5-minutes with... Chris Kalaboukis

The questions men aren't usually asked, answered without the armour.

I’ll admit, when I started this series, I wasn’t sure men would want to talk about midlife the way women do. So openly. So willing to admit where it’s actually landing.

Simon Salt, Marc Dupont, Paul Strobl and now, chris kalaboukis proved me wrong almost immediately.

Chris is a futurist, technologist, and philosopher, someone who’s spent a career thinking about what’s coming next. But what struck me most in his answers wasn’t anything about the future. It was how plainly he talked about the present. About strength, catching up with him in ways he didn’t expect. About needing rest in a body that, mentally, still feels exactly as sharp as it always did. About realising, almost by accident, that somewhere along the way, he’d already succeeded, and hadn’t stopped long enough to notice.

There’s something quietly important in hearing a man say that out loud.

Who are you, and what season of midlife are you in right now (work, health, family, identity)?

Chris Kalaboukis, and I’m a futurist, technologist and philosopher. I’m in my 60s, so early mid-life (for me, I’d say ;)

What surprised you most about getting older and being a man in midlife?

I’d say that the physical issues catching up to me are the hardest: loss of strength, pain, etc. Mentally, I feel just as fit as I was, but I get more physically tired.

What’s been the hardest part that men rarely say out loud?

The hardest part is being able to give myself time to rest and recuperate, things I never needed to have before.

What has helped you most (a habit, a mindset shift, support, therapy, community, lifestyle changes, medication if relevant)?

I get up at 5 am every weekday, and I need some alone time to meditate and think.

What are you unlearning about masculinity, success, or what it means to be a good man?

I’m go go go all day, and I find it hard to slow down. I realised at one point that even though I was still trying hard to succeed, I neglected to look back and notice that in some ways, I had already succeeded.

What do you wish you could tell your 35-year-old self?

I wish I could tell my 35-year-old self to be less careful about my reputation and take more risks.

What do you want other men to know they’re not alone in?

I’d like men to realise that it's okay for us to step back from our responsibilities if we have to. We need more time to rest.

What’s one small ritual or practice that’s keeping you steady day to day?

The meditation ritual and actually spending time connecting with people on Substack are great.

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The line that’s stayed with me is the one about reputation.

I wish I could tell my 35-year-old self to be less careful about my reputation and take more risks.

I think a lot of us, women and men alike, spend our 30s and 40s building something so carefully that we forget to ask whether that caution has ever served us. Chris’s honesty about that, and about needing to rest in a way he never used to, feels like exactly the kind of conversation this series exists for.

Thank you, Chris, for being so open.

And to everyone reading, if there’s a man in your life who’s never quite given himself permission to slow down, maybe this is the one you send him.

Kiran x

This series exists because when one woman tells the truth, another woman exhales. If something in this conversation made you exhale, if you recognised yourself in her words, there is a space where that feeling has a home.

The Midlife Circle is where the deeper conversation lives. Not just other women’s stories, but yours. Bi-weekly essays and The Midlife Edit, a private podcast, tools across all five areas of this season of life, from £19/month or £149/year.

And if you’re ready to go all the way in, the Midlife Inner Circle at £297/year includes the Midlife Manifesto Audio Training, The Midlife Reset course, and four quarterly 1:1 calls with me. Real, personal support for the redesign you’re already beginning.

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