Sentenced at 16, Free at Last: Cheryl Armstrong on 26 Years in Prison & Planting Purpose

“None of us are the worst thing that we’ve done in our lives. We get to wake up and choose the state of our mind every day. That’s going to completely change the entire course of your life.”

When Cheryl Armstrong walked into my studio for this interview, I was struck by her calm energy. Here’s a woman who was sentenced at 16 years old and spent 26 years behind bars. She could have become bitter. Instead, she became a two-time international bestselling author, keynote speaker, and founder of Plant Your Energy, a life skills and character development program that’s now being used in Colorado prisons.

Her story hit me hard because it’s a reminder that one terrible decision as a teenager can steal nearly three decades of your life. But it’s also proof that transformation is possible at any point.

The Night Everything Changed

Cheryl grew up in Colorado with a good family. Her parents divorced when she was two, but her stepdad stepped in. She had three older brothers who were military guys, tough guys. “I wanted to have that edge about me,” she told me. “I modeled their behavior as a teenager. It did not go well for me.”

At 14, they moved to a Denver suburb. Her parents ran a Mailboxes Etc. store downtown. She was alone a lot. Started smoking pot. Made friends who were ditching school. By 16, she was on juvenile probation, using meth, and dating a guy involved with rival gang members.

The crime happened fast. Threats were being exchanged. Her friends had guns. She drove them to the house. When she tried to drive away, they screamed at her to turn around. She did.

That was the moment. If she had kept driving, none of it would have happened. But she turned around. They ran inside. Two people died.

“I should have just kept going,” Cheryl said. “That’s the moment that’s been with me all my life.”

96 Years at 16

The courtroom sentenced her to 96 years. 48 years for each victim. The room erupted in applause.

“It was like some sick show,” she remembered. “But that was what I had created for myself.”

When Cheryl got to prison, she didn’t shrink. She dug into her worst traits. Embraced them. Ran her mouth. Challenged people. Built a reputation for having an attitude. “I was not the girl who got bullied,” she said. “I had such rigid boundaries. Stay away from me unless you’re in my tiny circle.”

But underneath all that armor was a broken 16-year-old who didn’t know who she was.

The Moment Everything Shifted

Years went by. Cheryl was miserable and taking it out on everyone, including her mother who visited every single week for 22 years.

Finally, her mom said: “If you don’t want me to come see you anymore, just say that. But you’re not going to keep talking to me like this.”

That woke Cheryl up. Her mom was the one person who loved her unconditionally. The visits were everything. So she enrolled in college classes. Started getting straight A’s. Found purpose in education.

“I was sick and tired of myself,” she said. “I was like, I cannot handle this anymore. But I didn’t know how to change it.”

She started reading Wayne Dyer, Tony Robbins. Noticed her patterns. Examined every ugly thing inside her. “Going through that process was almost as bad as going through my trial,” she admitted.

A friend with a life sentence said something that changed everything: “I’m kind to everybody and I feel like people respect me.” Cheryl realized her friend had real respect. She didn’t. She wanted that.

Earning Her Way Out

By 2016, Cheryl had earned a master’s degree. She spent eight years training dogs in prison. Facilitated Seven Habits of Highly Effective People. Ran circuit training classes. Taught others.

When Colorado’s juvenile sentencing laws finally changed, she was the first woman in the JCAP program. Three years later, she saw the parole board.

“I sat there in shock, just sobbing. 26 years almost to the day. I could finally just take a real breath.”

Building Plant Your Energy

Today, Cheryl works in peer support and runs Plant Your Energy, her life skills curriculum based on everything she learned transforming herself in prison. She pitched the program to the Colorado DOC and they greenlit a pilot immediately.

Girls who took her class have reached out after release to say how much it helped. That’s what it’s all about for her now.

“I want to reach back in, and even to people without a criminal background, and say: You can choose something different. You’re letting fear dictate the quality of your life. It doesn’t make sense.”

The Takeaway

When I asked Cheryl for her biggest lesson, she didn’t hesitate:

“None of us are the worst thing that we’ve done. We get to wake up and choose the state of our mind every day. That’s going to completely change the course of your life. Grasp the power in that. Even if it just means you’re a happier person, that in itself is a huge win. You have to take responsibility for who you are, the good and the bad. Sometimes more so the bad, because that’s what you need to change. That’s where real change happens.”

Cheryl Armstrong’s book, Plant Your Energy: Face Your Demons and Transform Your Life, is available on Amazon.