As men in midlife, many of us feel a weight: the sense that we should have everything figured out by now. We’ve lived long enough to think we ought to be the ones with all the answers, leading with clarity. But if we’re being honest with ourselves, the further we go, the more the ground beneath our certainties seems to shift. And maybe, just maybe, that’s the truest sign of our growth.
Charles Kettering once said, “Education is man’s going from cocksure ignorance to thoughtful uncertainty.”
When I first heard this, it struck me deeply because it captures something many of us already know in our bones. In our younger years, we were sure of ourselves—sure we knew what success looked like, what it meant to live a “good life,” and how the world worked. We were convinced we had the answers. But that certainty was often rooted in an oversimplified view of the world, a black-and-white perspective that couldn’t hold the complexities of life that midlife forces us to reckon with.
Carl Jung spoke about the midlife transition as one from the outer world of achievement to the inner world of self-awareness and meaning. As we shift inward, we come to understand that many of the “answers” we once relied on no longer serve us. And yet, this growing uncertainty isn’t a sign of regression—it’s a sign that we are finally seeing the deeper, richer truths that life has to offer.
In his work, Parker Palmer describes how finding our vocation—our true calling—isn’t about discovering definitive answers, but about listening to the quiet inner voice that guides us. He writes, “Vocation at its deepest level is something I can’t not do.” This work, this journey we are on, isn’t about mastering life’s questions. It’s about showing up, again and again, with a willingness to live inside those questions, even when the answers are nowhere to be found.
Richard Rohr also speaks about this second half of life; he refers to it as the time when we finally embrace mystery. Rather than needing everything to be clear-cut and defined, we begin to appreciate the wisdom of not knowing. Rohr reminds us that real growth comes not from certainty, but from the humility that accompanies uncertainty—from the ability to sit with the unknown and allow it to transform us.
So if you’re feeling uncertain right now, know that you are not alone. In fact, your uncertainty is a marker that you are on the right path. It’s a sign that you are growing, deepening, becoming. It’s a sign that you are stepping out of the oversimplifications of the past and into the richness of life as it truly is.
The truth is, being cocksure at midlife is a sign of immaturity, a refusal to face the complex, nuanced reality of the world we live in. It’s the man who embraces uncertainty—who lets go of the need for neat and tidy answers—who is maturing, who is stepping into the fullness of what life has to offer.
If you’re grappling with more questions than answers right now, it’s not a sign that something is wrong. In fact, it’s often a sign that you’re evolving in ways you may not even recognize yet.
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