Haskalah (Jewish Enlightenment) is a one-generation phenomenon. A maskil (an adherent of the Enlightenment) has certain characteristics: he is male, he comes from beis medresh (traditional house of learning), and he has learned Talmud on a high level. Somewhere along the way (usually when a teenager), he becomes exposed to secular knowledge through translation into Hebrew from German, Polish, Russian, etc. On his own, a maskil never attends a university and his knowledge is rather unsystematic once he begins to question Jewish belief. In Eastern Europe, maskilim directed their ire to the mystical belief systems of the Hassidim. Their children will not be maskilim any more in the strictest definition. Instead, their children go to universities and strike new paths out of the community and traditional learning. Though waves of maskilic thought occurred between 1810-1870, and each generation was affected, the trajectory of the maskil was largely the same.
Take the example of Isaac Bär Levinsohn (aka Ribal): he has a classic maskil biography. He is known as “the Russian Mendelssohn.” Born 1788 in Kremenets, Ukraine, a Hassidic stronghold and later a center of the haskalah. The Hassidic orientation of Kremenets in his youth makes the fact that he is a maskil very hard for him. He is emotionally unstable at times. He writes a tract published in 1828 – Teudah B’Yisroel (Testament Amongst the Jews). In it, with great erudition, he writes in both a biblical and rabbinic style. He claims that if a person really understands Torah Talmud, they would understand that there is no discrepancy or conflict between traditional Judaism and haskalah. He argues that Jews in Eastern Europe should speak the language of the land and uses himself as an example, since he had mastered the Russian language on his own and had become something of an autodidact in Hebrew philology. Levinsohn argues for educational reform for Jews: more Hebrew language and the study of the Bible – and does so in a less combative way than the “average” maskil. He argues Jews should move away from being merchants and become artisans and Landarbeiter because he believes merchantry has had a corrupting influence on the Jews. And Levinsohn uses satire to accomplish the tendentious points in his writing, especially satire against the Hassidim, for example in Dibre Tsaddikim (The Words of Tzaddiks) in 1830. Levinsohn was also not averse to writing in Yiddish to get to the target audience of his satirical writings.
In these early days of maskilic writing when Levinsohn wrote, rabbinical thought and maskilic thought were not so different from each other. Levinsohn was read and highly regarded in traditional circles by figures like Radal (Rabbi Dovid Luria). Though the Hassidim were not interested in Levinsohn, when he went to the Maggid of Vilne (Misnagdish), he got approving support there. Outside of Russia, the maskil-turned-reformer of Germany, Abraham Geiger, was a fan of Levinsohn’s writing and read several chapters of the German translation of Levinsohn’s Bet Yehudah in front of the congregation of the synagogue in Breslau, where Geiger was Chief Rabbi.