There are moments in life that seem almost impossible until you are living them.
The first time I entered the gates of FCI Aliceville, I arrived on a worn prison bus. Around my waist was a heavy black steel box with chains connecting it to handcuffs on my wrists and shackles around my ankles. Every step echoed with the sound of metal.
I believed I was beginning the next thirty years of my life.
This time, I was still wearing an ankle monitor, but almost everything else had changed.
Instead of arriving on a prison bus, I pulled into the parking lot in a rental car. Instead of being escorted through Receiving and Discharge, I walked through the front entrance, where I was greeted by the Warden and members of the executive staff.
I wasn't returning as an incarcerated woman.
I was returning as a Prison Professors Ambassador, a member of the Prison Professors team, and the founder of the Peer Success Team.
The contrast was almost overwhelming.
As I walked through the institution, memories flooded back. I remembered the uncertainty of my early years, but I also remembered the incredible culture we built through the Peer Success Team. Seeing so many familiar faces reminded me that leadership leaves a legacy. Programs evolve, people transfer, leaders come and go, but when a culture is rooted deeply enough in accountability and service, something of it remains.
One of the stories I wanted to share with the women was how Prison Professors became part of that culture in the first place.
When I was developing the curriculum for what would eventually become the Peer Success Team, I built workshops around each of the Eight Dimensions of Wellness. Emotional wellness, physical wellness, education, financial wellness, relationships, spirituality, purpose, and environment all had structure.
But when I reached the section on reentry, I stopped.
I didn't know how to write it.
The Bureau of Prisons traditionally introduces much of its reentry programming as release approaches. Having been sentenced to thirty years, I believed I still had another twenty years before reentry would become part of my own life. It wasn't that I didn't expect to go home someday. It simply felt like knowledge intended for a future so distant that I could barely imagine it.
That morning, sitting alone in my cell, I opened my journal and wrote one sentence:
“Find a structure for the reentry portion of the Peer Success Team.”
I closed my journal, walked out of my housing unit, and headed to work in the gardens.
Less than five minutes later, Amanda Young came running down the sidewalk calling my name. She caught up to me holding a workbook in her hand and said she thought I might want it.
The title was Preparing for Success After Prison.
Looking back now, I cannot help but smile at God's timing.
I thought I was looking for a curriculum.
What I found was a philosophy that would eventually change the way I served my sentence—and, years later, help change the trajectory of my life.
Michael Santos wasn't teaching people to begin preparing for release six months before walking out the gate.
He was teaching something much more powerful:
Prepare for success from the earliest possible moment.
That single idea fundamentally changed the culture we were building through the Peer Success Team.
From that point forward, reentry was no longer something waiting for us at the end of a sentence. It became part of how we lived each day.
Every journal entry could sharpen our awareness. Every biography could require us to look honestly at where we had been and intentionally at where we wanted to go. Every book could introduce a new way of thinking. Education could strengthen our skills. A release plan could begin years before release and evolve as we evolve. Mentoring another woman could turn experience into service.
Without realizing it at the time, we were learning to do what Prison Professors describe as becoming the CEO of our own lives: defining success for ourselves, setting meaningful goals, choosing our attitude, acting with intention, measuring our progress, and holding ourselves accountable for what came next.
We could not control our sentences.
But we could control what we did with the days inside them.
And Aliceville caught fire.
Prison Professors became woven into the culture of the Peer Success Team. We began running six-week Prison Professors content-development workshops on Saturday mornings in each housing unit, creating a rhythm that helped women move from simply hearing about the program to actually doing the work.
Week by week, they worked through the building blocks of a documented journey—defining success, developing biographies, journaling with purpose, writing book reports, strengthening release plans, and reflecting on the growth behind their accomplishments. Women who had already begun the process helped others get started, and the work naturally spilled beyond the workshops into conversations throughout the housing units.
At that time, Prison Professors was still a relatively small but growing community, with only six or seven hundred participants on the platform. There is a map in the Prison Professors Playbook from that period that shows institutional engagement by color.
Aliceville is deep purple.
The highest level of engagement.
I remember what it took to create that color.
It was not simply points on a leaderboard. It represented Saturday mornings spent doing the work. It represented women sitting together with notebooks and ideas, helping one another turn experiences into biographies, reflections, goals, and release plans. It represented a community beginning to understand that preparation for the future was not something we had to postpone until the end of our sentences.
Preparation became part of the culture.
Years later, returning to Aliceville as a Prison Professors Ambassador, I realized I had come back carrying the same message that had once found me on a sidewalk outside the gardens.
Only now, the movement had grown.
There were no longer six or seven hundred people building profiles through Prison Professors.
There were nearly 8,000.
The competition had become a lot stiffer.
I smiled when I told the women that, because I remember Aliceville in deep purple, and I know exactly what that community is capable of.
So I gave them a challenge:
Let's bring the purple back.
Not simply for a place on a map or a position on a leaderboard, but for what that color once represented—a community where women encouraged one another to write, reflect, prepare, document their growth, and take ownership of the lives they were building.
The field is much bigger now.
I expect Aliceville to rise with it.
The evening before my visit, I watched a video Michael recorded after attending a national conference. One message, in particular, stayed with me. He shared Alice Marie Johnson's remarks about the importance of institutional leadership when evaluating clemency candidates and the value of hearing from wardens and staff who have personally witnessed a person's transformation over time.
The next morning, standing in that room surrounded by Peer Success Team mentors, those words came back to me.
I looked out at the women in front of me.
These were not women waiting for someone to tell them how to change their lives. I knew what was happening in that institution. I knew about the workshops, the mentorship, the women stepping forward to serve, the problems being solved quietly every day, and the culture they continued to carry forward through the Peer Success Team.
Then I looked across the room at the executive staff.
And suddenly the significance of where we were—and who was in that room together—became impossible to miss.
I turned back to the women.
“You are sitting in a sweet spot.”
Then I gestured toward the executive staff.
“They already know the work you are doing.”
They did not need to be convinced that something meaningful was happening inside the Peer Success Team. Their presence in that room, their support of the program, and the fact that I had been invited back through those gates to stand there with everyone that day were evidence of something important: institutional leadership had seen the value of what these women were contributing.
“They see you. They know what you are doing. This program is proof that they are proud of and supportive of the work you do every day.”
For a moment, I wanted the women to recognize how powerful that position was.
Their transformation was not occurring somewhere beyond the view of the people around them. Their leadership, service, mentorship, and commitment to making their community stronger were unfolding in front of the very people who had the opportunity to observe their growth over time.
Now they needed to make sure that story could travel beyond the room.
Document it.
I could say that with conviction because I had lived the value of doing exactly that.
This is how I advocated for my freedom.
For years, I consistently documented my journey. I wrote about what I was learning, the goals I was pursuing, the work I was doing in my community, the programs I was helping to build, and the ways my thinking was changing.
No single journal entry told the whole story. No certificate proved transformation. No one accomplishment could capture years of growth.
But over time, those pieces accumulated.
They became a body of evidence.
When opportunities for advocacy eventually came, I did not have to reconstruct a story of transformation from memory or simply ask people to believe that I had changed. Years of documentation already existed. My record demonstrated consistency over time—personal growth, education, accountability, leadership, and a sustained commitment to community service.
That experience is why I believe there is no greater tool available to people inside prison than the ability to build and preserve a documented record of their journey.
Prison Professors give people a place to do exactly that while the transformation is happening.
Some of the women standing beside me in the photograph from that day are already demonstrating what this looks like.
Maureen Robbins, Sherida Nabi, Brooke Beckley, and Cleo Allen have earned places on the Prison Professors leaderboard while continuing their work with the Peer Success Team. They are documenting the work they do every day—the leadership, mentorship, service, lessons, challenges, and contributions that might otherwise remain visible only within Aliceville.
Their profiles allow that work to have a life beyond the moment in which it happened.
That is what I wanted every woman in the room to understand.
The work you do every day matters.
Build the record while you are living the story.
Write about the workshop you facilitated and what it taught you about leadership. Document the person you mentored and what the experience revealed about your own growth. Reflect on the certificate instead of simply collecting it. Write the book report and explain what you will actually do differently because of what you learned. Keep strengthening the release plan as your knowledge, relationships, and opportunities evolve.
And write about the setbacks too, because accountability is not a record of perfection. It is evidence that we can examine our choices, learn from them, and continue moving forward.
Over time, those pieces begin speaking to one another. They reveal patterns of action, consistency, service, and growth. They show what we value, how we respond to adversity, whether our daily choices support the future we say we want, and whether our commitment to growth survives long enough to become a way of life.
And now, something else has changed.
I explained to the women that Prison Professors have developed a tool that allows people connected to their journey—case managers, supporters, family members, and loved ones—to subscribe to their profiles and receive an alert each time new content is posted.
Think about what that means.
The work no longer has to sit quietly on a profile waiting for someone to discover it. As the record grows, the people who matter in a participant's life can choose to follow that growth as it happens.
What struck me most was something our team had shared with me: case managers have been among the strongest users of this feature.
To me, that signals an encouraging shift.
For years, incarcerated people have often felt that the most consequential parts of their identity were contained in documents describing the worst decisions of their lives. Yet here is a tool that can help the people working directly with them follow a different kind of record—one built entry by entry through reflection, education, accountability, service, and preparation.
A case manager does not have to see only what someone did years ago. They can also follow what that person is doing now.
That represents a powerful shift in the culture surrounding rehabilitation.
Transformation no longer has to be something a person simply claims at the end of a sentence. Through consistent documentation, it can become something others have the opportunity to witness unfolding over time.
And that is why documentation matters.
No one can predict who may someday read the record we are building. It may be a case manager or warden who has the ability to speak about our progress, an advocate helping us pursue an opportunity, an employer considering who we have become, or a judge or clemency decision-maker trying to understand the person behind an old conviction. It may be a family member witnessing our growth from a distance, or someone we have never met who is in a position to open a door we do not yet know exists.
We cannot know who will eventually encounter our work or when that moment will come.
That is precisely why the time to build the record is before we need it.
I know what it means for that moment to arrive and already have years of evidence behind you.
When I was incarcerated, I could not have known exactly how the record I was building would eventually be used. I could not have predicted that I would receive clemency, leave Aliceville years earlier than I once believed possible, join the Prison Professors team, and one day return through those same gates as an Ambassador.
I only knew to keep doing the work—and to keep documenting it.
That is why my message to Aliceville was not simply, “Get back on the leaderboard.”
It was:
Do not allow the evidence of who you are becoming to disappear with each passing day.
Document it. Build upon it. Let consistency give it credibility.
And when opportunity arrives, let the body of work you built over years already be waiting to speak for you.
That is the revival I want to see at Aliceville.
I have seen that institution deep purple before.
I know what that color represents.
And somewhere between the six or seven hundred participants we had known then and the nearly 8,000 profiles that exist today, Aliceville's voice had grown quieter.
I want it back.
The competition is stronger now. Thousands more people are documenting their journeys and preparing for opportunities they may not yet be able to see.
Good.
Let the competition be stiff.
I know Aliceville.
I expect them to shine.
We also talked honestly about reentry itself.
I reminded them that while they may have spent years growing, learning, healing, and becoming stronger, many of the people and circumstances they left behind have not necessarily shared that same journey.
That is why release planning must include independence.
You cannot build your future entirely on someone else's choices, promises, or stability.
Becoming the CEO of your life means preparing for the best possible outcome while also having the awareness to ask difficult questions. What if Plan A doesn't work? What if the person who promised housing changes their mind? What if the job falls through? What if the relationship you imagined returning to no longer fits the person you have become?
The Straight-A Guide teaches us that aspiration must be followed by action, and action must be measured through accountability. Reentry requires exactly that.
I could now tell the women something I understood differently from the other side of the gate: reentry is difficult under the best of circumstances.
Freedom brings extraordinary opportunity, but it also brings change, uncertainty, relationships that may no longer fit, unexpected setbacks, and the responsibility of making decisions in a world that continued moving while you were away.
That is why preparation cannot begin at the gate.
We must build the habits, skills, relationships, financial awareness, and multiple release plans that give us the ability to adjust when life does not unfold exactly as we imagined it would. Becoming the CEO of your life means preparing for the best possible outcome without assuming there will be only one path to get there.
True freedom requires autonomy, discipline, adaptability, and the courage to protect the identity we worked so hard to create.
One of the most meaningful moments of the day came when I saw my old Captain, Ora Mosby.
Years ago, she believed in the vision that eventually became the Peer Success Team. Before I left, she smiled and made me promise that her institution would be at the top of my list for future Prison Professors visits.
That conversation reminded me just how much had changed.
I was still on home confinement.
I was still wearing an ankle monitor.
I was still, technically, serving the same federal sentence that had brought me through those gates in chains.
Yet here I was, walking back through them as a professional representative of Prison Professors.
The significance of that moment was larger than my own story.
If someone still serving a sentence on home confinement could return to a federal prison as a Prison Professors Ambassador, welcomed back to encourage the very community I once lived among, then perhaps that return could become evidence of something we had been teaching all along:
We must prepare for opportunities before we know they exist.
That possibility had never occurred to me years earlier, when I sat in my cell and wrote one sentence in my journal:
“Find a structure for the reentry portion of the Peer Success Team.”
I could not see this day.
I could not have imagined that the search for a reentry curriculum would lead me to Prison Professors, or that the principles I discovered would become woven into the Peer Success Team and eventually into the way I prepared for my own future.
I certainly could not have imagined that years later, while still serving the very sentence that brought me to Aliceville in chains, I would walk back through those same gates wearing an ankle monitor—this time as a Prison Professors Ambassador.
I could not see any of that from my cell.
All I could do was take the next step.
That, to me, is the mission of Prison Professors.
We prepare before we know what the opportunity will be. We define success and work backward. We develop aspirations larger than our present circumstances, then connect those aspirations to action and accountability.
We document the journey while we are living it.
We build a record that allows our actions—not simply our intentions—to speak for the people we are becoming.
As I drove away from Aliceville, I wasn't thinking about being recognized as a success story.
I was thinking about responsibility.
Years ago, I believed I was writing a curriculum that would help other women prepare for release.
I never imagined I was also writing the blueprint that would prepare me for my own journey home.
And perhaps that is the most important lesson I could carry back through those gates as a Prison Professors Ambassador.
We do not prepare because we know exactly what the future holds.
We prepare because we don't.
The first time I crossed the gates of Aliceville, I entered in chains believing I knew what the next thirty years would look like.
Years later, I returned wearing an ankle monitor, greeted by the Warden and executive staff, carrying back the very message that had once changed my own life:
Do the work now. Document the journey. Prepare for opportunities you cannot yet see.
Because sometimes the future waiting for us is larger than anything we could have imagined when we began.