I've had Ben Werdmüller's post "What you're proud of" marked as unread since he posted it almost two weeks ago:

"I wish resumés told a story. I want to know the narrative of a person. The why is often more important than the where. Not why did I take this job?, but why do I make the decisions I do? What motivates me?
And most of all: what am I really proud of?"

I last had to update my CV almost three years ago and I hated it. I always hate it. It's such a false, fabricated representation that everyone knows is false - we just accept it as the norm and look for a few key words to establish some relevance to the role being applied for.
We make a big fuss about competency (rightly so) and want to ensure that someone will be be a good fit for the team (equally as important) but are not set up to demonstrate this beyond a few crappy questions in interview that are likely to have rehearsed "best fit" answers.
I've conducted at least a couple of dozen interviews (as one of the interviewers not the interviewee) over the past couple of years and they always go better when veering off script, when just talking and trying to get a feel for the person rather than ensuring they tick the boxes for the scoring system.
Ben goes on to say:

"I wish there was a place where I could read the story of a person. Everybody's journey is so different and beautiful; each one leads to who we are."

Blogs are (or should be) "the story of a person" if written well but it is not practical to trawl through the archives to see the bigger picture.
I was mulling this over until Chris Aldrich commented:

"Forget the ‘Now‘ page, or even the ‘About’ page, this sounds like the type of thing every personal website should have."

And that's such a good idea!
Whether it needs to be a separate page or could be incorporated into the About page doesn't really matter, but having something to more easily tell your story and what you're proud of would be so useful.
Conversely, some kind of "Failure Resumé" - those moments you're not so proud of and how you've dealt with them - could reveal more about you than you realise. (H/T Patrick Rhone)