1

What's the difference between the following sentences:

  1. Her career was beset with difficulties.

  2. Her career was beset by difficulties.

2

Not unique to the verb "to be beset", in general the two particles "by" and "with" imply different things. Consider the difference between these two requests:

Come stand by her.

Come stand with her.

By implies that you simply stand in the same physical space that she does. But with implies that you and she are standing together. To stand with someone connects the two of you much more than just to stand by them.

(That being said, the idiom "to stand by" can have several other meanings, which you have to determine from context. English is complicated.)

In the same way there's a subtle difference in the nuance between beset with and beset by. "With" suggests that the difficulties were connected to her career in some way -- that she ran into many problems as a consequence of the job. "By" suggests the difficulties were disconnected from her career, that they were not necessarily related to the job.

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