Which One Are You?

The Brisker Rebbe, zs'l, illustrates how most people prepare themselves before entering Rosh HaShana with the following parable:

A millionaire hires a driver to take illegal merchandise across the border. Who is taking the bigger risk, the millionaire or the driver? Of course the millionaire because he is taking a tremendeous risk losing all his merchandise. The driver is taking very little risk because if he gets caught, he'll say that he didn't know that it is illegal and blame it on the millionaire. But the horse has no fear at all, he couldn't care less if the driver or the millionaire gets caught, feeling it's definitely not his problem, even though he's the one responsible for carrying the illegal merchandise.

The Brisker Rebbe says that wicked people enter Rosh HaShana, Day of Judgement, like the horse. They think they have no worries and carry their sins into the following year, without any worries or remorse. The middle people (not Tzaddikim or wicked) are like the driver, they take the chance of entering Day of Judgment with little thoughts of remorse, comforting themselves that if they get 'caught', they will blame someone else. The Tzaddikim are like the millionaires; they understand the risk of getting 'caught' and its drastic outcome.