Why I’m Coaching the Machine
How I am rediscovering the joy of learning, building, and coaching — in tech and life.
For most of my career, I’ve helped organizations, especially in the public sector, tackle complex technology transformations. I had what many would call a dream job: leading high-impact programs that made a real difference across government and society.
And I still love that work — and continue to do it today.
But over time, I realized I was missing something: the hands-on experience of learning and creating.
I’ve always loved building things—systems, teams, strategies. But the more I led big projects, the more I moved away from the part of tech that first interested me: experimenting and making something useful. I tried to make space for that in my evenings and weekends, but the daily grind usually won.
So I made a decision.
I created the space to explore, learn, and experiment again—not instead of advising, but alongside it. I've learned that investing time in myself—learning, getting healthy, family, coaching youth sports, and now building with tech—is what makes me the best version of myself. This is the next step in that evolution.
Back to the Terminal
I didn’t just want to read about AI. I wanted to build with it. So I dove in—not as an expert, but as a student. I dusted off skills I hadn’t touched since university, opened a terminal, and started coding again.
It was intimidating at first—I hadn’t written real code since 2008. But with ChatGPT as my tutor, I started "vibe coding". I connected my learning to my love of sports, and soon, I was making working AI prototypes every few days. One prototype analyzes hockey skating videos & gave kids personal feedback. Another teaches kids baseball plays through guided AI questions.
I was hooked:
The joy of learning something new.
The pride of seeing something I built come to life.
The hope that maybe this could help someone.
What this Blog Is About
I’m calling this blog "Coaching the Machine" because that’s what it feels like I’m doing—guiding AI systems to reason, re-invent organizations, help kids to learn and play, and push myself to keep growing.
This is where I’ll share what I’m building, what I’m learning, and how I’m evolving as a builder, coach, and tech advisor. You can expect posts on:
Building with AI models, knowledge graphs, and reasoning agents
Lessons from 15+ years leading technology strategy and delivery — especially in the public sector
Coaching insights from youth sports, parenting, and endurance training
Reflections on making a bold (but thoughtful) mid-career shift
What’s Next
In my next post, I’ll share one of the first tools I built: a chat-based Baseball Tutor that teaches kids baseball plays through AI-powered guided questions. It started as a fun side project for my son’s team—and turned into something with a lot of potential.
If you're learning about AI, thinking about your next step, or just want to know how sport, systems, and software can work together—I'd love to have you join me.
Let’s build something meaningful. Together.