Ask HK: When do you know it is time to reinvent yourself?

I would say, as most of the times: "it depends". In terms of career, I like to think I reinvent myself constantly until I gather enough experience or capital and, arguably more important, convince myself that I can be that new me. This step is usually the visible one for the people around me, but in my mind I have already moved on by then. I doubt that just feeling bored would push me to this unless it would happen over a very long period of time.