Good Morning Players,

We’re now on our fourth edition of my revamped newsletter. I’ve been thoroughly enjoying writing for you all so far.

I think I finally narrowed down what The Game actually is.

Each newsletter will revolve around a central idea. That idea may be tied to a recent news event or a more general trend that I am seeing. Most will have to do with either business, media, or startups.

Then, I’ll do my best to bring in disparate threads to make you consider that central idea in unique ways. For instance, today’s piece starts with a Cherokee proverb then jumps to Taylor Swift.

The goal is to write a piece that gives you one or two “Aha!” moments each week.

Those are the types of pieces I enjoy reading the most, so I hope you will too.

Now onto today’s topic.

I am cringe, but I am free

There is an old Cherokee proverb that I want to start this piece off with. You may have heard it before:

One evening an elder told his grandson about a battle that goes on inside all people.

The Elder said, "Son, there is a battle between two "wolves" inside us all.

One is Evil. It is anger, envy, jealousy, sorrow, regret, greed, arrogance, self-pity, guilt, resentment, inferiority, lies, false pride, superiority, and ego.

The other is good. It is joy, peace, love, hope, serenity, humility, kindness, benevolence, empathy, generosity, truth, compassion, and faith."

The grandson thought about it for a minute and then asked his grandfather: "Which wolf wins?"

The old Cherokee simply replied, "The one you feed."

I like that proverb because it reminds us we are in control, we get to decide which wolf to feed.

But today’s piece is not about human nature or living intentionally. It’s about being cringe.

I want to amend the Cherokee proverb because I don’t think just one good wolf and one evil wolf live within us. I think there are two more wolves: cringe and not-cringe.

Taylor Swift is cringe

Taylor Swift's superpower is that she is not afraid of being cringey. If you really look at some of the songs she writes, they are balancing on a knife's edge of being so incredibly corny and cringey.

And yet, she pulls it off. She’s the biggest musical act of the 21st century. Her latest tour is probably going to gross $1 billion. All because she embraces the cringe.

“Learn to live alongside cringe,” Taylor told NYU’s graduating class of 2022 in a commencement address. “No matter how hard you try to avoid being cringe, you will look back on your life and cringe retrospectively. Cringe is unavoidable over a lifetime.”

Let’s break this quote down because Taylor is actually saying two things at once.

First, “Learn to live alongside the cringe,” meaning, don’t be afraid to look dumb in the moment.

Then, “You will look back on your life and cringe retrospectively.” That is a totally different thing altogether. No matter what you do in life, looking back, it will seem cringe.

So, not only do we have to learn to be cringe in the present, but we also have to make peace with the fact that the past will inevitably end up being cringey as well!

So what Taylor is truly preaching is practiced apathy. If cringe is the physiological and emotional response to an awkward or embarrassing situation, then the antidote is indifference.

Now apathy and indifference don’t sound like desirable traits to develop. But employed correctly, they are probably the single biggest difference between successful people and not.

Cringe mountain

The inspiration for today’s essay originally came from a TikTok I recently stumbled across. It starts with the line:

“What you are forgetting is that everyone who is now cool or good at something at some point had to climb cringe mountain.”

Cringe mountain is exactly what it sounds like, a mountain of cringe you have to scale before you can descend into the “land of cool.”

There are lots of famous examples of successful people crossing cringe mountain.

MrBeast started by counting to 100,000 in his room without stopping and now he’s the biggest YouTuber on the planet.

Paul McCartney is Taylor Swiftian when it comes to earnestness and simplicity of lyrics. If he, like Taylor, hadn’t owned it, he would never have set foot on cringe mountain and wouldn’t have become the biggest rockstar ever.

That’s the point she’s making in the TikTok—everyone who points and laughs and calls you cringe as you’re climbing the mountain is doing it from base camp.

They’ve never set foot on cringe mountain because it is far safer and gentler on the ego to judge people from the ground.

The perils of becoming Sisyphus

The tale of Sisyphus involves a mortal condemned by the Gods to forever push a heavy boulder up a mountain, only for it to roll all the way back down to the bottom once he reaches the peak.

There are plenty of people like Sisyphus who toil away endlessly on cringe mountain and never get a chance to descend into the land of cool.

In fact, most people don’t because the internet is governed by the Power Law, which means 1% of creators hoover up 99% of the success.

It’s why MrBeast has 100 million followers and you don’t.

But from this reality, a new class of Sisyphusian figures has emerged. Figures that our society has begun to reward for never leaving cringe mountain.

The biggest example that comes to mind were the original crop of TikTokers who rose to fame by wasting food on camera. Click here and here if you don’t know what I’m talking about.

They are truly the worst videos ever, not because of what they are doing, but because of how many views they get. These people film themselves dumping 10 gallons of syrup on one stack of pancakes because it absolutely racks up views. Views driven by outrage, but views nonetheless.

They are being cringe for the sake of being cringe and figured out that you don’t actually have to leave cringe mountain in order to gain success.

The difference between the food wasters and Taylor Swift is that Taylor’s end product has inherent value. It stays with you because there is real emotion and effort put into her music. Music itself is also a worthy art form to devote time to. Dumping food on a counter is not.

Final thoughts

This piece just scratches the surface on how important of a factor cringe is in today’s landscape. You can’t tilt too far toward either end of the spectrum. If you’re too afraid of being cringe, you’ll never set foot in the arena. If you’re too willing to be cringe then you lose sense of what is truly worth creating.

I think that figuring out how to arm yourself against the critics who aren’t climbing cringe mountain is extremely important—I wouldn’t be hosting a podcast if I hadn’t figured it out to some extent.

But I also think that selling your soul at the altar of cringe is possibly even worse. That means you are playing only vapid games by hopping on whatever trend floats your way. You are shameless in all the wrong ways. I touched on this during my last piece on Game Selection. 

Instead, be good shameless. Be like Taylor. Feed the right wolf hopefully we all see each other on the right side of cringe mountain.