Leanne Gillespie: Finding Inspiration in the Transformation of Young People

In celebration of Women’s History Month, the Center for Improving Youth Justice (CIYJ) proudly presents the remarkable story of Leanne Gillespie. Born in Melbourne, Australia, Leanne’s journey is a testament to resilience, compassion and an unwavering commitment to fostering positive change. Let’s delve into her transformative experiences and insights throughout years of work within the justice system.

A Journey of Resilience and Determination

Leanne’s upbringing in Melbourne and later Hawaii shaped her into the formidable advocate she is today. Despite facing challenges as a Caucasian, blonde newcomer with a distinctive accent, Leanne’s academic struggles and passion for athletics fueled her drive to succeed. “My mother was a Special Education Teacher and is a strong woman who always instilled in me that I could do anything I set my mind to.  When others thought I couldn’t do something, it made me work harder to prove them wrong.  I earned a bachelor’s degree in psychology at Swinburne University in Melbourne, and a master’s degree in Criminal Justice Administration at Chaminade University in Honolulu.  During my bachelor’s degree, I often worked transcribing psychological assessment reports and answering a suicide crisis line.  Both experiences were very eye opening and brought about a sense of compassion and need to help others.  Originally, I set out to become a child psychologist, but after watching Jodie Foster in Silence of the Lambs, I knew my future was somewhere in the field of criminal justice.”

From Adult to Juvenile Justice:

With nearly three decades of experience in adult criminal justice, Leanne’s transition to juvenile justice might seem surprising at first glance. “Honestly, I’m a bit surprised to be here (in December 2022, Leanne was named Executive Director of Hawaii’s Office of Youth Services).  I’ve worked in adult criminal justice for almost 30 years, working in jails, prisons, as a probation officer, and a parole officer.  I’ve worked mainly in sex offender management, prison re-entry and Americans with Disabilities (ADA) implementation and compliance.  Nearing the latter years, the work really started to wear me down.  Every time I walked into an adult prison, all I could think about was the unfulfillment of human potential and it overwhelmed me with sadness and failure – failure not only of the system, but of my life’s work to help people.” However, a growing sense of unfulfillment in adult prisons led her to explore the transformative potential of working with young people. Inspired by conversations with youth justice colleagues centered on compassion, care and potential, Leanne embarked on a new path dedicated to preventing young people from entering the criminal justice system. “I started to reach out to my juvenile justice colleagues to discuss their work and the youth and families they worked with.  The conversations were inspiring as they were always discussions encompassed in compassion, care and potential.  At first, I didn’t believe it, but as I had more and more conversations, I realized that this is where I needed to be to effectuate meaningful changes in both the system and in young people’s lives.  Change that would prevent them from entering into the adult system.”

Moments of Inspiration and Reflection:

Throughout her career, Leanne has been inspired by the young people and families navigating the youth justice system. Witnessing their positive choices and changes reaffirms her belief in the transformative power of compassion and support. Each day brings new opportunities to be inspired and to inspire others, driving Leanne’s commitment to her work.

Advice to Aspiring Women:

For young women starting their careers, Leanne offers timeless wisdom: Listen, work hard and seek out strong positive role models. Drawing inspiration from her own mother, a beacon of strength, independence and resilience, Leanne emphasizes the importance of learning from those who embody the values and qualities we aspire to emulate. Leanne continues to be inspired most by her own mother stating, “My mom is an amazingly strong, hardworking and independent woman who has made many sacrifices so that I can have the life that I have now. She still travels the world and lives life to the fullest.  I can only hope to be able to do the same.”

As we honor Women’s History Month, Leanne highlights the importance of sharing stories and experiences to inspire future generations of women in the youth justice field. By recognizing and celebrating the adversities, accomplishments and compassion of women like herself, we pave the way for a more inclusive and equitable future. Through her transformative experiences and insights, she inspires us to listen, work hard, and uplift one another as we strive to create a brighter future for justice-involved youth.

Kapiolani Kassal is the Communications Director for the Center for Improving Youth Justice. She has over 10 years of experience in various aspects of the Communication & non-profit industries. Kapiolani has her Bachelor's in Communications, Management, and Design from Ithaca College and her Master's in Television Producing from Boston University. Prior to working at CIYJ, Kapiolani worked as the Communications Administrator for MIT's Introduction to Technology, Engineering, and Science. She's had a passion and enthusiasm for the justice industry for as long as she can remember and is excited to be able to dive in as CIYJ celebrates the 20th Anniversary. In her free time, she loves playing social sports, attending weekly trivia, going to the theatre, and hanging out with her dog, Gatsby.

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