How To Be Cool (like Rihanna)

• 5 min read
How To Be Cool (like Rihanna)


I watched Rihanna's Savage Fenty fashion show this weekend with some friends. And one thing we all agreed on was that Rihanna was bad af.

See what I mean?

As we sat in the jacuzzi the next day the fashion show still fresh in our minds, my friend asked me:

"Would your style be different if you were super rich?"

I thought about it for a minute.

"Nah." I replied, "Style isn't about clothing. It's about attitude."

Rihanna is somehow simultaneously unique and relatable. She can be demure and seductive. She can be party loud and introvert quiet. She is a bag of contradictions. And yet somehow she is always authentically a 100% herself. She has so much swagger and bad bitch energy that women buy her clothes because they want to be her.

She is the epitome of cool.

As we sat in the jacuzzi, my friend told a story about two girls he knew.

One girl thought her friend was super cool. She asked her friend, "Can you teach me how to be cool like this?"

Her friend replied, "Unfortunately, you can't teach this."

I thought it was the perfectly sassy and true answer. Cool is about not trying.

It's similar to the Chinese idea of wu-wei

Wu-wei literally translates as “no trying” or “no doing,” but it’s not at all about dull inaction. In fact, it refers to the dynamic, effortless, and unselfconscious state of mind of a person who is optimally active and effective. People in wu-wei feel as if they are doing nothing, while at the same time they might be creating a brilliant work of art, smoothly negotiating a complex social situation, or even bringing the entire world into harmonious order. - Edward Slingerland.

Wu-wei is inherently attractive. It's attractive because we see effortless mastery. And it's something that most people don't think about. We tend to overuse the tools of cold rationalism and goal driven analysis.

We have been taught to believe that the best way to achieve our goals is to reason about them carefully and strive consciously to reach them. Unfortunately, in many areas of life this is terrible advice. Many desirable states — happiness, attractiveness, spontaneity — are best pursued indirectly, and conscious thought and effortful striving can actually interfere with their attainment. -Edward Slingerland.

This idea is something I'm obsessed with. Laziness is seen as un-attractive. But in all aspects of our life Embrace Our Lazy is what we should aspire to. Even if it takes hard work to get there.

I want to be great not because of what I do. But because of who I am.

Like Rihanna I don't want to do cool things, I want to be the embodiment of it. That's what I want for you too.

Here's this week's embrace your lazy to help you out...

This Week's Updates

A Blog Post From My Archives:

I wrote a  short blog post a while back about sprezzaturra, aliveness, and negative emotions. It's literally what I'm talking about above. The first step to becoming who you are is accepting your inner devil.

Why You Need to Love Your Inner Devil — Pranav Mutatkar
We are just as attracted to the devilish imperfections in others. We are attracted to charismatic people because they always do the right thing, but also because they do it with a twinkle in their eye.

Lazy Question of the Week:

Who are you when you aren't around people? Is it the same person who you are with people?

🧫This Week's Petri Dish


I keep harping about the lover archetype. Here is how I was introduced to the topic. A great (and surprisingly emotional) introduction to something that's difficult for all of us to find within ourselves especially men.


Some really cool images from Justin Peters


Since y'all liked that video a couple issues ago from Nerdwriter, here's another one of my favorites from him

Mastering anything (even the art of being cool) follows what I started calling the Sleep Paradox.

For people who struggle with sleep, they need to optimize as much as they can. They need to figure out reasons they can't sleep. They need to meditate, buy blackout curtains, etc etc.

But a certain point they have to stop trying. You can't try your way into sleep. Sleeping (like happiness, charm, etc) is about not trying.

Usually when people master anything they either don't try at all or never stop trying. Both will end up failures.

I remember coming across the biblical Matthew effect in Malcolm Gladwell's Outliers and being blown away:

For to every one who has will more be given, and he will have abundance; but from him who has not, even what he has will be taken away. - The Matthew Effect

I don't know if it's true, but I came up with a revised Matthew effect that I think is more accurate.

For to every one who does not care what will be given, he will have abundance; but from who cares, even what he has will be taken away.

This idea is something that's echoed by many of my favorite philosophers.

Ernest Becker said all of us are seduced by "infectiousness of the unconflicted person." It's one of the reasons why narcissistic individuals are so charming. Rene Girard put it this way,  

The indifferent person always seems to possess that radiant self-mastery which we all seek. He seems to live in a closed circuit, enjoying his own being, in a state of happiness which nothing can disturb. He is God.

To be cool we must be un-conflicted, have strong opinions, and not give a f**k on the front end. On the back end to be good humans, we must cultivate self doubt, introspection, and empathy.

Rihanna is admirable because has the seductive charisma of cool and all the supporting humanness.

If you want to get there try as hard as you can to become who you are. Reality is distorted by an extreme self assuredness.

And then at some point, stop.

Just be.

This week think about who the authentic you really is.

Quarantine gives us a good opportunity to be ourselves without performing for other people. It gives us a good opportunity to figure out who we really are.

Next week email me and let me know what you found!

Till then,

← Why You Should Admit that You Don't Know
Why You Should Embrace Your Inner Warrior →

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