The Lost Art of Millennial Boasting

Tre Vayne
Tre Vayne
Sep 5, 2019 · 5 min read

You’ve worked for it, no matter what that boomer tells you.

Image by freeillustrated from Pixabay

While I was at my on-campus job my first year of grad school, I decided to disregard the Geneva Convention and commit a crime against humanity by asking my friends what their plans were for postgraduate life. I only dared to ask such an empty, volatile question because the friends I was talking to were exceptional. One majored in the humanities, spent a year studying in Buenos Aires, consistently had internships and jobs throughout school, and was on the road to being published with research he was conducting in the humanities with a professor. One majored in communications and was quietly wrapping up an internship at a major fashion house all the while launching a media brand and getting amazing opportunities such as presenting at Google. And the other was a force within the New York theater scene. She was producing her own shows, getting cast in small roles Off-Broadway, and supplemented all of this with on-campus leadership positions and a side gig at a boxing gym.

After their respectful (and warranted) deflections about the question at hand, they started to lament the prospect of the future, feeling unprepared and unqualified for anything aspirational. And when I loudly protested, citing all the aforementioned impressive accomplishments, I was met with a collective disbelief, almost as if I had made up the points on their resumé.

“I didn’t do that much at the internship, I was only there three days a week.”

“The professor only let me on the research team because I bugged him, it’s his research to be honest.”

“I’m not even union, there are people out there with ten times the acting credits.”


Millennial Misconceptions, Debunked

This might be the most millennial thing to say, but millennials get a bad reputation. We are seen as these lazy, unmotivated individuals who would rather get an avocado toast than buy a house. How those are even remotely related, the mind boggles, but for starters, I’m allergic to avocados and secondly, I don’t even want to own a home. We get chastised for being spoiled, for being delicate nobles who have never had to work for anything and don’t even know how to change a tire. My mother did teach me how to fix a tire (which was nice of her), and she spoiled me to bits but considering millennials on average work more than previous generations, the spoiling does not translate to lack of work ethic. But every anti-millennial’s (antimil?) favorite metaphor, the all encompassing idol, is the participation trophy. It has become the strongest symbol of the source of millennials’ alleged entitlement, and that entitlement informs our relationship to the job sector, our consumer behavior, and our take on human rights issues.

The claim is that for our entire lives, millennials have been given participation trophies for everything. That we think we are entitled to the world because at every turn, we have been given an acknowledgement of our presence. Even ignoring the fact that participation trophies are nothing new and that rewards for participation are commonplace (i.e. jerseys, the after game snacks, name tags), I could see how the concept of a participation trophy can be detrimental. If everyone gets something for just showing up, what would motivate anyone for trying? What’s the use of striving for greatness when mediocrity is celebrated?

Image by Med Ahabchane from Pixabay

The Boasting Barrier

Unfortunately, this logic does not hold up in the real world. It’s not the trophies themselves that are damaging to the millennial sense of self, it’s the discourse around the trophies. The constant barrage of “you never worked for anything” is directly tied to why millennials are so bad at boasting. When we’re told that any small achievement is worthless, it numbs us to the successes that matter. The constant cynicism robs us of our pride, it plants seeds in our heads to recognize every token of achievement as merely participation. Now the first place trophy and the “If You Had Fun, You Won” medals start to look the same. Now the internship at a Fortune 500 company has the same value as the on-campus job. It all feeds into the cycle of feeling as if nothing’s impressive, so to make ourselves feel we have even a little headway, we nab that extra internship, we make sure each A is an A+, not because we think we deserve it, but because a warped sense of quality can be temporarily compensated for with quantity.

That’s why so many millennials are prone to freak out over the grading of every single assignment, why we will leave a job if we feel mistreated or stagnant (even after a short amount of time), why everything seems like a crisis. Our entitlement or spoiled nature doesn’t come from the silver spoon in our mouths, it comes from the paranoia that no single accomplishment actually matters. It derives from the gaslighting by some who claim we have never worked for anything or ever could. This isn’t to say that there aren’t some bratty, undeserving, insufferable pricks in the mix, there certainly are, but before you condemn the entire generation, have you ever seen an antimil get the wrong order at a fast food restaurant? It’s just mustard, wipe it off.

But this gaslighting is precisely why I’m making the case for boasting. Boasting doesn’t require critical thought about the quality of an accomplishment, it doesn’t care about the “grander scheme of things”, it’s brash, and proud, and it feels damn good. I am twenty-three and I have worked at record labels, luxury hotels, I have one degree and I’m working on another, and I’m really funny (like, very funny). Aren’t I impressive?

Now do the hours I spent doing absolutely nothing at my internship, my complete disdain for my undergraduate academic program or the mini-breakdowns I had at my hotel job matter? No! Because I’m boasting! Nothing but the simple fact that I did these things at all matters!


If at the end of this article all you took away was me chastising the older generation for how they raised us or for constantly belittling everything we do, you read this incorrectly. This is a call for hubris, a demand for grandiose sense of selves to counterbalance the white noise. All three of the friends I spoke about before are doing amazing, impressive things (as they have been). Millennials will always survive because something we certainly have in spades is adaptability, but take it from a charismatic, accomplished, effervescent icon, life’s much easier when you boast.

Tre Vayne

Written by

Tre Vayne

I am a writer, content creator, and comedian based in Los Angeles. Big fan of food, philosophy, and reality TV.

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