The Silent Glass Ceiling – Why High Performers Get Stuck and How to Break Through
“Until you make the unconscious conscious, it will direct your life, and you will call it fate.” — Carl Jung
We talk a lot about pushing past limits. Setting goals. Hitting milestones.
But what we rarely talk about—especially in entrepreneurial or creative circles—is the ceiling we don’t know we’ve built for ourselves.
Not the kind someone else puts there.
The one we quietly accept because we’ve been doing “well enough.”
Because things look good from the outside.
Most high-performers I know—myself included—have lived in that space.
What I call the 70% Zone.
You’re motivated. Respected. Seen as successful by most.
But deep down, you know you’re holding back.
You’re not burned out. You’re not broken.
You’re just… not all in.
What’s Holding Us Back?
It’s not laziness. And it’s not a lack of discipline.
It’s usually one of two things:
We’ve gotten comfortable doing well.
We haven’t stopped to question what we’re really aiming for.
And the longer we stay in that zone—where effort is high but clarity is low—the more it starts to wear us down.
You might start asking questions like:
“Why don’t I feel more fulfilled?”
“Am I really using my best talents?”
“Is this the work I want to be known for?”
Those questions don’t come from failure. They come from a deeper knowing—one you can only hear when you stop long enough to listen.
My Experience (and the Pattern I’ve Seen)
Over the years, I’ve started and co-founded businesses in finance and real estate. And today, I consult with a wide range of business owners—some in more traditional industries, others in creative or emerging spaces.
Lately, I’ve found myself helping more independent filmmakers who are trying to navigate direct distribution—many of whom are incredibly creative but feel stuck in systems that don’t serve them. The talent is there. The ambition is there. But they’re hesitating to go all in.
And I get it. I’ve seen that same hesitation in mortgage bankers, in entrepreneurs, in executives running eight-figure companies.
They all say the same thing:
“I want to take it to the next level.”
But very few are willing to make the internal leap it takes to actually do it.
The ones who break through?
They get a little obsessive.
They’re willing to take the risk.
And they’re honest with themselves about what’s working—and what isn’t.
Let’s Talk About the Real Reason People Stay Stuck
One of the biggest culprits?
Sunk cost.
You’ve already invested years—maybe decades—into building something.
It’s brought you some level of success. It’s your identity now.
So the idea of stepping into something new, or admitting your heart’s not in it anymore? That’s terrifying.
There’s also the emotional shield a lot of people hide behind:
“If I don’t give it everything, I can always say it wasn’t my best shot.”
It protects the ego. But it keeps you under that glass ceiling.
How to Spot the Ceiling Before You Hit It
It doesn’t always look like a breakdown. Sometimes it’s subtle.
Here are three signals I see in clients who are overdue for a breakthrough:
1. Sunday-Night Dread
Not the kind that comes from overwork, but from disconnection. The sense that what you’re doing just doesn’t light you up anymore.
2. Future-Self Nausea
You picture your life ten years from now… and it’s just a more tired version of today. Not exactly the inspiring vision you hoped for.
3. Over-Justification
You keep reminding yourself how good the benefits are. How other people would kill for your job. But if you’re honest, you’ve outgrown it.
These aren’t red flags. They’re invitations.
Invitations to take a closer look at what you’re building—and who you’re becoming in the process.
How to Start Breaking the Ceiling
Here’s a framework I often walk people through when they’re on the edge of something new but afraid to jump:
✅ Reverse Timeline
Imagine your life 10 years from now if nothing changes.
What’s your day-to-day look like?
Are you proud of where you ended up?
What do you regret not doing?
Write it down. Sit with it. If it makes you feel sick—that’s useful information.
✅ Micro-Quitting
You don’t have to blow up your life. Start by walking away from the things that are clearly misaligned.
Say no to the gig that doesn’t excite you.
Turn down the project that feels like a distraction.
Carve out a few hours a week to build what you do care about.
These small moves build trust with yourself.
✅ Run the Numbers
A lot of people don’t make a leap because they’re emotionally cloudy and financially vague.
Get real about your runway.
What are your monthly expenses?
What can you cut temporarily to buy time?
How many months of freedom could you fund?
Freedom doesn’t just come from courage. It comes from preparation.
🚀 Real-World Case Studies
1. Jeremy Wilson – JPMorgan to Climbing Empire
After 29 years at JPMorgan—leading mega-mergers like Exxon-Mobil—Jeremy finally listened to that inner pull.
He’d tried winding down to a one-day week, but said,
“I really wasn't very engaged. Then I just told him: it is time for me to leave.”
He financed Lakeland Climbing Centres, launching with one site in the Lake District.
Today: 15 UK venues, nearly £10M in revenue, profit, and a community-first ethos.
He didn’t do it for prestige—he did it to live his values and bring joy to others.
2. Stephany Kirkpatrick – From Goldman Offer to FinTech Founder
Stephany was on a linear path—financial planning to a job offer at Goldman Sachs. But another door opened:
“Counter to every piece of advice… I thought about what would make me happy instead.”
She chose SoulCycle—trading prestige and pay for skill-building. She later reflected:
“Choosing SoulCycle over Goldman allowed me to do something new… It unlocked incredible career growth.”
That shift equipped her to launch Orum, now a fintech scale-up with $82M raised—and she’s just getting started.
3. Genevieve Beyleveld – Journalist to Pilates Studio Owner
Genevieve swapped newsroom deadlines for client sessions—co-founding Reforming Pilates in South Florida. Her storytelling and community focus fueled a boutique success story, with multiple studios and a loyal client base.
These people didn’t just pivot.
They made the unconscious conscious.
And they bet on themselves.
Closing Thoughts
If you’re doing well but know you’ve got more in the tank—it’s not a midlife crisis. It’s a signal.
And ignoring it won’t make it go away.
You don’t have to burn it all down.
But you do have to stop pretending that “pretty good” is your ceiling.
The next chapter of your business—or your life—might not look like the one you imagined. That doesn’t make it wrong. That makes it real.
Bring it to the surface. Name it.
Make the unconscious conscious—and choose what happens next.
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Excellent piece, Michael. So many aha moments. You made me reflect on the comfort zone, especially the sunk costs we rarely acknowledge. And the insight about how our identities can trap us in a version of life we’ve outgrown was powerful. Thoughtful, practical, and timely. 👏