The New Testament never paints the Pharisees as the heroes of the story. Nobody wants to grow up to be a Pharisee. And nobody wants to be labeled as a legalistic Christian.

But to a certain extent, the Pharisees get a bad wrap. At least in my opinion.

I mean, think about it. These were some of the more well-respected men in the first century Jewish community. They were incredibly well versed in the Scriptures. They even memorized large passages and could recite them from memory. How many of us can say that we know entire pages of scripture by heart and can recite them at the drop of a hat?

Pharisees were theologians and teachers. They were family men. They prayed and fasted more than anybody. In many ways, they would put the rest of us to shame in how honorably they lived their lives.

This is why it was such a striking statement when Jesus said, “For I tell you, unless your righteousness exceeds that of the scribes and Pharisees, you will never enter the kingdom of heaven” (Matthew 5:20).

Cultivating Greater Righteousness

The natural response to Jesus’ statement would be, “Who could be more righteous than a Pharisee?” It seemed like an impossible statement. But what Jesus was talking about is cultivating a different kind of righteousness.

In their efforts to obey everything that God had commanded, the Pharisees had begun to legislate everything. It’s not as if they ever intended to be so uptight and even adversarial toward the Messiah they said they had been waiting for.

Everything the Pharisees did was an attempt to keep themselves pure by creating systems and structures that would help keep them from sinning. They thought they were being wise. But the systems and structures eventually became ends unto themselves.

What Jesus is calling for is transformation of the heart.

We’re often guilty of the same thing. It’s easy to follow rules that you establish for yourself. It’s harder to give your entire heart and life to Jesus. And so we’re all tempted to become legalistic. It’s a safety hatch we use to keep ourselves from having to surrender.

Here are four subtle signs to look for as you seek to avoid becoming a legalistic Christian. 

1. You See the World in Black and White.

When you have a legalistic mentality, your understanding of morality is often very reductionistic. It’s incredibly black and white. But the world is more grey than we give it credit for.

You may look at something like alcohol and feel as though it’s an absolute evil. You can’t understand why any good Christian would drink even one beer. Or maybe you can’t understand why any follower of Jesus would have a Netflix subscription, given some of the content they host. Or maybe you just can’t wrap your mind around voting outside your political party—your candidate is the only Christian choice.

And the problem isn’t that you have strong convictions about what you believe to be right. There’s nothing wrong with that. The problem is when you believe that there is no possible way to see an issue other than the way you see it. Your understanding is undeniable in its moral superiority. That’s legalism.

And this is what the Pharisees had done. Take the Sabbath for instance. God had commanded his people to rest on that day. But as the Pharisees began to interpret it, they dictated exactly how many steps you were allowed to take on that day before it was considered work. You could be punished and shunned if you took even one more step! I’m not sure this is what God intended. The issue is more open to interpretation than that.

To be sure, a great many commands of scripture are indeed black and white. I’m not saying that we all need to become moral relativists. But if secondary issues are primary to you, it may be because you have a legalistic streak in you.

2. You Constantly Compare.

The Pharisees were constantly comparing themselves with Jesus. And they always scored themselves higher than him. They were better at keeping all the rules they made up than Jesus was. And so the Pharisees ended up thinking that they were literally more righteous than God.

Do you constantly compare yourself to other people to see how you stack up against them in terms of how good of a person you are? We all do it to a certain extent. But if you’re constantly living in the land of comparison, you probably have some legalistic tendencies. You begin to fixate on where someone else is breaking the rules that you are successfully keeping. And you always score other people using the scorecard of your strengths.

But here’s the unfortunate news. God doesn’t grade on the curve. When someone else struggles with a sin, that doesn’t necessarily mean that you’re morally upright. And you aren’t better than somebody else just because you sin differently from them.

We often have blindspots when it comes to our own shortcomings. We tend to see the areas where we’re doing things right, and we take notice where others aren’t measuring up to our personal standard. We would do well to begin intentionally focusing harder on where we fall short and how we need God’s grace.

3. You Silently (or Not so Silently) Judge Other People.

Jesus once told a parable about a Pharisee and a tax collector who both went to pray to God. The Pharisee was the respected man of the community. The tax collector, not so much. People in his profession were known for stealing from and extorting their fellow countrymen.

So the Pharisee prays, “God, I thank you that I am not like other men, extortioners, unjust, adulterers, or even like this tax collector. I fast twice a week; I give tithes of all that I get” (Luke 18:11-12). Even in his prayer, he seeks judgment over the person standing next to him.

And we can tend to do the same. We see the ways that other people struggle, and we can silently judge them for being less holy, less righteous, less morally upright than us. We can be judgmental of people and mask it as a prayer request. “Pray for so-and-so. They really seem to be struggling with their faith.”

Other times, we take a more direct approach and harm people with the harshness of our words and the judgmentalism of our spirit. Christians ought to keep each other accountable, but always with an attitude of gentleness and a heart for restoration (Galatians 6:1-2).

Always seek to be more humble and gracious. And when you pray, pray like the tax collector. He confessed his own shortcomings, asked for mercy, and was the one who walked away right with God. The Pharisee, not so much.

4. You Believe That Blessing Comes to You Only When You’ve Had Your Quiet Time.

It’s important to realize how toxic legalism is. It’s toxic to your relationships, but it’s also toxic to your soul. At the heart of legalism lies a doubt. You get legalistic because you doubt that God’s grace really is big enough to cover all the sins you’ve committed. And so in order to supplement God’s grace, you work harder.

This is precisely what the Pharisees sought to do. Their intent was to purify their people. They believed that if they became righteous enough, spiritual enough, morally virtuous enough, then God would come and bless them.

They had been waiting for a Savior to come and deliver their people from the oppression of foreign empires. And they believed that if they tried hard enough, God would see their good works and save them faster.

We tend to believe something similar. We might believe that we will have a more blessed day if we’ve had our quiet time–which necessarily means that you’re less blessed on the days that you don’t.

But God’s love for you isn’t dependent on your bible reading plan. The measure of his provision and protection over your life isn’t determined by how many minutes you spend praying today.

Experiencing the tyranny of always trying to be good enough but never feeling like you measure up is an indicator that you have a legalistic view of the world. Jesus came to give you freedom from that. Don’t act like you’re enslaved when you have been called a son (Galatians 5:1).

There Is Grace for the Legalistic Christian.

The good news is that God’s grace is bigger than all of this. You only have to open yourself up to it. Admit that you are not good enough, and surrender to Jesus—because he is.

You will never be able to measure up. And that’s okay.

That’s why Jesus came and died in your place. And by the power of his resurrection, you can begin to become the person you were always intended to be. Not by keeping rules, but by the power of the living God.

And you’ll never fully get there this side of heaven. But it’s important to remember that we aren’t in a race against each other. We are on a journey together. When you trade your legalism in for grace, what you receive is safety, security, and community. When everything depends on Jesus, that’s when we really begin to be made whole.