In the latest Figure/Ground interview, Luciano Floridi has the following to say about deciding to become an academic:
In the humanities, and especially in philosophy, I would strongly urge the student to reconsider the choice. The positions are so few, the competition so high, the sacrifices before obtaining a permanent job (tenure) so many and tough, that pursuing an academic career looks unreasonable when, with half the brain and efforts, one would get a much better chance of enjoying the handful of decades at one’s disposal. So the advice is: do not do it, unless you absolutely cannot help doing it, in which case no advice is necessary anyway.
Not such a positive outlook.