Crying Boys, Confused Men, and the Box We Forgot to Draw

I was in a steam room the other day when a friend told me a story about his nine-year-old son.

His son had just finished a hockey game. The team lost 3–2. As the boys came off the ice, some of them were crying. They had given everything they had, and it hadn’t been enough.

Then a woman said to them, “You should be ashamed of yourselves for crying.”

That comment stuck with me.

Not because kids cried after losing a game, that part actually made perfect sense. What struck me was the idea that they shouldn’t.

Because if a nine-year-old boy isn’t allowed to cry after giving everything he has and still losing… what exactly are we teaching him?

Tears are part of passion.
They’re part of caring.

When you give everything you’ve got to something, whether it’s sport, a relationship, or a dream, and it still doesn’t work out, it hurts.

And that hurt is human.

The Container Men Carry

As men, many of us grow up learning to hold things in.

We become containers.

If we have families, we feel responsible to provide, to protect, to be strong. Even if we’re not perfect at it, the instinct is there.

And when someone asks how we’re doing, the answer is almost always the same:

“Good.”
“Fine.”
“Doing alright.”

Even when we’re not.

Lately, I’ve noticed how many men around me are going through difficult times: divorces, relationship struggles, and uncertainty about their place in the world.

And many of them have done exactly what they thought they were supposed to do.

Be a good guy.
Be kind.
Do the right thing.

With the hope, sometimes unconsciously, that if they did those things, life would respond in kind.

But life doesn’t always work like that.

Dr. Robert Glover talks about what he calls the “Nice Guy Syndrome.” The idea that many men make covert contracts with the world.

If I’m kind, people will be kind back.
If I do the right thing, things will work out.

But those contracts often exist only in our own heads.

And when reality doesn’t honour them, it can feel confusing.

The Missing Box

There’s another piece to this.

Right now, many young men are growing up without a clear sense of what it means to be a man.

That might sound controversial, but I don’t mean it in a rigid or prescriptive way.

I’m not suggesting there’s one correct way to be a man.

What I am saying is this:

Before you can step outside a box, you first have to know where the box is.

In business, I learned something interesting about creativity.

Everyone says they want “outside-the-box thinking.” But when you’re trying to win a client, you still have to present your ideas in a way they recognize. You have to fit inside the box first.

Once they trust you, you can push the boundaries.

Life is a little like that.

We need guidelines before we can meaningfully challenge them.

Freedom Without Structure Isn’t Always Freedom

Years ago, I spent time living in a monastery.

The schedule was incredibly strict.

Meditation at a certain time.
Meals at a certain time.
Work at a certain time.

You might think that kind of structure would feel restrictive.

But strangely, it felt incredibly freeing.

When the schedule said it was time to rest or walk or reflect, it felt genuinely enjoyable. There was no guilt attached to it.

Compare that with modern life, working whenever we want, from wherever we want.

Laptops on beaches.
Total freedom.

And yet many people feel overwhelmed rather than liberated.

Sometimes structure is what creates the space for freedom.

You need to know the rules before you can break them.

A Generation Without Reference Points

For many younger men today, the traditional “box” of masculinity has largely disappeared.

In many ways that’s a good thing. The old rules were often restrictive or unfair.

But removing the box entirely can also leave people without reference points.

It’s a bit like a mixing board in a recording studio.

Every trait, courage, compassion, ambition, sensitivity, strength, is like a fader. Everyone’s settings are different.

None of us are all one thing or another.

But if there are no reference levels at all, it becomes harder to understand where we stand.

The Value of Brotherhood

Something I’ve noticed in my own life is how important it is for men to spend time with other men.

Not because women aren’t incredible, they absolutely are.

But men understand certain things about each other instinctively.

Time with other men can be grounding.

It’s not exclusionary.
It’s not competitive.

It’s simply part of a healthy ecosystem.

Strength Still Matters

Another thing I’ve realized is how easy it is to become soft in modern life.

And “soft” can mean different things to different people.

For me, it means losing touch with challenge.

Cold exposure.
Physical effort.
Doing things that require grit and discipline.

There’s something deeply grounding about physical effort.

Zen philosophy often talks about this idea:

Before enlightenment: chop wood, carry water.
After enlightenment: chop wood, carry water.

There’s something important about engaging the physical world.

Pumping water.
Chopping wood.
Climbing a hill.

These things remind us we are part of nature, not separate from it.

Back to the Hockey Rink

So I keep coming back to that moment at the hockey rink.

A group of nine-year-old boys who cared enough about something to cry.

And someone telling them they should be ashamed.

I can’t help but wonder what happens to those boys over time if they learn that expressing emotion is something to hide.

Do they grow into men who can’t show how they feel?

Men who carry everything inside?

Men who no longer feel like they fit anywhere?

The Word That Matters Most

If there’s one word I believe matters right now, it’s respect.

Respect for women.
Respect for men.
Respect for differences in experience and opportunity.

Everyone deserves the chance to pursue their goals without being limited by their race or gender.

But respect also means recognizing that guidance matters.

Especially for young people trying to find their place in the world.

Still Learning

I’m 45 years old, and I’m still learning what it means to be a man.

I’m also the father of a sixteen-year-old boy.

So part of this reflection is simply trying to create a framework, something that might help him grow into the best man he can be.

A good brother to his sisters.
A respectful son to his mother.
And one day, perhaps, a thoughtful partner to someone he loves.

I don’t have all the answers.

But I do know this:

If a nine-year-old boy cries because he gave everything he had to something that mattered to him…

That’s not weakness.

That’s humanity.