Part of the MASK-ULINITY Series
(Enneagram 7: The Silly Boy)
Peter Pan Syndrome, Hook Syndrome, and the Journey to Wholeness
Let’s start with a scene—not from a textbook, not from therapy, but from Peter Pan.
Peter bursts into Wendy Darling’s bedroom in a whirlwind of chaos, chasing something he’s lost: his shadow. Tinkerbell buzzes. Peter zips around like a high-functioning child on too much sugar, trying to tape the damn thing back on. He presses it to his foot, stomps it, pleads with it. Nothing works.
Eventually, he collapses, frustrated, fighting back tears—though of course, he swears he’s not crying.
Wendy wakes up, sees the wreck of a boy in front of her, and says the most important line in the entire story:
“You can’t stick it on. It must be sewn.”
Peter, clueless and resistant, blurts out: “What’s sewn?”
And there it is—the crisis of masculinity in one innocent question. A boy who can fly, fight pirates, and rally the Lost Boys… but has no idea how to face himself. A master of fantasy, totally inept at reality.
You can watch the scene on YouTube. It’s whimsical, yes—but it’s also heartbreakingly familiar. Because a lot of men I know? They’re still trying to tape on their shadows with duct tape and a smile.
Peter, Jeff Spicoli, and the Mask of the Silly Boy
You’ve seen this guy before.
He’s Jeff Spicoli from Fast Times at Ridgemont High—laid back, stoned, surfer-cool, totally allergic to anything that sounds like effort, commitment, or introspection. You laugh at him. You like him. Hell, maybe you are him. He’s fun. He’s free. He’s absolutely empty.
Or maybe he’s Peter Pan—flying from one thrill to the next, surrounded by Lost Boys who reinforce his delusion that fun is enough.
This is the Silly Boy mask.
It’s the Enneagram 7 in reaction mode.
Fun. Funny. Flying around. Addicted to the next adventure. And off he goes—faster than you can say that dreaded word: R-E-S-P-O-N-S-I-B-I-L-I-T-Y.
He chases highs, novelty, distraction—anything but the truth. He tells jokes to avoid silence. He turns every wound into a witty anecdote. He reframes grief into “a lesson” before he ever actually feels it.
And if you challenge him?
He disappears.
But here’s the secret: underneath the party is pain. Under the mask is a man who’s terrified of stillness. Of sadness. Of shadows.
Hook Syndrome: When the Boy Dies and the Shadow Takes Over
Now, let’s swing to the other extreme.
You remember Captain Hook?
That grim, controlling, shadow-drenched man chasing Peter across Neverland?
Here’s what most people forget: Hook is in his 40s or 50s. He’s not ancient. He’s not mythical. He’s middle-aged. He’s what Peter fears becoming.
Hook is what happens when the Silly Boy dies and the shadow takes over.
He’s angry. Bitter. Controlling.
Obsessed with time—the ticking crocodile—and haunted by all the things he never became.
This is Hook Syndrome: a man completely consumed by responsibility, stripped of joy, dried out by duty. He’s not floating—he’s drowning. Not in play, but in pain.
And here’s the truth: most men either live like Peter—running from the shadow—or like Hook—completely overtaken by it.
Both are stuck. Both are masks. Neither are free.
Pete’s Crash Landing
I’ll never forget the day I met a guy whom we’ll just call Pete.
He was the quintessential 7—lightning-fast brain, big ideas, always moving. A startup guy. A podcast guy. A “what if” guy. His whole life was one big brainstorm on a whiteboard.
But when his father died, the whiteboard got erased.
He looked at me with tears in his eyes and said, “I couldn’t fly anymore. I wasn’t the man I wanted to be for my dad. And now it’s too late.”
Except it wasn’t too late. It was just the beginning.
The loss shattered his illusion of freedom. It brought him crashing out of the clouds and down into the depths. For the first time in his life, he stopped moving—and he started feeling.
That’s when we began the real work.
He wrote a letter to his dad. He started showing up—not just to his business, but to his wife and daughter. He stopped taping on old ideas and started sewing in something deeper: meaning, grief, truth, responsibility.
Not the kind of responsibility that weighs you down. The kind Dr. Viktor Frankl talked about—the responsibility that sets you free.
The Responsible Man: Frankl’s Freedom To
Frankl said it best:
“Freedom is only part of the story and half the truth… Freedom is but the negative aspect of the whole phenomenon whose positive aspect is responsibility.”
There’s freedom from—from rules, expectations, weight.
But the real transformation happens when a man discovers freedom to.
Freedom to commit.
Freedom to serve.
Freedom to love.
Freedom to carry the weight of others.
That’s what Pete found. That’s what the boy in every man must find if he ever hopes to grow into someone worth trusting.
This isn’t about becoming the “Serious Man.” No one needs more uptight, emotionally constipated, soulless men doing their duty. What we need is the Responsible Man.
Not a man buried by burdens.
But a man who chooses his burdens.
Who says yes—to meaning, to service, to others.
And who learns to carry that yes with integrity and presence.
The Invitation To Sew
So where are you in the story?
Still floating? Still taping your shadow on with sarcasm, spirituality, or success?
Still flinching at the word R-E-S-P-O-N-S-I-B-I-L-I-T-Y?
Or are you finally grounded?
Finally tired?
Finally ready?
You don’t have to become Hook.
And you don’t need to kill the boy.
But you do need to raise him.
It might hurt a little.
It might feel like dying.
But it’s not the end.
It’s the beginning of a man who isn’t flying above his life, or drowning beneath it—but walking through it.
Not bitter. Not boring.
But whole.
Real.
Authentic.
All in. Responsible
Shadows and all.
