I can understand the job market concern but that is why you get them in easily covered locations.
I'm a consultant to some of the largest insurance companies in the world. None of my clients know or have seen my tatyoos. Its none fo their business.
as far as the "cool now" concern, thats why i have designed mine.
I don't think you should just go get anything. I think they should be images that hold importance to you personally.
It is also a way to connect to the person you once were. We all change though out our lives. I have always looked on my tats as ways to remember who I was and how I got here.
But then again, I'm wierd.