When setting up the SSL certificate for workingninja.com, I made a mistake in my VirtualHosts configuration file that handled the redirect of the non-SSL site to the SSL site. The mistakes was simple: I forgot a trailing slash on the receiving end of the redirect. Without the trailing slash on the receiving end, http://workingninja.com/blog was redirecting to https://workingninja.comblog. The correct configuration (with trailing slash):
Redirect permanent / https://workingninja.com/
Because 301 redirects are cached by the browser, whenever I tried to hit workingninja.com/blog I would end up with my browser trying to go to workingninja.comblog. To fix this, I opened up "Web developer tools" and made sure that the option to "Disable Cache" was selected. This fixed the redirect issue until I closed out the Web developer tools pane.
The final solution was to dump my cache for the browser entirely. I was hoping for a solution with a bit more finesse but a cache flush every once and a while isn't too bad of a thing to do =)