A Conversation with Mike from Progressive Masculinity
There are some conversations that feel important.
Not performative.
Not algorithm-chasing.
Not “this will clip well for Instagram.”
Just important.
This week on Detention Diaries, I sat down with Mike from Progressive Masculinity to talk about something that is quietly (and sometimes loudly) shaping our classrooms, staffrooms and homes:
What does it actually mean to be a man in 2026?
And more importantly…
What does it mean to be a good one?
The Problem We’re Not Talking About Properly
In schools, we see it every day.
- Boys disengaging.
- Boys underachieving.
- Boys lashing out.
- Boys disappearing into screens.
- Boys struggling to articulate emotion beyond “I’m fine.”
At the same time, there’s a cultural tug-of-war happening:
On one side:
“Man up.”
“Don’t cry.”
“Be dominant.”
On the other:
“Masculinity is the problem.”
“Men need to do better.”
“Check your privilege.”
And somewhere in the middle?
Confused teenage lads trying to work out who they are.
Mike’s work with Progressive Masculinity sits in that messy middle. Not anti-men. Not anti-women. Not culture-war nonsense.
Just thoughtful, grounded conversations about how we raise boys and support men in a healthier way.
What We Talked About
This wasn’t a surface-level chat. We went deep.
We covered:
- Why so many boys feel lost right now
- The rise of online “masculinity influencers”
- What schools get right (and wrong) about behaviour and identity
- Why shame doesn’t build character
- The difference between strength and suppression
- How we can model better masculinity as teachers and fathers
We also talked about vulnerability.
Because here’s the uncomfortable truth:
You can’t ask boys to open up if the adult men around them never do.
Masculinity in Schools – The Reality
As a secondary teacher, I see the tension daily.
We want resilience.
But we don’t want aggression.
We want confidence.
But not arrogance.
We want independence.
But we panic when they fail.
Mike articulated something powerful:
Boys don’t need to be “fixed.”
They need frameworks.
Frameworks that allow:
- Strength with empathy
- Discipline with reflection
- Ambition without ego
- Leadership without domination
That resonated massively with me — especially in the context of behaviour conversations happening nationally.
We’re very quick to talk about sanctions.
We’re slower to talk about identity.
The Role of Fathers, Teachers & Male Role Models
We also explored something that I think a lot of men don’t say out loud:
Many of us are figuring this out in real time.
There was no “Progressive Masculinity Handbook” handed to our dads.
And there wasn’t one handed to us either.
So what do we do?
We model curiosity.
We model accountability.
We model emotional literacy.
We admit when we get it wrong.
And we keep talking.
🎧 Listen to the Episode
Below you can listen to the full conversation with Mike.
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Why This Conversation Matters
If you’re a teacher — this affects your classroom.
If you’re a school leader — this affects your culture.
If you’re a parent — this affects your home.
And if you’re a man trying to do better than the generation before you…
This one’s for you.
💬 Final Reflection
At one point in the conversation, we laughed about how awkward these conversations can feel.
But awkward doesn’t mean unnecessary.
If anything, awkward usually means important.
Mike isn’t shouting.
He’s not selling outrage.
He’s not building a brand off division.
He’s doing the quieter work.
And sometimes that’s exactly what we need.
🙌 Support the Show
If this episode resonated with you:
- ⭐ Leave a review wherever you listen
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- 📲 Share this episode with a colleague, friend or fellow parent
The more we talk about this stuff, the less power the extremes have.
And if you’re enjoying these conversations — your support genuinely makes a difference.
Thanks for listening.
Thanks for thinking.
And thanks for being part of the Detention Diaries community.

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