Why Every Generation Feels Like it's Failing Adulthood

I’m forty-six years old. I’ve been a regular rural mail carrier for about a year. Most of the people I work with are in their mid-to-late twenties. We’re at different stages of life on paper.

On paper.

In reality, we’re standing in the same break room, doing the same math. We’ll each have to put in roughly twenty more years to retire with anything that looks like stability. They’re just getting started. I’m halfway through adulthood. And somehow, we’re equally unsure that the finish line will hold.

That’s the part no one prepares you for. The shared uncertainty. The realization that age does not automatically translate into security.

No matter how old people are, many of them carry the same quiet fear.

They feel like they’re behind.

They look at their lives and wonder why things don’t feel settled yet. Why adulthood still feels provisional. Why they don’t feel the sense of arrival they assumed would come with time.

They assume everyone else figured it out.

That assumption is wrong.

People of all ages feel this way. Twenty-somethings, forty-somethings, retirees. The details change, but the feeling stays the same.

Something was supposed to click by now.

And it didn’t.

When that happens, people tend to blame themselves. They assume they made the wrong choices. They didn’t try hard enough. They didn’t grow up the way they were supposed to.

They scroll past milestones that look shinier than their own. They compare houses, savings accounts, career titles, energy levels. They edit their own story down to a list of perceived deficiencies.

But what if the problem isn’t you?

What if the map you were handed simply stopped matching the terrain?

For a long time, adulthood followed a recognizable story. You learned, you worked, you built stability. You became independent. You accumulated security. You aged into something solid.

That story was never accessible to everyone, but it existed strongly enough to orient people. There were clearer ladders. More predictable timelines. Fewer overlapping crises.

Then the conditions changed.

Wages stagnated. Housing became unreachable. Healthcare became fragile. Work stopped being stable. Crises overlapped without recovery time.

The markers people were told to aim for either moved out of reach or stopped meaning what they used to mean. A degree no longer guarantees security. Loyalty no longer guarantees stability. Hard work no longer guarantees arrival.

But no one thought to update the story.

So people are walking through a landscape that no longer matches the directions they were given, wondering why they feel lost.

Older generations feel like they failed to secure what they were promised. Middle generations feel permanently stretched and behind. Younger generations feel tired before life even begins.

Everyone assumes the problem is personal.

It isn’t.

When instability is treated as a character flaw, shame fills the gap where context should be. People hide their confusion. They minimize their struggles. They delay rest, joy, and satisfaction until they feel like they’ve earned adulthood.

They postpone living until things “make sense.”

But adulthood isn’t a finish line.

It’s a moving target that was never clearly redrawn.

So if your life doesn’t look the way you were told it should by now, that’s not evidence that you failed.

It’s evidence that the world changed faster than the story did.

Naming that doesn’t magically make things easier. But it does something gentler and more important.

It lets you stop measuring yourself against a version of adulthood that no longer exists.

And that relief matters.

I write about the quiet pressures we’re taught to internalize, and what shifts when we question them. If this resonated, there’s more of that work gathered in one place. You can find it through the link in my bio.