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For a time, Owsley taught at a country school, and in 1803, he married Elizabeth Gill, one of his students.
Gill was almost seventeen ; Owsley was twenty-one.
The couple had six children.
During his time as a teacher, Owsley also studied surveying and eventually became a deputy surveyor.
Later, he served as a deputy sheriff under his father, who was High Sheriff of Lincoln County.
While in this capacity, he attracted the attention of John Boyle, who offered Owsley the use of his library.
Owsley availed himself of this opportunity, and read law with Boyle.
In 1809, Owsley opened a legal practice in Garrard County.

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