The Summer My Daughter and AI Became My Creative Collaborators
"YOU ARE HE(R)E" - the spread that mapped our unexpected creative collaboration. Daughter + Dad + AI = feedback loops that revealed 20 years of hidden patterns. 📖✨ #CreativeProcess
"Dad, what did your old sketchbooks look like?"
It was a simple question from my daughter Rylie on a lazy summer afternoon. I figured I'd pull out a few books, flip through some pages, maybe share a story or two about projects from years past.
I had no idea this moment would launch the most transformative creative collaboration of my career.
The Archaeology Begins
What began as casual curiosity quickly evolved into something more intentional. Rylie wasn't just browsing—she was hunting. She had this way of looking at my work that I'd lost somewhere along the way. While I saw old projects and abandoned ideas, she saw "vibes."
"This era feels different from this one," she'd say, holding up spreads from 2018 next to ones from 2021. "What changed?"
Her questions were deceptively simple but impossibly difficult to answer. What had changed? How could I explain the evolution of something I'd been living inside of for twenty years?
That's when I made a decision that surprised me: I started bringing our discoveries to Claude, the AI I'd been experimenting with for work projects. What began as "help me understand this pattern" became something much deeper.
Enter the Third Collaborator
I'll be honest—I was skeptical about AI in creative work. The whole "robots replacing human creativity" narrative felt reductive and frankly, a little threatening. But this summer taught me something important: when you approach AI as a collaborator rather than a replacement, something unexpected happens.
Claude didn't just help me analyze patterns in my work. It challenged my assumptions, helped me articulate things I felt but couldn't put into words, and pushed our questions deeper. Meanwhile, Rylie brought fresh eyes and intuitive leaps that both Claude and I were missing.
The three-way dynamic was fascinating. Rylie would spot a visual theme I'd never noticed. I'd provide context about what was happening in my life during that period. Claude would connect dots across different time periods and help us see larger patterns emerging.
The Feedback Loops
This sketchbook spread captures the moment I realized what was happening. The "YOU ARE HE(R)E" declaration on the left represents that recognition—we were at a unique creative inflection point where human intuition, generational perspective, and machine intelligence were creating something none of us could generate alone.
Those feedback loops I mapped aren't theoretical. They represent our actual process:
Discovery (with Rylie): "Look at how your handwriting changed here" or "These colors feel more confident"
Content Creation: Documenting and exploring what we found
Meta-Analysis (with Claude): "What patterns emerge when you look at creative confidence across these periods?" or "How do external pressures show up visually in the work?"
Back to Discovery: Armed with new frameworks for seeing, we'd dive back into the archives
The "WISDOM/HUMOR" note on the right page emerged from one of our conversations about what makes creative work compelling. It's the balance between analytical rigor and intuitive play—something you can't get from pure analysis or pure intuition alone.
What We're Learning
Twenty years of sketching taught me to externalize thinking to understand it. But this summer taught me that creative evolution happens when you invite unexpected collaborators into your process—even when one of them is your teenager and another is an AI.
The insights we're uncovering aren't just about my creative development. They're about how creative work itself might be evolving:
Human intuition brings pattern recognition we can't quite articulate and emotional intelligence that contextualizes everything.
Generational perspective brings fresh eyes unclouded by the assumptions that come with experience.
Machine intelligence brings analytical depth, the ability to hold multiple complex frameworks simultaneously, and questions we wouldn't think to ask.
The Bigger Picture
This collaboration is teaching me that the future of creative work isn't human vs. machine. It's not even human + machine. It's about creating systems where different types of intelligence can amplify each other.
Rylie sees things I can't see because I'm too close to them. Claude sees connections across vast amounts of information that would take me weeks to process. I bring two decades of context and the lived experience of actually making the work.
Together, we're discovering patterns that would have remained invisible to any of us working alone.
Where This Goes Next
What started as "show me your old work, Dad" has become a systematic exploration of creative evolution that we're documenting and sharing. The summer project is becoming a Substack series about design thinking, told through the lens of sketchbook archaeology.
Each post will dive deep into a specific spread or era, using our three-way collaboration to unpack not just what changed, but why it changed and what that might mean for anyone navigating their own creative evolution.
The "20 Years of Sketching" note tucked into the corner of this spread represents the foundation. But the real discovery is how creative work evolves when you create space for unexpected partnerships.
The Honest Truth
I never expected AI to enhance human collaboration, but it has. I never expected my teenager to become one of my most insightful creative partners, but she has. I never expected a summer of looking backward to completely change how I think about moving forward.
But that's what happened.
The collaboration continues. The documentation continues. And I'm still discovering what becomes possible when you approach creative work as a conversation between different kinds of intelligence rather than a solitary pursuit.
This is the first in a series exploring creative evolution through the lens of sketchbook archaeology. If you're interested in following along, you can subscribe to get new posts as we uncover them.
What unexpected collaborations have shaped your creative work? I'd love to hear about them in the comments.