O that whips were set over my thoughts…! is literally “Who will set whips over my thoughts…?” (New Revised Standard Version; see the Revised Standard Version footnote). As in 22.27, this is a rhetorical question that expresses a wish. Good News Translation has “I wish I could be whipped for my thoughts,” but the Greek does not necessarily say this. The intent of the Greek could be the threat of punishment, so a better rendering is “I wish someone could threaten to punish me with a whip for my thoughts.”
And the discipline of wisdom [were set] over my mind!: Good News Translation expresses this line as the result of the first line. This is not misleading, although in Greek it is an additional wish, which may be rendered “I wish Wisdom could discipline my mind.” It may also be interpreted “I wish my mind could be disciplined so as to become wise” or “I wish someone could discipline me so that I become wise.” Discipline here refers to control that makes instruction possible. The writer is really talking about self-discipline, controlling his own actions so as to be able to learn.
That they may not spare me in my errors, and that it may not pass by my sins: In Greek these two lines are result clauses, the desired results of whips (they) being set over thoughts, and discipline (it) being set over the mind. Good News Translation expresses the two lines as wishes. This is not misleading, and works well in this context. The Greek noun translated errors is more fully translated by An American Translation as “errors of ignorance.” Pass by here means “ignore,” not “overtake.” Contemporary English Version provides a helpful model for these two lines by reversing them as follows: “to tell me when I have sinned, and to correct me when I am wrong.”
There is a problem in the last line. As the Revised Standard Version footnote indicates, the Greek says “their sins” rather than my sins. Presumably “their” refers back to errors, that is, “the sins of my ignorant errors.” (A few ancient witnesses omit this line.)
For a suggested approach to this verse and the first two lines of the next verse, see the model for the next verse.
Quoted with permission from Bullard, Roger A. and Hatton, Howard A. A Handbook on Sirach. (UBS Helps for Translators). New York: UBS, 2008. For this and other handbooks for translators see here.

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