The Art of Being Wrong First


By Jackie Overstreet November 23, 2025

Why spiritual maturity sometimes starts with a bad guess

We don’t talk about the ministry of being wrong.


But maybe we should.


Because somewhere along the line, people started believing that being “right” was the proof of spiritual depth.

As if God hands out gold stars for accuracy.

As if faith is an exam, not a relationship.


But here’s the thought most people never consider:


Being wrong is often the first proof that your soul is awake.


Not because error is noble,

but because teachability is holy.


Think about the disciples.

Half their greatness came from getting things wrong

spectacularly

publicly

and repeatedly.


They misread moments.

They misunderstood Jesus.

They jumped to conclusions.

They panicked.

They bragged.

They tried to call down fire on people who annoyed them.


They failed the quiz but passed the calling.


Why?

Because they didn’t hide from correction.


Correction is where soul esteem is forged.


Self-esteem says,

“I must be right.”

Soul esteem says,

“I must be teachable.”


Self-esteem tries to preserve its image.

Soul esteem tries to preserve its alignment.


There is a strange, holy intelligence in being the first one willing to say:


“I don’t know.”

“I misjudged that.”

“I assumed wrong.”

“I need to rethink this.”

“I missed it.”


Because the person who can acknowledge error

is the person God can trust with truth.


The spiritually fragile need certainty.

The spiritually strong can survive discovery.


And here’s the twist:

The enemy loves overconfidence more than ignorance.

Ignorance can be taught.

Overconfidence cannot be touched.


So what if the next breakthrough in your life

doesn’t come from what you know,

but from what you’re willing to un-know?


What if wisdom isn’t the accumulation of answers

but the willingness to release outdated ones?


What if your next level depends on your capacity

to be wrong faster

so God can redirect you sooner?


This is the part no one tells you…


Teachability is a weapon.

It humiliates the enemy because he cannot use pride to trap you.

It humbles the flesh because ego has nowhere to hide.

It honors God because submission always outranks certainty.


This isn’t about being passive or unsure.

It’s about being spiritually nimble.


Flexible.

Soft-hearted.

Quick to adjust.

Quick to pivot.

Quick to release the version of you that no longer fits.


Soul esteem is not noisy confidence.

It’s quiet adaptability.


It’s the inner posture that says,

“If God shows me a better way tomorrow,

I am free enough to take it.”


May you have the courage

to be wrong first

So you can be right in the end.


~Jackie

Share this with someone who’s tired of pretending they know everything.

Excavation Quiz Bar
Which of the 4 Invisible Crowbars will unlock your breakthrough?
Soul Chisel Bloodline Bolt Cutter Heart GPS Silence Hammer
Free Discovery

Which Invisible Pattern Is Keeping You Stuck?

Discover which of the 4 Crowbars will unlock your breakthrough. Takes 90 seconds.

Soul Chisel- Clear mental fog
Bloodline Bolt Cutter- Break generational cycles
Heart GPS- Find your true calling
Silence Hammer- Defeat inner critics
REVEAL MY PATTERN →
📖 DAILY WISDOM

Dig In: Excavation Letters + The Guide

This isn't another newsletter. It's a slow excavation of your soul.

The Excavation Letters land in your inbox with truth that hits home
Your Soul Trap Discovery Guide is already on its way
Join a community of deep feelers and truth diggers

Your inbox is sacred. No spam. Ever.

90-Day Transformation

Break Free From What's Been Holding You Back

The Soul Esteem Freedom Journal is your daily roadmap to lasting confidence and freedom.

Soul Esteem Freedom Journal by Jackie Overstreet

90 days of guided transformation

Pattern-breaking exercises

Scripture-rooted soul care

Proven by thousands

$27
Your freedom starts today
GET THE JOURNAL

Latest Posts

closed door
By Jackie Overstreet January 9, 2026
Closing doors that drain authority
slow leak
By Jackie Overstreet January 8, 2026
Recognizing subtle emotional interference
marriage-is-not-fear-it-is-wisdom
By Jackie Overstreet January 7, 2026
Marriage is not about pressure or perfection. Biblical wisdom before commitment.
Forgiveness Starts With You. finger pointing
By Jackie Overstreet January 6, 2026
Learning to forgive yourself creates space for growth and clarity.
The stuck layer
By Jackie Overstreet January 5, 2026
If space feels hard to clear, something deeper may need naming. Christ reveals truth with precision. The Soul Chisel restores clarity. Share this with a friend and subscribe to keep excavating.
Clear space/room
By Jackie Overstreet January 4, 2026
Gratitude clears mental clutter
Full plate of food
By Jackie Overstreet January 3, 2026
What is really on your plate this year? Calling begins with honesty. Christ invites reflection, not pressure. Share this with an accountability partner and subscribe to Excavation.
First step
By Jackie Overstreet January 2, 2026
A new year does not require speed, it requires clarity. Christ is our guide. The Heart GPS helps us choose direction before motion. Share this with someone you trust and subscribe for a grounded year.
narrow path
By Jackie Overstreet January 1, 2026
Focus grows when truth is faced
peace truce
By Jackie Overstreet December 31, 2025
Inner peace shapes relationships
Show More