Shikamaru doesn't seem like someone who looks to the future, but he has dreams. Extremely average, but very detailed dreams. And what are they?
He wants to be just a plain ninja (no visions of greatness) and earn an ok salary while he's at it. He also wants to marry someone that isn't beautiful or ugly, just normal, and have two children (preferably a girl first then a boy). Then he would retire when his son was independent and his daughter was married, then he would play Shogi and relax every day till his death caused by old ge (which he hopes to die before his wife).