My son: The writer is addressing the reader as teacher to student; see the comments on 2.1.
Glorify yourself with humility: This is not the contradiction it may at first seem. We are not forbidden from “glorifying ourselves,” that is, we are not to be ashamed of who we are. We may have a wholesome pride; we are simply told to keep that self-respect, that self-esteem, within the bounds of modesty. An alternative model for the first line is “Students, it is not wrong to respect yourselves, but you should remain modest [or, humble].”
And ascribe to yourself honor according to your worth: There is no reason not to give ourselves credit where we deserve it, but only to the degree we really do deserve it. We should not think higher of ourselves than we should, but we should not think any less of ourselves than we should, either. Good News Translation provides a good model here: “Value yourself at your true worth.”
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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