There's a version of this generation that did everything they were told - degree, internship, entry-level, work up - and arrived in their late 30s holding a résumé that still doesn't pay enough for a two-bedroom apartment

I want to talk about something that doesn't get said enough, mostly because the people it applies to are too exhausted or embarrassed to say it themselves.

There's a version of this generation that did everything right. They stayed in school. They got the degree. They did the unpaid internship and didn't complain about it. They took the entry-level job and worked their way up, just like they were told. They didn't job-hop too much because they'd heard that looked bad on a resume. They didn't take big risks because they'd been taught that stability was the goal.

And now they're in their late 30s, holding a resume full of experience and a bank account that still can't cover first and last month's rent on a two-bedroom apartment.

This isn't a failure of character. It's a failure of the deal they were offered.

The most educated, least rewarded generation in modern history

Pew Research Center's data on generational comparison makes the scale of this clear. About 39% of millennials aged 25 to 37 hold at least a bachelor's degree, compared to roughly 25% of baby boomers and 29% of Gen X at the same age. Millennial women in particular have surged ahead in educational attainment, outpacing men in college completion rates for the first time in history.

By every educational metric, this is the most credentialed generation the country has ever produced. And yet, as Pew's own data shows, millennials with some college or less are earning less in real terms than their counterparts in previous generations earned at the same age. Even those with full degrees are roughly treading water compared to college-educated Gen Xers.

CNBC reported on data from New America showing that millennials earn roughly 20% less than baby boomers did at the same age, despite being significantly better educated. The average millennial's wealth in 2016 was 41% less than those at a similar age in 1989. The generational wealth gap has reached what researchers called "historic proportions."

Read that again. More education. More credentials. More hoops jumped through. Less money. Less wealth. Less security.

The wage illusion

Here's the number that stops me every time I encounter it.

According to Pew Research, after adjusting for inflation, the average hourly wage today has roughly the same purchasing power it did in 1978. Real average hourly earnings peaked more than 45 years ago. The number on the paycheck has gone up. What it can actually buy has barely moved.

Meanwhile, during those same decades, the cost of housing, healthcare, education, and childcare has increased at rates that make those flat wages feel like a pay cut delivered in slow motion. Median home prices in the US increased roughly 50% between 2015 and 2024. Wages for young workers grew about 15% over the same period. The math doesn't work. It hasn't worked for a long time. And no amount of career advice or productivity hacking can close a gap that large.

This is the part that drives me slightly crazy when I hear people talk about this generation's struggles as though they're caused by avocado toast or poor financial discipline. The problem isn't spending habits. The problem is that the fundamental economic equation that previous generations relied on, work hard, get educated, and you'll be able to afford a decent life, has been quietly dismantled while the advice built on top of it has stayed exactly the same.

What the pathway was supposed to look like

The promise was simple and it was everywhere. Your parents said it. Your teachers said it. Your guidance counselors said it. The culture said it so consistently that questioning it felt irrational.

Get good grades. Get into a good college. Get a degree. Get an internship. Get an entry-level position. Work hard. Be patient. Move up. Buy a house. Start a family. Retire with some dignity.

Each step was supposed to lead naturally to the next. And for previous generations, it more or less did. A boomer with a bachelor's degree could reasonably expect to buy a home by their late twenties. Redfin's analysis of homeownership data shows that 40.5% of baby boomers owned their home when they were 27. For Gen Z at the same age, that number has dropped to 32.6%. Among 35-year-old millennials in 2024, the homeownership rate was 56%, compared to 61.5% for boomers at that age.

These aren't dramatic cliffs. They're slow erosions. And they're happening to a generation that, by every measure of effort and credential, has done more to earn economic stability than any generation before it.

The psychological cost nobody measures

What doesn't show up in the economic data is the psychological weight of living inside a broken promise. Of doing everything you were told and arriving at an outcome that doesn't match the effort.

I think about this a lot from the perspective of my own life. I'm Australian, not American, but the dynamics are similar in much of the English-speaking world. The same promise was made to my generation: get educated, work hard, the system will reward you. I was lucky in some ways. I found a path that worked for me by building a media business from scratch. But that path required ignoring most of the conventional advice I'd been given, which felt terrifying at the time because the conventional advice was the only map anyone had offered.

A lot of people I know didn't take that leap. Not because they lacked courage, but because the system explicitly told them not to. Stay on the path. Don't take risks. Be responsible. And they listened, because why wouldn't you listen when every authority figure in your life is saying the same thing?

Now they're in their late 30s, and the path has delivered them to a place that looks nothing like what was described. They have the degree. They have the resume. They have the years of experience. And they're still doing the mental arithmetic every month to figure out whether they can afford both rent and groceries without touching whatever thin savings they've managed to scrape together.

What I think needs to be said

If you're someone who followed the rules and arrived at an outcome that doesn't feel like it reflects the effort you put in, I want to be direct with you: it's not because you did something wrong. The rules were written for an economy that no longer exists.

The advice to get a degree made sense when a degree was relatively affordable and reliably led to wages that outpaced the cost of living. The advice to work your way up made sense when companies promoted from within and loyalty was rewarded with raises that kept pace with inflation. The advice to save for a house made sense when housing prices bore some recognizable relationship to median income.

None of those conditions hold anymore. The advice persists because cultural scripts are slow to update and because the people giving the advice, often parents and teachers from a generation where it worked, aren't lying. They're just working from an outdated map.

In Buddhism, there's a concept called upadana, which means clinging or attachment. One of the most painful forms of attachment is clinging to a version of reality that no longer matches what's actually in front of you. The promise of the traditional career path has become that kind of attachment for a lot of people. They keep holding onto it because letting go would mean admitting that the years they invested were guided by a framework that was already breaking down.

That's not easy to sit with. But sitting with it might be the first step toward building something that actually works for the world as it is, rather than the world as it was described to us when we were 17 and choosing a major.

I moved to Saigon partly because the economics of life here make more sense for someone running a digital business. My cost of living is a fraction of what it would be in Sydney or Melbourne. That's not a solution for everyone. But it was a decision that required me to let go of the script I'd been given and write a different one. And I think more people in this generation are going to have to do some version of that, not because the script was bad advice at the time, but because the economy it was written for has left the building.

The hardest part isn't starting over. The hardest part is accepting that you might need to.