventable obstacle—no meal plan, no laptop, no bus fare—it infuriates me. We can’t invite people into rooms where they have never been welcomed and then watch them fail because they lack the right tools. When we talk about leveling the playing field, that means more than just saying, “Sure, come in.” It means ensuring every participant has a fighting chance to stay in the room and thrive.

I do this work so that no one else has to survive the kind of hardships I did. I want to ensure we aren’t creating more “Skips”—people who struggle longer and harder than necessary because no one showed them the pathway to success. We need to open doors, and then keep them propped open with robust support so everyone who enters has a chance at completing their degree or training program.

Moving Forward, Together

Academically, I’ve come a long way. Right now, I’m completing my master’s in criminology with a 3.8 GPA. Not bad for someone who once believed a classroom wasn’t where she belonged! I’m proud of that achievement, not just because of the letters I’ll soon have after my name, but because it represents the power of possibility when people with lived experience step into leadership roles.

Some people ask me if I’m going for a PhD next. My answer is always a resounding yes. I’ve learned too much to stop now, and I still have more to contribute. Higher education may not have been part of my early life plan, but today I’m determined to keep expanding my skill set because each credential I earn is another tool I can use to advocate for others.

And one day, you will call me Dr. Skip.

A Message to Anyone Who’s Curious About CCF

If you care about empowering justice-involved women and creating real, transformative change, then supporting organizations like CCF should be at the top of your list. Everyone deserves the opportunity to learn, grow, and provide for themselves and their families. Women in particular often face compounded challenges, like trauma, childcare, housing instability. Together, we strive to fill in the gaps—from scholarships and academic counseling to career-focused training that meets people where they are. We’re learning that a one-size-fits-all approach doesn’t work, especially when every woman’s journey looks different. We celebrate the student who aims for a bachelor’s degree and the student who chooses a certification program leading directly to a well-paying job.

My story is just one example of what’s possible when an organization believes in the power of lived experience and invests in its people. If there’s a takeaway I want you to remember, it’s this: Don’t just open the door—show people how to walk through it, stay in the room, and eventually lead. That’s how we build a future that honors the resilience and talents of formerly incarcerated women and ensures they have the chance to flourish.

Thank you for taking the time to read my story. If you want to learn more about CCF, get involved, or donate, please explore our website. Your support matters.