The Good Boy Must Die So The Great Man Can Rise

He wakes up early. He works out religiously. He tracks macros. He organizes the garage by tool type and seasonal use. He follows the rules—not just because they work, but because they feel safe. He keeps a clean house, a clean calendar, and a clean conscience—or at least tries to. He does what’s expected of him and then some. He’s the one people rely on. Dependable. Predictable. Responsible. Respectable.

He checks the church box. He honors the flag. He doesn’t blaspheme. Doesn’t drink too much. Doesn’t cross lines—any lines. Especially not the double yellow ones. He doesn’t speak badly of others, but only because that would be wrong. Not because he doesn’t think it. He suppresses that, like everything else. His discipline isn’t noble. It’s a dam.

OK, fine—maybe it sounds like a caricature.
But you know who you are.
Eddie Haskell in your perfectly polished mask for the world to admire.

The one always looking like he has it together. The one who needs it to look that way. The Good Boy. A man who built his identity not around freedom or fullness, but around performance and control. You’re not witnessing virtue. You’re witnessing fear—socially acceptable, even praiseworthy, fear.

This is the third installment in the MASK-ULINITY series—where we name the lies men wear and give them the option to finally set them down. We started with the Nice Boy—Enneagram 9—who avoids conflict by blending into the background. We called out the Bad Boy—Enneagram 8—who protects his pain with a shell of swagger and aggression. And now, we step into the straitjacket of the Good Boy—Enneagram 1—who’s afraid that if he doesn’t hold it all together, it will all fall apart. That if he isn’t perfect, he’ll be punished. Or worse, exposed.

Because this man isn’t just trying to be a good man.
He’s terrified of being found out.
As weak. As lazy. But most of all, as flawed.

You see, the Good Boy doesn’t actually lack anger.
He’s full of it. Brimming with it. Boiling beneath the surface.
It’s just been buried under two decades of forced politeness, perfection, and “shoulds.”
He’s spent his life shoulding all over everyone and everything—but at midlife, he might finally wake up and realize the harshest truth of all: he’s spent his entire life shoulding all over himself.

The Good Boys are the angriest men I know.

Everyone else sees it. His wife sees it in the way he slams the cabinet doors. His kids feel it in the way he corrects their tone before hearing their words. His employees brace for it in his perfectly passive-aggressive feedback loops.

But he doesn’t see it.
Not until he does.

And look the hell out when a Good Boy blows his perfectly coiffed top right off.

I had a coaching client—let’s call him Brad. He didn’t come to me because he felt lost or broken. He came to me because he was furious. He just didn’t know why. His wife had said he was “emotionally unavailable.” His team said he was “intense” and “hard to read.” His therapist had suggested yoga. He wanted none of it. What he wanted was to stop feeling like a volcano that had to be managed every second of the day.

Brad was a textbook Good Boy. Structured. Disciplined. Methodical. From the outside, you’d think he was running a Fortune 100 company and a monastery at the same time. But when I sat with him, the rage was right there—coiled under his collar, burning behind his eyes. Rage at never being enough. Rage at always being the one who does the right thing while everyone else just gets away with it. Rage at how much he had sacrificed just to be seen as good.

And once it surfaced?
It didn’t trickle out.
It detonated.

Not in violence. Not in destruction.
But in clarity. In truth. In tears.
The kind of unraveling that only happens when you finally stop playing perfect and start telling the fucking truth.

So here’s what I tell the Good Boys:

Your perfection is killing you.
Your rules are just armor.
Your discipline is a disguise.

You don’t need to be better.
You need to be honest.

You don’t need more control.
You need more courage.

You don’t need anger management.
You need anger integration.

In my work, especially with men in midlife, I’ve found this mask to be the hardest to tear off. Because it doesn’t look like a mask at all. It looks like virtue. But it’s not. It’s fear dressed up as moral superiority.

I often draw from ancient Kabbalistic wisdom to help explain what’s going on underneath. The Hebrew word for “good,” tov, doesn’t mean what we think. It doesn’t mean moral. It doesn’t mean responsible. It doesn’t mean good in the tidy, Instagrammable way we’ve rebranded it.

Tov means something creative. Constructive. Alive.
And it only exists in tension with its opposite—rah. Chaos. Destruction. Wildness.

You don’t get to have light without dark.
You don’t get to be whole if you’re only playing half the instrument.
You don’t get to be alive if you’re still pretending you were ever meant to be perfect.

No matter how many rules you follow, you won’t outrun your darkness. No matter how rigid your schedule, how filtered your speech, how clean your house or controlled your emotions—there’s a part of you that is messy, raw, and unsanitized.

You weren’t built to be flawless.
You were built to be perfectly imperfect.
To be real. To be full. To be human.

So let this be the line in the sand:

You can stay the Good Boy.
You can keep the mask on. Keep getting the applause. Keep pretending you’re fine. Keep clinging to the double yellow lines and calling that “success.”
You can do that until you’re dead inside.

Or…

You can become a Great Man.
Not by polishing your perfection—but by owning your imperfection.
By stepping into the parts of yourself you’ve rejected.
By integrating your shadows instead of fearing them.
By letting go of the performance and stepping into presence.

You don’t need more control. You need more courage.
You don’t need to manage your life better. You need to live it.

And you won’t live it—not fully—until you embrace the dark, disgusting, beautiful mess of life.
Not just the chaos out there, but the chaos in here.
The rage. The grief. The shadow. The shame.
That’s the stuff of real transformation.

That’s your path to greatness.
Not through perfection—but through embracing the perfectly imperfect wholeness of who you really are.

Tear up the checklist.
Break the routine.
Burn the fucking handrails.

The Good Boy must die…
So the Great Man can rise!