I've been using Wordpress on various sites that I've maintained for probably the better part of a decade now. By most metrics, it's still very good blogging software; I'm not aware of any self-hostable alternative that can match Wordpress in terms of the union of ease of use, feature set and flexibility that it provides. That said, lately I've been feeling that perhaps Wordpress is no longer the right choice for my specific needs. These are my problems with it:

• It's not very good for sharing source code. There are a multitude of plugins available for syntax highlighting; the best of them seems to be Alex Gorbatchev's Syntax Highlighter, which is used by Wordpress.com and is also what I was using on my blog. But I've had problems with the Wordpress converting some of the characters in my code to HTML entities (e.g. & for & ) which are then printed literally by the plugin.
• I find that more often than not Wordpress' visual editor is insufficient for the formatting I want in my posts. That forces me to use the raw HTML editor. That would be fine, except that Wordpress has a strange sort of off-spec way of storing post HTML. Paragraph and line break tags are omitted in the editor and the database, and are added when the page is actually rendered to the client. This is okay, I guess, and I think Wordpress is smart enough to not insert extra paragraph tags if you do wrap your own paragraphs with them. Still, it leads to some unpredictability with regard to how a post with hand-written HTML will actually be rendered.
• A similar but worse problem occurs when you try to insert extra line breaks. Even if you're using the raw HTML editor to insert <br /> tags, Wordpress will just get rid of them unless you insert additional non-breaking spaces ( ) so that it thinks the lines are non-empty. But! If you switch back to the visual editor for any reason, even your &nbsp;<br /> lines will be wiped out. Even for "average" users I can't think of any situation in which this "feature" would be desirable. If I put a bunch of extra newlines into something I'm writing, it is because I want exactly that many newlines. I tend to not have much patience for software that thinks it's smarter than I am; that is why I still write most of my code in Vim and use hand-written makefiles in an age of IDEs.
• Never-ending updates. It seems like every time I log in there's a new update to download. Wordpress has updates down to a one-click install process, so this wouldn't be much of a problem except for the fact that every time I have to update Wordpress warns me that I should back up my database first. Why? Is there a significant possibility that the update might break everything? It's probably just a COA, and I back up my database daily anyway, but this whole aspect of Wordpress makes me uneasy and I don't want to have to deal with it any more. Even though I'm covered for backups, recovering from a botched update would undoubtedly be a nightmare.
• Vulnerabilities. One of the big reasons that Wordpress is updated so frequently is that it has a long history of security vulnerabilities, and more are still being discovered and patched. This also means that if I don't log in frequently enough to download new security patches, I'm at risk of having my site compromised, loaded up with malware and blacklisted by Google.
• It's written in PHP. PHP sucks. (I can't link to that enough.) I don't want to be dogmatic about technology choices; good software is good software regardless of what language it's written in, and my primary desire is always to use whatever is best for the task at hand. But lately I've been pretty vocal, both here and in person with friends and colleagues, about how bad PHP is. Continuing to rely on it undermines my credibility on the issue and makes me a bit of a hypocrite.

And while this might seem trivial or pedantic, it's actually one of the root causes of almost all of the issues above; the weird HTML handling, inappropriate entity conversion, and security issues are all due, at least in part, to bad design patterns popularized and perpetuated by PHP. Wordpress still uses raw non-parameterized SQL queries; blogging software built on a modern web framework with a proper ORM would not be plagued by SQL injection exploits as Wordpress has been historically and probably continues to be. - Wordpress supports themes so that you can customize the apperance of your site, but editing them kind of sucks, because they're all written in PHP instead of a proper templating language. Years ago I actually wrote a lot of PHP, but I still find Wordpress templates pretty ugly and difficult to understand; they seem more verbose than should really be necessary for what they accomplish, and have, on average, more <?php ?> sections than a keyboard has keys. (That analogy sucked. Sorry, it's late. What I'm trying to say is that there are a lot of them.)

So recently I got it into my head to switch over to Octopress. Octopress bills itself as "a blogging framework for hackers," which is an attractive description given my predilections. It uses Jekyll to generate static pages from a set of templates and content written in Markdown.¹ It is, without a doubt, harder to use than to Wordpress, but it has the following advantages:

• Rendering static pages once and serving dynamic content via AJAX is much more efficient than rendering entire pages dynamically for each visitor. This isn't really a concern for me because this is a very low-traffic site, and I have an entire quad-core VPS doing basically nothing besides serving this site. That said, it's nice to know that when I start doing other stuff on my VPS, I won't be contending for cycles with PHP and MySQL, so the site will always be very responsive. Plus, wow does the site load fast now (once you have that huge header image cached, anyway. I'll fix that soon.) Also not a huge concern for a blog, but I didn't expect the difference to even be noticeable, and it definitely is.
• Static pages significantly decrease the attack surface of the site; there is no database, so no SQL injection to worry about, and no scripts are being executed, so PHP vulnerabilities aren't a concern.
• Static pages means I get a nicely organized, easily navigable directory structure instead of God-awful rewrite rules.
• The default Octopress theme is very well designed and well-suited to customization. I was able to modify it to make it look almost exactly like my old custom Wordpress theme did, while retaining the fully fluid layout of the Octopress theme—meaning that the layout will resize to look beautiful at any screen resolution, including on mobile devices.
• Octopress has pretty nice built in Github and Twitter widgets.
• Comments are handled by Disqus, which provides a nicer comment system than Wordpress' built in comments. I was using Disqus anyway via a plugin, but now I don't have to worry about keeping the Disqus comments synced with the Wordpress database. Incidentally, Disqus provides a very nice system to migrate comments to new URLs by uploading a CSV file mapping old URLs to new URLs. They've really thought of everything, so props to them for providing a great service.
• All of the blog content is stored on my local machine, which means I can write posts in a disconnected environment using Vim, version control them with Git, and then push them to my server when they're finished. I have a nice deployment setup where everything is stored in a Git repository on the server and a post-commit hook copies the updated content to the web root for the blog subdomain. All I have to do is git push and the blog is instantly updated.
• Since Wordpress uses hand-written SQL queries, it is tightly coupled with MySQL and doesn't support any other database. PHP is similarly tied to Apache; while it's possible to run it with other servers, it's not particularly easy. By ditching Wordpress, I can also get rid of Apache, PHP and MySQL. This is nice since I was planning to use nginx and Postgres for my photo album project anyway.

Those are, give or take a few minor considerations, my reasons for switching blogging platforms. I'd be remiss to not mention that Octopress does have some noteworthy disadvantages even for "power users" to whom the above advantages might sound attractive. This post does a good job cataloguing a few of them. On the balance, though, I feel like it's a good choice for me, and although the switch took me considerably longer than I expected (the better part of an weekend where I'd expected an evening or so of work), I'm pretty happy that I did it.

In an upcoming post, I'll discuss the actual process of reconfiguring my server and importing all of my content (which is what I had planned to do before this turned into a 1,600 word diatribe against Wordpress.) For now, if I've inspired you and you're thinking about switching your own Wordpress site to Octopress, you can take a look at the ETL I wrote to ease the import process.