Kammala jumla mai zuwa: Makiyayi ya koma Amurka a 1929 kuma ya halarci Makarantar Jami'an Kasuwanci, Makarantun Marine Corps. Bayan kammala karatunsa, an sake tura Kyaftin Shepherd zuwa kasashen waje, a wannan lokacin yana aiki tare da Garde d'Haiti, yana aiki na tsawon shekaru hudu a matsayin kwamandan yanki da sashen a cikin
Amurka ta mamaye Haiti. Bayan janyewar Sojojin Ruwa daga Haiti a 1934, an tura Shepherd zuwa Gidan Sojojin Ruwa, Washington, DC, a matsayin babban jami'i kuma a matsayin mai rejista na Cibiyar Marine Corps.