Upon his admission to the bar the irresponsible young blade hung out his shingle in Martinsville, Guilford County, North Carolina, and sat down to wait for clients.  He was still less than twenty years old, without influence, and with only such friends as his irascible disposition permitted him to make and hold.  Naturally business came slowly, and it became necessary to eke out a living by serving as a local constable and also by assisting in a mercantile enterprise carried on by two acquaintances in the town.  After a year this hand-to-mouth existence began to pall.  Neither then nor in later life did Jackson have any real taste or aptitude for law.  He was not of a legal turn of mind, and he was wholly unprepared to suffer the sacrifices and disappointments which a man of different disposition would have been willing to undergo in order to win for himself an established position in his profession.  Chagrin in this restless young man was fast yielding to despair when an alluring field of action opened for him in the fast-developing country beyond the mountains.

The settlement of white men in that part of North Carolina which lay west of the Alleghanies had begun a year or two after Jackson’s birth.  At first the hardy pioneers found lodgment on the Watauga, Holston, Nolichucky, and other streams to the east of modern Knoxville.  But in 1779 a colony was planted by James Robertson and John Donelson on the banks of the Cumberland, two hundred miles farther west, and in a brief time the remoter settlement, known as Nashville, became a Mecca for homeseeking Carolinians and Virginians.  The intervening hill and forest country abounded in hostile Indians.  The settler or trader who undertook to traverse this region took his life in his hands, and the settlements themselves were subject to perennial attack.

In 1788, after the collapse of an attempt of the people of the “Western District” to set up an independent State by the name of Franklin, the North Carolina Assembly erected the three counties included in the Cumberland settlement into a superior court district; and the person selected for judge was a close friend of Jackson, John McNairy, who also had been a law pupil of Spruce Macay in Salisbury.  McNairy had been in the Tennessee region two years, but at the time of receiving his judicial appointment he was visiting friends in the Carolinas.  His description of the opportunities awaiting ambitious young men in the back country influenced a half-dozen acquaintances, lawyers and others, to make the return trip with him; and among the number was Jackson.  Some went to assume posts which were at McNairy’s disposal, but Jackson went only to see the country.