"High paying salary" and "continues to fail" are contradictions and very unusual.
At a certain level how much money you make doesn't really increase our happiness (http://blogs.wsj.com/wealth/2010/09/07/the-perfect-salary-fo...). It's tough, without knowing him, to know what his real goals and desires are, but it seems to me like "make more money" isn't the answer.
tldr. 250K isn't that much these days when you factor taxes, child care, housing costs and student loan replayments.