AI-Assisted Engineering Series

I've been building a habit-logging iOS app called ProjectDawn. Not because the App Store needs another habit tracker, but because I wanted a personal project that was genuinely mine and open source, and a project that can answer this openly: what does it feel like to build a real, modular, native iOS app with AI as a primary collaborator?

This post is part personal log, part technical retrospective. It covers the tools I used, what surprised me, where the AI fell flat, and the biggest shifts in how I think about building things now.

I’ve had the Umami + Ansible post in my head for ages, but it touched three different repositories and a whole bunch of code snippets. Totally doable, but undeniably tedious — which is why it kept slipping down the backlog. You can read the finished article here: Private Analytics With Umami, Docker Compose, and Ansible.

The idea that finally nudged it forward was simple: why not let GPT (Codex) do the heavy lifting while I steer?

For years, I thought of coding as something tied to my desk — Mac in front of me, full keyboard, full IDE. But recently, I found myself dreaming: what if I could carry my entire creative coding studio in my pocket? Not just SSH access, but a true AI-assisted environment where I could code, commit, and preview my projects anywhere.

This blog is half technical walkthrough, half personal reflection. It’s the story of how I explored Cloudflare Tunnel, discovered Tailscale, refined my workflow with tmux and iTerm, and ultimately unlocked the freedom of having a fully fledged Mac in my pocket.

Building small websites with GPT-5 Codex turned out to be less about typing code and more about collaboration. From crude sketches to polished sites, the model took on the heavy lifting while I guided direction and design.

Along the way I discovered both the joy of fast iteration and the limits of relying on an AI partner. These projects became less about the sites themselves and more about exploring a new style of programming — conversational, creative, and sometimes flawed, but always eye-opening.

Last month, my girlfriend mentioned she needed a sleek portfolio site, and I realized I’d been meaning to start a personal tech blog.

I wanted something lightweight—easy to spin up and even easier to tweak. So I dove in: building a small 11ty + Tachyons site from scratch, pushing every iteration live in under a minute, and watching her face light up with each update even though she’s halfway across the country.