Rebecca Schuman has written an entertaining piece about the impossibility of the current academic job market for Slate. Using the context of a family member with a PhD, she describes in excruciating detail the trials and tribulations of looking for an academic position. Parts of the piece are a bit overstated, but overall it is certainly close to the reality. Check it out. The conclusion, advice for talking to job-searching relatives in academia, sums up the article nicely.
You don’t have to be sympathetic about the life choices of a relative who’s a struggling early career academic—chances are she regrets them enough already for the both of you. But if you’re trying to help—or at any rate not actively trying to wound—when it comes to academics looking for jobs, it’s best to limit the conversation to a nice, light topic. I suggest religion. Or abortion. Or the inevitability of climate change. Anything but the job your relative very possibly will never get.