In a world awash with algorithms and automation, as a man in his fifties, it’s your emotional intelligence, hard-won wisdom, and storytelling ability that will keep you indispensable.

Everywhere you look today you will hear or read a story about a chatbot that can write a poem and an algorithm can crunch your finances or AI agent that can check your diary, go online to book your concert tickets and then alert your friends via your email that this has been done. It is tempting to think the machines have won. From customer service to investment advice, AI seems to be encroaching on once-sacred human territory. For professionals in mid-to-late career stages, the question looms large: Am I still relevant?

Here’s the good news: AI might run the data, but it can’t run the room. It lacks moral judgment, intuition, and—perhaps most importantly—the life-earned qualities that make a seasoned human being invaluable. This is the power move we have in our mid-life that comes home to roost in our favour. If you’ve got the following five skills, not only are you safe from being replaced—you will be in demand.

Trust-Building – The Original Operating System

Trust is a human characteristic that no one can see or touch, but everyone knows when it is present or missing from the relationship. Trust isn’t transactional. It’s built over years, in meeting rooms, lunch breaks, late-night calls, and hard conversations. AI might give you correct answers, but it can’t look into the eyes of a nervous client and reassure them reassure or mend a dysfunctional team dynamic.

• People trust people, not processors.
• Trust is nurtured through consistency, empathy, and credibility.
• Your ability to build relationships is your biggest leadership asset.

Heidi Badgery is the Chief AI Officer for Tech business, Alteryx, and she noted in an interview with The Australian newspaper, that leaders must move fast to close the AI trust gap—but no software update can replace a trusted human face in the room. “The soft skills will be needed in the AI process, including critical thinking, judgement and creativity,” she said.

Moral Judgment – Because Ethics Aren’t Coded

AI is great at optimising. But should it? How does AI understand nuance? If moral dilemmas are about knowing when to break a rule for a greater good, what does AI use to help determine that?

• Ethical dilemmas don’t come with binary answers.
• Real leadership requires principled decision-making.
• Empathy and accountability don’t fit into algorithms.

Peter Singer, the moral philosopher, recently shared his views with The Guardian. Peter had just retired from Princeton University, where he was professor of bioethics. Today he writes on Substack, hosts a podcast, and edits journals for print and online readerships. In the piece, he explores the moral dilemma about the source for ethical judgement, concluding that “machines cannot intuit the messy middle of human values.” That middle is where you live, and lead. His conclusion underscores the indispensable role of human judgment in morally complex scenarios.

Crisis Wisdom – The Benefit of ‘I’ve Been Through Worse’

American author Rita Mae Brown said “Good judgment comes from experience. Experience comes from bad judgment.” It is a pithy reflection on how wisdom is gained through mistakes and learning over time. In a former career working in cardiothoracic surgery ICU, I remember having to physically pump a patient’s heart with my right hand while a surgeon calmly under pressure, tried to find the source of the sudden rupture of sutures that had been put there during their heart surgery a few hours earlier. I have never forgotten that moment and the need to stay calm in moments of severe pressure. Anytime I have found myself in an anxious situation I have asked myself, “is this moment as severe as the moment I was pumping a patient’s heart”? The answer is always no!

Crisis separates data from judgment. In high-stakes moments, your ability to stay calm, think clearly, and act with authority can’t be downloaded.

• Experience gives you intuition: the ability to spot patterns in chaos.
• You’ve weathered industry shifts, financial downturns, interpersonal meltdowns.
• AI can alert you to a fire. It can’t lead people through the smoke.

Try asking ChatGPT how to handle a passive-aggressive CEO in the middle of a poor monthly financial reporting session—see how that goes!

Storytelling – Data’s Favourite Translator

Facts inform. Stories persuade. AI can generate reports, but it doesn’t know your audience’s fears, dreams, or attention span.

• Humans are wired for story, not statistics.
• The best communicators use narrative to shift hearts and minds.
• Data storytelling is what turns insight into action.

In a 2014 article by neuroeconomist Paul Zak called “Why Your Brain Loves Good Storytelling,” he explores how emotionally engaging stories stimulate oxytocin production. Oxytocin is a neurochemical associated with empathy, trust, and connection. This hormone makes us more likely to trust the storyteller and take action based on the story. Zak shared that “Narratives that are personal and emotionally compelling engage more of the brain and are better remembered than dry facts.”  AI can give you a plot. But it still can’t avoid a dad joke!

Lived Empathy – Not Just Simulated Concern

Elon Musk is not a fan of empathy. In fact, he publicly highlighted concerns about its potential misuse on an episode of the popular Joe Rogan podcast in 2025. Musk stated in that interview, “The fundamental weakness of Western civilization is empathy. The empathy exploit. They’re exploiting a bug in Western civilization, which is the empathy response.” Musk went on to express that while he believes in caring for others, excessive empathy can be detrimental if it leads to decisions that harm societal well-being. His perspective has sparked significant discussion and criticism. Former Vice President Kamala Harris responded to Musk’s remarks during a speech at the 2025 Australian Real Estate Conference, asserting that empathy is a strength, not a weakness, and cautioning against leadership models that dismiss compassion.

Empathy isn’t a feature. It’s a decision born of lived experience. You’ve grieved, you’ve celebrated, you’ve endured—and it shows in how you listen and lead.

• AI can mimic sympathy, but it can’t feel your heartbreak or hope.
• Real empathy builds connection, loyalty, and culture.
• Your presence, your story, your scars—they’re what make you human.

Maya Angelou, the famed poet, put it beautifully: “I think we all have empathy. We may not have enough courage to display it.”

Lean In, Don’t Log Out

So, the next time someone whispers, “AI’s coming for our jobs,” smile and remember: it’s not coming for trust. It’s not coming for empathy. And it’s definitely not coming for your story.

Yes, AI is reshaping how we work. But is it actively shaping you? You’re not going anywhere. In fact, your greatest value might just be what the machine can never mimic: your humanity.

Men- keep showing up. We still need you at the table.

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.

Pod O’Sullivan is the host 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.