I have discussed this question several times before. Here is my short answer. By all means, go to graduate school in philosophy, but only if you satisfy all of the following conditions.
1. Philosophy is your passion, the one thing you think most worth living for.
2. People in the know have advised you that you have philosophical aptitude.
3. Your way is paid in toto via fellowship including tuition remission or else you are independently wealthy. No student loans!
4. You are willing to live for 10-12 years, minimum, before relaxing with tenure. (I began grad school in '73 and received tenure in '84 = 11 years.) You will be under a fairly high degree of pressure during that decade or so, including such stressors as: living on a meager income as a grad student, writing a dissertation, earning the doctorate, landing a tenure-track position at a school where there is a real chance of getting tenure, surviving the tenure review.
5. You are willing to chance jumping though all the hoops, and then not get tenure, in which case you are no longer young somewhat damaged goods who may have to re-tool career-wise, or accept a lesser position. I know a philosopher who failed to get tenure at the University of Hawaii and had to take a job in Toledo, Ohio. It was a full-time philosophy position, but Toledo ain't Honolulu. It is easy to go up, hard to go down.
6. You understand that, if you do get tenure at Cleveland State, say, then you are stuck there for the rest of your career unless you are unusually talented. Tenure is a boon and a shackle, 'golden handcuffs' if you will. The security is purchased in the coin of a reduction of mobility.
7. You understand that the humanities are in trouble, the job market is bad, and that competition for tenure-track positions is ferocious.
In sum: if philosophy is your passion, you are good at it, have an opportunity to pursue it for free at a good school, and would not consider the years spent in grad school wasted if no job materializes — then go for it! Live your dreams! Don't squander your self for pelf!
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