English translations render Isaiah 53:3 as “a man of sorrows and acquainted with grief” (ESV) or the like (NIV, NKJV, KJV). But the word “grief” here perhaps should be translated as “sickness” (וִיד֣וּעַ חֹ֑לִי).
But There Are Good Reasons to Translate It As Grief
Yes, I know that grief could be a general translation of hali, but the idea of sickness and healing is prominent in Isaiah (Isa 1:5; 38:9 with Isa 30:26; 53:5; 57:18, 19). Sickness is also part of the covenant curse that comes before salvation (Deut 28:59, 61). And in two verses later, the servant heals the people (Isa 53:5). More than that, the translation in Isaiah 53:3 may also contribute to a misunderstanding of Isaiah 53:4.
Isaiah 53:4 reads, “Surely, he himself bore our sickness, and he carried our sorrows” (אָכֵ֤ן חֳלָיֵ֨נוּ֙ ה֣וּא נָשָׂ֔א וּמַכְאֹבֵ֖ינוּ סְבָלָ֑ם). Isaiah 53:4 shows that the servant who knew sorrow and sickness (Isa 53:3) carries these same things, sorrow and sickness for us.
Sickness has to be in view here because Isaiah 53:5 reads, “But he himself was pierced for our transgressions; he was crushed for our sins; discipline fell on him for our wholeness; and his wounds healed us.”
Yes, sickness here seems to mean sin as sickness. But Isaiah 1:5 has already introduced the idea that sickness is not merely physical but a matter of the heart: “The whole head is sick (לָחֳלִ֔י), and the whole heart faint.”
Translation of Isaiah 53:1–5
Take a look at the first five verses of Isaiah 53. I think you will agree that sickness makes better sense here. I’ve bolded words that refer to the servant in verse 3 and later to the people in verses 4–5.
 Who has trusted our report, and upon whom has the arm of Yahweh been revealed?  He came up like a shoot before him and like a root from the dry ground. No form nor splendour belonged to him that we should look at him. And he had no appearance that we should desire him.
 He was despised and rejected by men, a man of suffering, one who knew sickness, and one from whom men hid their faces. He was despised, and we esteemed him not.
 Surely, he himself bore our sickness and carried our suffering. But we did not esteem him—he who was afflicted, struck by God, and humiliated.  But he himself was pierced for our transgressions; he was crushed for our sins; discipline fell on him for our wholeness; and his wounds healed us.
What Does This All Mean?
(1) The emphasis on sickness and healing makes sense of Jesus’ healing ministry. Jesus is the great healer who has borne our sickness and suffering.
(2) But physical sickness is a metaphor for spiritual sickness. Already, Isaiah 1:5 has introduced the idea of a sickness of mind. And Isaiah 53:5 confirms that the healing here focuses on sin. Better: it shows that healing comes to the whole person whether in body or in soul.
(3) The servant dies as a substitute for his people. He takes the punishment of God (Isa 53:4) in place of his people. In Isaiah, God afflicts his people due to their sin as Isaiah 30:26 says:
Moreover, the light of the moon will be as the light of the sun, and the light of the sun will be sevenfold, as the light of seven days, in the day when the Lord binds up the brokenness of his people, and heals the wounds inflicted by his blow.
God afflicts his people and heals them. God wounds and heals (Deut 32:39). By his temporary wounding, God saves to the utmost. And he does so through afflicting the servant in place of his people.
(4) The final affliction (or death as in 53:8) of the servant is not only in view here. His life is also highlighted as being for us and for our salvation. In Isaiah 53:3, the servant suffers, is sick, and not esteemed. Why did he live this way?
The answer comes in Isaiah 53:4–5. The servant bore our suffering, our sin, and he was not esteemed by us! Or rather, he was not esteemed by those of his people who did not believe the report about him (Isa 53:1).
Isaiah portrays the life of the servant as something lived on behalf of the people, not only his climactic affliction or death.
What I’ve said here could also be said if “sickness” is translated as “grief.” Yet I think the biblical metaphor of sickness better captures the meaning of Isaiah.
The picture of sickness better accounts for the ministry of Jesus as the great healer of maladies. More than that, it captures the spiritual meaning of Jesus’ healing ministry because he came bear our sins and sickness of the head and heart.
Jesus’ healing in Isaiah 53 and in the Gospel witnesses show that, despite his form, he is powerful, bearing the arm of Yahweh. It also shows that he has the power to forgive our sins. As the Word from the Father, he lived and died for us and for our salvation. He is our great healer.