Having a philosophy degree holder in the family to give some inside perspective, this guy is doing it wrong. Philosophy degrees don't really stand on their own. They have to be paired with something else. Philosophy+education, philosophy+literature, philosophy+mathematics, philosophy+law. Those will all get you places.

Within the philosophy department at his university, they had an often shared joke that went, "How do you find a man with a philosophy degree? You sit down at a cheap restaurant and call, 'Waiter!'".