Accident, happily turned to his profit, served to introduce him to the townspeople of Winchester.  The morning after his arrival, he found a crowd in the public square and learned that an auction sale of personal effects was about to take place.  Everyone from the administrator of the estate to the village idler, was eager for the sale to begin.  But a clerk to keep record of the sales and to draw the notes was wanting.  The eye of the administrator fell upon Douglass; something in the youth’s appearance gave assurance that he could “cipher.”.  The impatient bystanders “’lowed that he might do,” so he was given a trial.  Douglass proved fully equal to the task, and in two days was in possession of five dollars for his pains.[29]

Through the good will of the village storekeeper, who also hailed from Vermont, Douglass was presented to several citizens who wished to see a school opened in town; and by the first Monday in December he had a subscription list of forty scholars, each of whom paid three dollars for three months’ tuition.[30] Luck was now coming his way.  He found lodgings under the roof of this same friendly compatriot, the village storekeeper, who gave him the use of a small room adjoining the store-room.[31] Here Douglass spent his evenings, devoting some hours to his law books and perhaps more to comfortable chats with his host and talkative neighbors around the stove.  For diversion he had the weekly meetings of the Lyceum, which had just been formed.[32] He owed much to this institution, for the the debates and discussions gave him a chance to convert the traditional leadership which fell to him as village schoolmaster, into a real leadership of talent and ready wit.  In this Lyceum he made his first political speech, defending Andrew Jackson and his attack upon the Bank against Josiah Lamborn, a lawyer from Jacksonville.[33] For a young man he proved himself astonishingly well-informed.  If the chronology of his autobiography may be accepted, he had already read the debates in the Constitutional Convention of 1787, the Federalist, the works of John Adams and Thomas Jefferson, and the recent debates in Congress.

Even while he was teaching school, Douglass found time to practice law in a modest way before the justices of the peace; and when the first of March came, he closed the schoolhouse door on his career as pedagogue.  He at once repaired to Jacksonville and presented himself before a justice of the Supreme Court for license to practice law.  After a short examination, which could not have been very searching, he was duly admitted to the bar of Illinois.  He still lacked a month of being twenty-one years of age.[34] Measured by the standard of older communities in the East, he knew little law; but there were few cases in these Western courts which required much more than common-sense, ready speech, and acquaintance with legal procedure. Stare decisis was a maxim that did not trouble the average lawyer, for there were few decisions to stand upon.[35] Besides, experience would make good any deficiencies of preparation.