Do You Doubt Yourself for Experiencing Doubt?

Every hyper-successful founder I've worked with at some point has confessed essentially the same thing to me behind closed doors:

"I just don't know if I have what it takes."

Not just occasionally. But more often than they'd ever admit.

They wonder if they're smart enough. If they're making the right calls. If they can actually pull this off.

Yet here's the paradox that traps most founders: they think this doubt proves they're different from the most extraordinary entrepreneurs like Elon Musk, Sam Altman, or Brian Chesky. Those titans must have felt confident all the time, right? They must have known exactly what they were doing.

So when doubt creeps in, your mind creates a devastating story: "I must not be like them. I can't do what they did."

But it's not the doubt that's destroying you. It's your relationship to the doubt.

Because when you make experiencing doubt mean something about your worthiness, you create the most vicious cycle imaginable: you start doubting yourself for having doubt in the first place.

This is where most founders get trapped. They can't tell the difference between doubt that serves them and doubt that sabotages them.

So they either fight all doubt (which is impossible) or listen to all doubt (which is paralyzing).

Here's how to tell the difference...

Judgment of Identity vs Functional Discernment

Destructive self-doubt makes it about your identity.

It sounds like:

• "Maybe I'm not really a good entrepreneur"
• "Maybe I can't do this"
• "Why did you think you could do this?"
• "Maybe I'm not good enough"

This kind of doubt attacks your fundamental worth as a person. It's binary thinking: either you're good enough or you're not.

Healthy self-questioning focuses on functional discernment.

It sounds like:

• "How could I be better?"
• "How am I awesome at this? And how am I not so awesome at this?"
• "Where do I have opportunities to improve?"
• "What am I doing that's going great and working really well?"

The difference is profound. Destructive self-doubt makes your identity dependent on your performance. Healthy self-questioning treats challenges as information you can work with.

Think about it this way: if someone told you that you weren't great at badminton, you probably wouldn't take it personally. You don't have "badminton player" as a core part of your identity. But when someone questions your ability as an entrepreneur – something you've tied your sense of worth to – you either get defensive or spiral into self-criticism.

The most successful founders I work with have learned to separate who they are from how they're currently performing.

Here's How to Make the Shift

When you catch yourself in the doubt spiral, try this three-step process:

1. Welcome the doubt without judgment - Instead of fighting it, try: "Of course I'm experiencing doubt. I'm human, and I'm attempting something difficult. This doesn't mean anything about my worth or potential."

2. Get curious about the function - Ask yourself: "What specifically could I improve? What's working well that I can build on? What would growth look like in this area?"

3. Apply the growth mindset filter - Challenge yourself: "Am I treating this as a fixed trait I either have or don't have? Or as a skill I can develop over time?"

The goal isn't to eliminate doubt – that's impossible and not even desirable. The goal is to use doubt as fuel for growth rather than evidence of inadequacy.

Most thoughts contain some truth. The key is not believing they're the complete truth or making them mean something about your fundamental worth as a person.

We're All Equal

This reminds me of a quote from Chamath Palihapitiya on the Lex Fridman podcast a couple years ago, which perfectly captures this exact struggle that founders face:

"I wish somebody had told this to me – we are all equal and you will fight this demon inside you that says you are less than a lot of other people... I am fighting this thing all the time... my biggest learning is I am equal, I'm the same as all these other people."

Think about that. One of the most successful investors in Silicon Valley – someone who's built multiple billion-dollar companies – still fights the same inner voice that tells him he's not enough.

Your doubt doesn't make you different from successful founders. It makes you exactly the same as them.

Now, I'm not saying you should be fighting this "doubt demon" all the time.

Rather, welcome and appreciate the doubt for being there. Because ultimately, it is just trying to keep you safe.

But with this understanding – and in seeing the difference between healthy doubt and destructive doubt – you can choose to only listen to the doubt that further empowers you.

You already have everything you need. You just need to remember that you're equal to every founder who's ever built something that mattered. Including the doubt they felt along the way.

With love,

- Dave Kashen

P.S. Have you had this realization that we're all experiencing the same doubts? I'm curious how you came to that understanding. Or if this newsletter was your first time hearing it, what stuck out to you?