Escaping the Cycle: Paul’s Antidote to Legalism’s All-or-Nothing Trap
Romans 9:30-33
What shall we say, then? That Gentiles who did not pursue righteousness have attained it, that is, a righteousness that is by faith; but that Israel who pursued a law that would lead to righteousness did not succeed in reaching that law. Why? Because they did not pursue it by faith, but as if it were based on works. They have stumbled over the stumbling stone, as it is written,
"Behold, I am laying in Zion a stone of stumbling, and a rock of offense; and whoever believes in him will not be put to shame."
No one was more circumspect in regard to righteousness through the law than the Pharisees. Yet Jesus taught that the path to true righteousness isn’t paved by human effort or legalistic striving, but by humble faith in God’s grace through Him.
In this passage in Romans, the Apostle Paul contrasts two groups, Gentiles and Israel, to illustrate how God’s righteousness is attained. The Gentiles, who weren’t actively chasing after righteousness through religious laws or rituals, surprisingly received it. Why? Because it came through faith, not achievement. Paul explains that Israel, despite zealously pursuing a "law that would lead to righteousness," fell short. Their mistake was treating righteousness as something earned by works, like checking off a divine to-do list, rather than receiving it as a gift through faith. This culminates in the imagery of the "stumbling stone," a reference to Jesus Himself, drawn from Isaiah 8:14 and 28:16. Israel "stumbled" over Him because He didn’t fit their expectations of a works-based salvation, they saw Him as a rock of offense instead of the cornerstone of faith. And we see these things even today now under the assumptions of the gentile congregations.
Paul promises here in Romans that "whoever believes in Him [Jesus] will not be put to shame," emphasizing security and freedom from condemnation for those who trust in Christ. It’s a reminder that God’s plan often upends our human logic, and that salvation flows to the unexpected, through our belief rather than our merit.
Jesus’ words at the end of his Sermon on the Mount echoes this theme with striking clarity.
He warns,
"Unless your righteousness exceeds that of the scribes and Pharisees, you will never enter the kingdom of heaven" (Matthew 5:20).
The scribes and Pharisees were paragons of religious observance, they tithed meticulously, fasted publicly, and followed the law to the letter. But their righteousness was external, focused on appearances and self-effort, much like Israel’s pursuit in Romans, and even like what we see in Christian churches from Orthodox to Roman Catholic, and even in every variation of the Protestant traditions. Each practicing their righteousness, displaying their godliness, doing their fundamentalist church works, putting on their righteousness for an hour every Sunday morning.
Jesus isn’t calling for more and more works or stricter rule-following; that would be impossible, as no one can out-Pharisee the Pharisees in legalism. Instead, He’s pointing to a different kind of righteousness, one that’s internal, transformative, and rooted in faith, worshipping God in Spirit and truth. This surpasses mere obedience to good works because it’s imputed to us through Christ’s perfect life and sacrifice, not our flawed attempts. In essence, the "exceeding" righteousness is the very faith-based righteousness Paul describes in Romans, where we trust in Jesus as the fulfillment of the law rather than stumbling over Him.
These passages converge on a central gospel truth: a works-based righteousness leads to failure and shame, while faith in Christ brings true attainment and security.
Reflection:
Are we pursuing God through our own efforts, good deeds, rituals, or moral checklists, or are we resting in faith?
The Pharisees’ righteousness was impressive but insufficient; Christ’s is perfect and accessible. These verses invite us to examine our hearts.
Where might we be relying on works instead of faith?
In a world obsessed with achievement, they offer liberating hope, true righteousness is a gift, waiting for those who believe.
Thankfully Paul doesn't leave it at that, for surely many in the flesh will continur to desire works that will make them out as good and godly people. And do he goes on...
Romans 10:5-11
"For Moses writes about the righteousness that is based on the law, that the person who does the commandments shall live by them. But the righteousness based on faith says, "Do not say in your heart, ‘Who will ascend into heaven?’" (that is, to bring Christ down) "or ‘Who will descend into the abyss?’" (that is, to bring Christ up from the dead). But what does it say? "The word is near you, in your mouth and in your heart" (that is, the word of faith that we proclaim); because, if you confess with your mouth that Jesus is Lord and believe in your heart that God raised him from the dead, you will be saved. For with the heart one believes and is justified, and with the mouth one confesses and is saved. For the Scripture says, "Everyone who believes in him will not be put to shame."
Paul's progression builds on the theme of righteousness by faith, addressing the human tendency to cling to works while offering a straightforward, accessible path to salvation. It’s as if he’s anticipating the reader’s question: "If faith, not works, is the way, then how do we access it?"
What Paul highlights regarding fundamentalism and legalism is, it’s an all-or-nothing system; one slip up, and it all crumbles, leading not to life but to condemnation, as no one can fully keep the law. Everyone slips up. So everyone everywhere needs to continually rinse and repeat. unforgiving system: it’s perfection or bust, and since "everyone slips up," it traps people in a relentless cycle of striving, failure, and "rinse and repeat" efforts to atone or measure up. This isn’t just ancient Jewish legalism, it’s echoed in today’s rigid religious structures, where rules and rituals become the focus, leading to exhaustion rather than true life in Christ. Paul, drawing from his own Pharisaic past, dismantles this in Romans and beyond, pointing instead to faith as the liberating alternative.
Paul echoes this in his letter to the Galatians 3:10
"Cursed is everyone who does not continue to do everything written in the Book of the Law,"
...underscoring that partial obedience isn’t enough. No human can achieve this flawless standard, as Paul admits in Romans 3:23: "All have sinned and fall short of the glory of God." Even the apostle himself, in Romans 7:14-20, confesses his ongoing struggle with sin, showing that legalism offers no real escape, only a perpetual treadmill of trying harder next time.
Paul is saying that religious people chase righteousness through repeated rituals, confessions, or rule-keeping, hoping to wipe the slate clean. Strict doctrines, repetitious checklists of behaviors, and a focus on outward conformity that breeds judgment and burnout, rather than genuine transformation.
Paul clears it up in Romans 10:6-8, reinterpreting Deuteronomy to show that faith doesn’t demand impossible feats or endless do-overs. Instead, the gospel is "near you, in your mouth and in your heart", accessible, not earned.
Do you see what he is saying?
He's saying what Jesus said.
Salvation isn’t about climbing to heavenly heights, or plumbing the depths; Christ has already done the work. As Jesus taught, by believing in your heart that God raised Jesus from the dead and confessing Him as Lord (Romans 10:9-10), you’re justified once and for all, no resets required. This faith ends the curse of the law, as Paul declares in Galatians 3:13
"Christ redeemed us from the curse of the law by becoming a curse for us."
Paul’s anti-legalism stance isn’t anti-law; he affirms the law as holy and good (Romans 7:12). But it’s a tutor leading to Christ (Galatians 3:24), not the savior itself. And that's the key to it all. And Paul he warns against man-made rules that "lack any value in restraining sensual indulgence," (Colossians 2:20-23) calling them shadows compared to the substance of Christ.
For modern believers, this means freedom from fundamentalist traps like equating spirituality with our attempts at perfect attendance, moral perfectionism, or cultural dos and don’ts, it’s about resting in God's grace. Faith avoids that pitfall, bypassing the all-or-nothing grind. Even in our slip ups, grace abounds (Romans 5:20), not requiring endless rinsing but offering continual access to God’s throne.
Hebrews 4:16
"Let us then approach God’s throne of grace with confidence, so that we may receive mercy and find grace to help us in our time of need."
Reflect:
Where in my life am I caught in this cycle, perhaps in guilt over failures, or in performative faith?
Prayer:
Father God, king of the Universe, free us from legalism’s chains. Help us to confess Jesus as Lord, with our words and with our hearts, believing in His resurrection, and resting in the righteousness You provide. We ask these things through the power of the Holy Spirit and in the Holy name of Jesus Christ, Amen.