After qualifying, Freeman spent a year as a house physician at the hospital. He married his childhood sweetheart Annie Elizabeth Edwards in London on 15 April 1887, and the couple later had two sons. He then entered the Colonial Service in 1887 as an assistant surgeon. He served for a time in Keta, Ghana, in 1887 during which time he dealt with an epidemic of black water fever which killed forty percent of the European population at that port. He had six months of leave from mid 1888 and returned to Accra on the Gold Coast just in time to volunteer for the post of medical officer on the planned expedition to Ashanti and Jaman.