Do not let anyone judge you by what you eat or drink, or with regard to a religious festival, a New Moon celebration or a Sabbath day. These are a shadow of the things that were to come; the reality, however, is found in Christ. Do not let anyone who delights in false humility and the worship of angels disqualify you. Such a person also goes into great detail about what they have seen; they are puffed up with idle notions by their unspiritual mind. They have lost connection with the head, from whom the whole body, supported and held together by its ligaments and sinews, grows as God causes it to grow.

Since you died with Christ to the elemental spiritual forces of this world, why, as though you still belonged to the world, do you submit to its rules: “Do not handle! Do not taste! Do not touch!”? These rules, which have to do with things that are all destined to perish with use, are based on merely human commands and teachings. Such regulations indeed have an appearance of wisdom, with their self-imposed worship, their false humility and their harsh treatment of the body, but they lack any value in restraining sensual indulgence.

Since then, you have been raised with Christ, set your hearts on things above, where Christ is, seated at the right hand of God. (New International Version)

“Moral stupidity comes in two different forms: relativism and legalism. Relativism sees no principles, only people; legalism sees no people, only principles.” – Peter Kreeft

There was once a pastor who found the roads blocked one Sunday morning and was forced to skate on the river to get to church, which he did. When he arrived the elders of the church were horrified that their preacher had skated on the Lord’s day.

After the service they held a meeting where the pastor explained that it was either skate to church or not go at all. Finally, one elder asked, “Did you enjoy it?” When the preacher answered, “No,” the board decided all was good.

Nothing can choke the heart and soul out of true spirituality like legalism – a precise extra-biblical list of do’s and don’ts. For many folks, it seems easier to live by the list than to pursue the harder road of developing character qualities.

Christian discipleship involves growing into spiritual maturity and allowing a seasoned character to shape how we make decisions. We must patiently and consistently follow in the way of Jesus, which is the way of grace and of life.

The Apostle Paul spent a lot of his time and energy trying to keep the churches he established from slipping into a soul-less legalism.

Legalism is a compulsion to spell out every detail of how everyone is to live a godly life, going beyond the stated commands of Holy Scripture.

The problem with this approach to the Christian life is that godliness is merely an outward expression of our ability to hold to the list. This legalistic way feeds human pride and boasting, going against the inner heart values of genuine humility and thoughtful service to others.

Biblical teaching thus gets lost in trying to do everything right or perfect.

There are only two alternatives: Choose the way of life and set your heart on things above – or choose the way of destruction through the legalistic list.

The legalist is like a wolf in sheep’s clothing. We need to be wary of people who seem pious and sincere, yet who do not quite pass the smell test. After all, Satan himself, the Apostle Paul once said, masquerades as an angel of light, appearing righteous, yet is intent on deceiving many (2 Corinthians 11:13-15).

So, how do we recognize a legalistic wolf who spiritually and emotionally devours people by judging them according to a contrived list, instead of altruistically helping them with grace? 

Look at the fruit of the tree. Anyone who fails to uplift others will be seen by the rotten fruit of boasting and pride. A telltale sign of such a person is their lack of connection with any spiritual body of people or faith community.

Bellicose boasters and nit-picking legalists believe they are above others because of their expertise at keeping the list of do’s and don’ts. 

A bogus disciple will always be shown by their profound lack of grace, gentleness, and genuine humility. They inevitably advocate for holding to their brand of religion and keeping the unscriptural list. Steer clear of such persons.

A sobering reality is that many people can be deceived with a devil’s bargain: take the nice handy list and you will become godly; here are twelve principles to change your life; follow these rules, pray this prayer, give your money to this, and all will be well.

It is, however, a highway to the grave. The so called “fruit inspector” comes along and goes on to judge everyone according to the legalistic list.

So, get rid of the extra-biblical and even unbiblical list. Stop judging others on whatever someone has deemed the nasty nine sins to avoid or the terrible ten things that will send you to hell. Don’t waste your time or energy on such persons.

The legalist holding to a contrived list of don’ts is not honest about their struggles. Because the bald fact of list-living is that it cannot be fulfilled; it’s unreasonable. So, when we know we are not measuring up to the list, the temptation is to keep up appearances as if we are. 

List-living eschews showing any weakness or imperfection. The legalist’s self-talk says:

• Always avoid admitting my sin to anyone because the list pronounces me a failure if I do. 
• Don’t ever enter a deep and prolonged grief over my loss because the list says I need to stay strong. 
• I cannot profess my doubts about God because the list says if I doubt, I am not a real Christian.
• Just tell me what is on the list, and I will do it – even though I cannot.

Here is my response to legalistic list-living: To hell with the list! 

You were raised from death with Christ. So, live for what is in heaven, where Christ is sitting at the right hand of God.

Grace transforms hearts, turns lives around, and provides genuine joy and satisfaction – not list-keeping.

If grace is not the answer, we are not asking the right question.

The greatest anti-legalistic prayer we can pray is the tried and true ancient prayer of the Church:

“Lord Jesus Christ, Son of God, have mercy on me a sinner.”