Planting Hope: A Journey From Prison to Purpose with Cheryl Armstrong

Meet Cheryl Armstrong, a remarkable individual whose journey embodies the power of resilience and transformation. After being incarcerated at just 16 years old and serving 26 years in prison, Cheryl emerged with a renewed sense of purpose and determination. Her remarkable achievements include earning a Master’s Degree in Humanities, founding the Plant Your Energy organization dedicated to inspiring others in need, and authoring the empowering book, “Plant Your Energy: Face Your Demons and Transform Your Life.” Through her unwavering perseverance, Cheryl has not only overcome immense challenges but has also become a beacon of hope for countless others seeking to overcome adversity.

In this emotionally charged episode, Cheryl sits down with Christina to discuss her sentencing, time spent in the correctional system, her inspiration for completing her education and starting her company while incarcerated, and many other reflective topics.

Cheryl’s narrative weaves together themes of resilience, forgiveness, and the pursuit of personal growth no matter what challenges you face. From her early struggles to her current endeavors in promoting positive change within the prison system, Cheryl’s story serves as a testament to the transformative power of self-reflection, education, and the relentless desire to obtain a purpose-driven life.

Rehabilitation and Reinvention

Cheryl Armstrong’s story is one of remarkable transformation and redemption. At just 16 years old, she found herself sentenced to 96 years in prison for her involvement in a crime that resulted in two deaths. Despite her troubled past and reckless behavior, Cheryl didn’t let her circumstances define her future. During her time in prison, she pursued education relentlessly, earning associate, bachelor’s, and master’s degrees while also becoming a leader within the prison system.

After 26 years behind bars, Cheryl was released and has since dedicated her life to helping others transform theirs. She now focuses on giving people second chances and advocating for rehabilitation and reinvention. Despite the difficult journey she has been through, Cheryl’s story serves as a powerful reminder that it’s never too late to change and make a positive impact on the world.

A Gradual and Purposeful Transformation

Cheryl’s journey from being an angry, troubled teenager to becoming a leader within the prison system is a story that inspires. Despite facing a nightmare scenario at just 16 years old, Cheryl’s determination to turn her life around helped her to write a new story.

Despite the initial shock of being incarcerated and facing immense challenges—including spending eight months in segregation in a tiny, insect-infested cell—Cheryl found ways to take ownership of her life while in prison. With the support of her family, especially her mother, Cheryl began a gradual transformation when she decided to pursue education while in prison. Initially, she felt resistant and saw no point in it, but eventually, she found purpose and enjoyment in her studies. Over a span of 14 years, Cheryl earned her associate’s, bachelor’s, and master’s degrees—all while incarcerated.

Throughout her journey, Cheryl defied stereotypes and found respect among her peers in prison. Taking college classes marked a turning point, as she began to be seen in a more positive light. Although she initially felt uncomfortable with the idea of being seen as a leader, Cheryl gradually embraced her role and realized the impact she could have on others. Despite the daunting prospect of spending decades behind bars, Cheryl persisted, pacing herself and focusing on personal growth and purpose.

Through self-reflection and a commitment to personal growth, Cheryl recognized that her circumstances didn’t define her character or her potential to make a positive difference. She saw education as a tool for transformation and took full advantage of opportunities to pursue her degrees while incarcerated.

A pivotal moment came in 2016 when Cheryl completed her master’s degree amidst personal tragedy and significant legislative changes regarding juvenile sentencing. She became the first woman accepted into the Juveniles Convicted as Adults Program (J-CAP), which provided a pathway to potential freedom for those sentenced as juveniles.

Although she faced challenges and frustrations within the program, Cheryl remained determined to seize every opportunity for a chance at a better future. She found solace and purpose in training dogs and even began contemplating starting her own business, demonstrating her unwavering commitment to growth and resilience.

Planting Her Energy

Christina and Cheryl discuss Cheryl’s journey towards preparing for life outside of prison and the inception of her business, Plant Your Energy. Despite uncertainties about her release, Cheryl was determined to be ready for any opportunity that came her way.

With the goal of living her best life, Cheryl channeled her energy into positive pursuits, including starting her own business. Plant Your Energy began as a concept focused on mindful living and a positive mindset, embodied in t-shirt designs with uplifting messages. Cheryl wanted to share her experiences and encourage others to realize the power of their choices and the importance of living with intention.

This drive for personal growth led Cheryl to write her book, “Plant Your Energy: Face Your Demons and Transform Your Life,” which serves as both a memoir and a guide for personal development. With practical exercises at the end of each chapter, Cheryl aims to help readers confront their own obstacles and unlock their full potential.

After her release in March 2021, Cheryl wasted no time in bringing her vision to life. She published her book, developed a curriculum, and pitched her program to key decision-makers, laying the foundation for the next chapter of her journey.

The Healing Power of Grace and Forgiveness

At the age of 16, Cheryl entered prison and spent 26 years behind bars. There was a stark contrast between life inside and outside the prison walls—the world saw many changes during her incarceration. Although she had worked hard, earned multiple college degrees, and developed an entrepreneurial mindset, Cheryl encountered anxiety and uncertainty as she navigated basic tasks like using a debit card or pumping gas

With the unwavering support of her mother, Cheryl found her footing, publishing her book and learning essential life skills. However, tragedy struck when Cheryl lost her mother and stepfather within months of each other, leaving her to learn to live without her biggest supporter.

Amidst the challenges, Cheryl found solace in reconciliation with one of the victim’s cousins, who forgave her and recognized the positive impact she was making both inside and outside the prison system. This forgiveness became a source of healing and validation for Cheryl, allowing her to move forward with a renewed sense of purpose and gratitude.

Resilience in the Face of Adversity

Even among recent challenges, Cheryl continues to demonstrate resilience in the face of adversity. She opens up about the struggles she’s encountered in her journey since leaving prison, including the loss of her mother and stepfather, navigating new relationships, and facing unexpected setbacks in her career.

Despite these obstacles, Cheryl reflects on her determination to make a positive impact in the world, particularly through her work in behavioral health and her efforts to create educational opportunities for incarcerated individuals. She shares her vision for expanding her program beyond prison walls to help people from all walks of life overcome their struggles and lead fulfilling lives.

Her unwavering commitment to her mission shines through even amidst personal tragedy, serving as a testament to her strength and resilience. Her story reminds us of the power of perseverance, compassion, and the ability to find purpose even in the darkest of times.

Breaking Cycles and Creating Positive Change

Cheryl’s story is one of incredible fortitude, requiring grace, forgiveness, and a growth mindset.

When asked where she sees herself in 10 years, Cheryl responds with unwavering determination and ambition. She envisions herself as hugely successful, aiming to become a motivational speaker and expand her business on a massive scale. Her ultimate goal is to transform the lives of hundreds of thousands of people, transcending limitations and leaving behind a positive legacy.

Through continued challenges, grief, and growth, Cheryl remains committed to honoring those she’s hurt and elevating herself to new heights. Christina offers her heartfelt support and well-wishes to Cheryl, acknowledging the impact she’s already making in breaking cycles and creating positive change in the world.

Watch the full episode here: