Episode #480
The Loneliness of Success: What Nobody Tells You
50% of CEOs feel lonely, and the more successful you become, the more isolated you feel. This isn't weakness—it's a real challenge that requires deliberate action to solve.
8 minUpdated:

The Loneliness of Success: What Nobody Tells You
0:000:00
Audio in Dutch
Key takeaways
- 50% of CEOs experience loneliness that increases with success—it's real and normal at this level
- Three reasons for leadership loneliness: your world shrinks as problems become more unique, leadership roles distance you from authenticity, and greater success creates greater vulnerability
- Your partner isn't the problem, but they're also not the right sparring partner for business challenges
- Attack loneliness like a business case: find equals, secure proper sparring partners, and embrace vulnerability as power
- True vulnerability is fearing others will discover your true self; true strength is being completely open from a place of confidence
Timestamps
00:00:00Introduction: The Hidden Reality of CEO Loneliness
00:01:15Peter's Story: Success Without Understanding
00:02:45Three Reasons Why Success Creates Loneliness
00:03:00Reason 1: Your World Shrinks as You Grow
00:04:20Reason 2: Leadership Role Creates Distance from Authenticity
00:05:30Reason 3: Greater Success Equals Greater Vulnerability
00:06:45Three Solutions to Combat Leadership Loneliness
00:07:00Solution 1: Find Your Equals
00:07:45Solution 2: Find the Right Sparring Partner
Show notes
Success often comes with an unexpected cost: profound loneliness. In this episode, we explore why 50% of CEOs experience deep isolation, and how this feeling intensifies with greater achievement. Through the story of 'Peter'—an entrepreneur who has everything on paper but feels fundamentally misunderstood—we uncover three critical reasons why success breeds loneliness: your world shrinks as you grow, leadership requires you to play a strong role that distances you from authenticity, and greater success makes you more vulnerable. More importantly, we provide three actionable solutions: finding peers at your level, securing the right sparring partner who isn't impressed by your success, and embracing vulnerability as strength rather than weakness. This isn't about complaining—it's about acknowledging a real leadership challenge and taking concrete steps to address it.
Topics
CEO lonelinessleadership isolationentrepreneurial successexecutive lonelinessleadership vulnerabilitybusiness leadership challengesentrepreneur mental healthsuccess and isolationleadership authenticityexecutive coaching
Full transcript
View full transcript
50 percent of CEOs feel lonely. And it's such that the more successful you become, the lonelier you become. And not just sitting alone on the couch once in a while. No, really deeply fundamentally feeling, feeling misunderstood. And this is the thing, you don't see that on Instagram either or it doesn't come up in masterminds.
It gets hidden away. But today I'm going to talk about it, because you're not crazy. It's really there. And the more success you achieve, the worse that feeling can play out. Last week I spoke with an entrepreneur.
I'll call him Peter. And Peter has everything on paper. A very nice house, detached. His dream car he told me, beautiful wife, a daughter. And he says yes, I love my wife too, but she doesn't get me.
She just doesn't understand what I'm dealing with. I told her that I was experiencing too much stress. And what did she say? Yes, then you should just work a little less. And his friends he told me, yeah, they just think it's cool that he has it all together.
But they don't see that stress and that fear. And he said, my team, I want to shield them. So all the worries, all the fear around every decision I make, I carry that myself and nobody around me understands it. And this is the loneliness of success. And it's really more real than you think.
Not to complain or to whine. It's important, you as a leader know, that feeling matters too. So naming the feeling of loneliness is just fine, is actually necessary to acknowledge it. And why does this happen? There are 3 reasons.
Reason number 1 is very logical. The more you grow, the smaller your world becomes. That sounds crazy, I said it before. But the moment you're turning over 300k for example, then you can easily find 10 others who are doing that too. You can easily spar with them about the same things.
If you've already grown further then you'll actually see in retrospect that it was already difficult then. But it matches. But do you grow to 1 or 2 million revenue per year? Or to 10 million? Or even further?
The world gets smaller and smaller. Your problems are of a greater magnitude than someone who turns over a hundred thousand per year. So to be able to talk about that with people, then you also just have to find people who experience those same problems of that magnitude. Because that connects and that's difficult. And 2, the role you play as a leader, that requires you to be strong.
Of course it's important to also show emotions and use them at the right moment or not. But it does require from you that you carry the business and the team. That you radiate confidence, because then your team can operate best. But that also causes, and I spoke with an entrepreneur about this recently, that you start playing a certain role in your own company that you can't get out of anymore. You also see this a lot with actors.
They play a role in such a way that they actually can't really snap out of it anymore. And as a leader this entrepreneur said, I just don't even know anymore what it's like to be really honest. And 3, more success also makes you more vulnerable. Because the bigger your success, the more there is that can break. You have the responsibility to carry for more success, but also for a bigger team.
So your choices affect many more people. Not only your team, but also cash flows, your customers. And you're responsible for it. And that makes you vulnerable. And also the question what happens if people on your team or customers find out that you don't know everything either, that you're also insecure sometimes.
And more status doesn't solve this. It only causes the gap to grow bigger and bigger. So you're going to keep more inside and maybe even slow yourself down in your success. What can you do about it? How can you solve this loneliness?
There are 3 things that are really all 3 equally important. The first sounds simple, but you really have to approach this like you would approach a business case. So really as that entrepreneur that you are just tackle it. Namely number 1, find equals. Actually go looking for that entrepreneur who can level with you at your level.
And yes, that takes some time. And many entrepreneurs also say I don't have time for that. But honestly, if you don't do it, it will cost you more than the time it takes you. You understand that too. So find those equals.
And 2, find a sparring partner. Someone who just isn't impressed. That the moment when you talk about a deal of 10 million or 100 million that they can just keep up with you. That they engage in conversation about it and treat you as an equal sparring partner. Very valuable to really make the right choice in that.
Because the moment when you sit at a table or get into a conversation with someone who becomes impressed by your success, then you really end up in a different pitfall. You really want to avoid that at all costs. And 3, realize that vulnerability isn't weakness at all. I always say when you are completely open, it actually comes across as very powerful. Whereas if you're afraid that people will discover your true nature, then you're vulnerable.
But that only has to do with how you look at it yourself. Of course it's not smart to show insecurity towards your team. You can perfectly radiate confidence, but the moment when you also just don't know something and you express that from confidence. I don't know that right now either and I'm going to work on it, that actually feels extremely powerful and strong. And that ensures that you stay much closer to yourself.
And that strength, that's where you draw confidence from yourself. And that's also a reason why many entrepreneurs feel lonely, because they are alienating themselves from themselves. Whereas if you just really stay with yourself and from there communicate openly and honestly with others, that you say, hey, I can be affected and I keep standing instead of no, I must not be affected, because that is actual vulnerability. Then you feel good in yourself and then you are extremely powerful, but you're also connected with yourself, which means that loneliness will occur much less. And if you recognize this, that feeling of loneliness, then tackle it as a business case and really do something about it.
Realize, you're not crazy, it's normal to experience loneliness at this level. That's completely logical. And it's also true as happened with Peter your partner is not the problem, but your partner is also not the right sparring partner. So get to work with this, attack it as a business case, think about the 3 ways to solve it and know that you are definitely not the only one and that there are therefore definitely others with whom you can share this. It's important that you take that first step.
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This transcript has been translated from Dutch.
Frequently asked questions
Why do successful CEOs feel more lonely as they grow?
As you achieve greater success, your world paradoxically becomes smaller. Problems at the million-dollar level are fundamentally different from those at the hundred-thousand level, making it harder to find peers who truly understand your challenges. Additionally, the leadership role requires projecting strength and confidence, which can distance you from your authentic self and create isolation even when surrounded by people.
Is feeling lonely as a leader a sign of weakness?
Absolutely not. Fifty percent of CEOs experience this loneliness, and it's a natural consequence of the unique position you hold. The isolation stems from having responsibilities and challenges that few others can relate to, not from any personal failing. Acknowledging this feeling is actually the first step toward addressing it effectively and doesn't diminish your leadership capability.
How can I find the right sparring partner or peers at my level?
Treat this like a business case and actively invest time in finding equals. Look for entrepreneurs operating at your revenue level or beyond who can discuss seven or eight-figure deals without being impressed. The key is finding someone who treats you as an equal sparring partner, not someone who's awed by your success. While this takes time, the cost of not doing it far exceeds the investment required.
Can I be vulnerable with my team without losing their confidence?
Yes, but it requires reframing vulnerability. True vulnerability isn't admitting uncertainty from a place of weakness—it's being open and honest from a position of confidence. When you tell your team 'I don't know this yet, and I'm going to figure it out,' you project strength and authenticity. The real weakness is fearing that others will discover your true self, which distances you from your authentic power.
Why isn't my partner the right person to discuss business challenges with?
Your partner isn't the problem, but they're typically not equipped to be your business sparring partner. As illustrated by Peter's experience, when he shared his stress with his wife, her response was 'just work less'—well-intentioned but not addressing the deeper challenges. Partners can provide emotional support, but they usually lack the context of operating at your business level to truly understand the unique pressures and decisions you face daily.
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