Let’s talk about confidence.

Women always say that they love confidence in guys. As I was growing up, it always felt like women would always go for the guys who were more confident and outgoing. Whenever I had a crush on someone, most of the time I would be too scared to ask her out. My mind would tell me things like “she probably already has a boyfriend,” and if I did try to talk to her then I would become super awkward and would barely even be able to say anything.

This makes it especially difficult because as a guy, you’re the one who’s expected to be the initiator. You’re the one who’s expected to approach her, begin the conversation, ask her out, and so on. This also means that you’re the one who risks being rejected every step of the way. If I tried to ask her out, I would never have enough confidence while talking to her to get her to out with me. And when she rejected me, this lowered my confidence even more and made it even harder to talk to the next person that I liked.

For guys that have had relationships in the past or who often go on dates, it’s easier to be confident because the fact that they’ve had a girlfriend before or have been dating a lot of women provides a confidence and self-esteem boost. They know that they’re attractive already. But what about those of us who have never had a girlfriend before or who struggle to even get a first date?

How are we supposed to be confident then?

I’m not going to give you some generic advice such as “man up” or “grow a pair.” You’ve probably already heard that enough times already. Instead, I’m going to show you how I learned to be confident. There are three steps, and along the way we’re going to gain the Triforce of Wisdom, Courage, and Power and become the hero that Hyrule needs.

Are you ready? I hope so. Zelda is counting on you!

Continue reading A gamer’s guide to being confident around women →

Today we’re going to talk about the things that make YOU awesome!

Aww, yeah!!

So, in my other life I’m also a private equity accountant and one of the things we studied in business school was the Johari window. Basically, there are AWESOME qualities about you that are both known/unknown to yourself, and also known/unknown to others:

We’re mostly interested in Quadrant 2 – your strengths that are known to others but not known by you (yet!) There’s an easy way to find out what they are but it IS going to push you out of your comfort zone. You’ve been warned!

Continue reading Try this DARING exercise to become more confident!! →

I’ve been reading a lot of self-books these days and it seems like many of them have a similar exercise–

(GOOD self-help books, I mean. Not those weird ones from other dating coaches with half-naked women on the cover, but reputable books like The 7 Habits of Highly Effective People by Stephen Covey or The Seven Principles for Making Marriage Work by John Gottman).

Books like these ask you to imagine your own funeral and write a eulogy for yourself. What do you want people to say about you when they talk about you? What legacy would you like to leave behind when you’re no longer here?

I’m gonna be honest and say that I’ve been resisting doing this exercise whenever I read it. Yeah, I know I should, but…

…holy cow, what a depressing thing to think about…

After reading this one, two, three times though, I started to get curious. Maybe it was worth thinking about it if several different authors were independently saying the same thing.

Turns out, it highlights an important part of being confident around women.

One of the best ways to become confident is to live a meaningful life. And thinking about what you’d like people to say about you when you’re not around is a great way to do just that.

Maybe it’s a bit much to ask you to imagine your own funeral. I mean, I still haven’t done that exercise myself. Who am I to tell you to do it?

Another great way to start moving toward a meaningful life is to choose what I call your “Awesome Alternative”, and it goes like this—

Continue reading Become confident by living a meaningful life →

Have you ever thought about how dangerous the modern world is?

You’re probably reading this email on your computer or phone right now. You would have had to plug in whatever device you’re reading this email on. If your fingers were just 1 or 2 centimeters off the mark, you could have fried yourself!

What an incredibly dangerous task! I’m sure you didn’t even think twice about pulling it off. That’s because you’ve already demonstrated to the part of your brain which controls confidence that you are capable of performing such a task.

The science behind where confidence comes from

That part of your brain is called the amygdala and it’s responsible for regulating your body’s emotional responses. One of those responses is fear and confidence. Its task is to keep you alive by making you feel unconfident around situations it believes you are not equipped to handle.

Continue reading The science behind feeling confident →

Lately I’ve been playing a lot of classic games using the NSO feature on the Nintendo Switch – you know, those old side-scrollers from the 80’s and 90’s.

When you play them on modern hardware, there’s often some Quality-of-Life improvements vs playing them on their original systems. For example, you can use ‘save states’ to reload at any time or even hold the trigger buttons together to rewind time on some games.

I try not to use those features when I play because I’m trying to capture the feeling of playing those games from my childhood – and that includes the tension of not screwing up at the end of a level.

Think about that. Why would I feel nervous at the end of a level?

It’s simple: if I screw up, I got to restart the whole level again!

This perfectly highlights where confidence comes from, and what factors can increase or decrease how confident we feel.

The ABC Confidence Principle

Being confident involves three factors. This is what I call the “ABC Confidence Principle”, and it goes like this:

[Ability + Belief + Curiosity = Confidence]

Generally speaking, how confident we are at any given task is a combination of 1) Our Ability to do the task, 2) Our Belief that we can pull it off successfully, and 3) Having a positive curiosity about your successes/failures (there are a couple of exceptions, but we’ll cover that later). Being confident around women involves both knowing how to talk to her, and developing a positive Belief in our Ability to do so.

Let’s start by talking about Ability.

Continue reading The ABC’s of being confident →

Welcome to 2026! Happy New Year!!

New year, new you huh. Have you made any New Year’s resolutions?

(More importantly, are you keeping them?)

Whatever you’re looking to accomplish in the new year – it all starts with being confident.

One of the best mindsets around confidence comes from a line you’re probably heard before if you watch any number of rom-coms:

“I just want you to be happy”

What does that line mean? Take a second and think about it.

Continue reading Let’s kick off 2026 with confidence!! →

The holidays are coming! It’s the time of year when you start seeing Christmas lights and other festive decorations.

It’s also the time of year that used to stress me out the most.

You see, I always used to put a lot of pressure on myself to find a girlfriend in time for the holidays. It’s the time of year that you spend with people you love, and I always wanted to find a nice woman and take her home to meet my parents during the holiday season.

What I didn’t realize is that I was actually making it harder on myself by doing this. Since I was putting all these arbitrary deadlines around when I “had” to find a girlfriend, I was starting to come off as desperate to the women that I talked to. As I’ve written before, women don’t want a man whose cup of life is only half full.

After trying to talk to women and striking out a few times, I began to ask myself…

“How do I stop coming across as desperate when talking to women?”

…which was a good start, but it was still the wrong question. Eventually, I started having more luck talking to women when I stopped asking myself that question and started asking this one:

“How do I stop being desperate when talking to women?”

Continue reading How to become confidently outcome-independent around women →

Sometimes, I think back to how dumb I used to be and it makes me cringe.

Back in high school, I used to have a crush on my locker buddy, Olivia. We only had a couple of classes together all throughout high school, but every morning before classes began and every afternoon when we left school at around 3:15 pm we would meet up at our lockers and shoot the breeze for a few minutes. I always looked forward to that.

Honestly, I don’t remember what most of our talks were even about. I guess that’s the thing about memories. Those small details tend to fade away after a while. I no longer remember what we used to talk about or what she wore or even what my own locker combination was. If I went back to my old high school and look at it today, it would probably be much different than how I remember it.

Details fade away, but you remember 1) the people who were there and 2) the way they made you feel. Maybe that’s what really matters.

Continue reading What pickup gets wrong about being confident →

Let’s talk about confidence.

When I first started looking for love, I always wished that I could be more confident around women. If only I were more confident, I could go right up to a woman that I was interested in and just start talking to her. No more feeling awkward or nervous. No second guessing myself.

However, I’d usually just find some way of talking myself out of it. I’d tell myself things such as, “She probably already has a boyfriend” or “Someone like her would never be interested in me”. If I had a crush on someone, I would try to psyche myself into asking her out beforehand but when the time came and I did see her I just told myself, “She’s probably busy. I’ll ask her out tomorrow.” Of course, when tomorrow came I would just tell myself the exact same thing.

How do you become more confident around women? Especially if you haven’t had a lot of success before?

Continue reading Three ways I made myself more confident around women →