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Isaiah 58:3,13-14 (ESV)

3 ‘Why have we fasted, and you see it not? Why have we humbled ourselves, and you take no knowledge of it?’ Behold, in the day of your fast you seek your own pleasure, and oppress all your workers.

[...]

13 “If you turn back your foot from the Sabbath, from doing your pleasure on my holy day, and call the Sabbath a delight and the holy day of the Lord honorable; if you honor it, not going your own ways, or seeking your own pleasure, or talking idly;

14 then you shall take delight in the Lord, and I will make you ride on the heights of the earth; I will feed you with the heritage of Jacob your father, for the mouth of the Lord has spoken.”

This is evidently a rebuke against selfish pleasure, but the lack of concrete examples in the chapter makes the concept a little bit vague to me. What is exactly meant by "seeking/doing one's own pleasure" in Isaiah 58? I'm especially interested in understanding how this selfish pleasure can simultaneously be the reason why fasting becomes ineffective (verse 3) and the Sabbath is broken (verses 13 and 14).

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The "seeking/doing your own pleasure" in Isa 58:13 has been the subject of (in some isolated legalistic circles) intense debate. However, the sense is clear even from ancient times.

The best explanation is actually provided by the LXX in its translation of Isa 58:13 which reads:

ἐὰν ἀποστρέψῃς τὸν πόδα σου ἀπὸ τῶν σαββάτων τοῦ μὴ ποιεῖν τὰ θελήματά σου ἐν τῇ ἡμέρα τῇ ἁγίᾳ καὶ καλέσεις τὰ σάββατα τρυφερά, ἅγια τῷ Θεῷ σου, οὐκ ἀρεῖς τὸν πόδα σου ἐπ᾿ ἔργῳ, οὐδὲ λαλήσεις λόγον ἐν ὀργῇ ἐκ τοῦ στόματός σου

This may be translated:

If thou turn away thy foot from the sabbath, so as not to do thy pleasure on the holy days, and shalt call the sabbaths delightful, holy to God; [if] thou shalt not lift up thy foot to work, nor speak a word in anger out of thy mouth

Thus, it appears that "not doing your pleasure" cannot be restraining from pleasurable things as this would immediately create a contradiction. Rather, the "own pleasure" is a reference to pursuing one's own pleasure in business or general work.

The same conclusion is drawn by numerous other commentators such as Ellicott, Cambridge, Pulpit, but note also Matthew Poole -

Not doing thine own ways, or works, or course of life; a man’s whole course being described by a way or walk, Genesis 17:1 Ephesians 5:8.

Thus, the sabbath was intended to be dedicated in time, function and celebration to the LORD to recall His great creation (Gen 2:1-3, Ex 20:11) and His saving grace (Ex 31:12-17). Under the definition of Isa 58:13, pursuing one's own business, farm or sales interests would dishonor the day dedicated to honoring God the great and only creator and re-creator.

Thus, the sabbath was to be "a delight" so that such people could "delight in the LORD" (V14).

APPENDIX - Example

There is a good example of this in Neh 13:15-22 where Nehemiah encouraged people not to work or engage in commerce on Sabbath

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