Millennials: Survivors with Numbers

Ah, Millennials. The generation immortalized in memes—tech-savvy, socially aware, perpetually underemployed, and forever misunderstood. We’ve been called “soft,” “rudderless,” and even “entitled,” but what those labels miss is the resilience we’ve developed after spending decades navigating a world that seemed determined to throw us off course.

And there are other more scathing tags like "underskilled", "underfunded", "underemployed"...and while we're here let's include "under the thumb" of Baby Boomers, the former largest living generation.

That's right. For five years, beginning in 2019, Millennials surpassed Baby Boomers as the largest living generation in the United States. Google it. You'll see.

Yes, Millennials are approximately six years underskilled compared to generational benchmarks. We didn’t get work experience until later in life. Hitting the job market later than previous generations, we’ll get back to your most basic question: “Why?”

Also factful… Millennials are epically underemployed and underfunded. The means of generating wealth were suspended during that period of delayed work experience at the same time capital and financial markets erased any morsels the oldest Millennials had gained. Born between 1992 and 1998, sucks to be you! And I’m not dismissing your trauma. This. Is. Not. Cool. Bro.

A generation of survivalists

Imagine this: you’re a Millennial born in 1994. When you were 7 years old, something historic happened. The terrorist attacks on your country. For you, this could be one of the most vivid memories of your first decade in life. Name me a generation with the same trauma. I’ll wait. A stateless, faceless, shadow adversary uses the products of your fascinating world—like airplanes and tall buildings—to kill thousands for no other purpose than spectacle. That’s what you faced as a 7-year-old in the U.S. Don’t think it had an effect? Think again.

That’s alright, you have a good core group around you, right? Right? Nope. During the years you went to elementary school, those late Boomer parents of yours were rat-racing (absent and climbing some personal or professional ladder — living out their best life and Winfreyian advice) or they were hovering, sometimes literally. Your two-income household helicopters always ready to mold their little bags of genes for a world that felt increasingly uncertain — and what better advice to give them than to “go to college”, “become an expert”, “join the technocracy”, and “compete for it all”.

This is also where you became a part of the most socially advanced generation — forged by the crucible of more non-family social interactions than any other generation in history. After-school programs and scheduled activities replaced unstructured free time of previous generations. You had to become more social, you had to become more conscientious, you had to care about…social justice. ?

Fast-forward to your high school years. Now, you’re about 14 or 15 years old, excited about what the future holds. Maybe you’ve even been told, like so many Millennials, that if you go to college, study hard, and follow the rules, you’ll have a bright future. But oh wait, it’s 2008, and instead of a red carpet into adulthood, you get an economy in free fall.

The Great Recession wasn’t just a financial blip — it was a tectonic shift that took out entire industries, millions of jobs, and wiped-out household wealth in the blink of an eye. For a Millennial born in 1994, this disaster hit at a critical moment. As you were starting to think about college or maybe even entering the job market, you faced a complete collapse of the world economy that your parents had been telling you to work toward. Remember those dreams of owning a home or finding a stable job with benefits? Yeah, about that…

Instead, you got rising tuition costs and a job market so tight that even entry-level positions required experience. Cue the existential dread.

Adulting blindfolded

By the time you’re ready to leave high school in the early 2010s, the economy is technically “recovering”—though that probably felt more like watching someone who just got hit by a truck say they’re "fine." Wages were stagnant, but college tuition was skyrocketing. If you were born in 1994, it felt like the whole system was rigged against you, and in a lot of ways, it was.

I can hear it, or maybe that’s just my own voices: “Well, not every Millennial went to college”. You’re right. And if you’re one of those didn’t go to campus, buckle up for a world of unpaid internships and retail jobs with no health insurance. Either way, debt was your constant companion. For the class of 2016, the average student loan debt was around $37,000. So, you’ve got your degree and that new wardrobe you bought for interviews, right? Time to launch your career and start paying down those loans.

But instead of getting a real job with a decent paycheck, you were more likely to get trapped in the gig economy, cobbling together freelance work, side hustles, and low-wage jobs to make ends meet. Uber, TaskRabbit, Etsy—these were the lifelines Millennials turned to when the promised jobs with benefits were nowhere to be found.

That’s if you found work at all. You were entering a world where wages for entry-level positions were a joke, housing prices were out of reach, and oh, yeah, there was still that student loan albatross hanging around your neck. And sure, the job market was better than in 2008, but compared to the stability Boomers had when they entered the workforce? Well, it wasn’t great, Bob.

Your parents, teachers, preachers, coaches, and counselors put you on a path they expected to be your best bet. It was the bet they wish they had made. The thing is, while they were encouraging you to compete, they didn’t want to once you came into the workforce. Boomers stuck around, expanding their wealth and holdings and positions of power (the average age of a US Senator is 63.9 years, the oldest in history). They just didn’t want to let go, and you were locked out of the workspace and years of work experience.

Go to college, they said.

Get a job, they said.

Get a house, they said.

Debt is investment, they said.

They. Were. Wrong.

Climate, COVID, Courtship, and Contempt

In February, 2020, you’re now 26 years old. Trump is kind of weird, but things are starting to get better. Some serious relationships, moved out on your own, getting good at work. Then, smack. Just when you were beginning to feel like you were getting a foothold in their 20s or 30s, COVID totally wreck the show. For you, this meant another seismic disruption right as you were entering your prime working years — work that will take a whole new form (and attempts to get wealth in other ways), from Zoom to work-from-home to retail collapses, to time-consuming gigs, to crypto scams, to sports gambling addictions, to seeking subscribers on OnlyFans.

Layoffs, furloughs, remote work, and a brand-new set of challenges in an already volatile job market—it felt like déjà vu. The pandemic accelerated changes that were already underway, like the rise of automation and the gig economy, leaving you once again to adapt and survive in a system that wasn’t built for you and is guarded by those before you are constitutionally incapable of letting go—I’m looking at you, Boomers.

Now that you could work remotely, location flexibility became the new currency. This reshaped your residential choices — that is, if the residences existed. You guessed it, in 2024, Baby Boomers real estate holdings valued more than $18 trillion. That’s trillion with a “T”. And when it comes to single family residences, well…they hold nearly half of it (43% of single-family residences are in the hands of Baby Boomers, while making up only 21% of the U.S. adult population). ?

You packed up and headed for places with lower living costs or more space, while urban centers—previously the Millennial dreamscape — started feeling like pricey relics of a pre-pandemic era. Rent? Ridiculous. So why not flee to the suburbs? Except, oh wait, that housing market? Still out of control, still dominated by Boomers who were in no rush to leave their homes — or drop the prices. Buying a home continued to be a distant dream for you, unless you were lucky enough to be part of the tech elite who rode that remote-work stock market boom.

And you got even worse off when all that crypto-chasing and sports betting seemed like your only way to just catch up to the mirage you were promised.

Cue inflation. Now even the basics started to feel like luxuries. Gas, groceries, rent — everything cost more, and your paycheck? Not growing at the same pace. Add to that student loan repayments that were paused during the pandemic? Yeah, those were coming back. It’s like the financial system was programmed to wring every drop from your wallet.

Starting to pick up skills in the trades? Awesome, you can work on-contract (no benefits, no paid time-off, no professional development, sink or swim). But you persevered and got skilled up. Great! When you go to start your new company, the market barriers legislated into place lock you out from getting started. Regulations, taxes, insurance, state and local fees, licenses (all artifacts of the hyper-intense Boomer generation in power) prevent you from leveraging your skills for upward mobility.

But wait, there’s more. The climate crisis didn’t go on pause either. Wildfires ravaged the West Coast, floods became an annual event, and hurricanes were like clockwork. Every year felt more like a dystopian blockbuster, but instead of Bruce Willis saving the day, we got the ?? emoji.

Meanwhile, automation didn’t stop evolving either, that 12-to-6 curveball is always nasty. But AI and robots takes it to a whole new level — not just the factory floor stuff, but white-collar gigs too. If you thought the gig economy was precarious, wait until your job can be done by an algorithm. Some Millennials managed to pivot into tech-adjacent fields, but for many, it felt like no matter how much you upskilled, the rug could still be pulled out from under you.

And let’s talk about relationships. You are part of the first generation to grow up with dating apps, which turned swiping right into a sport, but as they hit their 30s and 40s, it became clear: this wasn’t the same dating landscape as their parents. Marriage and kids? Sure, some Millennials went that route, but for a huge swath, those things felt optional, maybe even impractical. Raising kids in this economy? No, thanks. Plus, by the time they got to the point where they could even consider starting a family, fertility issues and the insane costs of childcare made the decision even tougher.

This is all assuming your profile pic was compelling enough to swipe right. The lopsided imbalance among heterosexual people is staggering with less than 10% of men attracting 90% of the women. This model excluded things like tone of voice, pheromones, vibe, energy, character, and left a whole generation with nothing but the superficial to assess friends, causes, values, and now….mates.

Conclusion: a generation of survivors, not snowflakes

Millennials are emerging from decades of instability, broken promises, and systemic failures with a growing sense of urgency. If you were born in 1994, or anywhere near it, you've been sucker punched time and again — I mean, we don’t even like answering the doorbell. From growing up in the shadow of 9/11 and entering adulthood during the worst financial crisis since the Great Depression to dealing with a gig economy, climate change, social justice struggles, class warfare within your generation, stupefying debt, with a pandemic on the side.

The 2020s aren’t the end for you — they are the dress rehearsal for the 2030s, where Millennials will either finally break the cycles of dysfunction or sink further into the quagmire left by Boomers. ?

But here’s the twist: you aren’t the rudderless, entitled snowflake you’re often portrayed as. You’re a survivor. You’ve learned how to adapt, how to make do with less, and how to fight for a future in a world seemingly set up against you.

The thing is, you’ve never had the numbers. Now you do. Game on.

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