I'm not sure this is exactly what Drekin was getting at, but a related question I've sometimes thought about is "How do you 'break in' to certain sets of careers that have certain hard to acquire skills as prerequisites?"
In NEW and in (forthcoming) OLD v1.2, standard run-of-the-mill humans have "Skill Choice: any." So I guess this problem is limited to NOW at the moment. And I don't know NOW enough to know how big a problem this is. Is it really the case that no Origin career provides the skill you need to take the career you want? It seems like they cover most if not all of the entire set of skill groups.