I see some problems here but it doesn't seem quite as intractable as Alicorn suggests.

If your beliefs are highly correlated with those of your teachers then you need to immerse yourself in the best arguments of the opposing side. If you notice that you are not changing your mind very often then you have a deeper problem.

To give a few related examples. One of the things that gives me confidence in my major belief structure is that I am an Atheist Capitalist. But, as I child I was raised and immersed in Atheist Communism. I rejected the communism but not the Atheism. At least in the small set my parents/early teachers were only 50% right in their basic belief structure and that doesn't sound too unlikely.

On the other hand I have been troubled by the extent to which I have become more sensitive to liberal arguments over the past 2 years. My social and professional circle is overwhelmingly liberal. It is unlikely that this does not have an effect on my beliefs.

To compensate I am attempting immerse myself in more conservative blogs.

Now of course there is no way to be sure that the balancing act is working. However, if we take as a starting point that errors among well informed people are randomly distributed then as a rough approximation your adherence to the beliefs of your community should be proportional to the number of intellectuals who hold those same beliefs.