When Humility Looks Like Insecurity

What is something you are really good at?

Several years ago I couldn’t answer that question. Even today sometimes I hesitate. I still have moments where I go, Well, I’m good at this… but there are so many people so much better than me.

I get stuck comparing, and questioning whether I’m enough.

When I do work for others I tend to freak out and ask…

• “What if I mess it up?”

• “Maybe I should just not do anything for anyone else so they don’t judge me…”
  

I know it sounds ridiculous, but it’s the truth. And I want to encourage you that if you’ve ever thought things like that — especially as a leader or business owner — you’re not alone.

Sometimes we’ve been told those thoughts are okay. That they’re a badge of humility.

But let’s pause and ask:

What does biblical humility actually look like?

Because I think our culture has confused humility with insecurity.
And confidence with pride.
And in doing so, we’ve lost the heart of biblical leadership.

The Modern Trap

Today’s culture says lots of things depending on what circle you’re in. You may have heard things like:

• “You have to earn your worth.”

• “Don’t take up too much space.”

• “Success equals pride.”

• “If you’re confident, you must be arrogant.”
  

With all these voices, we often respond in one of two ways:

• Overcompensate with hustle and ego — trying to prove we’re good enough.

• Undercompensate with fear and passivity — pretending we’re not good enough.
  

But both of those are rooted in the same thing:
Self-reliance.
Not covenant alignment.

Undercompensating Isn’t Humility — It’s Hidden Self-Reliance

When we shrink back, play small, or stay silent because of insecurity or fear, it feels humble (I should know, I’ve done it)…

But often, it’s rooted in this belief:
“I’m not enough, so I better not mess this up.”

Which, if we’re honest, is just another version of:
“It’s still about me.”

Just like the person who overcompensates says:
“I’ve got this. I can make it happen.”

The undercompensator says:
“I don’t got this… so I won’t do it at all.”

Both are fixated on self — not yielded to God.

What Humility Really Means: The Covenant View

In the Hebrew mindset, humility wasn’t self-deprecation.
It was clarity of position.

The word עֲנָוָה (anavah), which is the Hebrew word for humility, carries a deeper meaning than what we usually think of.

The letters of anavah paint this picture:

• To see yourself clearly (Ayin)

• As one who is yielded and dependent (Nun)

• Connected to the Source through covenant (Vav)

• And open to God’s breath and leading (Hei)
  

Think about it this way:
“I am not the source,
But I am joined to the Source.
And because I know who I’m not…
I can fully become who I was made to be.”

David: A Portrait of Humble Leadership

David was anointed king — but he never acted entitled to the throne.

Even when people praised him, he never assumed he deserved it. He wrote:

“You are my Lord; I have no good apart from you.” (Psalm 16:2)

Later, after years of victory and favor, he still prayed:

“Who am I, O Lord God, and what is my house, that You have brought me this far?” (2 Samuel 7:18)

Even when Absalom rebelled and David was forced to flee, he didn’t cling to control. He didn’t manipulate the outcome. He simply said:

“If I find favor in the Lord’s eyes, He will bring me back… but if not, let Him do what seems good to Him.” (2 Samuel 15:25–26)

That’s the heart of anavah — the willingness to occupy your God-given space, nothing more, nothing less.

Don’t shrink smaller than what God has given you.
Don’t expand beyond what He has entrusted to you.
Just fully live in your assignment.

It’s about alignment, not self-diminishment.
It’s obedience, not outcome.

This Is What It Means to Lead in Covenant

To lead a business…
To raise a family…
To build anything meaningful…

It must come from this posture:
“It was never about me to begin with.
I will rise when He says rise,
Speak when He says speak,
And rest when He says rest.
Because I trust that my worth is not up for debate.
It was decided in the covenant.”

That means:

• You don’t have to overcompensate with hustle.

• You don’t have to undercompensate with fear.

• You just have to stand in your space — the one God already gave you.
  

This also means you don’t have competition — not because others can’t do what you do, but because if they aren’t called to serve the people you’re called to, the rest is irrelevant.

And if you feel unworthy? So what! We all are.
The only qualification is that God called you, and you are willing to obey and serve where He has put you.

A Final Word to the Leader Who Feels Small

You might feel like you don’t know what you’re doing.
You might think someone else could lead better.
You might feel like a fraud.

But if God assigned the portion…
If He gave you the space…

Then don’t give it away.
Don’t hide in false humility.
Don’t pretend He made a mistake.

Instead, say:
“Lord, I’m not here to prove.
Not here to perform.
Just here to obey.”

And that…
That’s leadership in covenant.

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