ויאמר עשו הנה אנכי הולך למות ולמה-זה לי בכרה
Eisav said: “Behold, I am going to die! Why then do I need this right of the firstborn?”
Chazal teach us a formula to defeat our yetzer hara, our evil inclination. First, use your yetzer hatov, your inclination for the good, as a weapon to battle the yetzer hara. If that works, great. If this doesn’t work, Chazal say to toil in Torah. If that works, great. If it doesn’t, we are told to say the verse of Shema Yisrael. If that works, great. If this doesn’t work, then we are to remember the day of death. Considering this is the final suggestion, it sounds like it’s foolproof. If all else fails, remembering the day of death will surely silence a person’s yetzer hara. If that’s so, why is it the last in the list? Shouldn’t it be the first thing people try out?
There are those that suggest that such a strategy is specifically a last resort. Thinking about the day of death could lead to depression. The thought that life is short, and a person could die at any moment, is not the easiest of messages to digest. Therefore, this thought exercise is to be used sparingly. First a person should try the other suggestions. Only if all else fails should they focus on the fact that life is fleeting.
Eisav and Yaakov were having a discussion about the right of the firstborn. Although Eisav was born first, Yaakov felt that the religious rights reserved for a firstborn were more appropriate for himself. Eisav responded that he was going to die, so he personally had no need for these rights. We see that Eisav took for himself this lesson of Chazal, but jumped right to the final strategy. He constantly kept in mind that he could die at any time. Therefore, he didn’t need the rights of the firstborn. However, besides seeming to not cause him depression, it also appears like the strategy failed! Eisav was one of the most wicked people to walk this earth. His yetzer hara was in total control. If he constantly remembered the day of death, why didn’t Chazal’s stategy prove effective?
It could be that Chazal had a different intent. They didn’t put remembering the day of death as the last suggestion to avoid depression. Rather, everything was meant to be a process. A person is having a hard time fighting their yetzer hara. First, they have to activate their yetzer hatov. Then, they should learn Torah. Subsequently, they should say the Shema. Doing these things will give a person the proper perspective. Learning Torah will help them tap into the Divine Will. Saying the Shema is a proclamation that everything comes from Hashem. A sincere effort to inculcate these messages should prove effective. If all else fails, remember the day of death. By this point, the proper perspective, with a healthy dose of morbid levelheadedness, should do the job.
What was Eisav’s mistake? He jumped to the final suggestion. He focused on the fact that he was going to die. What was the problem? He took out of this focus the wrong message. If someone is going to die at any moment, that means that they should take advantage of the limited time they have left. Now, “taking advantage” can mean different things to different people. For someone without the proper, Torah perspective, that means Carpe Diem, seize the day! Maximize the worldly pleasures, as much as possible. For life is short, and we may die tomorrow. Eisav took this message very seriously. There was no worldly pleasure that was out of his reach, and nothing could stand in his way. This focus on his day of death was in fact his downfall.
On the other hand, someone who follows the formula of Chazal will see true success against their yetzer hara. If they followed the steps properly, they’ll have the proper perspective. If someone realizes that life is short, they won’t “take advantage” like Eisav did. They’ll realize that there’s limited time to earn eternity. The number of mitzvos a person can accomplish is finite. The reward for each mitzvah however is limitless. How could a person then listen to their yetzer hara? There’s no time! Life is short, and we better use the time we have wisely.
 Based on something I heard from Rabbi Elimelech Reznick in the name of Rav Eliya Lopian zt”l. I believe the idea is printed in Lev Eliyahu, but I don’t have access to that sefer at the moment
 Genesis 25:32
 Berachos 5a
 Rabbi Reznick quoted this from the Ba’alei Mussar, the Rabbinic masters of the human psyche. I couldn’t find any examples. However, I saw the chassidishe Rebbe the Penei Menachem parshas Lech Lecha quote his father the Imrei Emes as saying that remembering the day of death could lead to depression. Although, he didn’t mention that this is why it is last in the list
 This popular Latin phrase has its roots in Tanach: Isaiah 22:13 says: …הרג בקר ושחט צאן אכל בשר ושתות יין אכול ושתו כי מחר נמות, …kill bulls, slaughter sheep, eat meat and drink wine; eat and drink, for tomorrow we die!