There’s a moment in the lives of many men — often somewhere between 45 and 60 — when the maps run out. The success you once chased feels hollow, the roles you’ve played seem ill-fitting, and the horizon that once stretched endlessly now whispers of limits, not boundlessness.

David Whyte, in Midlife and the Great Unknown, doesn’t offer tidy answers or ten-step programs. Instead, he invites us into the fertile discomfort of unknowing. “The only way to find the path is to walk it,” he suggests, with the voice of a poet and the grit of someone who’s walked it himself.

Whyte argues that midlife is not a crisis but a passage — a frontier where old identities dissolve and new, more authentic selves emerge. It’s the time when a man is asked, not by the world but by his own soul, to stop performing and start listening. The rewards? A richer, more meaningful life. The cost? Letting go of certainty.

This is deeply relevant for men in Australia, where the cultural blueprint for masculinity still leans heavily on stoicism, productivity, and control. From the boardroom to the barbie, men are taught to soldier on, to hold it together. But midlife refuses to be muscled through. It asks for a different kind of courage: the courage to surrender.

In this space of unraveling, Whyte’s poetic reflections meet beautifully with Derek Mahon’s quietly powerful poem, Everything is Going to be All Right. Mahon writes:

There will be dying, there will be dying,

but there is no need to go into that.

The sun rises in spite of everything…

Everything is going to be all right.

These lines offer no easy comfort — but something better: a deep, lived assurance. Yes, life is finite. Yes, you’ve made mistakes, missed chances, and fallen short. But also: the kettle still boils. The sea still sparkles. You are still here. And all is not lost.

In Whyte’s view, midlife is the point at which we’re invited to shed borrowed ambitions and begin again, this time aligned with what truly calls us — not just what impresses others. It may mean stepping away from roles you’ve mastered, into uncertainty. It may mean returning to passions left dormant, or learning to be present in your relationships in a way you never were before.

For the Australian man — who might’ve been raised on bush stoicism, hard yakka, and a quiet beer over introspection — this can feel confronting. But it’s also liberating. You don’t have to have it all figured out. You just have to be willing to stand still, to listen, to be changed. Because midlife isn’t The beginning of the end. It’s the beginning of becoming real.

And in the quiet that follows — perhaps with a cup of tea in hand and the surf humming nearby — Mahon’s words may return, not as consolation, but as truth: Everything is going to be all right.

There’s a reason the podcast Don’t Let the Old Man In resonates with thousands of men in their 50s. It speaks to the quiet war many fight against obsolescence, irrelevance, and a determination to navigate life’s crossroads with clarity and confidence. And likewise, if you’re reading this, you haven’t given up. You’re still curious. Maya Angelou once said, “If you’re always trying to be normal, you will never know how amazing you can be.” Midlife career change isn’t about being extraordinary. It’s about being aligned—with yourself.

Stephen Keys is the Producer of the Don’t Let the Old Man In podcast. Listen on YouTube, Apple, Spotify or wherever you tune in. Find more thoughts on living gracefully (and disgracefully) in the second half of life at The Wisdom Vault, on LinkedIn, Substack and even (!) Instagram.