Boris Trajkovski was born on 25 June 1956, in Strumica. In 1980 he received a law degree from the University of St. Cyril and Methodius in Skopje, afterward specializing in commercial and employment law. Until 1997, he headed the legal department of the Sloboda construction company in Skopje. He has also been a member of the Macedonia America Friendship Association, and he served as leader of the United Methodist Church's youth branch in the former Yugoslavia for 12 years. Trajkovski is married and has two children.