For at first she will walk with him on tortuous paths: This verse describes how difficult the search for Wisdom is, and warns those who seek her that at times they will wonder if it is worth the effort. Translators may ignore the connector For since a new idea begins here. This particular line does not speak literally of paths; that is simply a convenient figure of speech. However, in some languages it will be a very natural metaphor, and Good News Translation‘s model may be followed. Tortuous becomes “difficult” in Good News Translation. This is a rather weak word. The Greek word here, which is a rare one, speaks of something twisted. The writer is probably speaking of the difficulty of study, how hard it is to figure some things out, how hard it is to understand things that have to be learned. Those translators who cannot personify Wisdom may say “At first the path leading to understanding the Lord’s ways will be tortuous [or, twisting] and difficult to walk on.”

She will bring fear and cowardice upon him refers to that stage in learning when the student is ready to give up, believing that he will never, ever, be able to understand the lessons. Good News Translation has a good translation, but “She will make you so afraid that you will think you cannot go on” does not refer to fear of physical dangers. Wisdom does not entice people to do things that are inherently dangerous. A spirit of adventure may do so, but it is not wisdom. Wisdom does not prevent a person from being brave, but it does preclude recklessness. An alternative model for the first two lines is “At first it will be difficult to follow Wisdom. She will give you hard lessons to learn, and you will get to the point that you want to give up; you will think you cannot go on.” Contemporary English Version reorders the two lines as follows:

• At first, Wisdom will test you
with her commands,
and you will walk in fear
along twisting pathways.

And will torment him by her discipline: This is well put in Good News Translation (“The discipline she demands will be tormenting”), but we may also translate “The hard work she requires will torment the learner.” In languages where Wisdom cannot be personified, we may say “You will suffer much as you strive to learn the Lord’s difficult commands.”

Until she trusts him, and she will test him with her ordinances: These last two lines are something of a problem. It seems like the last line is out of order, that the verse should conclude with the line about trust. Several translations rearrange them in translation; for example, Good News Translation has “and she will put you to the test with her requirements until she trusts you completely” (similarly New English Bible, Revised English Bible, New American Bible).

Until she trusts him is literally “until she trusts his soul.” As Good News Translation indicates in its footnote, this can be translated “until you trust her.” Literally this would be “until he trusts her in his soul.” This can be argued either way, but the Handbook prefers the alternative, and understands the Greek verb translated trusts as interpreted in verse 16, where Revised Standard Version renders it “has faith” (see the comments there). A possible model is “until you are fully committed to her.” Contemporary English Version follows this interpretation with “until you are truly faithful.”

Another way, and we think a better way, of understanding the last line of the verse, and she will test him with her ordinances, is not to rearrange the order of lines, but to take this line as the first line of a new thought continuing into verse 18. This could be signaled “Oh yes, Wisdom will put you to the test with her requirements….”

For translators who cannot personify Wisdom, an alternative model for this verse is:

• At first, the paths leading to the understanding of the Lord’s commands [or, laws] will be twisting and difficult to walk on. As you walk along them you will be very afraid. You will suffer much as you strive to learn the Lord’s difficult commands, until finally you truly commit yourself to him. Oh yes, you will be truly tested as you learn the Lord’s laws.

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.