The Daily Check-In That Changed Everything

5-minute habit… Here’s how it works

Something I get told regularly by the men I work with is a version of the same thing. They have friends. They know plenty of people. Their diary is rarely empty and their phone is full of contacts. And yet underneath all of that, they feel quietly isolated, because they never actually get to say how they’re really doing to anyone.

Not because their friendships aren’t real. But because nobody ever quite creates the space for it, and after a while you stop expecting it to happen.

This is something I’ve been doing for years now, quietly, with my mate Phil. And I’ve been sharing it with the men I coach ever since because the results are consistently the thing they thank me for most.

One STORY

Me and Phil started a daily WhatsApp voice note check-in during lockdown.

We did it as an experiment to see what would happen if we just asked each other three honest questions every single day and actually answered them. That was a few years ago now and we haven’t missed a day since.

Some days it’s five minutes. Some days it stretches to twenty-five. It doesn’t matter. What matters is that every morning, usually between half seven and half nine, one of us hits record and checks in honestly with where he actually is. And the other listens, properly, and sends one back.

The three questions are simple.

How am I doing physically?
How am I doing emotionally?
And how am I doing spiritually?

By spiritually, I don’t mean anything religious, I mean how am I doing in myself, that old-fashioned phrase your grandparents might have used, the one that points to something underneath the surface that the other two questions don’t quite reach.

What surprised me wasn’t how much came up in those check-ins. It was how little it took to make both of us feel genuinely less alone. Not because we were solving problems or offering advice. Because we were being heard. Consistently. By someone who was actually paying attention.

Men do talk. We just need the container, the permission, and the safety. That’s it.

The men I’ve introduced this to, coaching clients, mates, men who’ve seen it on the YouTube channel, they all say the same thing after a week. I didn’t realise how much I needed this. And almost all of them carry on long past the week I ask them to try it for.

One SHIFT

There’s a story a lot of men tell themselves about why they don’t have this kind of conversation.

That their mates aren’t the type. That it would be weird. That they don’t have time. That they’re fine really, so what would they even say.

But that story isn’t really about their friends or their schedule. It’s about the fact that nobody ever designed a space for it to happen. Because without design, without a container and a structure and a clear set of rules about what this is, most men default to fine. Not because they are fine, but because fine requires nothing of anyone and keeps everything safely on the surface.

The shift this practice creates isn’t dramatic. It’s quiet and cumulative. You start to know yourself better because you’re checking in with yourself every day rather than running straight past what’s actually there. You start to know your friend better because you’re hearing him honestly rather than at the level of pub chat.

And slowly, almost without noticing it, you stop carrying everything alone. Which for most men in midlife is the thing that was quietly exhausting them more than anything else.

I've create this video below to support this weeks challenge!

One Challenge

This week I want you to try this for seven days.

One person.
Five minute checkins.
Seven days. That's it.

Here’s exactly how to set it up:

Step one — choose your person. It doesn’t have to be your closest mate. It just needs to be someone you have a quiet sense could hold space without immediately trying to fix something. Send him this email if that helps explain it, or just ask if he wants to try something for a week.

Step two — agree the design together. Before you start, have a quick conversation about the rules. No advice unless asked. No fixing. No judgment. No pressure to respond the moment it comes through. And absolute confidentiality — what goes into the check-in stays there. That last one is non-negotiable.

Step three — hit record each morning. Keep it to five minutes to start. Answer these three questions honestly, in order:

How am I doing physically? Your body, your energy, your sleep, what you’re noticing.
How am I doing emotionally? Check in from your chest, not your head. What’s actually there?
How am I doing spiritually? Not religion. How am I doing in myself underneath everything?

Step four — listen properly. When his message comes through, give it your full attention. Listen like you're going to be tested on it afterwards. Then send a short reflection back — “I really hear that, that sounds tough” is enough. You are not there to solve anything.

Step five — keep going. Do it again tomorrow. And the next day. The practice builds its own momentum within a week.

If you’re not sure where to start with any of this, the Midlife Audit is a good first step. Not because it solves the belonging problem, but because getting honest about where you actually are is almost always where everything else begins.