Rebuilding keithposehn.net
A Human + AI Creative Collaboration
// 24 design iterations, 2 days, 1 very patient AI
The Problem
My personal site had become a ghost town. Built on Jekyll with a basic template, every update felt like a chore. No CMS, no AI integration, and a Ruby environment that broke more often than it worked. Content had stagnated since 2023.
The irony? I work with AI every day, yet my own site was stuck in 2015.
The Experiment
What if I approached a site redesign as a genuine creative collaboration with AI? Not just “generate me a website” but an iterative, conversational process where I could push, challenge, and be surprised?
The rules were simple:
- Be honest — Tell the AI what’s working and what isn’t
- Push boundaries — Ask for things that might not work
- Stay curious — Let the process surprise me
The Journey
Round 1: Finding Direction
The first batch of iterations explored different vibes: Explorer (adventure/discovery), Growth Rings (organic/evolving), and Thinker (philosophical/contemplative). These were interesting starting points—thoughtful, but perhaps too safe.
Round 2: Back to the Drawing Board
Nothing from round two quite landed. I asked Claude to push the envelope and “surprise me!” Sometimes the best creative direction comes from explicitly asking for boldness.
Round 3: Terminal Tugs at My Heartstrings
This is where things got interesting. Terminal hit something deep—the developer aesthetic I’d been unconsciously craving. Lab Notes brought a scientific curiosity that resonated with my values.
I pushed further: “Show me what you can do.” And I asked to dial up the humor around my core values: curiosity, understanding, and growth.
Round 4: Now We’re Cooking
The gloves came off:
- Code Review — A literal code review aesthetic, complete with a Monaco editor feel. Meta and clever.
- Debug Mode — Hilarious debug output as design. Error messages as personality.
- Peer Review — Academic paper vibes with marginalia and citations.
- Mycelium Network — Organic networks and interconnected ideas. Beautiful and weird.
Round 5: The Synthesis
I asked Claude to take the best of Terminal and Debug and see what emerged. The results included Logbook (ship’s log aesthetic) and Annotated (scholarly notes in margins).
But Syntax was the clear winner. It combined:
- The terminal aesthetic I loved
- Debug-style humor and personality
- A command palette (Cmd+Shift+P) with easter eggs
- Tab-navigable autocomplete navbar
- Dark mode by default (obviously)
The Tech Stack
The rebuild wasn’t just visual—it was a complete platform change:
| Before | After |
|---|---|
| Jekyll (Ruby) | Astro (TypeScript) |
| No CMS | Keystatic CMS |
| Manual deploys | Cloudflare Pages |
| Basic CSS | Tailwind CSS |
| No AI | Claude-assisted everything |
Key technical wins:
- Keystatic for content that’s actually editable
- Cloudflare Pages with instant deploys
- YouTube sync that auto-imports from @ItsTheKeith
- Command palette for power-user navigation
- 24 preserved iterations at /iterations
What I Learned
On AI Collaboration
The magic wasn’t in the first response—it was in the conversation. Pushing back, asking for more, saying “surprise me” and meaning it. The AI got better as I got more specific about what I wanted emotionally, not just functionally.
On Design Iteration
Seeing 24 different visions of the same content was revelatory. Each iteration revealed something about what I actually valued. The Terminal theme resonated because it’s honest about what I am: someone who lives in the command line.
On Personal Sites
Your personal site doesn’t have to be “professional.” It can be playful, opinionated, and weird. The .env.local easter egg on the homepage? The fake debug output? The command palette that lets you trigger Matrix rain? That’s the stuff that makes it mine.
Timeline
Day 0: The Before Times (2020-2023)
The site existed on Jekyll—a Tumblr import from 2020 that I’d occasionally update when I could wrangle Ruby into cooperating. Last meaningful content update: August 2023.
Day 1: The Rebuild Begins
January 9, 2026
- Scaffolded Astro + Keystatic + Tailwind
- Generated 12 initial design iterations
- Added 6 more after pushing for bolder ideas
- Added 6 more after asking for “developer aesthetic”
- Built the Syntax theme from Terminal + Debug DNA
- Added command palette with easter eggs
- Migrated all pages to the new theme
Day 2: Polish & Launch
January 10, 2026
- Fixed mobile responsiveness (iPhones are picky)
- Added projects section (you’re reading it!)
- Fixed Keystatic CMS integration
- Added YouTube subscribe links
- Cleaned up legacy content issues
- This very page you’re reading
See the Full Journey
All 24 design iterations are preserved at /iterations.
Favorites worth exploring:
- Syntax — The winner
- Terminal — Where it started clicking
- Debug Mode — Pure comedy
- Code Review — Meta and clever
- Mycelium — Beautiful and strange
- Peer Review — Academic vibes
This project is ongoing. The site will continue to evolve, and I’ll keep pushing the boundaries of what a personal site can be. If you made it this far, we should probably talk.