The Teacher Who Failed: How Setbacks Forged an Unbreakable Educator
If you’ve ever felt like giving up on a dream, a goal, or just making it through a tough week—you need to hear the story of Cherish Jackson.
When we think of inspiring educators, we often picture a natural-born teacher, someone who aced every test and walked into the classroom with effortless grace. But what if the most impactful teachers are forged not in success, but in repeated, brutal failure?
That’s the powerful and surprisingly vulnerable journey we explore in the latest episode of the STEAM Studio Spotlight. Our host, Russ Devereaux, sits down with the incredible Cherish Jackson, an educator whose path to the classroom was anything but straightforward.
A Hero’s True Origin Story
Cherish’s dream started with a deeply personal spark: her brother, who was born with autism. Seeing her family navigate that world ignited a passion in her to support students with disabilities. She enrolled in college, determined to become an educator. And then she hit a wall. Again and again and again.
For years, Cherish consistently failed the test required to get into her university’s education program. She took prep classes, bought the books, retook it, and even moved to a different state to try a new program—only to fail again. Imagine the mental toll of that. The voice in your head that whispers, “Maybe this isn’t for you.” Most of us would have listened. Cherish did not.
But here’s the twist: she eventually discovered she wasn’t failing because she didn’t know the material. She was failing because of her heart.
A Heartfelt Lesson
In a moment that will change the way you think about teaching, Cherish reveals the well-intentioned flaw that kept her out of the classroom: a “savior complex.” She explains how her instinct to immediately “fix” a student’s problem—to move a distracted child away from a sunny window, for example—was a disservice. True teaching, she learned, isn’t about saving students from discomfort in the moment; it’s about equipping them with the tools to navigate life’s distractions long after they’ve left your classroom.
Endure the Chaos
This episode is a masterclass in resilience, but it’s also a raw look at the beautiful chaos of education today. Cherish talks about throwing away the perfect planner, embracing the unpredictable nature of each week, and finding victory not in grand, sweeping gestures, but in the tiny, email-worthy triumphs—a student reading five more words than they could three weeks ago.
She shares unforgettable stories from her classroom, including the time a student told her she was a terrible teacher and how she turned that moment into a life-changing leadership opportunity for him—a story so good it’s still echoing through his school district years later.
Beyond the classroom, we get to know the whole person: the small business owner focused on mental wellness, the avid concert-goer, and the woman who lives by the mantra, “I just want to know that I was here.”
This conversation is more than a podcast episode; it’s a dose of perspective. It’s for anyone who has ever felt behind, for the parents who worry about their child’s progress, and for anyone who needs a reminder that failure isn’t a stop sign—it’s the most important part of the map.
So, if you’re ready to be inspired, to rethink what it means to truly help someone, and to hear a story of breathtaking perseverance, you know what to do. Press play on this episode. You’ll come away not just admiring Cherish Jackson but feeling a little more capable of eating your own bowl of chaos, one spoonful at a time.
