When one of my most hard-working and self-aware clients looked at me with bewilderment and said, “Why do I feel so empty? Shouldn’t I be celebrating with my team — with you? This is supposed to be a day of celebration… yet I feel nothing,” I knew my real work with him had just begun.
He had just successfully led his company through an acquisition. On the outside, it was a massive achievement, the kind of milestone founders dream about. But beneath the surface, a hidden iceberg was beginning to emerge. What lay underneath felt like a thousand bricks on his shoulders.
Like many founders, he had spent years chasing growth. Endless effort, sleepless nights, cutting costs at every corner, missing weekends with family, all for the sake of outperforming competitors. That lifestyle became his norm. So when he finally reached the summit, he expected to feel euphoric. Instead, he told me he wasn’t prepared for the silence.
The recognition and accolades that once fueled him now felt like empty trophies. What used to elevate his ego to superhuman levels had become reminders of a deeper void. As he put it: “The higher I climbed, the heavier the loneliness.”
This wasn’t burnout. It wasn’t a lack of ambition. It was something deeper: a misalignment between his success and his identity.
The Illusion of Arrival
He’s not alone. Studies show many executives, founders, and CEOs face this same disconnection. They believe achievement equals fulfillment, until they arrive, only to be confronted with unsettling questions:
- Why am I feeling like this?
- Why am I still doing what I do?
- Does my work still have meaning for me?
- Where do I go now?
Even I remember moments in my own career when I questioned whether success was truly mine, or whether I was just carrying out expectations and loyalties mapped out long before me.
Leaders I work with, especially women, often describe the same experience:
- Feeling imposter syndrome despite clear evidence of accomplishment.
- Questioning whether the sacrifices were worth the goals achieved.
- Realizing the summit didn’t bring the satisfaction or bliss they imagined.
Yes, the success was real. But it felt meaningless.
Why the Void Appears
Psychologists Robert Kegan and Lisa Lahey (2001) describe this as a misalignment of our “meaning-making systems.” In plain words: when our inner growth doesn’t evolve at the same pace as our external success, we become estranged from ourselves.
That’s exactly what my client was experiencing. His world was expanding too fast on the outside, while his inner self hadn’t caught up. That mismatch created a quiet, almost invisible suffering.
It’s not about competence. It’s not about strategy. It’s about identity.
How to Reconnect (And How You Can Too)
The void doesn’t have to define you. It doesn’t have to stay. You have the power to change what no longer works.
Here are three practices that helped my client reconnect, and that you can apply, too:
- Re-ground in Purpose. Ask yourself: If no one was watching, what would I still fight for? What is truly mine? These uncomfortable but powerful questions help strip away inherited goals that don’t belong to you.
- Do the Identity Work. Exploring family dynamics, money stories, roles, and generational narratives is unsettling but essential. This psychodynamic work surfaces unconscious patterns and helps you see the forces that have been shaping your choices.
- Allow Evolution, Not Just Execution. Leadership is not only about getting things done, but also about allowing yourself to be reshaped by your teams, markets, and life experiences. Invite challenges to your perspective. Give yourself permission to adapt, to change, to grow.
For my founder client, re-grounding in purpose was transformative. He realized that half of his goals weren’t even his — they were his father’s. Letting go wasn’t easy and it wasn’t quick, but as he continued the work, his own definition of success began to emerge. Together with his family and his team, he created a new vision of what truly mattered. That’s where reconnection, and transformation, began.
Closing Thought
Success without alignment feels empty.
But when achievement meets identity, success feels whole: alive, authentic, and deeply human.
True growth isn’t only upward. It’s inward — to the sacred place where real leadership begins.
Reference:
Kegan, R., & Lahey, L. (2001). The Real Reason People Don’t Change. Harvard Business Review.