Inside the Legalist Mindset, Part 4: Gluttons for Punishment

After my exodus from legalistic fundamentalism several years ago, someone, appalled at our “compromise,” asked my wife, “So what’s he going to preach about now, love?” They were sure that if I wasn’t going to preach about women in pants, going to the movies, listening to “ungodly music,” how terrible Southern Baptists were, and the rest of fundamentalism’s hot buttons, then I must be abandoning the faith and would just preach a bunch of “sloppy agape.”

Preaching about love, well, that was what “liberal compromisers” do. That’s all they’re worried about, because, I mean, they don’t have anything else to say, right? If you don’t preach against sin, what else is there to preach about?

That’s one of the main reasons legalists attend church (I mean, “the preaching hour”) – to hear the preacher preach against their sin. The hope is to have some sin pointed out to their life that they can go to work on. Weep at the altar, add a new rule, or find some other form of penance. Everything else is peripheral, secondary. If you can’t find a reason to feel convicted from the sermon, then the preacher didn’t do his job.

This is also why legalists are always on the lookout for new rules. The Christian life is meant to be harder and harder, stricter and stricter. Because sin always finds new ways to overcome us, it needs to be met with newer, better, tougher rules.

And yet again, this serves to perpetuate the vicious cycle of legalism. It takes a major intervention of grace to break free – and then only over time. It takes time to decompress from this mentality. You’ve lived under so much pressure for so long, that it feels strange to come out from under it.

This is why so many stay locked in. It’s too insecure of a feeling to walk away from all those rules you’ve been convinced so long were so right, and by which you measured your spirituality before God. It feels like you’re sinning when you stop keeping a few of those man-made rules, so you immediately run back to the place where you feel comfortable, back where you felt “godly,” back to the pressure that “kept you in line” for so long.

It’s like a slave not knowing how to feel or act when he’s set free. That’s why so many slaves to legalism stay in it. It feels safer. So they pile up the standards like a fortress of emotional safety. Too afraid to break free. That’s why I would encourage you to pray for your brothers in bondage (Heb. 13:2).

For the other parts of this series: Part 1, Part 2, Part 3


9 Responses to Inside the Legalist Mindset, Part 4: Gluttons for Punishment

  1. newcolors says:

    Questions…How do you define sin? And what am I set free from…living in sin…or obeying God?


  2. TN says:

    Extra-biblical notions of holiness and the heart’s inclination to rest in them for righteousness is a powerful thing. Praise God for the gospel. And thank you for these posts. I’ve enjoyed reading them.

  3. Fundamentalist preaching often aims to heap guilt on the hearers. It condemns the hearers and calls for them to “do better”. They are left with guilt and a call to recommit to Christ. They need to just “grit their teeth and do it”.

    Fact is, they can’t. By themselves, in the power of the flesh they will ALWAYS fail.

    Biblical, Christ-centered preaching should do its share of convicting too. But it should point people away from their sin and toward Christ. It should give them hope in the Gospel. It should make them leave, not resolving to double their personal efforts, but aiming to rejoice in Christ and love him all the more.

    See my post on this topic here.

    Great series by the way. You are being somewhat general, and I think newcolors’ critiques don’t really apply. I think you would agree with what he’s saying, but he may not be familiar with fundamentalist-style legalism.

    Blessings from Christ,

    Bob Hayton

  4. holmegm says:

    Fundamentalist preaching often aims to heap guilt on the hearers. It condemns the hearers and calls for them to “do better”. They are left with guilt and a call to recommit to Christ. They need to just “grit their teeth and do it”.

    Not just fundamentalist preaching. Counterintuitively, liberal and “emergent” preaching does the same thing.

    After all, a command to “be like Jesus” – without any supernatural help, substitutionary atonement, and so forth – is just legalism in drag.

  5. Carla says:

    Without superhuman help, it’s impossible for a mind to hold onto this slippery truth of real Christianity without slipping either into legalism (the 20th centuries’ version of Pharisee-ism) or “sloppy agape” (the 20th century version of Sadducee-ism).

    I think it was Henry Cloud who talked once about making peace between the way things are and the way things ought to be.

    I’ve always wanted to start “Pharisees Anonymous” and see if anyone would come.

  6. Kim says:

    You may want to consider listening to Scott’s series on The Greatest Commandment found here, He isn’t advocating license at all; it is about living a holy life thru grace and esteeming others higher than ourselves. It is so hard to sum up in a few words but I think you’d be blessed by hearing the messages.

  7. Newcolors says:


    Thank you for the suggestion but I think I will pass for now. Scott has never answered my question concerning the definition of sin. The answer I was looking for was one based upon the truth of the Scriptures. 1John 3:4 says quite plainly “Whoever commits sin also commits lawlessness, and sin is lawlessness”.

    Scott talks about freedom, but in Scripture I am taught that I am not free from obeying God…but free from the life of sin and death. Is this not true??? Does Paul teach disobedience to God’s Law? Or does he instead say in Ephesians 4:17 that we as followers of the Messiah, should no longer walk as Gentiles?

    While I praise God for His grace poured out thru His sacrifice of His Son..when it comes to knowing how to live….the definition of right and wrong….the defintion of sin…I do not listen to men. I cannot afford to…neither should you. The Bible teaches that in the end times people would heep up for themselves teachers who tickle their ears…men who would turn the grace of God into lewdness.

    Scott…I have not meant to offend…please forgive me if I have. If you wish…I will refrain from commenting at your request. God bless…

  8. Scott W. Kay says:


    Thanks for the comments. I apologize for taking so long to respond. I’ve been out of town and unable to check up on things here. The posts have posted automatically. Sorry!

    In your last comment, you gave my answer to the definition of sin, actually you gave God’s: 1 John 3:4 – sin is the transgression of God’s law.

    I’m not arguing freedom from obeying God’s commands, but from obeying man’s laws that go BEYOND God’s laws. That is the legalism I have experienced and observed, namely, adding to the restrictions Scripture places on us so as to over-ensure we don’t violate God’s clear commands. It’s called “fencing the law.” It’s going beyond Scripture and over-defining sin; calling things sin that are not.

    I’ve got more to post on this. It sounds like I need to fill out the issue a bit more.

  9. […] An examination of this mindset has recently been well-written by Scott Kay. […]

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