✝️Why “Not Enough” Keeps Winning

Good morning, my brothers!  Comparison doesn’t motivate most men—it drains us. I know, because it hollowed me out. If you’ve ever felt behind or not enough, this story might hit closer than you expect. Let’s go!

This week: 4-minute, 54-second read

The Comparison Trap

These last few weeks have been painful for me, but necessary, as I’ve opened up a lot to you guys about areas I struggle with. Here’s another one, and I don’t think I’ll be the only one who will resonate with: The Comparison Trap.

You see, for years, I walked around with a quiet, persistent ache in my heart and mind that whispered, You’re not enough.

I didn’t say it out loud. I didn’t post it online. I didn’t even fully admit it to myself. But it was there. And if I’m honest, it shaped far more of my decisions than I ever realized.

I looked around at the other guys and constantly compared myself to them. And I rarely measured up. I ran the race to prove myself – to be seen as enough by others, but more so, to myself, as I’ve learned.

First, there was my Dad, who was successful and well-respected in my hometown of Youngstown, OH. Big shoes to fill. I thought it was my job to be more successful and more respected than he was. And this led me to a number of stupid situations and decisions.

I was running in my Dad’s lane, not the one God intended for me.

And then there was social media.

Scrolling on Facebook or LinkedIn had become a form of slow self-sabotage. Every post felt like evidence that other men were doing life better than me. Better careers. Better bodies. Better confidence. Better faith. At least it sure looked this way on the surface.

I compared their highlight reels to my real life and always came to the same conclusion:

I’m behind. I’m lacking. I’m not enough. Do more. Run faster. Not realizing that in comparing myself to others, I was running their race, in their lanes. Not mine.

Even in church, I would look around and see other guys from my outside perspective, seemingly further along on their walk with Jesus, leading their families more Biblically, serving more than I was.

When Comparison Becomes a Way of Life

Here’s the thing about comparison: it doesn’t usually feel sinful. It feels responsible. Motivated. Ambitious. Outwardly religious (or should I say Pharisaical?).

It tells you that you just need to work harder, grind longer, push more. And if you do, maybe—just maybe—you’ll finally measure up.

But that voice never stops talking.

For me, comparison didn’t lead to growth. It led to discouragement. It hollowed me out.

I became less reliant on the Lord. Less present with my wife. Less patient with my kids. Less grounded as a leader.

On the outside, to others, I would guess my life looked successful. Inside, I felt like I was constantly coming up short.

That’s what comparison does. It creates a private downward spiral that no one else can see, but you feel every day.

The Reckless Race to Prove Myself

In the early 2000s, I met a guy who was absolutely crushing it flipping houses. From my perspective, he had it all. Momentum. Money. Freedom.

Without ever saying it out loud, I decided that my definition of success would be catching him and then passing him. I’d flip more houses than he would.

At first, the chase was exhilarating. It felt like purpose.

But comparison always demands a price.

I started taking risks I shouldn’t have taken. I ignored warning signs. I justified decisions that put my family, my employees, and my financial future in jeopardy. And then came the financial collapse of 2008.

I ended up within a breath of bankruptcy.

That moment stopped me cold. I had to face the truth I’d been avoiding: my need to prove myself was threatening everyone and everything I loved.

The Truth I Had Been Ignoring

As I crawled out of that crater, something finally broke through.

I’d known Scripture for years. I could quote verses. I believed the Bible was true. But I hadn’t been living as it applied to me. I didn’t know who I was in Christ. I knew who I thought the world wanted me to be, though.

The Bible says I am made in the image of God (Genesis 1:26–27).

Yet I was constantly trying to remake myself in the image of whoever impressed me that week.

The Bible says I am fearfully and wonderfully made (Psalm 139:14).

Yet I was fixated on what I believed were my deficiencies.

The Bible says God arranges each part of the body just as He wants it (1 Corinthians 12:18).

Yet I resented the roles He had given me because they didn’t look like someone else’s.

Here’s the truth that finally landed in my heart: Success is not becoming more than another man.

Success is becoming more the man God created YOU to be. And this is the message I try to share each week in our newsletter.

Not louder. Not richer. Not more “religious”.

Just abiding. Faithful. Submitted. Obedient. Trusting.

Why Comparison Is So Dangerous

Comparison doesn’t just steal joy. It quietly undermines surrender.

When we compare, we stop asking, “Lord, what are You calling me to?” And we start asking, “Why doesn’t my life look like his?”

Scripture cuts straight through the noise:

“Each one should test his own actions… without comparing himself to someone else” (Galatians 6:4).

God never asked you to carry another man’s assignment. He asked you to be faithful with yours.

Breaking Free from the Trap

Escaping comparison isn’t about willpower. It’s about truth.

When the not enough voice shows up, answer it with Scripture.

When comparison creeps in, return to gratitude and obedience.

When you feel the urge to scroll and spiral, shut off your phone and ask a better question:

Am I being faithful today with what God has placed in front of me?

More The Man exists because I stopped chasing someone else’s calling and started surrendering to my own. Imperfectly. Sometimes two steps forward and one step backwards.

And thus, if I’m honest, I still have to make that choice, over and over again.

A Purpose In My Struggle

Brother, learn from my mistakes, my stupidity, my sin. I’m happy to share what He has taught me through the mess. Every week.

You are not behind.

You are not unworthy.

You are not lacking what God needs to work through you.

You are uniquely created, intentionally placed, and fully equipped for the life God has called you to live.

Step off the exhausting treadmill of comparison. Lay down the measuring stick. And live surrendered - not striving to be more than another man, but faithful to be the man God made YOU to be. You are God’s masterpiece.

Insert your name in the following statement. Maybe write it down somewhere to remind yourself:

I am exactly the [YOUR NAME HERE] that God created me to be. Made in His image with unique talents for a purpose that is uniquely mine. I will be more the man that God has called ME to be. Holy Spirit, you become more and I less.

-Will