Could It Be Imposter Syndrome?

It Shook My Confidence

A few years ago, I would have told you I was a confident executive.

Then my last role ended.

What surprised me was not losing the position. It was how much of my confidence seemed to disappear with it.

For decades I had built a successful career. I had led teams, solved difficult problems, and earned a reputation I was proud of. Yet without the title, the organization, and the daily validation that came with them, I found myself questioning things I had never questioned before.

At first, I called it imposter syndrome.

Now I think it was something else.

The uncomfortable truth is that I had spent much of my career chasing someone else’s approval. Promotions. Bigger titles. Recognition. The next opportunity. I believed those things reflected my confidence. Looking back, they had quietly become the source of it.

That was my first mistake.

The Creation of Self Doubt

My last boss did not create my self doubt. He simply exposed how much of my confidence depended on someone else believing in me.

Walking away became one of the hardest decisions I have ever made.

It also became one of the best.

Not because I had another job waiting.

Not because I knew exactly what came next.

I walked away because I realized I could no longer build my life around earning approval from people who could withdraw it at any moment.

That decision became the beginning of something entirely different.

As I have reflected on that experience, I have come to believe I am not alone.

Today, workers over 55 are one of the fastest growing segments of the labor force. Gen X is now the highest earning generation in the United States and holds many of the leadership positions shaping business today. Yet nearly two thirds of workers over 50 say they have seen or experienced age discrimination in the workplace. We are more experienced than ever, but many of us feel we have to work even harder to prove we still belong.

Then came AI.

For most of our careers, expertise was measured by what we knew. Experience was valuable because knowledge was difficult to acquire.

Today, information is everywhere.

Knowledge has become abundant.

Judgment has not.

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The Shift and the Answer

That shift can make even accomplished professionals wonder whether decades of experience still matter. I do not think we are suffering from an epidemic of imposter syndrome. I think many of us are navigating a world that has changed the way expertise is recognized.

The more I thought about it, the more I realized my confidence had never actually disappeared.

I had simply outsourced it.

I had allowed my identity to become inseparable from my employer, my title, and someone else’s opinion of my value.

That realization changed everything.

I still believe in ambition. I still believe in building meaningful careers. But I no longer believe a career should become the place where we seek our worth.

Careers evolve.

Companies change.

Leaders come and go.

If our confidence depends on any of those things, it will always be fragile.

The Belief

Building RestlessUrban has reminded me that the most valuable things I have accumulated over three decades were never the titles on my business card. They were perspective. Judgment. Curiosity. Relationships. The ability to connect ideas and people. No employer can give you those. And no employer can take them away.

I promised myself I would never build my confidence that way again.

And again, thank you to the boss who did not believe in me.

Because now, I do.