A coworker had recently moved her family blog from WordPress to Octopress. I already migrated from Google Sites to Blogger to Tumblr, ugh! I was fed up and wanted to control my content and own my own platform.

I use Ruby for Windows, the Ruby DevKit, and PowerShell. You do not need a Ruby version manager to install Octopress. There is no great alternative for Windows users, anyway. You can get these all setup and configured using Chocolatey. If the DevKit is not properly installed and configured, bundle install will fail to build certain gems.

Deploying to GitHub:Pages was not fool-proof. Your GitHub user page is just a repository called <username>.github.io. GitHub then knows that it should render any index.html in the root of that repository. If you create the wrong repository and try to visit the address, you’ll get a 404.

Octopress’s Rake tasks for configuring, generating, and deploying your site are generally ok. However, the setup task, rake setup_github_pages, asks for your “GitHub Pages repository URL”. That means the SSH URL, the one that start with git@github.com. If you enter the wrong URL, you get a useless Rake error.

I plan to continually edit and expand posts. So, I removed the date portion of the post permalink resulting in permalink: /blog/:title/. I don’t intend to enable many widgets, I think text is the future of the web ;)