While there are pedagogic lessons to be learned from every line in the Torah, the lessons from Parashat Toldot are particularly straightforward. Rabbi Samson Rafael Hirsch wrote a powerful essay entitled "Lessons From Jacob and Esau" in which he analyzed the educational message of this story.
I first was introduced to this essay in an article by Dr. Joel Wolowelsky that appeared in Ten Da'at that is accessible at http://www.lookstein.org/articles/moral_ed.htm; I was reminded of it today when Professor Yitzchok Levine emailed me, suggesting that it be shared on Lookjed. He has posted it at http://www.stevens.edu/golem/llevine/rsrh/lessons_jacob_esau_col_vii.pdf
Here is an excerpt:
Down to our present day we have been able to observe the disastrous consequences of a one-sided approach to the unique task of being a Jew. Many a son of a pious talmid chacham has been totally lost to Judaism because his father insisted on training him to become a talmid chacham without considering whether his personality and inclinations truly lay in that direction. Thus he is exposed to Jewish life in only one context: that of a quiet existence of study and meditation for which he has neither talent nor desire. What attracts him instead is the busy, colorful life of the world outside. But as a result of the narrow view of life in which he has been trained he gets the impression that in order to participate in the active, variegated life for which he yearns, he must give up his mission as a Jew. He consequently abandons his Judaism in order to fling himself into the maelstrom of excitement and temptations offered by the world outside.
The story of such an individual might end quite differently if only, instead of forcing him into the mold of a talmid chacham, his father would raise him from the very beginning to become a man of the world who, at the same time, is faithful to his duties as a Jew; if only that father would teach this son that the activities of the world outside, too, have their place in God's plan, that it is possible to preserve and to demonstrate one's complete loyalty to Judaism even as a sophisticated man of the world. He should make his son understand that, as a matter of fact, many, if not perhaps the most important, aspects of Jewish living are intended primarily to be practiced amidst the conditions and aspirations of everyday life, in the midst of the world and not in isolation from it. He should make his son understand that the Taryag Mitzvos are not meant to be observed in the klaus [Judeo-German equivalent for a small synagogue. (Ed.)] or in the beth hamidrash but precisely in the practical life of the farmer or the public-spirited citizen. If only that father would make it clear to his son that the spirit and the happiness of Judaism are just as accessible to a Zevulun "in the world outside" as they are to an Issachar "in the tents,"—who knows whether that son might not stand by his father's deathbed and gently close his father's eyes as a loyal, pious Jew?
The above is from RSRH's essay "Lessons From Jacob and Esau" that appears on pages 319 - 331 of his Collected Writing VII. This volume deals with his thoughts on Jewish Education. For the rest of this most insightful essay on Chinuch, see http://www.stevens.edu/golem/llevine/rsrh/lessons_jacob_esau_col_vii.pdf