On Confidence

2025.12.14

CXXX

[Shallow & Deep Confidence; Leading & Lagging Indicators; Disproving Your Doubts; Healthy Delusion; Slow & Steady]

Thesis: The best way to build confidence is by doing the thing.

[Shallow & Deep Confidence]

When we first started BirdDog, I had a really hard time closing anyone in 3 phone calls for even a $100 per month commitment. Now, I'm able to close low five figure annual contracts in 2 or 3 calls.

The reason for this change is a LOT of things. Our product is better, our marketing is more tight and dialed, and our value prop is a lot more clear.

But, what's most interesting is the increase in my confidence level.

Now, I believe so deeply that BirdDog is worth at least what we are charging for it, and almost always far more.

Back when we were selling it for $100/mo on month to month contracts, on the surface I “believed” that we were way under charging… but it wasn't a very deep belief. You could push and pull on it and it would fall apart pretty quickly.

This was a very "Shallow Confidence."

Now, my belief is very, very deep. You can tell me I'm wrong and I'll calmly stare back at you and clearly articulate why you're in fact the incorrect one, even though I am asking you for over 100x the amount of money I struggled to ask for a year ago.

This is a much more "Deep Confidence".

That's not to say I nail it every time or never lose my frame! I still have bad sales calls. And, beyond that, I still have moments of doubt. But, I’m much more sturdy than I was in the past. It’s really a night and day difference, and it goes down to the core.

This post is a reflection on confidence and how (and perhaps why) I've seen it increase in myself overtime.

[Leading & Lagging Indicators]

In the past, I've written about how in some very rare cases, your competence level matches up with your confidence perfectly. Really, though, most people are chronically ahead of or behind that match. In other words, the confidence lags behind competence or leads in front of competence.

If you are like me, confidence is a lagging indicator of competence. Meaning, you might find yourself often getting told that you’re underselling or are humble.

Tangibly, this looks like clients telling me, "We would've paid a consultant a boatload of money to show us this" or asking "Why are you charging so little" immediately after signing a contract.

I don’t know if there’s anything particularly “wrong” with that, but there are definitely trade offs to it.

The drawback is it might make you collect resources more slowly. The benefit is that it decreases the probability of overpromising and under delivering (but it certainly does not make this probability 0!). This is good for reputation.

For others, confidence is a leading indicator of competence, meaning they are more confident than they are competent. Again, I don’t think this is particularly “wrong,” it’s just a question of trade offs. While they are more at risk of over promising and under delivering, they might acquire resources a lot more quickly, which can possibly make the bold claims a self fulfilling prophecy.

I do tend to think that having confidence as a lagging indicator of competence makes the confidence a lot deeper and harder to push on; as you’ll see below, you’ll have a stack of evidence to fall back on.

[Disproving Your Doubts]

Whatever your doubts are, there is a way to empirically disprove each one.

First, you need to break down your doubts into something real and tangible. “I’m not good enough” is too murky and nebulous to handle.

Why are you “not good enough?” Going deeper and being clear helps with that.

Do you think you can’t start a business that can support yourself? If you haven’t started a business that can support yourself, you might be right. Once you have, you can’t really think that any more. You start to evaporate your self doubt.

Do you think you can’t sell? If you haven’t sold anything, you might be right. So go and sell things. And keep selling them. As a(n) (completely hypothetical) example, if you yourself have personally sold 6 figures in software subscriptions in under a year, the notion that you “can’t sell” would start to seem absurd.

Do you think you can’t commit to something? Write a blog every Sunday for 130 weeks in a row and see if it’s still possible to believe that.

I could keep going on and on…. but I think you get the point. Whether it’s about art or music or work or relationships, you can outwork your self doubt, no matter what it is. Make it tangible, then keep stacking evidence until it’s gone.

[Healthy Delusion]

Interestingly enough, even when my day to day confidence is shallow, I have a deep, borderline delusional belief in my long term ability to figuring things out.

I fully and deeply believe that BirdDog is a new kind of hedge fund, which, if you unpack that, is an incredibly bold claim. I've believed things this bold in the past, even when my confidence was shallow.*

When I was 18 or 19, I wrote out a list of things I wanted to do. I'll spare you each of them, but here are some:

• Open a hedge fund

• Publish a best selling book

• Direct a Movie

• Become a millionaire

• Go to Space

I've actually only done 1 of 5 of these things (and another on the list I will not share), which is still pretty cool. (If you haven't been keeping up with my adventures, I am not a millionaire or an astronaut. I started a hedge fund. I’ve written & published a number of books, none of which were “truly” best selling, and I have not yet directed a movie, but I have acted in one, which scratched a similar itch).

It has taken me longer to do these things than I thought I would, I still have a rock solid amount of confidence that I will do each. I over estimated what I could do in a long time period.

And, on the other hand, I under estimated what I could on a day by day or week by week basis.

All of that is to say, you can be the kind of person who generally has confidence as a lagging indicator and still over estimate yourself.

This doesn't seem to be a terrible place to be, in all honesty.

Founders and people who do pretty crazy things are full of juxtaposition. In some cases, one of these is an incredibly optimistic and borderline delusional forward looking belief with an incredibly skeptical and realistic analysis of the immediate situation, bordering on the word “harsh.”

This really does seem to be a powerful combination.

_{*This seems to be related to the notion of Hyperbolic Discounting}

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[Slow & Steady]

My first Jiu Jitsu instructor had a philosophy that he would not promote until you were already performing well within the band of the next level consistently. In this sense, when I got my blue belt, he had been viewing me as a blue belt for months already.

I like that a lot… If the fabric is dyed another color too early, then a faux confidence will get ahead of your competence. If the fabric is dyed later, then a deep confidence follows competence.

Even though this means I move slower than some of my peers, I am fine with that.

If you are deep in the trenches on something, and are doubting yourself, try this:

1. Breathe in deeply through your nose, and out through your mouth

2. Take stock of all you've achieved

3. Gently remind yourself to keep believing in the big thing

4. Keep taking the steps to get there, every day

Eventually, there will be so much evidence that you have no choice but to be confident & believe.

Live Deeply,