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The Happiness Trap: Why Am I Not Happy Despite Success?

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Not long ago, during one of my leadership retreats, a participant,let’s call him Ravi, approached me during a tea break. A CXO at a leading tech firm, he technically had ‘made it in life. ”
But his question was anything but casual:
“Sir, I’ve ticked all the boxes… So why am I not happy?”
This wasn’t a man who lacked ambition or grit. On the contrary, he’d built his career brick by brick. Yet there it was, emptiness, hiding behind all the success and accolades.
His question isn’t rare. In fact, it’s become so common that I’ve given it a name: the happiness trap.

Chasing Happiness Is a Marathon With No Medal

From a young age, we’re taught to chase milestones. Get good grades. Land a job. Buy a house. Move up the ladder. The world whispers: “Once you get there, you’ll be happy.”
But no one tells us what to do when we get “there” and still feel restless.
The happiness trap is precisely this,when the pursuit of happiness becomes a substitute for actual joy. And it sets in very subtly.

It’s the voice that says:
  • “I’ll be happy when I earn more.”
  • “I’ll feel fulfilled after this project.”
  • “Just one more milestone…”

But here’s the catch : the faster we run, the further away happiness seems.

The Science Behind Why You Still Feel Empty

There’s actually a term for this in psychology: hedonic adaptation. It means that no matter how exciting something is initially,be it a new job, a new car, or a promotion,your brain eventually normalizes it.
That initial high? Temporary. And when it fades, we start wondering again: “Why am I not happy?”.
That’s when we jump into the next pursuit. A bigger goal. A better gadget. Another title..
And unknowingly, we fall right back into the loop, chasing happiness without ever fully catching it.

Happiness and Success: Not Always Best Friends

We love linking happiness and success as if one guarantees the other. “If I’m successful, I must be happy,” we assume.
But real life tells a different story.
I’ve worked with people across industries, from Navy officers to corporate leaders to entrepreneurs, and I’ve seen something time and again: You can be wildly successful and still feel deeply unfulfilled.
You see, success is often measured, but happiness is felt. And when our lives are filled with achievements but empty of meaning, we find ourselves stuck in a silent question:
“Is this all there is?”

A Sailor’s Wisdom: True Happiness Meaning in Its Simplest Form

Let me share a story from my Navy days.
We had a sailor, Rajesh, who was always the first to wake and last to complain. No fancy degrees, no big ambitions. He made the morning chai with care and kept the deck spotless, for him everything he did, really mattered
One day I asked him, “Rajesh, you’re always cheerful. What’s your secret?”
He chuckled and said,
“Sahab, I don’t chase happiness. I live it.”
That moment hit me harder than any leadership theory ever could.
That’s the true happiness meaning, not something to be chased or conquered, but something to be lived, moment to moment.

From Chasing Happiness to Choosing: The Real Shift

So how do we escape the happiness trap?
Start by changing the question.
Instead of asking, “What will make me happy?”, ask:
“What brings me peace?”
“What aligns with who I am?”
“Where do I feel most alive?”
True happiness often hides in ordinary moments:
A walk without your phone. A laugh shared with your child.
A task done with full presence.
And most importantly, in knowing that your worth isn’t tied to your next achievement.

Final Reflection: Slow Down to Feel Full

If you’re reading this and thinking, “This is me,”that's good. You’re aware. And that’s where all meaningful change begins. You don’t need to abandon ambition. Just stop outsourcing your joy to it.
Let’s be clear: Chasing happiness is addictive and exciting, but it’s also exhausting.
When you stop, breathe, and simply be, you’ll often realize, you weren’t missing happiness.
You were missing yourself.
So pause today. Pour that cup of chai. Watch the sky. Hug someone tight.
And remind yourself:
Happiness isn’t ahead of you. It’s within you, right now.