Why Every Executive Woman Needs A Mastermind: Leadership Without Loneliness

A group of seven people stand confidently with arms crossed in front of a modern glass building. The person in front wears a light coat and appears to be in a leadership position for the group.

When you think of someone in the C-suite or at the executive level, what image comes to mind? For most people, it’s power, prestige, prosperity and influence…like something out of a movie. But there’s another side of that perfect puzzle that many don’t see.

I call it The Lonely Leader.

Maybe the position you’re in is something you’ve dreamed of for years. Maybe it was the next logical step. Maybe you were in the right place at the right time…or maybe, just maybe you were the most qualified person for the role.

Whatever brought you here, one thing is likely true:

Along with pride in your achievement, you might feel isolated, disconnected or no longer “one of them.” You’ve moved up or over…but you’re on your own.

The Truth About Leadership Loneliness

Most leaders don’t fail from lack of talent. They fail from lack of connection and support.

Survey after survey shows the same pattern. More than half of CEOs report feeling lonely in their role, and of that group, 61% say it hinders their performance. First-time CEOs are especially vulnerable. Nearly 70% of them say loneliness negatively impacts how they lead.

And it’s not just CEOs. Women in senior leadership roles, particularly those labeled “the first” or “the trailblazer” often carry the extra weigh of being the only.

And through this, there are also questions that quietly haunt us.

  • Who can I trust with my frustrations?
  • Is there anyone I can talk to about confidential matters…openly?
  • Who will give honest feedback on ideas that I haven’t even spoken aloud?
  • Will I be judged if I show uncertainty or emotion?
  • Where can I be vulnerable…without being considered weak?
  • Am I seen, and valued…for the right reason?

These aren’t hypothetical. They’re the lived experience of so many women leaders. I’ve surveyed hundreds and when they hear they are not alone in these feelings, there’s a visible sigh of relief. It’s not just me.

Vulnerability Is Leadership

Gone are the days of “never let them see you sweat.” Today’s leaders, especially women, are embracing vision, empathy, courage, generosity and yes, vulnerability. But even with that shift, the loneliness still creeps in.

And when it does, self-doubt follows.

No matter how prepared you feel, something will always arise that makes you question your worth. And just like that, our old companion Imposter Syndrome shows up again…didn’t we evict her already?

There’s no manual for being in the top spot. No playbook for what you do when you’re no longer “one of the team”…so where do you turn?

The First Step: Reconnect With Your People

Here’s what I teach my clients (and I do it myself):

Observe. Ask Questions. Listen. Affirm. Know Your People

These may sound like kindergarten lessons, but they’re leadership gold:

Observe everything. What’s working? What needs work?

Ask questions. I’ve been called “The Question Queen” for a reason. Curiosity builds connection.

Listen. Not just to the answers you expect, but to what’s really being said.

Affirm what you hear. Reflect it back. Show that you understand and that you care.

Know your people. What drives them? What excites them? What would they change?

These aren’t just warm fuzzies. They’re your foundation for sustainable leadership…and authentic connection.

The Second Step: Find Your People

That’s where the concept of Masterminds comes in.

A mastermind, or a strategic RoundTable, is a trusted circle of peers who challenge, support and grow together. It’s not a networking group or a coaching session. It’s a space for women leaders to be real, visible, bold and heard.

In a mastermind, you can share an insight without someone rolling their eyes. You can celebrate a win without being accused of bragging. You can ask questions, voice doubts and test ideas without apology.

Let me be clear…Talking about your accomplishments isn’t bragging. It’s letting people know what you’ve earned. Bragging is when you tear others down to build  yourself up. Know the difference and never apologize for your brilliance.  

I know there is some confusion about why Masterminds work. Let me break it down for you:

  1. They offer strategic peer-to-peer growth-not surface-level networking.
  2. They connect you with women who understand your challenges, pace and pressure.
  3. They accelerate breakthroughs through accountability, clarity and shared wisdom.
  4. They are curated intentionally because chemistry matters
  5. They create a ripple effect: stronger confidence, deeper relationships and greater impact.

The truth is…you don’t need more people. You need the right ones. Being in the C-suite is a milestone. But it’s also the beginning of your next great chapter…one that shouldn’t be navigated alone.

Asking for support is not weakness. It’s wisdom.

Leadership can be joyful. It can also be heavy. Masterminds are where that weight becomes shared, and that journey becomes lighter.

Women who lead with intention reflect often. They take responsibility for their outcomes. And they don’t play it safe. They trust their gut. They act with purpose. And they surround themselves with others who do the same.

You don’t need more people in your corner. You need the right people.

A mastermind is where transformation happens.

The time is now.

More importantly, your time is now.

Empower Your Journey with Judy Hoberman

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