Rubuta ci gaba ga wannan sakin layi - Woodlock ya sami digiri na digiri na digiri na digiri daga Kwalejin Yale a 1969, inda ya kasance memba na Skull da Bones, kuma mataimakin shugaban "Yale Daily News". Ya fara aikinsa a aikin jarida a matsayin mai ba da labari a "Chicago Daily News", wanda ke rufe Babban Taron Kasa na Democratic na 1968
a birnin Chicago. Woodlock ya zama mai ba da rahoto a "Chicago Sun-Times" daga 1969 zuwa 1973, inda ya yi aiki a Chicago da Springfield, Illinois, kafin ya koma Ofishin Washington na "Sun-Times" a 1971-1973, inda ya rufe Kotun Koli. Daga nan Woodlock ya halarci Cibiyar Nazarin Shari'a ta Jami'ar Georgetown, inda ya kasance memba na "The Georgetown Law Journal". Ya sami J.D. a shekarar 1975.