First, how did we get here? As I proposed in my previous post, in order to cram more learning into a fixed number of years of schooling, information compression is essential. We have to abstract, generalize, distill and quite frankly omit details that once were deemed fundamental knowledge every educated person should have.
But there are limits to how much compression is possible. A 128 kilobit per second mp3 file sacrifices music quality, as the compression drops below 64 kbps the song quickly becomes unidentifiable. Similarly, we may never be able to teach advanced computer science to babies in order to make way for later learning that builds upon that knowledge.
After approaching the limits of compressibility, we need other strategies. Like specialization.
Given a fixed number of years of instruction, specialization in a particular subject can sacrifice breadth in favor of greater depth. That's the fundamental information theoretic reason why the idealized liberal arts education is fading away. Put simply, there's just too much to know for a generalist to reach the forefront of any given field without sacrificing depth in another.
To answer the question I posed in the title, yes, specialization is at odds with the ideal of a well-rounded education, and perhaps they are irreconcilable.