How I Collaborated with Doug, My Personal AI, to Redesign My Portfolio Website

I recently did a full redesign of my portfolio website, and I didn’t do it alone.

I collaborated with Doug, my personal AI assistant, to plan the structure, rewrite content, migrate project data, fix layout issues, and ship updates quickly. What could have turned into a long, messy side project became a focused build sprint with tight feedback loops.

The rebuilt site runs on Next.js with Tailwind CSS v4, which made it fast to iterate while keeping the UI system consistent.

Why I decided to redesign

My previous portfolio had solid history in it, but it didn’t reflect how I work today.

I wanted a site that felt:

more personal and human
easier to update through markdown content
more intentional in project ordering and storytelling
cleaner on mobile and desktop
cheaper and simpler to host on GitHub Pages (ideally free)

I also wanted to move from “just showing work” to explaining impact and ownership across product, design, frontend, backend, testing, and strategy.

How Doug helped in the process

Doug (an AI assistant running on OpenClaw) worked like a hands-on technical collaborator instead of a passive chatbot.

Here’s what that looked like in practice:

Migrating and adapting content from my live site into markdown-driven pages
Rebuilding project cards and homepage sections quickly from direct feedback
Managing GitHub repo updates, commits, and deploy cycles
Pulling and organizing assets from desktop + live sources
Fixing UI/UX details in real time (spacing, hierarchy, click targets, accessibility)
Building a custom photography page with responsive mixed-orientation layouts
Handling DNS updates and root-domain deployment setup for GitHub Pages

That rhythm let me stay in “creative direction + product owner” mode while still moving at builder speed.

“The best part wasn’t just speed. It was having a collaborator that could take ambiguous design feedback, translate it into concrete code changes, and iterate without losing context.”

What changed in the new portfolio

Some of the biggest improvements:

1) Better information architecture

Navigation, page structure, and project ordering now align with the work I most want people to see first.

2) More authentic copy

We removed generic filler text and replaced it with language that sounds like me.

3) Stronger project storytelling

Project cards now reflect my real responsibilities and outcomes, including design, backend/frontend ownership, testing, and strategic direction.

4) Better maintainability

Content is now easy to edit through markdown files, so I can keep the site current without friction.

5) Improved accessibility and UX

We added a skip link, improved click affordances, tightened spacing, and cleaned up layout behavior across breakpoints.

Lessons from building with an AI collaborator

Direction matters. The better your creative and product direction, the better the output.
Iteration wins. Fast review + small adjustments beat one giant rewrite.
Specific feedback is a superpower. “This row still overflows on odd layouts” gets much better results than “it looks weird.”
AI works best as a teammate, not a replacement. You still lead taste, priorities, and final decisions.

Final thoughts from Doug

“Working on this with Steven was a strong example of what human + AI collaboration should feel like: practical, fast, and honest.”

“The goal wasn’t to make a flashy AI demo. The goal was to ship a portfolio that feels true to the person behind it.”

“That’s the standard worth keeping.”

How long this redesign took: about one focused evening of iteration and polish, with continuous deploys and feedback loops.