Rubuta ci gaba ga wannan sakin layi - Bayan nazarin doka na ɗan lokaci, Woolsey ya shiga Navy a matsayin mai kula da jirgin ruwa 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 na ɗan gajeren lokaci a Yaƙin Barbary na Farko
Kafin karshenta a shekara ta 1805. A shekara ta 1807, sabon Woolsey ya karbi umarni zuwa Washington, DC, inda ya ci gaba da lambar sigina don Navy.