On Assertiveness

2025.10.12

CXXI

[Becoming Assertive; A Misleading Résumé; Bird-Dogging; Getting Rejected; Relentless Sustaining; A Powerful Weapon; A Means, Not an End]

Thesis: Competence is not enough--you have to be assertive, too.

[Becoming Assertive]

You might not realize it, but I used to be a pretty passive person.

Over the last three years, I've been become a lot more assertive, and it's a very good thing.

The trouble is, I used to focus myopically on becoming more competent. I thought that when I was eventually 'competent enough,' everything else would just sort itself out.

While becoming more competent is very important, it is not enough on it’s own to get what you really want.

It doesn't actually matter how competent you are if you don't exercise that competence to achieve some goal.

And it becomes a lot easier to achieve goals when you’re assertive.

[A Misleading Résumé]

If you look at my résumé, it appears to be anything but passive.

Self published a book at 18. Started an options club at one of the most competitive business schools in the country. Spent a month driving from San Diego to Washington and then lived in Maine instead of getting the job I was supposed to. Launched a hedge fund in college.

There is no doubt that I have high agency. Don't confuse agency with assertiveness, though.

I was doing a lot of things I wanted, I became way more competent, and I achieved some pretty cool things. But none of these things felt like "success" to me, and in a lot of ways, they were not.

I was missing was a certain aggression and assertiveness--the belief that I could keep at something long enough and with enough force and compounding that the world actually updated it's beliefs to agree with me.

Back then, I was still praying for Deus ex machina--divine intervention, someone to come along and say that what I did and had become was finally enough and I had made it. An investor to randomly drop a big check into the fund or a volatility spike to validate our strategy or a publisher to read one of my books and want to pick it up, or a fintech company to buy the not so good software we had pieced together.

Now, I know that waiting for something like that means I wasn’t really convinced I could have great success on my own.

The people who win are the ones who don't wait for anything.

[Bird-Dogging]

It's funny that the first venture in which I've been able to maintained a concentrated and increasing assertiveness is called BirdDog.

'Bird-Dogging' has a lot of funny meanings, but broadly, we can take it to mean aggressively pursuing someone or something, synonym with 'hounding.'

Many other journeys of mine had been focused on building either capacity in myself or something strong and valuable that stood alone, whether it be writing that I still thinking is good or positive expected value trading strategies.

Even if those things really were as good as I thought, it doesn't matter; I wasn't interested in spending much if any time showing the right people that I was correct.

Convincing the world that you're right requires a certain level of unrelenting aggression. It won't work the first time, or the second, or the third.

I got on over a hundred sales calls before I closed a single customer for BirdDog. Yes, over one hundred no's before we had a single yes.

After that first yes, I got on hundreds of more calls before my win rate was above 10%, and then hundreds more before it was strong (over 30% in the last month).

In the past, I may have 'quiet quit' at that point and went back to the product drawing board and iterated on it, thinking that I needed to make it better.

You do need to make it better, but you don’t need to leave the market to do so. The truth is, going to market and leaving as soon as you fail is almost as bad as not going to market in the first place.

You will fail.

No matter how good or competent you or your product are, you will get rejected.

It’s by maintaining a general level of aggression and assertiveness and tenacity and solving (or sometimes ignoring) each no that you keep going and start to find things that won’t get rejected.

[Getting Rejected]

I used to have a certain fear that if I explicitly stated what I wanted I might upset some people or rub them the wrong way.

What if other people disagreed or thought you were wrong?

Sure. As I became more assertive, some people stopped liking me.

It's usually not the assertiveness itself they dislike, though. Rather, it's something else about you that is disagreeable to then.

The thing is, that thing that was already there; it’s just easier to see when you’re open about who you are.

Having it out in the open is actually useful, because it helps other people who you wouldn't click with self select away from you and draws in more people who you would get along with better than you thought you would.

[Relentless Sustaining]

I've always been opinionated, but I've also been insecure and apologetic at some of the times when it mattered most.

In the back of your head, you may hope that everything comes easy, but it doesn't. Sometimes, you have to keep going and keep digging until you find what you're really looking for.

In jiu jitsu, if you go in for a submission that you're very excited and optimistic about, and your opponent ends up getting the dominant position because you messed up, that's not an invite to stop. That just means you have to keep going and gain some ground back.

Likewise, when you're selling something, there is a certain judo that can lead to your prospect asking YOU how they can buy the product and get started. This is kind of like a girl asking a guy on a date. Early on, I had a fantasy that BirdDog's product and offering would be so good, that the person would always ask us out to the next date.

It’s not ‘always’ going to happen, even if you are good. And as a founder who hasn't sold the product you're selling before, or who is selling something that maybe NO ONE has sold before, you're probably not good.

This is where your assertiveness matters most, especially when the prospect is not being clear with you.

When you're assertive, you have the determination and honesty to know that "I don't know" or "I'll think about it" isn't an answer. It's a no buried under some pleasantries.

It's okay if someone is thinking no.

It's better if you can have the confidence to accept that fact and the assertiveness to get them to explain why. Because maybe it's not too late to turn that no into a yes. And even if it is, it gives you brilliant context for the next time you get a similar no.

[Waking Up]

All of this talk of being more assertive with BirdDog than before, but what changed?

I learned the consequences of not being assertive.

All of that competency I talked about building up before? While I don’t regret building it up at all, it also means I've put so much time into building things that I think are good, only to watch them get murdered in the cradle before they have a chance to become objectively great.

Jiu jitsu has helped me with this quite a bit.

When you're grappling with someone, opportunities will present themselves for you to gain ground. Like in chess, some of those opportunities are traps, and should not be taken.

If you never ever take any opportunities, however, then those opportunities might as well have never been there.

While learning to not lose is a good first step when you want to get good at something, the next critical step is actually taking risks and trying to win.

[A Powerful Weapon]

If you make yourself competent, but don’t order it towards something that you’ve believe is meaningful, you’ve just made yourself into a very expensive tool, or maybe even a weapon.

That’s fine, that’s a good way to get paid; it’s far better to be an expensive tool, than a cheap one.

But, if you don’t want to be ordered towards someone else’s objectives, then you need to have your own, and “becoming more competent” is not sufficient in itself.

If you liked this post, I’m going to be assertive enough to ask you to subscribe—I’m here every week!

[A Means, Not an End]

Becoming more competent and capable is a good goal, a good end, for certain seasons of life.

But, there are other, longer seasons where the competency itself is not the end, but a means to a greater end.

There are seasons where you leverage your competency to build or create something meaningful that will have more direct impact than you yourself ever could.

Or perhaps, building something like that is the real definition of 'competency,' and the rest is just a stepping stone to that.

Live Deeply,