On Millennial Cringe

Are We Really as Bad as Gen Z Thinks We Are?

The other day, I was scrolling TikTok when I came across something called a “millennial cringe compilation”, which is essentially a mashup of millennials being playful in ways that can best be described as childlike.

@cakeinme1#core #millenial #fy #joke

Tiktok failed to load.

Enable 3rd party cookies or use another browser

The comments were brutal, and most looked like this:

“Why do they want to be kids so bad?”

“They can’t cope with adulthood.”

Admittedly, some of the videos were undeniably “cringe,” and watching them gave me a shudder of secondhand embarrassment. But beneath that reaction was an undeniable self-consciousness.

In recent years I’ve worked hard to reconnect with my inner child and peel away a mask that became suffocating, so seeing my peers mocked for embracing their own version of childlike playfulness unsettled me.

That said, I get the impulse of these Gen Zers. In my early twenties, I would have rolled my eyes at the kind of overt earnestness those videos put on display.

I actually have a memory that haunts me to this day.

In my early 20s, I sublet an apartment from a woman who was about the age I am now. I’d host pregames there before my friends and I went out drinking ourselves into oblivion. One night, we discovered a fill-in-the-blank journal on her bookshelf, the kind meant as a therapy tool, guiding you to write about your feelings and goals. My friends and I passed it around like a party game, laughing at her earnest answers.

I am still embarrassed by how mean we were, and by how little respect I showed for her privacy. It is one of those moments from before I began real self-reflection and healing, before I understood how to respect other people’s boundaries, that I now look back on with deep shame.

And the irony is, I’ve essentially become the woman we mocked: therapy-going, self-reflective, and middle-aged, with shelves full of earnest books and journals.

If a group of 22-year-olds got into my place today, they would for sure mock me into oblivion.

They’d laugh at the obvious self-help titles, the way I write my excited little breakthroughs in the margins. They’d see it all as evidence of someone trying too hard and caring too much. And that’s exactly what I would have thought back then too. It’s exactly what I did think.

I’m aware that this dress looks like something a toddler would have worn in 1994, but maybe that’s why I was drawn to it?

At 22, you don’t really know who you are, so choosing a mask and clinging to it can feel thrilling and relieving. You want to be perceived as cool, detached, unbothered. But what you’re really doing is outrunning yourself, and you haven’t yet lost steam.

Eventually, the mask starts to feel unbearably stifling, and you realize it’s left you out of touch with yourself and profoundly unhappy.

That’s when the real work of self-discovery begins, and the best route there is through work that is embarrassing, earnest, and yes… 'cringe.'

Because you didn’t actually lose your authenticity, it was right there when you were a kid, and it’s since been buried.

Which is why the quickest way back to yourself is through what looks most childlike: silliness, curiosity, play for its own sake. That’s where you rediscover who you are and what lights you up, and where authenticity finally rises again after years of being pressed down by the performance of coolness.

And honestly, this is what I want to lean into more here in this newsletter: creativity, play, and the practices that bring us back to ourselves.

More journaling, more art projects, more experiments in being a little weird and childlike as a way of getting closer to authenticity.

So my question for you, dear reader, is this: would you be into that sort of thing?

Think prompts, creative exercises, little experiments to spark playfulness? It’s a side of me I’ve spent so much time on in recent years and would love to share more of with you!

As always thank you for being here. Your support means the damn world to me!

xoVC