I've added things like "topics" (sub-blogs based on links to a topic page) and "people" (ditto). A topic is a page and automatically shows (via ikiwiki inline) all the blog posts that link to the topic page. A person is also represented by a page, and similarly lists linking blog posts. Topics are usually using a meta link directive in ikiwiki, whereas people use a person/lastname.firstname link to achieve the same.
I wrote a little tool to make admining topic and person pages easier, and to easily add new blog posts and attach images or other files to the blog post. http://git.liw.fi/cgi-bin/cgit/cgit.cgi/jt/ has the code; I should probably write this up some day.
I've published some of my journal, related to one of my hobby projects. http://liw.fi/obnam/journal-dump/ if you're curious, though from server access logs I know nobody is.
I keep my journal private mostly so I can be more honest when I write. If I need to, I can be rude and impolite and use quite dirty language, which I wouldn't if I was writing in public. Also, some topics are private and nothing good will come from disclosing them.
So far my best answer is to do Jekyll, with every post 'published: false'. I like it because I can include LaTeX and probably even Lilypond.
Flaws are I haven't figured out easy photos, and haven't figured out how to journal from a mobile device.
I'd also like to encrypt my journal but I'm not sure how to combine that with git and searchability.
I have a capture template that automatically catalogs the entry to the right date. It comes up in a new window and I just write whatever I'm thinking. It works for me because it's so easy to hit C-c j when I'm doing anything at the computer and then I can write all I want. And if I want to make two entries on the same day, I can. The template has a little area for a title.
I've managed to journal a few times a week every week for over a year now.
Picked up from jrnl.sh. One text file per year. Single-line title starts with timestamp. No specific daily routine, just making an entry whenever I want to take notes. Usually plans or work log for personal projects.
What I like is the fact that I can just grep the whole thing to find relevant information.
I've been considering trying to put together an org-mode compatible mobile app that would support photos (syncing them to the same Dropbox folder), but that's tricky.
I guess you/we will have to find a compromise.