The Lonely CEO

Someone said - it’s lonely at the top. Turns out, they weren’t kidding. Sure, being a CEO comes with the perks—power, influence, the ability to shape a company’s future. But it also comes with a level of solitude that’s tough to explain until you’ve lived it.

The Weight of Leadership

Being a CEO isn’t just about hitting growth targets and making bold moves. It’s about carrying the weight of an entire organization. Every decision—good, bad, or somewhere in between—lands squarely on your shoulders. And while you might have a great leadership team, the final call? That’s all you.

1. You’re No Longer “One of the Team”

Remember when you were part of the team, cracking jokes, closing the bar, sharing frustrations, and feeling like you truly belonged? That dynamic shifts the second you step into the CEO role. You’re no longer just a colleague—you’re the boss. And that changes everything.

You used to have a support system in your peers, but now? Employees filter what they say around you. Decisions you make—big or small—carry weight in ways they never did before. Even your closest colleagues may hesitate before giving you unfiltered feedback. It’s a weird, unsettling shift. I try to be myself—self-deprecating and approachable—but it’s a balancing act. You want to instill confidence while remaining accessible. No one wants to work for a joke.

2. Who Actually Gets It?

Here’s the hard truth: the higher you climb, the lonelier it gets. You can’t vent to employees about boardroom pressure. You can’t share every uncertainty with investors. And even among peers, opening up can feel risky.

I’ve been lucky to find someone I can share almost everything with, someone who gives me unvarnished feedback. That person happens to be on our board. He’s a straight talker, which helps immensely. But I can’t share everything - see below.

3. Decisions That Keep You Up at Night

Being a CEO means making calls that impact people’s livelihoods, the company’s future, and your own sanity. Layoffs, restructuring, major pivots—none of it comes with a playbook. And no matter how many advisors you have, in the end, you’re the one who signs off on the tough choices.

One mistake I’ve made? Talking about a singular topic too much with the board. They say don’t bring up a problem unless you’ve got an answer—well, mistake made. I was socializing to develop an answer, but the board isn’t the right place to do that. Lesson learned.

4. Even Winning Can Feel Lonely

Here’s the ironic part—success doesn’t always make it better. While your team is celebrating a big win, you’re already thinking about the next challenge. You’ve got that gap to make up, those bonuses to pay out. There’s no finish line, just another goal to chase, another crisis to manage. That constant forward motion? It can be exhausting. I have plans to get ahead of it, but I need time to make them happen.

Connection Over Isolation

But loneliness doesn’t have to be inevitable. Some of the most successful CEOs fight isolation by staying connected to the people who matter most: employees, customers, and peers.

How I Stay Connected

To bridge the gap, one of the first things I’ve committed to hosting is virtual and in-person coffee chats with every employee. No agenda, no pressure—just real conversations. These sessions give me unfiltered insight into the company while helping employees see me as more than just “the CEO.” It feels like a good way to break down barriers and make myself approachable.

According to a Forbes article on customer-centric CEOs, leaders like Brian Chesky (Airbnb) and Satya Nadella (Microsoft) prioritize direct engagement with customers and employees. Why? Because staying involved at the ground level prevents CEOs from becoming detached in their own bubble. I love this as well! I get more energy talking to customers and prospects than any other way.

Ways to stay engaged:

• Work the Front Lines: Like the CEOs in the Forbes article, spend time with customers, join sales calls, and engage in real conversations.
• Be Accessible to Employees: Hold open office hours and company-wide check-ins to keep communication flowing.
• Listen More Than You Speak: Create an environment where people feel comfortable giving you unfiltered feedback.
• Find Your Peer Network: Join CEO roundtables or executive groups to discuss challenges without posturing. Still Looking.

External Relationships

Loneliness isn’t just an internal struggle—it also extends to external relationships. Many CEOs spend a significant amount of time networking, negotiating deals, and forging strategic partnerships. But what happens after the handshake?

According to Harvard Business Review, one of the biggest mistakes CEOs make is failing to nurture relationships post-deal. Partnerships require ongoing engagement, yet many executives move on too quickly, leaving opportunities—and critical alliances—to wither. This part is a bit easier for me as our projects happen over time where we help our customers all the way through to the final solution with checkins, etc.

How to Avoid Relationship Decay

• Follow Up With Intent: Bring new ideas, updates, or value to every check-in.
• Treat Partnerships Like Customers: Relationships require continuous effort, just like customer retention.
• Turn Transactions Into Collaborations: Find ways to work together beyond the initial deal to build lasting rapport.

Don’t Go It Alone

Yes, leadership is isolating. Yes, the buck stops with you. But the best CEOs don’t just manage from the top—they stay engaged at every level of the company. The ones who break the cycle of loneliness are the ones who make connection a priority—whether with employees, customers, or trusted peers.

So if you’re feeling the loneliness? Step off the pedestal, roll up your sleeves, and reconnect. Because the best leaders aren’t just at the top—they’re in the trenches.

References

1. Forbes – 10 CEOs Who Work on the Front Lines

   • Examines how top CEOs stay engaged with employees and customers to prevent isolation.

2. Harvard Business Review – After the Handshake

   • Explores why CEOs struggle with maintaining strategic relationships and how to stay connected post-deal.

3. McKinsey & Company – The Mental Health Challenges of CEOs

   • Analyzes the mental health pressures of leadership and ways to manage CEO stress.

4. Stanford Business – CEO Loneliness and Decision Fatigue

   • Research on how isolation impacts CEO decision-making and leadership effectiveness.

5. The Wall Street Journal – The Emotional Burden of Leadership

   • Real-world accounts from CEOs discussing their personal experiences with leadership loneliness.

6. Fast Company – 6 Ways to Battle That Lonely CEO Feeling

   • Practical advice for CEOs to combat loneliness, including joining peer networks and staying visible.

7. You Are Not Alone In The Journey: The Isolation Of Millions Of CEOs Facing Growth Pains

   • Published: February 28, 2024. Discusses the prevalence of loneliness among CEOs, noting that 30% of executives report feeling lonely frequently.

8. Heavy Is the Head that Wears the Crown: The State of CEO Mental Health

9. Is There Mental Health Support For Your CEOs?

10. Transcript: Why being a CEO is so lonely (and how to fix that)

• Published: January 2025. Features insights from former CEOs discussing the inherent isolation at the top and strategies to mitigate loneliness through self-awareness, coaching, and peer networks.