It happened in a fleeting moment. I was walking out of a conference room today, half-scrolling through Slack, half-wondering what my next caffeine fix would be, when I saw him.
My client’s CEO.
He didn’t see me. He walked right past, heading down the corridor with a pace that wasn’t rushed but was sharp, precise. There was a weight in his steps that didn’t come from urgency. It came from purpose. From knowing exactly why he was walking and where he was walking to.
He looked almost 60. Silver streaks in his hair, a lined but confident face, wearing a well-tailored suit and an air of control. Not the kind of control that screams authority, but the quiet kind that doesn’t need to.
And in that brief moment, I had a question echo in my head: Why is he still doing this?
He’s made his money. His LinkedIn glows with success. He’s spent decades climbing, building, leading. What more could possibly be left to chase at this stage? Why take the pressure calls at 8 AM? Why navigate another board meeting? Why solve yet another fire someone else lit?
And more importantly: Would I ever want to be like him?
What Drives Men Like Him?
I started unpacking it.
1. Legacy Over Livelihood
When the paycheck no longer changes your lifestyle, the only currency left is impact. These leaders want to leave a mark — not just on balance sheets, but on people, culture, institutions. Retirement is not an exit; it feels like erasure.
2. Identity and Ego
Work is not what they do. It’s who they are. Titles, meetings, and strategy decks become affirmations of relevance. To step away is to answer the haunting question: Who am I without this?
3. Power and Influence
Being the person who moves the needle, who commands rooms, who shapes futures — that’s addictive. There’s a buzz in being at the centre of the action.
4. Responsibility as Meaning
Some carry the pressure not out of ambition, but stewardship. A belief that they are the stabilizers of the ship. That if they leave, the system might tip.
5. Fear of Emptiness
With everything already achieved, many fear what remains when the emails stop and the applause fades. The real monster isn’t work. It’s silence.
Where I Am
Me? I’m still choosing the game.
I crave freedom — to move cities, to create, to feel. I’m asking questions, sometimes existential ones. I start projects, pause them, doubt them, love them again. I look for work that feels real, not just rewarding.
I don’t walk with purpose. I walk with curiosity. And occasionally with confusion.
And maybe that’s okay.
The Character Arc: A Life in Phases
I imagine that this man too, once walked like me.
Here’s how I see his journey:
Phase 1: The Seeker (20s-early 30s)
- Tries different things. Gets lost. Gets found. Wonders if he’s meant for this at all.
Phase 2: The Climber (30s-40s)
- Sharpens ambition. Plays the game. Starts winning. Chooses strategy over soul sometimes.
Phase 3: The Believer (40s-50s)
- Invests deep into one vision. Starts carrying others. Feels responsibility, and pride.
Phase 4: The Steward (50s-60s)
- Legacy time. Becomes the voice in rooms, the mentor, the symbol.
Phase 5: The Reflector (60+)
- Either lets go with grace. Or holds on a bit too tight. Either way, life slows, questions deepen.
Two Possible Futures for Me
✨ Path 1: The Deep Dive
I double down. I find my space in the system, my version of purpose within the pressure. I rise. I lead. I shape. Over time, I learn to love the game I once questioned. Maybe I don’t just play it — maybe I redesign parts of it. And one day, I’m the one walking down that corridor, sharp suit and soft smile, with 30 years of stories in my stride.
🌊 Path 2: The Divergence
I step off. I move towards a mosaic life: part creator, part wanderer, part strategist. I collect cities and conversations. I build small but meaningful things. Maybe I write, maybe I teach, maybe I start something of my own. I’m not the CEO of a corporation. But I’m the CEO of my time. I walk with a different kind of purpose. Not louder. Not bigger. Just mine.
Final Thought
That man today walked like he owned time.
Maybe he earned it. Or maybe, it was all he had left to own.
Me? I’m still figuring out my pace. But I’m beginning to realise that walking with purpose doesn’t always mean knowing where you’re going.
Sometimes, it just means walking wide awake.