You know what’s funny? When I quit my 16 years tech career to start on a totally new journey – to guide and work with the biggest changemakers & leaders on this planet, I thought the hard part was getting there.
Landing the big CEO clients. Hitting the numbers and building a reputation. Being known for bringing people together and helping them go beyond even their own wildest dreams – both personally and professionally.
Turns out, I had no idea.
The real challenges of success? They’re the ones nobody talks about at conferences. They’re not in the Harvard Business Review case studies. They’re the 3 am thoughts, the conversations you can’t have with anyone, the slowly growing sense that you’re living someone else’s life while everyone congratulates you on yours.
I’ve sat across from people who look like they have it all figured out—the title, the impact, the respect—and watched them break down because they finally found someone who wouldn’t judge them for admitting: “I don’t know if I can keep doing this.”
Let me walk you through what success actually looks like from the inside. Not the Instagram version. The real one.
When You Become a Role, Not a Person
I’ll never forget this CEO I worked with—let’s call him Raj. Built an incredible company from scratch. 300 employees. Lives changed. Real impact. And he came to me completely burned out.
“I can’t remember the last time someone asked me how I actually am,” he said. “Not how the company’s doing. Not how the quarter looks. Just… me.”
Here’s what happens: You achieve something significant, and suddenly you’re not allowed to be human anymore. You’re “The CEO.” You’re “The Founder.” You become a symbol, an inspiration, a beacon—and all of that is beautiful except you’re still just a person who gets scared and tired and confused.
Raj told me about going to a friend’s birthday party—people he’d known for years—and spending the whole evening answering questions about his company. Nobody asked about him as a father or about his painting hobby. Nobody noticed he’d lost weight from stress. The entire conversation was about his role, never about him.
This is the identity prison. You get trapped in the character you’ve created, and the bars are made of other people’s expectations and your own success.
I see this constantly. A leader can’t admit they’re struggling with a decision because “leaders are decisive.” They can’t show uncertainty because “leaders inspire confidence.” They can’t have a rough day because everyone’s watching.
The exhausting part? You start believing it too. You internalize that you should always have answers. You should never waver. And slowly, you lose touch with the actual human underneath—the one who’s allowed to not know, to be tired, to need support.
The Loneliness Nobody Warns You About
Let me tell you about Priya. Brilliant executive. Everyone wanted to work with her. Her calendar was packed 7am to 8pm. And she was profoundly, achingly lonely.
“I’m surrounded by people all day,” she told me. “But I can’t actually talk to any of them.”
This is the cruel irony of success: The higher you go, the fewer people you can be real with.
Your team needs you to be strong, so you can’t share your doubts. Your board wants confidence, so you can’t express fear. Your old friends feel distant because your life looks so different now. Your new “friends” might want access more than connection.
I remember Priya describing a moment when she was in a meeting with her executive team, discussing a major strategic pivot. She was terrified it was the wrong call. Her stomach was in knots. But everyone was looking at her for certainty, so she projected it. The decision went through. It worked out. And she felt more isolated than ever because nobody knew how scared she’d been.
Who do you talk to when you can’t talk to anyone?
This is why our work together mattered so much. Not because I had magic answers, but because I was someone she could actually be honest with. Someone who didn’t need her to be anything other than human. Someone who could handle her uncertainty without panicking or judging.
I remember one conversation where she spoke for 55 minutes of the 60-minute session. Internally, I was almost blaming myself because I didn’t get a chance to coach her or solve her problems. I was wondering if I added value because the only thing I did was I listened to her. At the end of the session, she said, “This was the best conversation I have had in a long time. Nobody has listened so deeply to me.” This feedback helped me understand the other side of success.
The loneliness of success isn’t about being alone. It’s about being surrounded by people and still feeling like nobody sees you.
When Success Stops Feeling Like Success
Here’s something wild: I’ve worked with people who hit goals they’d been chasing for years—goals that would change their lives—and they felt… nothing. Or worse, they felt empty.
There was this founder I coached who finally closed his Series B. Eight million dollars. Validation from top-tier investors. Everything he’d been working toward for three years.
He called me the next day. “Is this it?” he asked. “I thought I’d feel different.”
This is the moving goalpost syndrome, and it’s brutal. You think hitting the target will bring peace, satisfaction, that sense of “I made it.” Instead, it brings relief for about 48 seconds, and then your brain is already moving to the next thing.
The Series B becomes “we need a Series C.” The VP title becomes “I need to be in the C-suite.” The successful exit becomes “but what’s my next thing?”
You become addicted to the chase, to the achievement, to the validation—but you never actually feel satisfied. Success becomes this treadmill you can’t get off because stopping means facing the emptiness you’ve been running from.
I see this with executives who work 80-hour weeks not because they have to, but because they don’t know who they are without the work. The hustle became their identity. The achievement became their drug. And now they’re trapped in a cycle that’s slowly killing them but they can’t imagine life without it.
The Weight of Other People’s Lives
At 2am one night, I got a text from a client—a CEO of a mid-sized company. Just two words: “Can’t sleep.”
I called him first thing the next morning. He’d been lying awake thinking about a restructuring decision. Twenty people would lose their jobs. Twenty families. Kids. Mortgages. Dreams.
“I know it’s the right business decision,” he said. “The numbers are clear. But these are real people. How do you sleep when you’re making choices that impact lives?”
This is something most people never consider about success and leadership: Every decision carries weight that goes far beyond you.
You’re not just responsible for results. You’re responsible for people’s livelihoods, their sense of security, sometimes their entire identity if they’ve wrapped it up in their job. One wrong strategic call and you’re not just missing a target—you’re affecting dozens or hundreds of lives.
I’ve seen this weight crush people. The executive who can’t stop thinking about the single mom on their team who’s about to be laid off. The founder who feels guilty about every 5-star hotel stay because their employees can’t afford one. The leader who lies awake calculating how many people they’re affecting with each decision.
The privilege of impact comes with the crushing burden of consequence. And you carry that alone because who else can understand it?
When You Don’t Know Which Version of You Is Real
I worked with a leader once—a woman who’d built an incredible reputation in her industry. Confident. Inspiring. The person everyone wanted to be.
In our third session together, she said something that broke my heart: “I’ve been performing for so long, I don’t remember what I actually think or feel about anything. I don’t know who I am.”
She’d spent years crafting the right image. Saying the right things. Showing up the right way. And somewhere along the line, the performance became the reality. Or rather, she lost track of which was which.
This is the authenticity gap. The distance between who you are and who you show up as. And it grows every time you:
- Project confidence you don’t feel in a meeting
- Give an inspiring speech when you’re terrified inside
- Act like you have it together when you’re falling apart
- Smile and say “everything’s great” when it’s not
The gap gets wider and wider until you feel like a fraud in your own life.
I see this especially with introverts who’ve learned to perform extroversion. With people from cultures where showing vulnerability is seen as weakness. With anyone who’s had to “fake it till you make it” for so long that they forgot there’s a real person underneath the performance.
The work we do together often starts with simply creating space to let the real person emerge. No performance. No image management. Just “what’s actually true for you right now?”
When Everyone Wants Something From You
“I don’t know who actually likes me anymore,” a client told me once. He’d just sold his company for a stupid amount of money, and suddenly he had more “friends” than ever.
This is the trust deficit. When you’re successful, every relationship gets complicated. Is this person genuine or do they want funding? Want a job? Want to be associated with your success? Want to network through you?
You start filtering every interaction through suspicion. It’s not paranoia—you’ve been burned. The person who seemed so supportive suddenly had an agenda. The friendship that felt real turned out to be transactional.
I’ve watched this make people incredibly isolated. They want connection but they can’t trust it. They want friendship but they can’t tell if it’s real. And the sad part? Sometimes they’re right to be suspicious. Success attracts people who are more interested in what you can do for them than who you actually are.
This is why finding people who knew you before, who don’t need anything from you, becomes so valuable. Or working with someone like me, where the relationship is clear and boundaried and there’s no hidden agenda.
When You Have Everything Except Time
The most painful irony of success: You finally have resources but no time to use them.
You can afford the vacation but can’t take it. You can hire help but you’re too busy to let them help. You want to be present with your family but you’re always mentally somewhere else.
I remember this executive—father of three—who realized he’d missed every single one of his daughter’s soccer games that season. He could afford front-row tickets to anything. But he couldn’t afford the three hours on a Saturday afternoon.
Success promised freedom. Instead, it delivered a different cage—one made of opportunities you can’t say no to, obligations you can’t drop, expectations you can’t ignore.
“I thought making it would mean I could finally relax,” he told me. “But I’m more trapped than ever.”
The Imposter in the Room
Here’s the wildest part: The more successful people become, often the more like an imposter they feel.
You’d think it would be the opposite. You’d think results would build confidence. But what actually happens is this: The stakes get higher, the spotlight gets brighter, and that voice in your head gets louder: “When are they going to figure out I’m making this up?”
I worked with a woman who’d been promoted to SVP. Huge company. Incredible opportunity. And she was terrified.
“Everyone else seems to know what they’re doing,” she said. “I’m just figuring it out as I go.”
The truth I shared with her? Everyone is figuring it out as they go. But at higher levels, you’re expected to hide it better.
The imposter complex doesn’t go away with success. It just gets more sophisticated. More subtle. More isolating because you think you’re the only one who feels this way.
What Actually Helps
After years of sitting with people going through all of this, here’s what I’ve learned: The antidote to these challenges isn’t working harder or achieving more. It’s finding people and spaces where you can be fully human.
Where you can admit you’re scared and it doesn’t shake anyone’s confidence in you.
Where you can say “I don’t know” and it’s not a crisis.
Where you can drop the performance and just be yourself, whatever that looks like today.
This is why people come to me. Not because I have all the answers (I definitely don’t), but because I can hold space for the full reality of their experience. The fear and the confidence. The doubt and the vision. The exhaustion and the commitment. My promise to them is that I will never judge them (even when feedback is very honest and direct) and they can always count on me – for the rest of their lives.
They come with their lights dim—frustrated, stuck, low on energy. And through our work together, something shifts. Not because I fix them (they’re not broken), but because they finally have space to be honest. To reconnect with themselves. To remember who they are underneath all the roles and expectations.
They leave empowered, confident, ready—not because the challenges went away, but because they’re no longer carrying them alone.
(All names have been changed and details in this article have been anonymised)
The Real Conversation
If you’re reading this and recognizing yourself, know this: What you’re experiencing is real. It’s valid. And you’re not alone in it, even though it feels like you are.
The challenges don’t get easier with success—they just get more invisible and more isolating. And that’s exactly why finding someone who can see the real you, who won’t need you to be anything other than human, becomes absolutely critical.
There are moments in every leader’s life when they need someone they know they can count on. Someone who gets it.
Maybe that’s why you’re still reading this.
If any of this resonated, send me a note. Better yet, record a voice note or a video msg. Let yourself be seen.
Because here’s what I know for sure: You don’t have to carry all of this alone. And on the other side of being real about what’s actually happening? That’s where you let the burden of leadership go and acknowledge the privilege and grace of leadership. You deserve it.