What If They Realize I'm in Over My Head?

Here's what most founders won't admit out loud:

They spend an embarrassing amount of time crafting the perfect investor update. Rehearsing answers to every possible board question. Curating their LinkedIn presence to project unwavering confidence.

All to avoid one terrifying moment – someone discovering they don't actually have all the answers.

I see this pattern constantly. Brilliant founders driving themselves into the ground, not from the actual work of building a company, but from the exhausting performance of pretending they know exactly what they're doing every minute of every day.

But your team can sense the pretense. And it's eroding the trust you're trying so hard to protect.

The Problem Isn't Being In Over Your Head

Most founders think the problem is that they're in over their head. But being in over your head is literally the job description. You're doing things you've never done before, facing challenges that have no playbook, making decisions without complete information.

If you have any kind of ambition, you are, by definition, an imposter. You're attempting things today you haven't mastered yet.

The real trap is thinking you shouldn't be in over your head. That thinking you need to have all the answers is your job as CEO.

That belief creates a vicious cycle: You don't know what to do > You think you should know > You pretend you know > Your team senses the pretense > Trust erodes > You feel even more pressure to perform.

Meanwhile, the intelligence and perspective of your entire team sits unused because you've signaled there's no space for collaborative problem-solving.

Where "I Should Know This" Comes From

This pressure to have all the answers usually traces back to school. We learned early that getting the right answers brought praise. Getting them wrong brought shame.

But we forget something crucial: In school, they taught us the material before the test. We weren't expected to know it from thin air.

Yet as founders, we somehow believe we should know answers to problems we've literally never encountered before. Problems that may not even have known solutions yet.

The deeper issue? Many of us unconsciously sourced our sense of worthiness from getting those good grades. From being the smart one. From having the answers.

That conditioning runs deep. When you believe your worthiness depends on knowing everything, the stakes of admitting "I don't know" feel existential.

But here's what actually creates confidence: being yourself and seeing that it's enough.

Not projecting an image of having it all figured out. Not putting on a performance of certainty you don't feel. Just showing up authentically – including with your confusion, your questions, your uncertainty – and discovering that people actually respect you more for it.

But What If This Image Gives Me Security?

I know what you're thinking: "Okay, Dave, but if I start sharing the truth with everyone, it feels like all my security is just going to crumble. Everything I've worked towards and built, they'll see I shouldn't even be here."

This fear makes sense. When you believe your image is key to your security, dropping it feels dangerous. Like investors will regret backing you. Team members will quit. Everything will fall apart.

But maintaining that image is exhausting you more than the actual work of building your company.

It's a really hard way to live. The constant pretending. The performance. This is probably some of what leads to burnout in founders – not the hours, but the exhaustion of trying to be something you're not all the time.

And if you think you need to project a certain image to be loved or approved of, even if it works (even if investors adore your image and your team respects it) you still don't feel like you're loved or respected for who you actually are.

So what have you really gained?

What feels safer than knowing you can just be yourself? If you feel like you have to pretend in order to feel safe, that's not safety at all.

Here's something else to consider: the feeling of insecurity is really a function of not being present. The mind lives in the past and future, constantly making up stories about what might happen. But if you get fully present and look around – right now, in this actual moment – can you find any lack of safety?

In the present moment, you're safe.

And when is it not the present moment? Never.

So in every present moment, you're safe.

How to Actually Break This Pattern

So how do you actually move out of this pattern? Here's the process:

1. Identify The Pattern: Notice it. Bring it to consciousness. "Oh yeah, I'm constantly trying to uphold this image to feel safe, to win approval, to feel worthy."

Until you make the unconscious conscious, it will direct your life and you'll call it fate.

2. Look At What The Pattern Is Designed To Give You: What's the intended positive outcome? This pattern is designed to help you feel something – safe, worthy, confident, respected. Name it specifically.

3. Get Fully Present And Notice You Can Feel That Right Now: Not conceptually, but viscerally. Can you feel safe now? Can you feel worthy now? Not because of some external condition, but just by being present with yourself as you are?

When you can genuinely feel those feelings now it lightens the grip of the pattern. Because why would you go do a bunch of inauthentic things to avoid not feeling safe if you already feel safe?

4. Welcome The Feelings You've Been Avoiding: The confusion. The fear. The vulnerability. The sense of helplessness or powerlessness.

These are the feelings that pretending to have all the answers is designed to help you avoid. But here's what changes everything: feelings aren't actually painful. Resistance to feelings is painful.

When you fully allow confusion – when you welcome it instead of fighting it – it's no longer a problem. It's just what is. Same with fear. Same with the sense of not knowing.

The moment you stop resisting these feelings, you no longer need the pattern that was designed to protect you from them.

What Happens When You Do This

I've watched this transformation dozens of times. A founder finally gets exhausted enough to drop the act. They walk into a board meeting and say, "Here's what I know. Here's what I don't know. Here's what we're doing to figure it out."

And the investors... lean in. They ask better questions. They offer actual help instead of scrutiny.

Or they go to their team: "This is the challenge we're facing. I'm not clear yet on the best path forward. What are you seeing?"

And suddenly the team's intelligence gets activated. Someone proposes an angle the founder hadn't considered. The problem-solving becomes collaborative instead of hierarchical.

Here's the paradox: People are far more willing to follow a leader who admits when they don't know than one who pretends to know everything.

Because authentic leadership creates safety. And in that safety, teams do their best work.

The founders I work with who make this shift report something remarkable: They feel lighter. More creative. More connected to their teams. And counterintuitively, more confident – because they're no longer exhausting themselves maintaining a facade.

The Leader Your Team Is Waiting For

Your job as CEO isn't to have all the answers. It's to ask powerful questions. To create the conditions where the best answers can emerge. To lead your team in discovering what none of you know yet.

The confidence you're looking for doesn't come from finally having all the answers. It comes from being willing to show up as yourself (uncertainty included) and trusting that's enough.

Because here's what I've learned after years of this work: The version of you pretending to have it all figured out is far less compelling than the version of you authentically navigating the unknown.

Your team already knows you don't have all the answers. They're just waiting for you to stop pretending so they can actually help.

With love,

- Dave Kashen

P.S. The next time you catch yourself rehearsing the perfect answer to avoid looking uncertain, try this instead: Get present, feel the fear of not knowing, and then simply tell the truth. You'll be surprised how much respect that actually earns you.