Grit, Grace, and GPT
Recovery and Rediscovery in Midlife
Welcome to My Story (and Maybe Yours)
Hi, I’m Kerry Draper.
I’m 59. I’m in college. I’m in recovery. I’m neurodivergent. I’m a father. I’m a former VP in the software world. I’m a GED graduate. And I’m just getting started.
This Substack isn’t polished or pretentious. It’s not an expert's guide to anything. It’s a lived story—one I’ve never fully told until now.
If you've ever felt invisible or arrived too late...
If you've ever felt broken...
If you’ve climbed the steel stairs of humiliation, stepped into classrooms built from shame, or hid in closets constructed from judgment—I'm writing this for you.
This is the story of how I rebuilt my life—piece by piece, chapter by chapter—through luck, grit, grace, and the strangest twist of all: artificial intelligence.
AI didn’t just help me learn; it made learning joyful again, rekindling my curiosity and lighting paths I never knew existed. Through AI, assignments became adventures, mistakes became discoveries, and learning became an act of smiling defiance against a lifetime of doubt.
Wherever you are in your own story—struggling student, weary parent, compassionate teacher, someone bravely recovering, or simply feeling you've missed the boat—this space is for you. Let’s rebuild something lasting together.
💔 The Wreckage
My early life was a maze of fear and shame. School was a relentless nightmare, a daily walk through humiliation. I vividly remember those brightly painted mobile trailers sitting isolated in the school parking lot—special ed classrooms that separated me from everyone else. Every morning, climbing those cold steel stairs felt like an ascent into a world that reminded me I didn’t belong. Band class brought another lesson in isolation: relegated to a tiny closet crowded with instrument cases, I practiced alone, hidden away to spare others from my mistakes. In that dimly lit closet, I learned less about music and more about shame.
Despite it all, I stumbled into a successful tech career, driven by brute determination, self-teaching, and pretending I belonged. But then came September 22, 2006—the day my 16-year-old son committed a horrific crime. In a single moment, everything shattered. I quit my job, lost over a million dollars, fell deeply into addiction, and nearly lost myself completely.
✨ The Turning Point
After multiple stints in rehab, I finally found sobriety in November 2022—and that's when everything started to change.
I earned my GED.
I started college.
One night, exhausted and overwhelmed with college work, I hesitated to ask my professors questions, afraid they'd see through my façade of confidence. Instead, I discovered something remarkable right at my desk: artificial intelligence. Tentatively, I typed my questions into ChatGPT, expecting judgment. What I received instead was astonishing—patient explanations, endless encouragement, and something I'd rarely experienced before: genuine clarity.
AI became more than a tool; it became a companion who didn't care that I was neurodivergent, in recovery, or in my late 50s. It met me exactly where I was, gently guiding me toward understanding, rekindling my curiosity, and returning joy to my learning.
🌉 The Bridge
AI became my bridge—between past and future, confusion and clarity, who I was and who I’m still becoming.
AI didn’t see labels; it saw potential. Assignments turned into joyful journeys, questions became explorations, and side trails were delightful detours of discovery. AI reminded me that true learning isn’t about merely grasping facts—it’s about connection, laughter, and the joy of every small triumph.
With AI’s help, I began to dream again, realizing I could author my own next chapter filled with clarity, connection, and countless smiles.
🎯 What This Series Is About
This series is part memoir, part manifesto, fully dedicated to anyone who believes it’s never too late to start again.
I’ll be sharing:
· Personal stories of trauma, resilience, recovery, and the power of second chances.
· Reflections on education, the transformative potential of AI, and how they can empower nontraditional, neurodivergent learners.
· My ongoing college journey—unexpected discoveries, joyful adventures, and hard-earned insights.
· Honest thoughts on justice, purpose, and building a meaningful future.
Whether you're a struggling student, a parent navigating complex loss, a teacher seeking deeper connections, bravely recovering, or someone simply feeling you’ve missed the boat—this space welcomes you.
🛠️ Coming Soon
· Chapter 1: School Was My First Trauma
· Chapter 2: The Day My World Collapsed
· Chapter 3: Connection, Recovery, Rehab, and the Wild Idea of College
🙏 Thank You for Being Here
I don’t know exactly where this story ends, but I deeply understand why I’m writing it.
Because we need honest conversations about the courage it takes to rebuild. Because education must evolve. Because second chances matter. Because AI doesn’t need to replace us—it can empower and accompany us, turning learning into a joyful journey.
If any part resonates with you, please subscribe, share your experiences, or simply stay awhile. Let’s rebuild something meaningful together.
Thank you for joining me—you’re now part of this story.
Post Discussion: Google Gemini
Author’s Note 🖋️
This essay was shaped in collaboration with ChatGPT, my steadfast writing partner. Any wisdom is shared; any errors are human.