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Christian legalism does not imply a works righteousness because true Christians know they are saved apart from their works (Ephesians 2:8-9). But there is a type of legalism that stifles and suffocates authentic Christians from the unspeakable joy that comes with their inheritance. It doesn’t always come with loud demands—it often arrives quietly, cloaked in “discernment,” preferences, and good intentions.
A few years ago, I was sitting with a friend in a parking lot just after lunch. We were chatting. He was sharing with me how contemporary Christian music was worldly. I found it instructive that he could discern worldliness by external observation. I decided to draw him out about how he could know what worldly music is by listening to it, so I asked him to define worldliness for me. He stated that it was the style that made it worldly. He believed modern music was worldly, and he viewed worldliness as something out there in the world rather than something in our hearts (James 1:14-15; 1 John 2:15-16). This framing reveals a common thread in legalistic thinking: that worldliness is primarily about externals.
His perspective made me more curious, so I asked him about drums. He said that drums were worldly, too, but not in all contexts. For example, having a drum in your home is not necessarily worldly. A Christian living in Africa playing drums in a church meeting is not worldly either, but having a drum in a church building in America would be. His interpretation of worldliness depended on context and culture. It reminded me of my first Greek class during my undergrad program. My professor told me about a rule in Greek and said that it was always the same in every case, except in “this” particular case. Then he talked about this other rule that applied all the time, except for certain exceptions. I thought, “Greek is going to be impossible to learn. Why can’t they make one rule that applies universally?”
After a few minutes with my friend, I was thinking similarly about worldliness. He believed that a woman who wore pants to a church service would be worldly. But she could wear pants while camping or working in her backyard. She could also wear a swimsuit to the pool or beach, but she needs to cover her body in other places, like shopping or going on a picnic, because it would tempt men to sin if they saw her immodesty. (I silently wondered if men don’t lust while near an ocean.) What I was hearing wasn’t a biblically reasoned theology of modesty or cultural engagement. It was a shifting, unpredictable list of expectations where righteousness was gauged by appearance, location, and preference.
My friend would not go to a public movie theater but would watch a movie on his television. He would not look at a woman in a swimsuit but view a similarly attired woman doing gymnastics or ice skating on the television. He had an extensive list of rules to live by, which changed depending on the setting, context, or the situation. I appreciated his honesty and transparency, particularly his desire to live a Christian life before God and others. In that way, he was refreshing and inspiring to me. However, his Christian mentors trained him to base worldliness on stylistic issues, personal preferences, and community expectations.
I agree with him in a sense: Christians should be discerning about how we live in God’s world. We must discipline ourselves while always pursuing righteous ways (Ephesians 4:22-24). Holiness matters. But a significant point in which I differed from my friend was how he defined worldliness. He could look at a person and determine if that person was worldly based on external observations. Perhaps you can do that too. I do not have that gift. I have found it nearly impossible to look at a person externally and accurately judge them as being a lover of Christ or the world. The length of a person’s hair or their personal music preferences are shaky assumptions for determining the spiritual condition of an individual’s soul. It’s not that fruit can’t be examined, but fruit without context can be misleading.
It would be challenging to pick Jesus out of a crowd of Israelites because He was so much like them (Matthew 26:48). Others accused Him of sin because He hung out with unsavory people (Matthew 19:14; Luke 7:37–39). It becomes confusing and subjective when style preferences are the criteria for discerning worldliness. Jesus hung out with His world, He ate with His world, He drank with His world, and He dressed like His world. But Christ was not worldly. My friend’s approach to discerning worldliness was precarious because he judged external appearances while missing the heart’s motives (Luke 6:43-45).
He elevated his preferences to conscience-binding authority, e.g., drums in an African church are okay, but not in an American church. Is this the Bible speaking? Or is it white, American, conservative Christian-speak? A comparative religious culture is not wise (2 Corinthians 10:12). It tempts Christians to compare my list with your list of standards. In my friend’s system, each Christian would have different lists depending on their interpretation of worldly. His perspective is why Christian communities draw more attention to the stylistic distinctions that make them look different from the culture in which they live.
Though fruit inspection is a Christian assumption, there must be wisdom and humility when doing it because external observations do not always tell you all that you need to know about a person. Christians who are externally-centered tend to embrace a gnostic approach to discerning folks, albeit they would never say they have a gnostic worldview. Though the Lord calls you to be a fruit inspector, you must challenge your assumptions with humility, wisdom, and charity. The Gnostics believed—in part—that the world was terrible and knowledge was good, the earth was corrupt, and the spiritual was good. They put an accent on the internal—the gnosis (knowledge). They stayed away from earthly things because those would defile them.
Legalism borrows from this worldview. The legalist figures out what is wrong, primarily through external observations, and stays away from those things. As a double measure, the legalists do not associate with anyone who associates with the person who does “evil stuff.” This extra fence keeps them from contamination. There is a contrived theology that communicates this methodology. It is called the doctrine of separation, which can domino into multiple iterations that separate from the person who associates with the person who associates with the person who associates with the evil thing. It can become quite convoluted and confusing for the novice legalist.
The New Testament Pharisees were proficient at living out this separated and structured lifestyle. They had gnostic tendencies, which Jesus was not reluctant about condemning. (Read Matthew 23:1-39.) The Pharisees’ doctrine of separation led them to hold the Law up as the paragon of life, and then they placed hedges around those 600-plus laws. They feared breaking the Law, so they erected safe barriers (doctrine of separation) to keep them from breaking the Law.
The sad consequence is that they were noted for their “spirituality” by the number of hedges they set up, all of which were extrabiblical. Their severe asceticism led to a breakdown in their practical theology—spiritually, logically, practically, and relationally. As the generations passed, the succeeding followers forgot the intent of the hedge, and due to their ignorance, they elevated these tertiary rules and practices to the place of the Law. Thus, the Law expanded into a strict traditionalism that bound people in their consciences to maintain something that God did not demand. As you might imagine, there are many dangers to ascetic practices. I have seen three recurring ones: fear of others, erratic lifestyles, and cultural irrelevance.
Legalism is a fear-based culture. Being afraid is one of the strongest temptations for external rule-keepers who live in a culture rife with insecurity. It is a list culture. Everyone has a list to live by, and seemingly no one lives according to the same set of rule-ish preferences. Because they hold their standards at the level of the conscience, the list becomes a matter of authority for a legalist. But it is worse than that. When these legalistic Christians interact with other legalistic believers who do not practice the same things, there is a temptation to judge them uncharitably because the assumption is that they are sinning, according to their legalistic list of rules to live by to be right with God. These legalists are always awkwardly (if not dogmatically) explaining why they do this or that or why they don’t do what others do. They are painfully careful about what they say within their circles because harsh and punitive judgments are absolute. They don’t want to be known as a compromiser or liberal, according to how others within their rule-based community interpret their beliefs. It’s not just a fear-based culture, but it’s an exhausting one too.
God does not call us to instability or double-mindedness (James 1:5-7). He is not calling us to create a culture that draws more attention to our styles and preferences than to our Lord. It is not wise to develop choices for statement-making, even if that was not your intent. Drawing attention to yourself through immodesty or over-modesty is not necessary or prudent. The Lord is not the author of this type of confusion. Imagine if you gave your permission to a friend to go to a movie theater, but your other friends believed it was a sin to do what you did. But these same friends would watch a video at home. Because they live in a fear-based culture where the majority controls what they do or don’t do, this scenario is a picture of erraticness. For example, you can’t go to a movie, but you can watch one at home. What is worldly here? The movie? The building? The event? Some Christians travel to another town to watch a film so their Christian friends will not see them at a movie theater. They would say that being seen at a theater would be a stumbling block to their legalistic friends. And are they correct? Yes, in a sense, you don’t want to be a stumbling block. But are you to leave your friend in bondage?
Knowledge puffs up, but love builds up (1 Corinthians 8:1).
Our lives are sideways when we’re hiding from the Christians but are less concerned about what non-Christians see, think, or say about us. Suppose you met a pagan in another town while attending a movie and led him to Christ. Ironically, my buddy, who watched a movie in another town, was more concerned about hiding from the Christians than the non-Christians. What would you do when your new Christian friend invited you to a movie? What would you say? Would you say it was a sin to watch movies in a theater? Would you go with him? Would you ask him to go to another town because it is wrong for you to watch it in a locale where you are known? Do you know how not to be a stumbling block while not leaving a legalist in bondage? Jesus was a relevant man. He always connected Himself to His culture. He intentionally embedded Himself within the milieu of His day. Jesus was not a white, blue-eyed, pristine robe-wearing, purple sash-bearing, halo-supporting kind of guy. Christ was not out of step with His community. He blended with the people. He was different, but the differences were not culture-centered style choices.
Ironically, Jesus had more anti-religious rules than anti-cultural ones. He would work on the Sabbath (Matthew 12:1-2). He would trash a church building (John 2:13-16). He condemned religious people (Matthew 23:1-39). He hung with a harlot (John 8:1-11). Though He was out of step with the so-called holy people, He was not out of step with His community.
He had a gathering ability when it came to the culture. They flocked to Him. They wanted to be with Him, not because He was externally different, but because He was like them, albeit a much better version of them. The fundamental difference was that Jesus Christ was internally different. The legalistic Christian has created a subculture that is rife with insecure people with a bent toward rule-keeping. This Christian subculture believes they bring glory to God by not engaging the folks that Jesus came to save. In this way, they are anti-Jesus by separating themselves from their culture. And their culture has separated from them because the legalistic Christian is weird and uncompelling. Their separation creates and perpetuates isolation and irrelevance.
If these thoughts stirred conviction, confusion, or clarity in your thinking, take a moment to assess your current path with the Lord. The solution to legalism isn’t rebellion—it’s repentance. The way out isn’t throwing off all restraint but surrendering to Christ’s leadership and embracing the freedom He gives through the gospel. You don’t need fewer convictions—you need biblically anchored, love-motivated ones. Here are some questions for reflection:
Legalism doesn’t just distort our view of others—it distorts our view of God. It reshapes Him into a rule-keeper instead of a Redeemer. But the gospel doesn’t lead to license or legalism. It leads to love.
Rick launched the Life Over Coffee global training network in 2008 to bring hope and help for you and others by creating resources that spark conversations for transformation. His primary responsibilities are resource creation and leadership development, which he does through speaking, writing, podcasting, and educating.
In 1990 he earned a BA in Theology and, in 1991, a BS in Education. In 1993, he received his ordination into Christian ministry, and in 2000 he graduated with an MA in Counseling from The Master’s University. In 2006 he was recognized as a Fellow of the Association of Certified Biblical Counselors (ACBC).
