Cheryl Armstrong

Cheryl Armstrong is a life‑skills educator, distance‑learning coach, and justice‑impacted leader whose story of transformation has inspired audiences nationwide. Sentenced at just 16 years old, Armstrong spent 26 years incarcerated, an experience that shaped her deep commitment to personal development, accountability, and purpose‑driven living. Her powerful journey has been featured on national platforms, including the Nightmare Success In and Out podcast, where she shared how discipline, intentional mindset work, and radical ownership helped her rebuild her life from the inside out.

Today, Armstrong is a two‑time international bestselling author, keynote speaker, and founder of Plant Your Energy, a personal‑growth initiative focused on helping individuals cultivate self‑awareness, emotional resilience, and sustainable life change. Her work centers on the belief that no one is defined by the worst thing they’ve done — and that every person has the power to choose a new mental state, rewrite their narrative, and create a future rooted in clarity and purpose.

Armstrong’s coaching approach blends trauma‑informed practice with practical life‑skills development, guiding learners through mindset shifts, emotional regulation, healthy decision‑making, and personal accountability. She is known for her ability to connect authentically, speak truth with compassion, and help individuals confront the internal barriers that keep them stuck in cycles of fear, addiction, or self‑defeating behavior.

As Advisor for Life Skills & Distance Learning at Ben Free, Armstrong brings her lived experience, teaching expertise, and transformational coaching framework to help shape curriculum that empowers system‑impacted individuals. Her leadership ensures that Ben Free’s life‑skills and distance‑learning programs remain grounded in dignity, emotional growth, and the belief that change is always possible — no matter where a person begins.