I’ve been writing to this blog for over 20 years, publishing nearly 600 posts spanning everything from FoxPro to C#, from Evernote to Obsidian, from testing practices to personal growth.
From two decades of writing and reflection came my book 20 Lessons in 20 Years of Blogging, where I share insights gathered along this journey. Check it out!
There’s something I’ve known for a while: my blog was a mess.
The Problem
Over time, I had built up a tangled web of tags and categories. Some categories had a single post. Some posts were assigned to multiple categories. About one-third of all posts were completely uncategorized. I even had overlaps like Testing as both a category and a tag. On top of that, many posts didn’t have any tags at all.
So, finding things was hard. Understanding my main areas of focus was hard. Even sharing relevant content with others took longer than it should have. I wanted a clean tag cloud that truly reflected what I write about.
The Goal
I needed a way to:
- Make tags and categories consistent.
- Understand what topics I write about most.
- Easily group and share posts by topic.
- Streamline the process so I could keep things tidy going forward.
The Plan
I turned to AI for help. Using ChatGPT, I started by exporting my blog’s data from WordPress — tags, categories, and post metadata. I fed it a prompt explaining my goals:
“You are a blogging specialist. My blog uses tags and categories inconsistently. I need analysis, cleanup recommendations, and automation to fix this.”
ChatGPT responded with a structured plan:
- Project goals and data extraction.
- Cleanup rules for tags and categories.
- Automation options.
- Next steps for exporting and analyzing posts.
That gave me the roadmap to begin.
From Analysis to Action
I worked iteratively with ChatGPT to identify tag frequency, category overlaps, and consolidation opportunities. For example:
- Merge Personal Growth and Personal Development.
- Remove tags used on only one or two posts.
- Keep categories under ten total, focused on the type of content rather than the topic.
The AI suggested a clean set of top-level categories:
- Software Development
- Testing and Quality
- AI and Productivity
- Career and Mentoring
- Improving and Community
- Personal Growth
- Newsletter Archive
- The Blank Page Podcast
That structure made sense, so I moved forward.
Automating the Cleanup
To handle the automation, I switched over to Cursor, an AI-powered coding environment. ChatGPT summarized the project so I could continue in Cursor, where it helped me write scripts for:
- Reassigning uncategorized posts.
- Cleaning up old categories and tags.
- Using the WordPress REST API to apply updates.
Cursor then built scripts that parsed the XML export from WordPress, ran posts through AI categorization (using LM Studio with a local model), and automatically reassigned posts based on confidence scores. High-confidence suggestions were applied automatically; low-confidence ones went into a CSV file for manual review.
Running the AI Locally
Running the models locally with LM Studio (using GPT-OSS) was a breakthrough — no API costs, full transparency. The AI processed each post, explaining its reasoning:
“This post reflects on blogging habits and tool preferences — categorized under Personal Growth (80% confidence).”
Seeing the AI’s reasoning helped me trust its choices. Out of 210 uncategorized posts, 182 were confidently assigned (85%+ confidence). The remaining 28 I reviewed manually.
Refining Tags
Once categories were clean, I moved on to tags. The AI generated per-category tag suggestions and automatically assigned 3–7 tags per post, based on context and confidence. For instance:
“This post showcases advanced C# LINQ usage — tags: C#, Refactoring, Patterns.”
After a final dry run, 517 posts had tags automatically applied with over 70% confidence.
The Result
Now my blog feels fresh again. Categories are tidy and meaningful. The tag cloud reflects what I published. Here are a few examples of new posts after the cleanup:
- Balancing Input and Output — tagged with habits, productivity, reading, reflection, time tracking. Perfect.
- Capturing the Human Side of Software with AI Tools — tagged with AI, Creativity, Reflection, Storytelling.
- BDD, but Not the Way You Heard It Before — tagged with bdd, communication, teams, testing.
Now I have the tools to continue maintaining my blog with minimal effort.
Looking Back (and Forward)
Funny enough, I found an old post from 2010 when I first moved my blog from Microsoft Live Spaces to WordPress. In that post, I wrote:
“I’ll go through my old posts and backfill categories soon.”
It only took 15 years.
This whole cleanup — nearly 600 posts — took just a few hours over a few days using today’s AI tools. Work I had avoided for over a decade finally became doable (and even fun).
The Takeaway
There’s probably something in your world you’ve been putting off because it felt like too much work — maybe an old project, or something you didn’t have time or skill for before. Now, with tools like ChatGPT, Cursor, and LM Studio (to name a few in a sea of options), you can revisit those ideas, automate the boring parts, and finally get them done.
🎥 If you’d like to see how this all came together, check out the complete video walkthrough.
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