After years of blogging across different platforms and technologies, I’ve finally found a setup that makes sense. My journey from manually crafting HTML files to embracing static site generation taught me valuable lessons about simplicity, ownership, and what actually matters when you’re trying to share ideas online.
The Humble Beginning: Text Files and HTML Templates
My first blog was beautifully primitive. I maintained a collection of text files on a server running in my parents’ basement, manually converting each post to HTML using templates I’d created. My daily routine involved RDPing to my home machine from work, writing posts in Notepad, then copying and pasting content into HTML templates before uploading files to my site.
This lasted about a month before I realized the obvious: there had to be a better way.
The Platform Migration Years
Like many bloggers in the mid-2000s, I bounced between platforms searching for the perfect solution. I started with MSN Spaces, moved to Blogger, and eventually settled on DasBlog for several years.
DasBlog was my first real breakthrough. Combined with Windows Live Writer, it created a workflow where converting thoughts into published posts became genuinely quick and easy. For the first time, the technology got out of the way and let me focus on writing.
After a while, I decided to join the WordPress migration that seemed inevitable for serious bloggers. I spent considerable time converting my DasBlog content, though looking back, I’m not entirely sure why I thought this was necessary.
The Jekyll Revolution: Back to Text Files
Then I discovered Jekyll, a static site generation tool that changed everything. Instead of managing databases and server-side applications, I could write posts in Markdown and let Jekyll generate clean HTML files.
I fell in love with this approach for several reasons. First, I could use my preferred editor (Vim) instead of web interfaces. Second, and more importantly, I could finally put my blog under version control. No more worrying about losing content or tracking changes—my entire blog lived in a Git repository.
The revelation was powerful: no backend database, no heavy infrastructure, just text files that generated a complete website.
I briefly considered Octopress, an enhanced blogging framework built on top of Jekyll, but ultimately stuck with plain Jekyll. I preferred the lighter weight system that I could control completely. Though if I were starting fresh today, Octopress might be worth exploring for its additional tooling.
My Current Setup: The Sweet Spot
Today, my blog lives as Markdown files in a private Git repository. Jekyll generates the static site, which I deploy to hosting. It’s beautifully simple and represents a full circle from my original text file approach—but this time with proper tooling and version control.
What I Learned About Blogging Technology
Through this evolution, I discovered what actually matters when choosing a blogging platform:
Speed matters most. The best blogging system is the one that gets out of your way. If the friction between having an idea and publishing it is too high, you simply won’t write.
Own your content. Platforms come and go, but files on your hard drive are forever. Having your posts in a format you control means you’re never locked into a particular service.
Version control is non-negotiable. Once you’ve experienced tracking changes, branching content ideas, and never losing work, you can’t go back to systems without proper versioning.
Simple workflows win. Complex publishing systems might seem powerful, but they often become maintenance burdens that discourage writing.
The Deeper Lesson
My blogging journey taught me something important about technology choices in general. The newest, shiniest solution isn’t always better. Sometimes the answer is going back to basics with better tools.
Text files were my starting point because I didn’t know better alternatives existed. Text files are my endpoint because I now understand they’re often the best alternative. The difference is that I now have proper tooling—version control, automated generation, and deployment pipelines—that makes the simple approach powerful.
Whether you’re choosing a blogging platform, a development framework, or any technology stack, the question isn’t “What’s the most advanced option?” but rather “What’s the simplest thing that accomplishes my actual goals?”
In my case, that turned out to be text files, a static site generator, and Git. Sometimes the best path forward is a thoughtful step backward.