Behold, I am sending you like sheep in the midst of wolves;
so be shrewd as serpents and simple as doves.
Serpents were known for all sorts of negative qualities, since the first serpent encountered in Scripture was a manipulative liar, seeking to harm God's creatures. But there was one quality sheep would need to study and appropriate from the image of the serpent, that being shrewdness. Shrewdness may seem to have a negative connotation but it actually only implies "clever discerning awareness" or "artful ways of dealing" according to Merriam-Webster. It is true that it is easy to employee shrewdness in the pursuit of self interest but it was not in this way that Jesus recommended it to the sheep. He was not commending any actions that would result in deceptiveness or lies or the harm of others. He only praised a shrewdness that was at the same time as simple as doves. He did not necessarily recommend the simplicity of doves as sufficient in itself however. He only spoke of it together with sufficiently sharp powers of judgment. It was a simplicity that was not naive but was rather fully engaged and single hearted.
The Lord unites these two things; because simplicity without wisdom might be easily deceived, and wisdom is dangerous unless it be tempered with simplicity that does no man hurt.- Saint Regimus
Disciples were called to be attentive to the dangerous circumstances and situations they would encounter as they attempted to spread the Gospel message to the world. They were meant to be aware that many would regard them as hungry wolves may regard unguarded sheep. Shrewdness might well have been a skill that could have kept the disciples from any danger. But if they used it primarily as a means of escape they may also have been prevented from spreading the Gospel. No doubt Jesus did intend that it would prevent them from throwing their lives away wastefully. But it was not meant to prevent them from being witnesses, even if the cost of that be their lives.
When they hand you over,
do not worry about how you are to speak
or what you are to say.
The disciples weren't called to be overly clever about their words. Instead of shrewdness, the main thing that was meant to mark their speech was openness to the Holy Spirit. The words that were needed were not human words. For human words, however clever, were not sufficient to change hearts. It took divine revelation to do that. And human words could be a vessel for divine revelation, but human cleverness was not its origin.
You will be given at that moment what you are to say.
For it will not be you who speak
but the Spirit of your Father speaking through you.
The primary thing to which the disciples were being called as they were sent on mission was dependence on God. God himself would provide what they needed when they needed it. They were to employ what we might call human skills such as shrewdness, but only in a secondary and contingent way, as they were guided by the dynamic leadership that Jesus himself promised would be provided for them.
You will be hated by all because of my name,
but whoever endures to the end will be saved.
Popularity was not the success criterion of missionary activity. If anything, it was the opposite. After all, James would later write that "friendship with the world is enmity with God" (see James 4:4). Not that one could try to insight hatred or antagonize the world as his missionary strategy, as though merely being provocative was equivalent with proclaiming the Gospel. But nevertheless, becoming too comfortable with the world or being too popular in the eyes of society ought at least to be viewed more as potential warning signs than indications that we necessarily did something right.
We should read the command of Jesus to endure to the end as indicating that there will be temptations to give up along the way. But while he does not necessarily promise it will be easy, he does assure us that he himself will always arrive in time to save us.
Give me back the joy of your salvation,
and a willing spirit sustain in me.
O Lord, open my lips,
and my mouth shall proclaim your praise.
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