Molly Oliver

I definitely attribute my success to God—along with a lot of hard work, perseverance, and the willingness to walk through doors that opened while accepting, with humility, when others closed. From a young age, I was deeply inspired by Mother Teresa. I remember reading about her life and her work, and those stories stayed with me, shaping how I understood service, compassion, and purpose. While people often ask, “What would Jesus do?” for many years I found myself asking, “What would Mother Teresa do?”

Just as importantly, I recognize the role of mentors and support systems along the way. Although I grew up in a dysfunctional home, I was fortunate to have several adults—teachers, community members, and mentors—who saw potential in me and encouraged me to imagine a life beyond a small town in Indiana. They challenged me, believed in me when I didn’t fully believe in myself, and helped guide me toward opportunities I might never have pursued otherwise. Their encouragement made a lasting difference and continues to influence how I try to show up for others today.

The best career advice I’ve ever received was to slow down when an opportunity presents itself—to explore it, sit with it, and avoid making rash decisions. An opportunity may be a door that won’t open again, or it may be a door that leads somewhere entirely different—and even better—than you expected. Taking the time to reflect has helped me recognize when to step forward, when to pivot, and when to trust that growth sometimes comes through paths I hadn’t originally planned.

I would tell young women entering this field that empathy and accountability can—and should—coexist. Too often, this work is approached with a rigid tone, but real impact comes from taking the time to understand people as individuals rather than reducing them to their background or past mistakes. When you come alongside someone, listen to their story, and see their humanity, you’re not only better able to help them—you’re also protecting yourself from burnout. Leading with compassion while maintaining clear expectations creates stronger outcomes for everyone involved.

One of the biggest challenges in my field is funding—it’s a constant reality for nonprofit organizations. Beyond that, the individuals we serve face significant barriers when reentering society. When someone is released from jail, they are often quite literally released with no clear plan, limited resources, and little support. Access to housing, transportation, employment, and basic stability is often lacking, leaving many people vulnerable to being left behind before they’ve even had a chance to restart.

Employer stigma remains another major challenge. While progress has been made and more employers identify as “fair‑chance,” there is still a disconnect between intention and action. We frequently see individuals apply for jobs, only to be excluded once their background is disclosed. At 2nd Chance Indiana, we’ve participated in studies comparing the work performance of justice‑impacted employees to those without criminal records, and the data consistently showed no significant difference. In some cases, individuals who had spent longer periods incarcerated actually demonstrated stronger performance and commitment than their counterparts.

Despite these challenges, the opportunities in this field are powerful. There is a tremendous opportunity to change how we view people with criminal backgrounds—not as risks, but as individuals with potential. This work allows us to build more inclusive communities, strengthen the workforce, and meaningfully reduce recidivism. As one of my team members often says, when people get out, they have to go somewhere—so the real choice is whether we want individuals cycling back into incarceration or contributing to society through stable employment.

Building community and connection is one of the strongest protective factors against returning to jail. This field offers an opportunity to go beyond words and truly put values into action. Justice‑impacted individuals represent a largely untapped talent pool, and employers willing to invest in them often gain dedicated, resilient employees. For me, that’s not just an opportunity—it’s a responsibility.

My personal and professional values are deeply rooted in my Christian faith, which shapes how I approach people, leadership, and challenges. At the core of that faith is a belief that every person deserves dignity—regardless of who they are, where they come from, or what they’ve done. While offering grace and respect isn’t always easy, I believe we were all created by God with inherent worth and purpose. That belief guides how I show up in my work and reminds me to see the humanity in everyone, even in the most difficult moments.