From homelessness and incarceration to CEO. One woman's empowering story of resilience and transformation.

Welcome to Own Your Ambition, the weekly newsletter designed to empower and give professional women the tools they need to be successful. As a former CEO who made it to the C Suite from an entry level, I know first hand what it takes for women to realize their ambition and reach their career goals.

Empowerment comes from many different sources. Sometimes, we find the strength and courage from within to stand in our power and own our ambition. Sometimes it’s an external source that inspires us to be the best we can be. Perhaps a mentor or role model.

This newsletter is a story of empowerment and resilience from the streets of San Francisco. It’s an intense journey from the depths of despair and helplessness to one of rising above life’s struggles and owning one’s talent.

I hope this story will inspire you to rise above what holds you back from reaching your potential to living a full life and owning your personal power.

Jessica Nowlan’s story began on the streets of San Francisco’s Tenderloin neighborhood, an area of the city known for its high crime rate, drug use, and homelessness. There, as a young girl, Jessica experienced living on the streets, life in the underground economy, and being incarcerated seventeen times. A young woman caught up in a cycle of violence, poverty and incarceration, her experiences not unusual for many marginalized women and girls.

Approximately 582,462 people in the U.S. are homeless, with more than a quarter of those women, some with children. Nationwide, women make up about 34% of the homeless population.

As of 2022, women make up roughly 10% of the total incarcerated population in the U.S. with about 88,000 in state and federal prisons and about 93,000 in local jails.

Breaking the cycle of homelessness and incarceration is extremely difficult. With just a 7^th grade education, Jessica not only broke out of the homeless trap, she founded Reimagine Freedom, with the goal of using her story to empower and inspire others.

The turning point?

Jessica knew she had the power to turn her life around when she was hired directly from juvenile detention by the Young Women’s Freedom Center (YWFC), paid double minimum wage, giving her the opportunity to escape the underground street economy. It was then that for the first time, she was in an environment that didn’t just see her struggles or blame her for them but recognized her potential.

YWFC introduced her to a community of poor, mostly Black and Brown women, girls, and trans young people who had lived through similar circumstances. Together, they began to develop a powerful political analysis of the systemic issues impacting their lives, building an organization that would be a safe haven and launching pad for their collective power. California Congresswoman Lateefah Simon, who was YWFC’s Executive Director and Jessica’s supervisor, earned a MacArthur Genius award for her work leading and building YWFC as a 19-year-old Executive Director. By then, Jessica had been promoted to Deputy Director of the organization.

Jessica left YWFC to pursue entrepreneurship and searched for other organizations that shared a commitment to creating true pathways to power for people who had been through society’s hardest trials. But too often, she found that many organizations operated through a charity model—focused on “helping” rather than empowering, offering services while simultaneously criminalizing people for being poor, victims of violence, women, or trans. Frustrated by the lack of true investment in people’s growth and leadership, Jessica set out to make a change.

“Women and girls and gender-expansive people don’t need saving but investment.”

This understanding became Jessica’s life work: creating opportunities for these individuals to build skills, advance their leadership, and develop solutions born of their lived expertise.

When YWFC needed a new leader, Jessica returned as Executive Director, and over seven years, she led a remarkable transformation. She built an organization on the brink of closure into a nationally recognized movement, growing the team from 3 to 75 people and increasing the budget from $500k to $15 million! Under her leadership, YWFC expanded beyond San Francisco across California, launched the Sister Warriors Freedom Coalition with over 10,000 members, developed the Beloved Village housing project, and ultimately led a group of 500 women who have experienced the worst of what society has to offer in the drafting of the Sister Warriors Freedom Charter—a vision for systemic change based on self-determination, justice, and community. Jessica did all of this while living in public housing, raising kids on welfare, and even starting a small business of her own to help support her family.

The Sister Warriors Freedom Charter became the north star for Jessica’s next chapter, ReImagine Freedom. At ReImagine Freedom, Jessica aims to build the infrastructure to make the Sister Warriors Freedom Charter’s vision a reality, things like a right to be free from violence, to have basic access to medical care, to be treated with dignity, to take care of their children, and to have the right to economic opportunities. ReImagine Freedom is an engine of empowerment dedicated to creating sustainable pathways like small business opportunities and more for women, girls, and gender-expansive people to thrive.

Jessica shared her story with me. “My journey has been long and full of twists, with many pivotal moments along the way. The most significant one was being hired by the Young Women’s Freedom Center at 17. I was hired directly out of incarceration, paid double minimum wage, and told that my personal experiences—trying to survive on my own on the streets—were not something to be ashamed of but instead a source of power.

Another major turning point was starting my entrepreneurial journey. My goal was to become a millionaire—not because I wanted to be rich, though I didn’t want to struggle forever—but because I wanted to become a philanthropist who could fund programs to interrupt cycles of poverty, build community wealth, and decriminalize women and girls. At the time, I didn’t know what I didn’t know. That period of my life was incredibly hard and intense, but I learned so much.”

“I believed if I just worked harder and did more, I could crack the code.”

“While I didn’t immediately break my cycles of poverty and struggle, I was propelled forward in transformative ways—lessons I could only fully appreciate in hindsight. Even though I had a political analysis of poverty, meritocracy, capitalism in the U.S., and the falsehoods around ‘pulling yourself up by your bootstraps’, I still internalized those narratives about myself. I believed that if I just worked harder and did more, I could crack the code. This was during a time when Silicon Valley was pouring vast investments into tech startups. Co-working spaces were everywhere, and you could sit in a coffee shop next to someone building the next unicorn startup. I thought I could do the same thing. What I didn’t take into account was that I lacked formal training. I was a college dropout—not from Stanford, but from a semester at Laney College after getting my GED, following a formal education that ended in 7th grade. I had no family or personal networks in finance or business. In contrast, I was a single mom who had just left an abusive relationship. I was living in Section 8 housing with a slumlord landlord, and my only income was cash aid and food stamps. After leaving the coffee shop, I wasn’t going home to a safety net—I was returning to a precarious reality. There have been many turning points, but these moments propelled me forward when I felt stuck in survival mode. They helped me shift my focus from merely navigating systems and violence to envisioning real possibility and change—not just for myself, but for my community.”

Using my personal story to empower others.

“For a long time, I struggled to see how my personal story could inspire or empower others. I had the rare privilege of working in deep community with women who had similar experiences. We had all learned to survive some of the worst conditions, so it didn’t feel extraordinary—it was just our reality. We always recognized each other’s brilliance and strength, even when we couldn’t yet recognize it in ourselves.

Before I found my voice, I couldn’t yet imagine what I could do, though I somehow knew I was more than my circumstances. As I grew in leadership over the past decade, it has been humbling to realize the impact I can have. I believe the primary duty of leadership is to develop and uplift emerging leaders, opening doors for them. Now, I understand what it means for people to see themselves in me—it allows them to imagine new possibilities for their own lives. It’s not just about getting into different rooms or scaling our work. It’s about how I show up. Some of the most transformative moments in my life have come from my mentors and heroes. It’s wild to think that the girls I grew up with on the streets of San Francisco are now leading movements, making change, and lifting others up.”

I discovered the power of my own voice

“The first time I felt the power of my own voice was at 17 or 18 when I was newly hired at the Young Women’s Freedom Center. My supervisor at the time—now Congresswoman Lateefah Simon—was probably only 19 herself. She brought me to San Francisco City Hall for a public meeting on the incarceration rates of girls in the city. She elbowed me to get up and speak, and when I hesitated, she called me out in front of everyone, lifting me up next to her. She said, ‘We need to hear from this young woman, Jessica Nowlan—maybe the only formerly incarcerated young woman in the room. I was terrified, but I spoke my truth. I remember all these powerful people listening to me. That moment was transformative. It was the first time I found my voice, and over the years, I came to understand just how powerful we—the people closest to the problem—truly are. I realized it is our duty to stand up, speak the truth, and lift up our voices. Another transformative moment was when we launched the Sister Warriors Freedom Coalition. We were frustrated that our experiences were always sidelined, even though we bore the brunt of mass incarceration, the war on drugs, and the war on poor people.

We gathered in Oakland to answer one question: How are women and girls criminalized? If we could understand our own experiences, we could create solutions. Over 200 women, girls, and trans folks came together that day. Elders in their 70s and 80s sat beside 14-year-olds. Leaders like Lateefah Simon, Susan Burton, Topeka Sam, and Andrea James were there. We read letters from women serving 25-to-life sentences. Some women had just come home after decades in prison. We held our babies in our laps, and we sat in a circle. That day, we created the Sister Warriors Freedom Charter—our collective vision of freedom. There’s a video of that moment where Lateefah says, “This is our church.” And it was. That room was filled with hope and power. It was our collective brilliance and our ancestors’ prayers coming to life. That was ten years ago, and everything we’ve built since stems from that day.”

The systemic issues that cause this crisis for women.

“The crises facing the women and girls we work with are rooted in racism, patriarchy, gender-based violence, and poverty. These forces don’t just exist in theory—they shape and constrain our lives daily, keeping us one step away from crisis. Families have been systematically torn apart, and women—especially Black, Brown, and poor women—have been criminalized simply for trying to survive. Violence is a constant factor.

Since 1996, I have worked with over 40,000 directly impacted women, and 100% of them have experienced physical or sexual violence—whether from family members, partners, in their communities, or at the hands of police, prison guards, and the foster care system. Economic opportunity remains scarce, especially for those who are unstably housed, navigating violence, or trapped in survival relationships. We see it time and again: as women and girls begin to stabilize, find their voice, and build personal power, the violence in their lives often escalates. The women, girls, and trans folks we work with have always been the backbone of our families and communities.

As the U.S. built the world’s largest prison system and waged the "war on drugs," it wasn’t just men being incarcerated—women and girls were also swept up, criminalized, and left to hold everything together. That reality still persists today. But we refuse to be erased. We are organizing, building power, and creating a new future—one where survival is not criminalized and where every woman and girl can thrive.”

The solutions

The solutions are clear, and in many ways, we've been implementing them for years. The answers to these complex issues have always existed in our communities, and the proof is in the leaders who came through the Young Women’s Freedom Center. They built community, personal strength, and collective power. ReImagine Freedom exists to scale what we already know works: deep investment in the leadership, economic power, and collective brilliance of directly impacted women, girls, and gender-expansive people. We don’t need saving—we need resources, power, and ownership.

We’ve seen what happens when you invest in young women like the Young Women’s Freedom Center did for me. Look at the leaders who came through this work:

Lateefah Simon—my first supervisor at 17, now a Congresswoman.

Marlene Sanchez—locked up at 15, now leading the Ella Baker Center for Human Rights.

Julia Arroyo—homeless at 11, incarcerated, now leading the Young Women’s Freedom Center.

Amika Mota—formerly incarcerated, now leading a policy team of formerly incarcerated women fighting sexual violence in California prisons, and Sister Warriors, with a robust electoral program that involves endorsing impacted people from the ground as a strategy to change laws. Lateefah Simon was their first congressional endorsement.

There are countless others. We are not the exception—we are the outcome. This is what happens when we invest deeply in women and girls from the margins. We transform our own lives, change the circumstances of our families, and go on to transform our society. This is a powerful strategy with lasting impact.

We know what happens when we stop trying to “save” people and instead equip them with the tools they need to transform their lives, their communities, and our society.

Through ReImagine Freedom, we’re scaling this model. We're supporting the powerful work that’s been happening on the ground for the past 30 years, and we’ll never stray from that core work. At the same time, we're expanding our impact, focusing on shifting narratives and telling the story of what’s possible when we invest in women and girls.

We’re working to change society’s thinking and spread that message far and wide. We’re also building economic power and creating real pathways to economic freedom because none of this is possible without true access and opportunities.

I realized that I was powerful, had everything in me already, and had gifts to bring to the world. This is the model we scale through ReImagine Freedom. We meet people where they are and work with them over time to find their voice, realize their power, and build collective power. We create beloved communities and invest deeply in their leadership. We recognize our experiences as expertise to transform the structural conditions that keep us stuck in cycles of poverty, exploitation, and incarceration, and we create access and opportunities toward economic freedom. How we have survived the worst conditions in our society has forced us to develop a combination of complex problem-solving skills and resilience. While we do not glorify resilience, we recognize this as a core building block and a highly transferable skill.

This foundation allows people to dream about what’s possible, passions emerge, and we support them along the way to increase their skills and leadership, empowering them to show up powerfully in the world.

Imagine the possibilities if, across the nation, women, girls, and trans people who have experienced the worst parts of society receive this kind of investment.

What would they dream?

What would they create for all of us?”

What’s your biggest takeaway from Jessica’s story?

Leave me a comment.