The second Chapter of Avos is about paths. What is the proper path on which a person should walk? Which is the Straight path? The Good Path? The Bad path?

The chapter begins with the advice of Rebbe: Seek Tiferes. Tiferes is the combination of strict and flexible. It is the ability to be, like Rebbe, a person that can live in luxury and yet live only for G-d. Rebbe was a person that could live at a time when the Torah is being forgotten and build a legacy by transcribing the oral law.

Rebbe says to find a path that is a Tiferes to the person himself and also a Tiferes to those around him.

While there is much talk about people who are “off the Derech” (or “off the Path”), this chapter discussed the Derech itself. It is a special balance between motivation and expectation; the art of weighing every mitzvah and every action that we do; and the constant recognition that G-d is watching us and recording all of our actions.

Rav Chaim Vital, a disciple of the Arizal speaks of “walking through the Valley of the Shadow of Death”. He explains that everyone, even the most righteous, spend the first three days after death on a path that passes alongside Hell. At every juncture he or she is met with another turn-off to Gehenom and it is only by focusing that he can continue on his path to his just reward in the Garden of Eden.

To my mind, these are the turn-offs to the “paths not taken”. They are the jobs we didn’t take, the people we didn’t help, and the moves we never made. At each juncture we are plagued with self-doubt and even granted a vision of “what could have been”. It is a very frightening path and we can only hope that we made the proper decisions and that we will be able to continue to our reward. King David prayed, “Even as I walk in the valley of the shadow of death, I will not fear, for you are with me.”

Rabban Yochana ben Zakkai was a mysterious figure and we don’t know much about his family. Zakkai was an appellation and not the name of his father. His brother-in-law was the head of the Zealots in Jerusalem and Rabban Yochanan became head of the Pharisees when the traditional family of leaders (the descendants of Rabban Gamliel, Hillel, and King David) were forced into hiding. Whe Rabban Gamliel was allowed to emerge from hiding Rabban Yochanan be Zakkai worked to put Rabban Gamliel back into a leadership position and made himself scarce so as not to infringe on Rabban Gamliel’s position.

Rabban Yochanan be Zakkai’s years of leadership were difficult ones for the Jews of Jerusalem. The Roman army had laid siege to the city and the Zealots within the city were not allowing anyone to negotiate for peace. Rabban Gamliel met with his brother-in-law and hatched a plan to sneak out of the city in a coffin and meet with the General Vespasian. When they met, he foretold Vespasian’s rise to the crown and indeed as they were speaking a horseman cam and informed Vespasian that he had been crowned Emperor of Rome. Before he left, Vespasian granted Rabban Yochanan three requests: The Academy at Yavneh was spared, the family of Rabban Gamliel was no longer threatened, and doctors were procured for Rabi Tzadok who had been fasting for forty years.

When Rabban Yochanan ben Zakkai returned Jerusalem, he was criticized by his colleagues. Rabi Akiva quoted a verse claiming that Hashem had caused him to err. He should have requested that Jerusalem be spared and not settled for the granting of three comparatively minor requests.

Jerusalem was destroyed and the academy at Yavneh prospered. Rabban Yochanan ben Zakkai retreated with a handful of students to Bror Chayil. While he had acted to the best of his knowledge and abilities, one can imagine the constant fear of “the path not taken”. We need to be careful not to project our own feelings onto so great a personage as Rabban Yochanan, but we do know that on his deathbed, Rabban Yochanan ben Zakkai cried in fear.

“I see two paths before me”, he told his students, “and I don’t know which one I am going to take”. Rav Chaim Vital explains that Rabban Yochanan ben Zakkai was describing the aforementioned “Gei Tzalmaves”, the path through the valley of the shadow of death.

Although we are accustomed to saying that G-d only expects us to do our best, one can imagine the fear of standing before G-d who knows what was truly best. He knows what the options were and what the best decision would have been. He knows what destruction we caused and what destruction we avoided. It is frightful to be standing before G-d.

Rabban Yochanan, who had stood before a human king without fear, was scared of a G-d who truly knew everything. As he lay on his deathbed he described a G-d who knows the true and everlasting ramifications of our actions, whose anger lasts forever and whose decisions are final. How could any mortal know that he had walked the proper path all his life and how could anyone stand without fear and the final day of judgement before a G-d who knows that “our best” was not actually good enough?

It was in this context that Rabban Yochanan ben Zakkai implored his students to find the proper path. He was not satisfied with the suggestion of Rebbi that one find a path that worked well for him and those around him. Rabban Yochanan ben Zakkai wanted a path that he could walk upon comfortably in the context of eternity and the world that G-d had created.

He challenged his five students: Go out and find the proper path upon which a person should walk. “Going Out” is an instruction to rethink everything from the very beginning and to avoid all bias of previous thoughts or teachings.

In many editions of Pirkei Avos, the language is “Derech Tovah” – the Good Path”. In identifying good, each of the students examined the first instance of “Good” in the Torah: “And G-d saw the light, and it was Good”.

Rabi Eliezer ben Hukanus said the Tov can be achieved through a good eye, a utilization of Hashem’s creation of light to take in the world around us in an accurate and fair way. Rabi Yehoshua and Rabi Yosi focused on the relationship between Light and Dark. The Torah tells us that before light, there was a “Darkness on the face of the deep, and the spirit of Hashem was hovering above the water” The world was not yet good. It was with the advent of a Chaver Tov V’Shachein Tov – “a good friend and neighbor”, in this case light, that life was good.

Rav Shimon considered the Midrashic light and talked about seeing the future. The Medrash tells us that the Light of creation was a divine light. It allowed us to see from one end of the earth to the other; from the beginning of time to the end of time.

These four aspects of Light were on the minds of Rabban Yochanan ben Zakkai’s four students and the basis of their description of the “Proper Path”.

Only Rabi Elazar ben Arach chose to go back to the beginning of the Torah. The world didn’t start with Light. It started at the Beginning. All of the ingredients from the word Bereishis went into Hashem description of Tov. We can’t work on our eyes or our neighbors or our friends our ability to predict. We need to start from the very beginning and work on our hearts.

As a matter of fact there are exact thirty two words from the beginning of the Torah until the word Tov. All thirty two of those components (with the numerical value of Lev or Heart) were important to achieve Tov.

Perhaps all of this connects Rabban Gamliel’s original teaching in this chapter. “If you have studied a lot of Torah, don’t keep the Good for yourself, for that is why you were created.”

The Good that we have is a product of everything that we have had since creation and it something that we need to share with chose around us. We are just one piece in a very large puzzle. Our creation began in the womb when we were taught the whole Torah and instructed to do our best and not to be swayed by the opinion of the world around us (Nidda 32b).

When Rabban Yochanan ben Zakkai was on his death bed he said that there were two paths before him, one led to Gehinnom and the other to Gan Eden. Rabban Yochanan ben Zakkai was acutely aware that his actions were not the whole picture. He was scared of coming before G-d who would see the ramifications and results of all of his actions. There is nothing we can do about that except to follow the direction of Rabi Eliezer ben Arach: we need to make sure that everything that we do is rooted in a Lev tov. And we need to recognize that we are the sum total of all that preceded us.

The Avos Derabbi Nosson tells of a time when rabban Yochana ben Zakkai sat in mourning for his son. Four of his students tried to comfort him but they were unsuccessful. Finally Rabi Elazar ben Arach was able to comfort his teacher with the following analogy: “imagine that he king had given you a precious item to watch. You would have lived all your life in distress, worried that you might mistreat or ruin the item. G-d has taken back your son. You will no longer be plagued with the responsibility of maintaining His precious jewel.”

Rabban Yochana benm Zakkai was comforted because Rabi Elazar’s words reflected his teachings.

This approach did not work for Rabi Elazar. After the death of Rabban Yochanan his wife convinced him to move to Damascus. After all, he was an “overflowing spring”, he had a Lev Tov and did not need his colleagues for support.

In the end Rabi Elazar forgot all of his Torah. His colleagues returned and taught it to him once again. In the continuation of the chapter Rabi Elazar teaches that while a Good heart is paramount, we must be anchored in this world as well and we must remain confident that G-d will lead us down the proper path to our rightful reward:

“Be assiduous in your study of Torah”. He said, “Know how to respond to someone who does not respect Torah, and always remember that you are serving G-d. G-d can be trusted to give your rightful reward”.

These were the consoling words of King David: “Even as I walk in the valley of the shadow of death, I will not fear, for you are with me.”

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Devarim Nechmadim is a commentary on Pirkei Avos by Rav Tzvi Elimelech of Dinov. This essay is loosely based on his work as well as on the classes and writings of my father, Rav Yaacov Haber , Shlita.