YOU SAID:

He always said to cross the street without looking both ways

INTO JAPANESE

彼はいつも左右を見ずに通りを渡るように言った

BACK INTO ENGLISH

he always told me to cross the street without looking left or right

INTO JAPANESE

彼はいつも私に右も左も見ずに通りを渡るように言った

BACK INTO ENGLISH

he always told me to cross the street without looking left or right