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Cassandra Grube
Cassandra Grube
00:27

Cassandra Grube

The Last Mile

Indianapolis, IN USA

"You know you, more than anything. If you really are just like, ‘I love what I do,’ that’s where you’re supposed to be. You’re meant to be there and everything else will fall into place."

Career Roadmap

Cassandra's work combines: Education, Technology, and Teaching / Mentoring

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Day In The Life

Classroom Facilitator

I teach coding and personal development, empowering incarcerated women to succeed after reentry into society.

02:14

Day In The Life Of A Prison Classroom Facilitator

My Day to Day

I check in with my students and we review their work from the previous week. After we say morning mantras, the students start their work. I'm available for them if they need additional resources, need to watch a YouTube video on a lesson, or if they need to talk about anything—that's where I come in.

Skills & Education

Advice for getting started

I turned down the position with The Last Mile twice before I actually accepted it. I didn't know how to code, so I didn't think I'd be able to help them. I really doubted my abilities. However, when I finally did accept the position, it was the best decision I could've made. Empowering women to rewrite their narratives has become my life's passion.

Here's the path I took:

  • High School

Life & Career Milestones

My path in life took a while to figure out

  • 1.

    Growing up as a military kid, I moved across the globe—from Seoul, Korea, to Germany, then the U.S.—learning adaptability early on​.

  • 2.

    I began my career in the medical department at a correctional facility but soon realized I wanted a more direct way to help incarcerated people​.

  • 3.

    A warden encouraged me to shift to education, where I started teaching basic business tech skills like Microsoft Word and Excel to inmates​.

  • 4.

    I became a site manager at a men’s facility, helping people in their 50s and 60s earn their GEDs.

  • 5.

    I transitioned to working with incarcerated women, where I was invited to teach coding through the Last Mile program.

  • 6.

    Stepping into the classroom, I embraced the challenge of teaching JavaScript and fostering personal development for women striving for reentry​.

  • 7.

    I found my purpose in empowering women to rewrite their narratives, celebrating every win—whether coding a website or overcoming self-doubt​.

  • 8.

    My passion for rehabilitation deepened, leading me to advocate for the expansion of the Last Mile program to more correctional facilities nationwide​.

Defining Moments

How I responded to discouragement

  • THE NOISE

    Messages from Myself:

    I can't help these women. I won't be good at this.

  • How I responded:

    I turned down the position with The Last Mile twice before I actually accepted it. I didn't know how to code, so I didn't think I'd be able to help them. I really doubted my abilities. However, when I finally did accept the position, it was the best decision I could've made. Empowering women to rewrite their narratives has become my life's passion.