If I understand correctly, I think you're looking for the CASE statement:
SELECT User_id,
(CASE
WHEN YEAR(DOB) < 1980 AND Job_Title = "manager" THEN "Old Fart"
WHEN YEAR(DOB) < 1980 AND Job_Title = "associate" THEN "Old Timer"
...
ELSE "Unknown Title"
END) AS Real_Title
FROM users;