Why Freedom Feels Wrong at First
Another UnBound Letter to Brother & Sister Bondage
Dear Brother & Sister Bondage,
One of the strangest parts of leaving legalism is that freedom can feel like sin. You finally discover that some burden you carried for years was never placed on your back by God. It came from men. It came from tradition. It came from fear. And yet, when you finally begin to lay it down, you do not always feel free at first.
You feel guilty. & You feel uneasy.
You feel like you are doing something wrong.
But brother, sister, that does not mean freedom is wrong, it means bondage leaves bruises.
The Prison Comes With You
When a man spends years in a dark room, sunlight hurts his eyes. The problem is not the light. The problem is that he has grown accustomed to darkness. Legalism works the same way, in that it trains your soul to fear what God has not forbidden. It makes man-made fences feel like divine commandments.
Chains leave marks long after they are removed.
For years, you may have been taught that holiness means more rules, spirituality means less joy, and maturity means greater restriction. Then, one day Scripture opens the door, and you realize Christ offers something far better.
But the freedom still feels dangerous. The cage is gone! But, part of you still lives inside it!
Israel Wanted Egypt Back
Israel left Egypt physically long before Egypt left Israel mentally. God broke Pharaoh’s power. God split the sea. God drowned their enemies. Yet, when hardship came, they looked backward.
They remembered slavery as if it were safety and bondage; as if it were comfort. Freedom often feels uncertain because it requires faith. The old chains were familiar. The wilderness was not.
“They said to Moses, ‘Is it because there are no graves in Egypt that you have taken us away to die in the wilderness?’”
— Exodus 14:11, ESV
The Lord had delivered them, but they had to learn how to live as free men, and so do we.
The Spirit of Slavery
Paul gives us the category we need.
“For you did not receive the spirit of slavery to fall back into fear, but you have received the Spirit of adoption as sons.”
— Romans 8:15, ESV
Slavery produces fear, but adoption produces confidence.
The legalist approaches God like a servant terrified of punishment. The Christian approaches God like a beloved son brought near by grace.
The legalist asks, “Have I done enough?”
The son asks, “How can I honor my Father?”
Those are not the same question. One is driven by fear and the other is born from love.
Freedom Must Be Learned
Many Christians leaving legalism expect freedom to feel natural immediately. It usually does not, why? Freedom is a muscle!
For years, your conscience may have been trained by tradition instead of Scripture. Your instincts were shaped by church culture instead of God’s Word. Your reflexes were developed by fear instead of faith….. So, be patient.
You are not trying to silence your conscience. You are trying to disciple it.
“Do not be conformed to this world, but be transformed by the renewal of your mind.”
— Romans 12:2, ESV
The mind must be renewed and the conscience must be retrained. Also, the soul must learn the difference between the voice of God and the echoes of men.
A Weak Conscience Is Not a Holy Conscience
Romans 14 is a mercy to bruised believers. Some saints had consciences that restricted things God had not restricted. Paul did not mock them. But, he also did not make their weakness the rule for the whole church.
“One person believes he may eat anything, while the weak person eats only vegetables.”
— Romans 14:2, ESV
A weak conscience is real, but it is not the standard of holiness.
The conscience is a wonderful servant, but a terrible master. It does not create truth. It responds to what it believes is true (or what it has been fed), and often gives bad warnings.
A misinformed conscience is like a smoke detector that screams every time someone makes toast.
You do not smash the detector. You retrain it with the Word.
I have taught regularly in my counseling practices, that you must learn to preach the gospel to yourself and stop listening to the voice in your head speaking lies!
The Fear of Becoming “One of Them”
Many people leaving legalism carry a hidden fear. They do not want to become liberal or worldly. They do not want to drift.
That is a good instinct.
But, here is the mistake: they assume every step away from legalism is a step toward compromise, but it is not.
Sometimes a step away from legalism is simply a step toward biblical Christianity.
The opposite of legalism is not lawlessness. The opposite of legalism is liberty under Christ.
Christ did not free you from man-made rules so you could become your own god. He freed you so you could gladly live under His lordship.
The Older Brother Syndrome
Jesus told a story about two lost sons.
Most people focus on the prodigal. But the older brother was lost too, see the younger brother ran from the father through rebellion. The older brother ran from the father through rule-keeping.
One said, Give me my inheritance. The other said:
“Look, these many years I have served you, and I never disobeyed your command.”
— Luke 15:29, ESV
Both misunderstood the father’s heart. Legalism often creates older brothers. Yes, they obey, they work, and they “keep the rules” (externally anyway). But deep down, they believe acceptance must be earned.
Joy Feels Suspicious
One of the clearest signs that legalism still has roots in your heart is that joy feels suspicious.
You start enjoying God’s gifts.
You laugh more.
You rest more.
You stop living in constant fear.
But, then a voice whispers, “This cannot be right.”
But Scripture says otherwise.
“For everything created by God is good, and nothing is to be rejected if it is received with thanksgiving.”
— 1 Timothy 4:4, ESV
The God who made sunsets is not offended when you delight in them. The God who made laughter is not threatened by your joy. The God who made feasts is not honored by perpetual gloom. Joy is not worldliness when it bows before the King.
Learning to Walk Outside the Cage
As I wrap up this letter, I want you to imagine a prisoner who spent decades in chains and then has them removed. The prison door opens and Sunlight pours in. Yet, he hesitates. Why? Because, freedom feels unfamiliar.
Brother, sister, that may be where you are. You love Christ, you love Scripture, and you are not looking for excuses to sin. You are learning how to walk outside the cage.
So walk slowly if you must, but walk.
“For we walk by faith, not by sight.”
— 2 Corinthians 5:7, ESV
Let Scripture retrain your instincts. Let the Spirit renew your mind. And, let the gospel teach your heart how to breathe again.
The Freedom Christ Purchased
Never forget this: Jesus did not die merely to forgive your sins. He died to free you from every false master.
That includes the tyranny of man-made religion. It includes the crushing weight of legalism. And, it includes the endless treadmill of trying to earn what God freely gives.
“For freedom Christ has set us free; stand firm therefore, and do not submit again to a yoke of slavery.”
— Galatians 5:1, ESV
Freedom feels strange at first. Sunlight always does after a long imprisonment.
But, stay in the light. The air is better outside the cage.
Enjoy the light of Christ and shake off the cold moisture that made your spiritual bones creak!
Love in Christ,
Brother UnBound




What a freeing truth it is to live in the grace Christ purchased for us in His perfect life and His painful death! When we have the freedom of Christ, why would we want to live by man's rules anyways? I hope letters like this help folks see that.