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The Heart of the Matter

When are you enough? Addressing insecurity in the workplace


There’s a reaction I’ve come to expect when I’m speaking to executives. I’ll share this statistic, “In 2016, a Gallup poll found that only 18% of managers demonstrated a high level of talent for managing others, meaning a significant 82% of managers were not very good at leading people.

It’s like the air gets sucked out of the room.

Seriously; people go quiet. You can see them start mentally auditing the leaders they’ve been comparing themselves to, only now, those people seem a little less impressive.

The statistic hits hard because it calls into question a narrative so many of you have absorbed: that the higher up someone is, the more competent they must be. That success equals skill. But the people you’re striving to become? Their teams don’t even think they’re good at their jobs.

And still, you’re torturing yourself, trying to become a version of a leader that isn’t even working for most people in leadership positions.

Insecurity starts earlier than you think.

I was about 15 when my parents came home from a parent-teacher conference. "Your teachers think you're great," they told me. "Just remember, you're no better or worse than anyone else."

My parents, products of the civil rights era, meant well. Humility was protection. Don't stand out. Don't make waves.

But I was already nearly six feet tall. I stood out whether I wanted to or not. And to my teenage mind, their well-intentioned advice registered as: Play small.

That became part of how I moved through the world. I've realized since then that insecurities often begin long before adulthood, shaped by messages we receive early on, even caring ones.

I had great parents guiding me. They had their foibles but were loving, wise, and supportive. Not everyone gets that. Most people are left to figure themselves out within systems that profit from their insecurity, confronting the constant belief that they're behind or inadequate, that if they could just fix their personality, body, résumé, they would finally be “enough.”

I’ve seen this every day in my work. High performers chase someone else's idea of excellence to overcome insecure feelings, believing their worth is tied to their output.

What insecurity looks like

It’s not always easy to spot insecurity, even in yourself. It can feel like a drive to overachieve or control, instead of the more familiar signs of hesitation or self-doubt. You may recognize it as:

  • Pushing yourself past exhaustion, because rest feels like weakness.
  • Avoiding conflict, because being liked feels safer than being respected.
  • Micromanaging, because it’s too risky to let go.

I've seen people work themselves to illness trying to prove their worth, leaders fail to set direction because they fear being questioned, and talented people sabotage their teams because they're too insecure to delegate.

I almost feel sorrier for those who've climbed the ranks but still feel inadequate. They spend more energy managing how they’re perceived than being present.

You’re buying into a myth.

When I work with clients who are consumed by self-doubt, I start by naming their achievements. It’s good to be reminded that you have, in fact, accomplished a lot.

Then I ask a harder question: "Have you looked critically at the system you're a part of?"

So often, that doubt stems from believing you need to be someone else to succeed. You look at who dominates your organization, your sector, and your society, and to the extent you’re not that, you assume you're at a disadvantage.

You may still believe that if you work harder, you’ll be rewarded. But that belief belongs to a meritocracy that doesn’t exist.

Advancement isn’t just about merit. It’s about pattern recognition. Pedigree. Proximity. People rise because they resemble what those in power already trust. They don’t disrupt the archetype.

So if you’re looking at someone in a position you want and thinking, I’m better than them, I deserve that job, you might be right. It’s a sign that your institution still selects for sameness, not readiness.

I knew early on that I didn’t fit the mold. I had to stop wasting energy trying to contort myself into one. Coming to terms with that was incredibly freeing.

Feeling is a choice.

That doesn’t mean your insecurities aren’t real, but you don’t have to let them steer. You’ve learned to feel this way about yourself, but you can unlearn it.

You can decide: I’m going to feel powerful. Even if I don’t believe I am yet.

You’re already worthy of making that choice. You don’t need to earn it.

When I see someone stuck in patterns fueled by insecurity, I ask them: Is this working for you?

You can agonize about your problems all day. But what are you doing to disrupt them? You could try:

  • Pausing to name your feelings. Where is this coming from?
  • Questioning yourself. Is this my truth, or someone else’s expectation?
  • Choosing what serves you. Power. Sufficiency.

You deserve to feel grounded and free to move through the world without second-guessing. That comes from knowing who you are, building self-worth that isn’t dependent on recognition, and (dare I say) loving yourself. If you weren’t taught how to do that, it’s never too late to learn.

Something to consider as you move forward: When are you enough?

You don't need to be perfect. But you do need to stop performing someone else's idea of success. Start with honesty. Stay with compassion. Try being different.

It’s not easy, but it makes the peace you’ve been chasing possible.

Sending love and light,

Ginny

1440 W. Taylor St #1055, Chicago, IL 60607
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