Chapter 57, Verse 14: Clearing the Path Isn’t the Same As Getting There
The opening verse of the haftarah has Yeshayahu calling to pave the way, remove the obstacles from the way of God’s nation. Radak takes that somewhat literally, noting that the navi had earlier predicted the removal of the enemies who would keep us away from Yerushalayim.

Rashi sees the stumbling block as the evil inclination, a reading that connects it better to what is to come. For all that the verse is included in the previous section in the traditional text, Rashi (and Hazal, who read “michshol, stumbling block” as “yetser hara”) gives it a more forward-facing feel.

Verses 15-21: Greatness and Humility Go Together
Yeshayahu announces that Hashem, who is high and exalted, dwells with the downtrodden and lowly of spirit. While being downtrodden by physical circumstances is a problem, Hashem’s attitude towards such people suggests that they develop personality traits worth cultivating.

Megillah 31a cites this verse as the one that makes it appropriate for Yom Kippur morning. These two aspects of a personality seem to hold the key to finding Hashem’s presence, and regaining the closeness we so desperately seek on this special day. According to the navi, at least some of us will succeed at repenting properly; even before that, Hashem promises not to punish us forever. Radak thinks the verse means that Hashem has been punishing us since just about the beginning, which assumes that the Jewish people have never managed to live up to Hashem’s standards for us, lenient as they have been.

When some of us will be properly humble, Hashem will heal and comfort them, and then change the way that the other nations approach us. Note that Hashem promises to heal us by removing our stone heart; since Rashi identified that as the yetser hara, it sounds as if Hashem is promising to take that away. As I recently noted elsewhere, that may sound attractive, but it means we will have failed to overcome our baser instincts and build a noble life, a central human task.

Changing Those Around Us; The Meaning of Peace
Once having healed us, Hashem promises that He—Who creates the whole ability to communicate—will get those around us to approach us differently, in that they will say shalom, shalom, peace, peace to us. More than Hashem promising that those around us will no longer try to attack or hurt us, Radak thinks the verses mean that Hashem will change the nature of people, so they are interested in peace.

Evildoers’ being closed off from shalom must refer to more than just a lack of violence. Yeshayahu predicts the evildoers will crash like the sea, finding mud and dirt. Finally, Hashem’s promise of peace for “near and far” leads R. Abahu to famously assert that even the fully righteous cannot stand where penitents do, again making this shalom more central than we might otherwise think.

I suspect that shalom here refers to a peace in which the universe is operating smoothly and efficiently, all its parts—physical and metaphysical—in harmony with each other. Avoiding violence is a necessary first step on that path, but only that. Hashem is promising us that He will bring us to that goal, once we are truly penitent, humble of mind and of spirit.

Chapter 58; 1-5: A Fake Religiosity, the Central Sin
The chapter opens with a call to the navi to tell the Jews their sin, specifying that the people ask questions as if they care about observance, but don’t follow what they’re told, and then wonder why they aren’t answered on their fast days. The navi seems to me very modern in being bothered by the nation’s selective interest in halachic observance, where they pick and choose parts of halacha they accept as important. The details of their sin support that view, since Yeshayahu bemoans their gathering for fast days, when on that very day they are collecting loans at interest, and fighting amongst each other.

Verses 6-12: From Hashem’s Perspective, It’s Easy
Note that He does not reject the idea of fasts, He only wants the rituals to be accompanied by a true resolve to leave our paths of sin. Once we rectify our sins, which for Yeshayahu included feeding the hungry, bringing them to our home, and clothing the naked, our light will burst forth like the dawn, our prayers will be answered, and we’ll be like a well-watered garden that never lacks for water.

Yevamot 62b-63a thinks that those who love their neighbors, are close to their relatives, marry off their nieces, and lend to the poor will be answered when they pray. There could be many reasons to name those acts, but I wonder whether bringing about peace with one’s relatives—no easy task—is where the gemara imagines each of us can make the greatest contribution to universal peace.

Verses 13-14: Switching to Shabbat, Not as Abruptly as it Seems
The turn to Shabbat here seems jarring. Until now, we had been discussing how the Jews could achieve proper forgiveness, get God to accept their fast days, and usher in an era of world peace and closeness to God. In that light, though, Shabbat is a ritual that offers an excellent opportunity to show that we are humbly submitting ourselves to God’s goals, not using mitsvot to advance our own. We can use Shabbat to enrich our lives in the way we want (using our day off to thinking about our business, to walk places we want for mundane reasons), or we can turn Shabbat into a time of focus on Hashem and honoring His holy day.

Summary
Our challenge on Yom Kippur is to see whether we can cultivate the humility that will earn us God’s comforting Presence, whether we can free ourselves of the chains of our evil inclination and find our way to a true engagement with God’s goals, the key to unbelievable blessings—of true peace, of true pleasure, and, we can hope, of true freedom from sin and all the distractions that have led us so far astray in the past. Read as we have, the haftarah emphasizes all of those points. With best wishes for a Gemar Hatimah Tovah, an end to the curses of last year, and a year filled with blessing and peace.

Isa.57
[[14] And shall say, Cast ye up, cast ye up, prepare the way, take up the stumblingblock out of the way of my people.
[15] For thus saith the high and lofty One that inhabiteth eternity, whose name is Holy; I dwell in the high and holy place, with him also that is of a contrite and humble spirit, to revive the spirit of the humble, and to revive the heart of the contrite ones.
[16] For I will not contend for ever, neither will I be always wroth: for the spirit should fail before me, and the souls which I have made.
[17] For the iniquity of his covetousness was I wroth, and smote him: I hid me, and was wroth, and he went on frowardly in the way of his heart.
[18] I have seen his ways, and will heal him: I will lead him also, and restore comforts unto him and to his mourners.
[19] I create the fruit of the lips; Peace, peace to him that is far off, and to him that is near, saith the LORD; and I will heal him.
[20] But the wicked are like the troubled sea, when it cannot rest, whose waters cast up mire and dirt.
[21] There is no peace, saith my God, to the wicked.
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Isa.58
[1] Cry aloud, spare not, lift up thy voice like a trumpet, and shew my people their transgression, and the house of Jacob their sins.
[2] Yet they seek me daily, and delight to know my ways, as a nation that did righteousness, and forsook not the ordinance of their God: they ask of me the ordinances of justice; they take delight in approaching to God.
[3] Wherefore have we fasted, say they, and thou seest not? wherefore have we afflicted our soul, and thou takest no knowledge? Behold, in the day of your fast ye find pleasure, and exact all your labours.
[4] Behold, ye fast for strife and debate, and to smite with the fist of wickedness: ye shall not fast as ye do this day, to make your voice to be heard on high.
[5] Is it such a fast that I have chosen? a day for a man to afflict his soul? is it to bow down his head as a bulrush, and to spread sackcloth and ashes under him? wilt thou call this a fast, and an acceptable day to the LORD?
[6] Is not this the fast that I have chosen? to loose the bands of wickedness, to undo the heavy burdens, and to let the oppressed go free, and that ye break every yoke?
[7] Is it not to deal thy bread to the hungry, and that thou bring the poor that are cast out to thy house? when thou seest the naked, that thou cover him; and that thou hide not thyself from thine own flesh?
[8] Then shall thy light break forth as the morning, and thine health shall spring forth speedily: and thy righteousness shall go before thee; the glory of the LORD shall be thy rereward.
[9] Then shalt thou call, and the LORD shall answer; thou shalt cry, and he shall say, Here I am. If thou take away from the midst of thee the yoke, the putting forth of the finger, and speaking vanity;
[10] And if thou draw out thy soul to the hungry, and satisfy the afflicted soul; then shall thy light rise in obscurity, and thy darkness be as the noonday:
[11] And the LORD shall guide thee continually, and satisfy thy soul in drought, and make fat thy bones: and thou shalt be like a watered garden, and like a spring of water, whose waters fail not.
[12] And they that shall be of thee shall build the old waste places: thou shalt raise up the foundations of many generations; and thou shalt be called, The repairer of the breach, The restorer of paths to dwell in.
[13] If thou turn away thy foot from the sabbath, from doing thy pleasure on my holy day; and call the sabbath a delight, the holy of the LORD, honourable; and shalt honour him, not doing thine own ways, nor finding thine own pleasure, nor speaking thine own words:
[14] Then shalt thou delight thyself in the LORD; and I will cause thee to ride upon the high places of the earth, and feed thee with the heritage of Jacob thy father: for the mouth of the LORD hath spoken it.