Not all arrogance is the same.

He got a big ego

Such a huge ego

I love his big ego

It’s too much

He walk like this ’cause he can back it up

-Beyoncé Knowles, “Ego”

I’m not naming any names. Instead I’m just going to leave this here in case you happen to know someone who could benefit greatly if this article were to somehow show up in their newsfeed.

Extreme confidence can be ballsy and compelling or just plain irritating. If “he can back it up…” more power to him. But we’ve all known someone with misplaced arrogance; a kind of ill-fitting bravado that fails to persuade.

There’s a particular flavor of cockiness that one often sees in the relationship business, that arises when someone evolves rapidly. The best way to describe this is to use an example… so ladies and gentlemen, I present to you Exhibit A.


When I was young I was shy and timid around the opposite sex. I was also desperately lonely and hungry for connection. Like many people I encounter now as clients, I was suffering unnecessarily because there wasn’t anything fundamentally wrong with me.

Mind you, I’m not rich. I’m not tall. I’m not notably athletic or handsome. In fact back then I came off as pretty nerdy. I wouldn’t say I’m particularly charming, socially adept, or outgoing. My path to transformation did not involve learning to skillfully pick up chicks in bars. I can’t claim a fancy pedigree or highly exclusive credentials.

Fortunately none of these qualities stood in the way of me having a great relationship, a fantastic sex life, a deeply gratifying web of social connections, or worldly success. But I didn’t know that at the time.

This meant several things were true of me:

  • An ounce of connection was like a glass of water in the desert.
  • The fundamentals of human relating were within easy reach.
  • I wasn’t far off from having very, very different experiences with women than I’d been having.
  • My newfound ability to connect rapidly outpaced my emotional capacity to handle what I was experiencing.

In other words, my biggest problem was growing into the new me. You see, I was highly impressed with my own success. My tiny little triumphs were monumental to me. I had no perspective.

Or more accurately, my perspective was very different from everyone around me. My new relationships, my sex life, and my social life weren’t at all impressive to anyone else.

So this presented a big problem to anyone trying to deal with me. Especially if they were teaching or training me — whether it was a girlfriend who had the graciousness to be honest with me, or a mentor trying to steer me toward manhood. In either case they genuinely wanted me to become a better man. And had to deal with my suddenly huge, gigantic ego, with a head so big it could hardly fit through the door.

(The path from fragile arrogance to humble confidence is worthy of a whole other article.)

So this is our first flavor of cocky: misguidedly impressed with himself after a rapid up-level.

The second type is more common but more subtle. I’ve known a lot of guys who are genuinely dicks toward those who are drawn to them. And I always wondered why.

If it’s easier for us to recognize it for what it is — a defense mechanism — when a woman does it… well, that in itself reveals something about us and our stereotypes.

Whenever I spoke to these guys, there was something they weren’t saying, something they weren’t aware of within themselves. They were full. They didn’t have much actual hunger for connection. They acted like they did. They believed that they did. But the amount of interaction that was available to them was surpassing the amount they could ingest. They were deliberately, but unconsciously, holding people at bay. And the way they did it was through becoming increasingly, intolerably arrogant. Having gotten adept at chasing women they were now unconsciously chasing women off.

It may look paradoxical to the people around him. Like, why is he doing this? Until you realize that his capacity for connection, or intimacy or sex or love or whatever, is about the size of an eyedropper. He has a small amount and then, unbeknownst even to him, he’s had as much as he can take. In fact he will likely be the last one to recognize or admit it. Instead he becomes an asshole, an arrogant prick.

So that’s the second flavor of cockiness: arrogance as a cover for overwhelm, deliberately warding people off.

The third flavor I’ll just name: clueless. Let’s return to that list of all the things I’m not. Because I am now the guy who women bring their tall, rich, hot, athletic, charming guys to, in the hopes that I can train them in all the relating skills that they never had to learn in order to be well-liked and frequently fucked.

The single biggest question that will determine whether I can help turn this guy — the one with all the checkboxes, who basically has what we’ll call “great advertising” — into someone she would want to spend the rest of her life with, is whether he has sensed that there’s something beyond what he’s had up till now.

Let’s imagine he’s become bored with surface-layer relating. He’s popular but not gratified. At this point it’s possible he gets fed up with the whole relating game and turns his attention to financial success or some such. But maybe he craves something deeper. Perhaps there’s a woman in his life that he knows has ton of depth and he’s discovering that he has no idea what to do or how to be with her. He’s starting to realize that his playbook is useless in this arena.

Underneath their cocky exteriors, these guys are some of the most humble, beautiful men I’ve ever known.

Flavor number three — has all the checkboxes, clueless when it comes to relating with any depth.

And finally I want to talk about the self-help guy of the twenty-first century: the life-hackers, pick-up aficionados, flow junkies, do-it-yourselfers. These guys take on grand confidence as an x-game. Confidence is the decisive factor of success or failure in so many realms of life, and they see it as a brain hack, a life optimization. They’re not hard to spot because you can sense the shakiness underneath their bravado. But I always root for them because, holy shit, they’re really going for it. It’s the very definition of ballsy. You can see them fall flat on their faces, learn, get back up, and try again. I always find them inspiring. If they can do it, I can do it.

Flavor number four — life-hack bravado.

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