At milestones, I update a mindmap of my strengths, weaknesses and interests.
I've just quit what I expect to be my last job ever as an employee. That probably counts as a milestone.
So, here's the latest mindmap: [embiggen]
Sadly, it looks as if the company that made my mind-mapping software is now defunct. The lesson: if you back up your on-site backup with a remote backup, make sure you back up /Applications.