Should Have Syndrome
Have you ever heard of “should have syndrome”?
Maybe that’s not a clinical term or one you’ll find in the back of a Christian
bookstore on a laminated bookmark, but I bet you know what I mean. It’s that
quiet ache that whispers, "You should have done better." It’s
the subtle drip that turns into a flood if you’re not careful. It’s the echo of
regret bouncing off the walls of our soul.
I know it well.
I should have prayed more. I should have
forgiven faster. I should have reached out. I should have tithed. I should have
spoken truth when I stayed silent. I should have stayed home. I should have
gone.
You get it.
For me, this “should have” spiral starts
small, like forgetting to text someone back or skipping church one weekend. But
then it grows. Like an invasive weed, it winds itself around my peace, chokes
out joy, and whispers that I’m never going to be enough. And maybe that’s the
point. Maybe I’m not supposed to be enough. Maybe grace starts where my
should-haves end.
Let’s take a step back.
Jesus,
Juice, and the Gemstones
Now, before we go much further, I want to get
real for a moment. I’ve previously written about the show The Righteous
Gemstones—and no, it’s not exactly a series you'd find on PureFlix or
tucked in your church's video library. It’s raw. It’s extreme. It pokes at the
bloated underbelly of televangelism and paints characters who are painfully
flawed. And yet, I keep watching. Why?
Because somewhere in the chaos of the satire
and the over-the-top ridiculousness, there’s a mirror. And sometimes that
mirror is cleaner than we’d like to admit. I see parts of myself in the
struggle to be righteous while stumbling over my humanity.
I don’t profess to be a righteous and perfect
godly man. I don’t wear a halo, and I sure as Sunday morning don’t float two
inches off the floor when I walk. I’m a bachelor. A sometimes-lonely one. There
are nights when I ache for the comfort of a woman’s hand or her voice praying
next to mine. There are evenings when I sit down with a buddy and have a glass
too many of Jesus juice—and this time I do mean red wine, not spiritual
awakening.
I’m just a broken vessel. One that leaks
sometimes. One that spills grace as fast as it tries to collect it. And yet, I
love Jesus. I try my best to keep the Holy Spirit in the room and the Word on
my lips. And when I fall short—because I do—I try not to let “should have
syndrome” write the final chapter.
But that’s the trap, isn’t it?
When we live under the shadow of our
shortcomings, we start believing lies about ourselves. That we’re disqualified.
That we’ve missed the window. That God’s promises were for someone else,
someone who did all the things they should have done.
Let’s not pretend the Bible doesn’t have
something to say about this.
Grace
Doesn’t Whisper—It Shouts
One of the most comforting verses I come back
to is in Romans:
“But God demonstrates his own love for us in
this: While we were still sinners, Christ died for us.” — Romans 5:8 (NIV)
He didn’t wait for us to fix our lives. He
didn’t require us to clean the kitchen of our hearts and put out fresh linens
for His arrival. While we were still sinners, Jesus showed up with grace.
It’s not a polite grace. It’s not a fragile
grace that cracks under pressure. It’s a scandalous, rugged, holy grace that
barges in and redeems what should have been ruined.
This doesn’t mean we have a license to live
however we want. That’s not grace. That’s entitlement. Paul addresses this
directly in Romans 6:
“What shall we say, then? Shall we go on
sinning so that grace may increase? By no means!” — Romans 6:1-2 (NIV)
But the point remains—grace doesn’t wait for
perfection. It meets us in the messy middle.
Let me remind you of Peter. One of Jesus’
closest. One who swore he would never deny Christ. But when the pressure came,
when the rooster crowed, Peter had denied Him three times. Imagine the weight
of the “should have” in Peter’s heart.
I should have stayed with Him. I should have
said something. I should have trusted.
But then, post-resurrection, Jesus doesn’t
punish Peter—He restores him. He sits him down by the fire and asks, “Do you
love me?” And He asks it three times. One for every denial. Grace keeps
count—not of our failures, but of our potential.
The Old
Testament Echoes It Too
David. Adulterer. Murderer. Liar. Psalmist.
Worshiper. Man after God’s own heart.
Talk about contradictions.
David lived many “should have” moments. He
should have been at war instead of on the rooftop. He should have confessed
earlier. He should have disciplined his sons more intentionally. And yet, God
still chose to use him. Psalm 51 is the cry of a man who knows the weight of
guilt—but also the depth of mercy.
“Create in me a clean heart, O God, and renew
a right spirit within me.” — Psalm 51:10 (ESV)
That’s not the voice of someone who has given
up—it’s the voice of someone who knows he can’t do it without God.
3 Ways to
Not Be Overcome by the Guilt of Your Mistakes
1. Acknowledge but Don’t Dwell
Guilt, in healthy doses, is a teacher. It
shows us where we’ve veered off track. But when it moves from conviction to
condemnation, it’s no longer from God. The Holy Spirit convicts to bring us
back, not push us down.
Romans 8:1 declares:
“Therefore, there is now no condemnation for
those who are in Christ Jesus.”
Feel the guilt, let it teach you, then let it
go.
2. Replace Regret with Repentance
The devil loves to trap us in circular
thinking. Regret replays our sin like a broken record. Repentance hands the
record to Jesus and asks Him to write a new song.
Repentance is active. It’s not just saying
sorry—it’s turning around. It’s aligning your life again with God’s path. Joel
2:13 reminds us:
“Rend your heart and not your garments. Return
to the Lord your God, for he is gracious and compassionate.”
3. Speak Truth Louder Than the Lie
When the “should haves” start piling up, speak
Scripture over them. Let truth interrupt the lies.
Lie: I’ve sinned too much.
Truth: “Where sin increased, grace increased all the more.” — Romans 5:20
Lie: I missed my chance.
Truth: “I will restore to you the years the locusts have eaten.” — Joel 2:25
Lie: I’m too broken to be used.
Truth: “God’s power is made perfect in weakness.” — 2 Corinthians 12:9
The enemy thrives in silence and secrecy.
Speak God’s promises out loud. Drown the whispers with the roar of grace.
Final
Thoughts
As I sit here, single again tonight, with Max
(my red Boston Terrier) snoring in the corner, I feel the weight of some
should-haves pressing in. I should have written this piece sooner. I should
have reached out to someone I hurt. I should have trusted God more with my
finances, my relationships, my direction. But then I remember—grace has
entered the room.
The cross isn’t a decoration—it’s a
declaration. That we are loved. That we are covered. That we are free.
Should have syndrome will try to write your
obituary in failure. But grace rewrites it in faith.
Let’s stop beating ourselves up and start
leaning into the One who was beaten for us.
Your story’s not over. Your sin is not your
name. And your should-haves are not your chains.
They’re just reminders that you’re human. And
that God’s not done with you yet.
Let the
“Should Have” Become a “Still Can”
You see, “should have” doesn’t have to end in
shame. It can become the spark of transformation if you hand it over to God.
It’s not too late. It never is with Him. If there’s still breath in your lungs,
there’s still a calling on your life. God doesn’t wait for you to finish fixing
yourself before He uses you—He steps into your mess, wipes your eyes, and
whispers, “Let’s go.”
I’ve found in my life that the enemy doesn’t
waste time with the apathetic. He goes after the ones still trying. He wants to
bury the passionate ones in guilt so they never reach the people they were
meant to love. He wants us distracted by our past, so we’re immobilized in our
present, and robbed of our future.
But we serve a God who specializes in
reversals.
From
“Should Have” to “Still Chosen”
Take Moses for example. Talk about a man with
a rap sheet of regrets. He killed a man. Ran away. Hid for forty years. You
think he didn’t whisper in the desert, “I should have waited”? But God didn’t
let Moses’ “should haves” define him. He let obedience refine him.
And what about Jonah? That guy literally
ran away from his calling. Boarded a ship in the opposite direction. Ended
up in the belly of a fish. A prophet with the spiritual GPS of a squirrel. And
still, God brought him back.
Do you think God didn’t know about your
mistakes when He called you? When He gave you your spiritual gifts? When He put
that idea in your heart? He knew. And He still said yes.
Because it was never about your perfection. It
was always about your availability.
God doesn’t need flawless vessels. He needs
willing ones.
Guilt Is
Not Your Guide
We’ve made guilt our default setting in the
church far too often. Somewhere along the way, we confused conviction with
self-hatred. But let’s be honest—beating yourself up doesn’t make you holy. It
just makes you tired.
I know that feeling. Laying awake at night
with reruns of conversations I should have had, prayers I should have prayed,
love I should have given. It eats away at you. Slowly. Quietly.
But guilt doesn’t lead you to healing. Jesus
does.
That’s why Paul said in 2 Corinthians 7:10:
“Godly sorrow brings repentance that leads to
salvation and leaves no regret, but worldly sorrow brings death.”
There’s a difference. One drives you back to
God. The other drives you deeper into the dark. We’ve got to learn to let guilt
do its job—and then release it. It’s a signal, not a sentence.
You’re Not
the Only One
Let’s just say it plain: being a Christian
doesn’t mean you’re going to get it all right. Not even close.
Sometimes, I think the church sets up this
pressure cooker of expectations. And as a single Christian man, it hits
differently. There’s this unspoken assumption that if you’ve made it this far,
surely you’ve got your spiritual act together.
But the truth is, some days I’m full of faith,
and other days I’m full of doubt. Some days, I’m walking on water. Other days,
I’m sinking like a rock. I crave companionship, I miss intimacy, I wrestle with
what-ifs. And yet—I’m not disqualified. Neither are you.
Even Paul, the writer of much of the New
Testament, said this in Romans 7:19:
“For I do not do the good I want to do, but
the evil I do not want to do—this I keep on doing.”
That’s not an excuse to stay stuck. It’s an
invitation to keep going.
We’re not alone in our struggle. We're in good
company. We belong to a faith of flawed heroes and redeemed rebels.
A Little
Confession About Max
Let me tell you something lighthearted but
kind of deep. My little red Boston Terrier, Max—he’s got this thing. Every time
I bring out food, this dog stretches up as tall as his squat body will let him,
like he’s trying to reach Heaven itself. His eyes get wide, and there’s this
frantic hope in them: Will I get some this time?
He doesn’t know I already have a little treat
set aside for him. He’s going to get fed. I’ve never let him go without.
And maybe, just maybe, that’s how God sees us.
Reaching. Stretching. Worried. Frantic.
Thinking we “should have” been better to
deserve His provision. But the whole time, He’s already prepared something for
us.
Grace Is
Already on the Table
I’m reminded of the parable of the Prodigal
Son in Luke 15. You know it. The son squanders everything. He lives wildly. He
regrets. He rehearses his speech to the Father—his own personal list of “should
haves.”
But when he gets home, the Father isn’t
standing there with crossed arms and a ledger of wrongs.
He’s running. He’s weeping. He’s celebrating.
“But while he was still a long way off, his
father saw him and was filled with compassion for him.” — Luke 15:20
That’s grace. That’s your God. That’s the
gospel.
How to
Trade “Should Have” for “Still Can”
Let me leave you with three more steps that
have helped me when the “should have” voice gets too loud:
1. Start the Day with Surrender, Not a
Scorecard
Every day, choose to begin not by measuring
what you did or didn’t do yesterday, but by reminding yourself that today is
new. His mercies are new every morning. You don’t need to earn your
place at the table. You just need to show up.
2. Speak With Someone About It
The worst thing about “should have syndrome”
is that it often festers in silence. Speak to a mentor, a friend, a pastor.
Name your regret. Drag it into the light. You’ll find that its power fades when
it’s exposed.
3. Choose Worship Over Worry
You can’t worship and wallow at the same time.
Put on a song, pray, read the Word aloud. Let God’s voice be the loudest in the
room. Replace your inner critic with the Comforter.
A Closing
Prayer for the “Should Have” Soul
If you’re still reading, I want to bless you
with a prayer—not a fancy one, but one that comes from the same kind of tired
soul that’s found hope again.
Father,
Thank You for grace. Thank You for not
requiring perfection. Thank You that while I was still a sinner, You called me,
loved me, and died for me. I confess that I’ve lived too many days weighed down
by what I should have done. But today, I choose to hand that weight to You.
Redeem the regrets. Heal the wounds. Help me
move from guilt to gratitude. Speak truth over every lie the enemy has planted
in my mind.
I believe You can still use me.
I believe You’re not done.
I believe that grace has entered the room—and
it looks like Jesus.
In His name I pray,
Amen.
So here’s the truth, my friend:
You’re not your past. You’re not your worst
decision. You’re not a lost cause.
You’re a child of God.
And even if you didn’t do what you should
have yesterday—you still can today.
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