I’m Matteo Cassese. For most of my life I believed I was my performance, and it nearly cost me the business.
Boardrooms are full of people performing confidence. You can feel it. Organizations do not lose their edge because of bad strategy. They lose it because their leaders are performing confidence they do not feel, telling stories they do not believe, and navigating disruption with maps that stopped working years ago.
The answer to imposter syndrome is not more knowledge. But better communication. Confidence isn’t something you perform. It’s what’s left when you stop performing. Trying to be confident is the perfect way to feel insecure. Confidence isn’t something you have. It’s something you do.
Being smart and working hard got you this far. Now you’re stuck. Your analytical mind brought you this far. Now it’s the thing standing in your way.
The advice that makes it worse
If you want to get rid of imposter syndrome, read this. You can’t fake it. The whole world will tune out if they think you’re a phony.
Stop piling knowledge in the hopes that more facts will turn you into a more confident person. Start learning different skills. You won’t figure it out by doing more research or analyzing more options. You won’t figure it out by reading guru’s books or best practices. Not through any new technology or study. This is not an engineering problem for you to solve. It doesn’t work like that, and you know it.
You are the only one that knows how much you know. We can only hear how you talk. It’s not about what you know. It’s about what you can share. Deep down you will always know what you don’t know.
Think more research makes you a pro? Think again. If you can’t simplify, you know nothing.
What’s actually happening
For most of my life, I believed that I was my performance. I measured myself by my output, like a machine. From the outside, it looked perfect. Inside, I was exhausted. Always not good enough.
Your personal brand is not what you say about yourself. It is the residue of every story you have ever told, every promise you have kept, every moment where you showed up as yourself instead of performing a version of yourself. Most storytelling coaches help you perform better. I help you be.
I realized that trying to be confident is the perfect way to feel insecure. True confidence comes from showing up as yourself. Being willing to be vulnerable instead of hiding. Jumping head first into conflict instead of avoiding it.
Because I know a fundamental truth: if you are not ready to deal with your own vulnerability, you will never benefit from any knowledge imparted from the outside. Theory is useless without the courage to act.
Why founders get it worse than employees
It took me 34 years to give myself permission to start inventing my job. Even as I left corporate and started my own business, the old habit of asking for permission followed me. I had to burn this business to the ground twice to unlearn it.
You’re lonely at work. After your more formative years, you stop seeking mentors, helpers, and coaches. You’ve decided to rely on yourself and nobody else.
Founders must introspect more than everybody else. They must look inside, understand their biases, figure out their blockers, explore their mindset, realize their potential by understanding that the mind is full of layers and functions using symbols and archetypes. Now that everyone has the same AI tools, what really distinguishes a founder from the other is how uniquely they know themselves, and therefore how uniquely they know how to communicate.
It’s not consulting: no one’s handing you a playbook. And we’re not here to fix you. It’s a safe space where you can finally stop performing and start listening to what you actually know. Your chaos is the curriculum. It’s not a technical problem. It’s a problem of meaning.
A consultant looks at your business and tells you what to fix. I look at you and ask what’s in the way.
The fear underneath
Imposter syndrome is a real nightmare. I’m not enough. I don’t even know what I’m doing.
Nobody innovates with high confidence. We don’t have any confidence about the future.
When I was 16, I grabbed a microphone in front of 500 teenagers to lead a protest. Did I have experience? No. Did I have natural confidence? No. I was terrified.
Most organizations can’t tell the difference between vulnerable, confident, and overconfident leaders. They end up promoting the wrong ones and creating a toxic culture.
What actually helps
I stopped putting my confidence in outcomes. Started betting on myself instead.
Confidence, if you take it right, won’t be something that you have. It won’t be something that people give to you. It won’t come from experience. It’s going to be a decision that you make.
I stopped copying other people’s playbooks. Started writing my own. What I found on the other side was that confidence doesn’t come from a better playbook. It comes from knowing who you are. So drop the how-to and even the what, and start asking who.
I take people into uncomfortable places and make them feel safe there. Because here’s what I’ve learned after thousands of coaching hours: the answers you’re searching for already exist within you. They’re just hiding in places you don’t want to look.
Ask yourself:
- Do you feel like a fraud, or do you feel like you’re maintaining something?
- Does discomfort spike when you perform, or stop?
- Has more proof ever actually helped you?
- Do you know what your own job is?
Common questions about founder imposter syndrome
Is imposter syndrome normal for founders?
Imposter syndrome is a real nightmare. “How hard can it be?” and “I feel like such a fraud” are two sides of the same coin. Boardrooms are full of people performing confidence. You can feel it. Nobody innovates with high confidence. We don’t have any confidence about the future.
Does imposter syndrome ever go away?
You can be an expert inside. And never feel like one. You can be an expert outside. And enjoy the validation of your peers. Deep down you will always know what you don’t know. Confidence isn’t something you have. It’s something you do.
Why does “fake it till you make it” make it worse?
The answer to imposter syndrome is not more knowledge. You can’t fake it. The whole world will tune out if they think you’re a phony. Stop piling knowledge in the hopes that more facts will turn you into a more confident person. Trying to be confident is the perfect way to feel insecure.
How is founder imposter syndrome different from an employee’s?
It took me 34 years to give myself permission to start inventing my job. You’re lonely at work. It’s not consulting: no one’s handing you a playbook. Your chaos is the curriculum. A consultant looks at your business and tells you what to fix. I look at you and ask what’s in the way.
What actually helps with imposter syndrome?
Confidence, if you take it right, won’t be something that you have. It won’t be something that people give to you. It won’t come from experience. It’s going to be a decision that you make. Clarity. Not the kind you get from a strategy deck, the kind you feel in your bones.
Someone less talented than you is growing faster and charging more. Business problems are almost always identity problems in disguise. I’m here for the ones ready to stop treating the symptom. Give one hour to your deeper self. Start with the free Leverage assessment.
What you should do next
Discover what’s holding you back from the inside out. Understand where you naturally have leverage and where it eludes you.
Take the free founder mindset course.
If you want to talk it through with me, my coaching for founders starts with a first session at EUR 490, fully refundable.
About Matteo Cassese
Business coach, keynote speaker, and mythmaker, Matteo helps leaders thrive in chaos and conflict. Twenty years across tech, film and consulting, seven of them at Warner Bros., founding-team at Netflix Italy, and advisory work for Sony, LinkedIn and Heineken. Berlin based. His unique perspective as a queer nerd passionate about mythology and technology creates a safe space for leaders to be vulnerable and reach their full potential. Read more about Matteo.
