Ka cika wannan magana: Bayan ya yi karatun shari'a na ɗan lokaci, Woolsey ya shiga rundunar sojan ruwa a matsayin ɗan aji na biyu a ranar 9 ga Afrilu, 1800. Ayyukansa na farko shi ne jirgin ruwa, wanda ya yi tafiya zuwa West Indies a 1800 da 1801. Ya yi aiki a takaice a cikin
Yaƙin Barbary na Farko kafin ya ƙare a 1805. A shekara ta 1807, sabon Woolsey ya karbi umarni zuwa Washington, DC, inda ya ci gaba da lambar sigina don Navy.