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My journey through leadership’s loneliest moments

Mar 20, 2024 | Leadership, Motivation

When I’m coaching CEOs or Senior Executives, there’s one phrase that almost everyone says at the end of our first session. And it goes something like this:

“It just feels so nice to be able to talk to someone about this stuff.”

Because as leaders we carry a lot, and we don’t want to dump it on our partners, our people, or our pets. 

Let’s get real for a moment. Leadership isn’t all standing ovations and high-fives in the hallway. It’s also those 2 AM stares into the fridge, wondering if you’re the only one feeling like you’re navigating a ship through a storm without a compass. Yes, leadership can be incredibly lonely. And since we’re being honest here, I’ve had my share of those moments, those stretches of road that felt more like walking through a desert than leading a team to victory.

The Weight of Decision-Making

It hit me hard early on. The realization that every decision I made didn’t just affect me but an entire team, their families, and our collective future. It’s like carrying a backpack filled with bricks up a hill, except the bricks are decisions, and the hill never really flattens out. There were days I wished for a co-pilot, someone to share the load, to bounce ideas off, or just to say, “Hey, I think you’re doing the right thing.”

The Echo Chamber of Doubt

Doubt is a tricky companion; it loves to whisper in the quiet moments. “Did I handle that right?” “Could I have done more?” “Should I have let them go?” And when I didn’t have someone to share those with, they intensified. I found myself in an echo chamber of my own making, where the doubts grew louder, bouncing off the walls I’d put up to protect my team from my uncertainty.

Finding Solitude in the Crowd

Ironically, the loneliest moments often came when I was surrounded by people. In meetings, at company gatherings, smiling and nodding, yet feeling an ocean of distance between me and everyone else. It was as if I was standing on one shore, my team on another, and no bridge between us. I was the leader, yes, but also an island. I know I’m not the only one whose felt like this as I hear this repeated over and over again by executives we work with.

The Turning Point: Embracing Vulnerability

The game-changer for me was embracing vulnerability. It sounded counterintuitive—weren’t leaders supposed to be invincible? But the more I opened up, shared my uncertainties, and admitted I didn’t have all the answers, the less lonely leadership felt. It was as if admitting my vulnerability gave others permission to share theirs, bridging the gap I’d felt for so long.

Building Bridges, Not Walls

I learned that leadership isn’t about having a fortress around you; it’s about building bridges. I started having real conversations, not just about targets and objectives, but about fears, dreams, and the messy middle we all navigate. These conversations didn’t weaken my leadership; they fortified it with trust, respect, and a sense of shared purpose.

The Light at the End of the Tunnel

Looking back, those lonely moments were also my moments of greatest growth. They taught me resilience, empathy, and the power of genuine connection, and that I’m often not right. Leadership might be a journey you start alone, but it doesn’t have to be a lonely one. It’s about finding your tribe, your fellow travelers, and realizing that vulnerability isn’t a weakness—it’s your strongest bridge.

Climb with Us!

If you would like to surround yourself with a tribe of amazing leaders then consider joining our Natural Born Leaders Program. Think Mastermind, but way more fun. I’ll leave a link below for you in case you’d like to jump on a call to find out more about it. 

Closing Thoughts

To anyone walking through leadership’s loneliest moments, know this: you’re not alone. The road might feel deserted, but it’s lined with others who’ve walked it before and are walking it now. Don’t be afraid to reach out, to share the load, to be vulnerable, beautifully human. Because on the other side of loneliness is a community waiting to embrace you, scars and all.


There’s a better leader inside all of us.

Hi, I’m James Robbins and i’ts my life’s work to help leaders reach their highest potential. Click below to get free tools and resources to help you become the leader everyone wants to follow.

About James Robbins

James is a rare mix of management consultant, change specialist, adventurer and motivational speaker. He speaks to audiences worldwide, helping them raise their performance to match their potential. He has been helping equip and transform leaders for over 20 years.

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I hope you enjoy reading this article.

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