Our investment follows our educators regardless of what they do afterwards. I do think that less educators would re-train if they had more financial security in their chosen profession.
Going into even more debt for a second degree is a dangerous decision. I'd hope that they retrain for a career that at least has the potential for paying them a wage that would make them financially independent. I know too many people in my generation who didn't take such prosaic economic considerations into account until it was too late, and are staring down the barrel of a couple hundred k in student loans in their late twenties.