Those who know me know that Jesus’ teaching to be “shrewd as serpents and innocent as doves” (Matthew 10:16) is one of my favorites. It’s been tattooed on my body twice now. I was a teenager when it first started resonating with me, and I don’t think I fully understood why it has stuck with me since then until recently. Today, when understood in its context, it is a bit controversial because we aren’t aware of how we get it wrong. We’ll come back to that after a little etymology.
The NASB uses “wary” while the KJV goes with “wise” to translate this word. The Greek word is “phronimos.” It’s the same word used in the parable of the Shrewd Servant in Luke 16 (one of my favorite parables for pretty much all the same reasons). The root word of “phronimos” is “phrēn,” which specifically refers to the part of a human that perceives and makes judgments. The only time “phrēn” is used in the New Testament is 1 Corinthians 14:20 – “Brothers, do not be children in your thinking. Be infants in evil, but in your thinking be mature.” The second part of “phronimos'” etymology is “synetos,” which means to be prudent and mentally put together (cf. Acts 13:7). Thus, “phronimos” conveys the idea of being intentional and thoughtful with our thinking and actions. The difference between someone who is smart, maybe even wise, and someone being aware, controlled, and intentional is the difference between “phrēn” and “phronimos.”
In Matthew 10, Jesus was providing instructions for his twelve apostles on the trips he was sending them on (cf. Matthew 11:1). Generally speaking, Jesus’ directions were for his apostles to be sagacious and not naive when they face opposition, just as Jesus was facing opposition. He uses a lot of Old Testament references and allusions throughout, as he always did. We will just focus on verse 16, but it’s important to remember that there’s more going on here.
In Matthew 10:16, he first said, “Behold, I am sending you out as sheep in the midst of wolves, so be wise as serpents and innocent as doves” (ESV). Notice the structure: sheep – wolves/serpents – doves. It’s chiastic in structure, and the last half teaches how to be a sheep among wolves. Yet, his answer for how to be a sheep (a common metaphor for God’s people in the Bible) is to be a wise serpent.
Straight away, Jesus’ words should strike us as bordering on controversial. There is only one place, just one, where a “shrewd” serpent appears in all of the Jewish scriptures, and it is in Genesis 3 when the serpent talked Eve into eating from the tree of the knowledge of good and evil. Genesis 3:1 introduces this talking snake as “more crafty than any other beast of the field.” The word “crafty” shares a very similar etymology as the word for “naked” which was used in the immediately preceding verse to describe the state of humans before this story: “And the man and his wife were both naked and were not ashamed” (Genesis 2:25).

Nakedness is a central theme from Genesis 2:25 through 3:21 when God covers Adam and Eve’s nakedness. The idea behind this theme is about how we perceive and interact with the vulnerability of ourselves and others. When Jesus taught to be “shrewd as serpents,” he was unashamedly making a reference to Genesis 3:1, teaching that we should be like that serpent: aware, intentional, engaging, and phronimos. In essence, Jesus was teaching his apostles to be like “that ancient serpent, who is called the devil and Satan, the deceiver of the whole world” (Revelation 12:9). However, the catch is that we must also be “innocent as doves.”
The word “innocent” is akeraios, which means to be unmixed and pure. It carries the same idea as being “sincere” or “without wax.” This Latin word referred to clay pots that weren’t patched up with wax to deceive buyers. Jesus’ use of the dove as a metaphor may allude to the contrast between the raven and the dove in the Flood narrative. Even if not specifically referring to that story, the use of the dove in contrast to the Genesis 3 serpent conveys a similar idea to what “naked” represented in Genesis 2:25. The serpent used its own nakedness against Eve’s vulnerability. This sets the stage for Cain and Abel, and the subsequent downfall of humanity in the biblical narrative. It is, in many ways, the central issue that the Bible teaches about how we humans mess things up.
Instead, Jesus teaches us to be “unmixed.” We should be who we present ourselves as, and our words and actions should align with who we are, rather than hiding behind craftiness to manipulate the world and people around us for our own protection and gain. We all engage in such behavior. We protect ourselves from others, play mind games, use subtle tactics to influence others, avoid confrontations, dodge responsibility, gossip, hint, exaggerate, deceive, and so on. We tend to justify our own beliefs and behaviors while discrediting others. This dynamic isn’t “unmixed” but rather a messy one. It’s why we find it difficult to trust people since we don’t truly know what we are getting from them due to the mixed signals.
I struggled with Imposter Syndrome for as long as I can recall. It wasn’t until this year that I realized it had disappeared. In the middle of a conversation with a friend about it, I suddenly realized that I didn’t have it anymore. Upon reflection, I now understand why Jesus’ teachings have resonated with me all along. I longed to be safe from others, and I desired to be understood, known, and accepted. In a world full of humans, some acting like wolves and snakes, it is challenging to trust a different metanarrative and adopt a different posture than what is typically expected. Even spouses, children, and parents can and have hurt us, and they may do so again in the future. Our inability to apologize for our wrongdoings is perhaps a global pandemic. Our tendency to draw lines, take sides, victimize ourselves while vilifying others is truly remarkable.
Both innocence (sincerity and vulnerability) and shrewdness (intentional mental awareness) were crucial for Jesus’ apostles’ mission trips. If they were to accomplish what Jesus wanted and what he himself was attempting to accomplish, and if they were to convey this understanding to future followers, they needed to embody these qualities. They were to be aware and cautious, but not to protect or advance themselves over others. They were called to believe something different from what we often choose to trust. There may be countless excuses for not following Jesus’ words, but deep down, I believe we all understand why it’s better: because we wish others would treat us in the same way.
Kant’s Categorical Imperative serves as a logical trap that urges us to give Jesus’ words a chance. We expect others to exercise control and awareness while avoiding the behaviors of snakes and wolves. Therefore, we too should act in the same manner, even if, and perhaps especially when, others are not acting that way. In fact, in the context of Matthew 10, that is precisely Jesus’ point. People will reject, refuse, and even abuse and kill. We should be aware of them and exercise wisdom, but we must not become predators ourselves. That is what is wrong with the world, and perpetuating such behavior only deepens the problem. It never truly solves anything. In the end, such snakes meet the same end as that of Revelation 12.