Health & Wellness

What Happens When the Life You Planned Never Arrives?

June 9, 2026

Millennial Midlife Crisis: Grieving the Life You Imagined — Image: Vasilis Caravitis on Unsplash

When you’re younger, it’s easy to imagine life unfolding in a neat sequence of milestones. The world is your oyster, and everything seems possible. It’s the version of adulthood that somehow feels both inevitable and just around the corner. Then one day, you wake up and realize you’re old enough to take stock of what actually happened.

On Girls Gotta Eat, Ashley Hesseltine and Rayna Greenberg tackle the very millennial experience of looking around and asking, “Is this it?” They speak about the things many of us are experiencing—from changing friendships, career pivots, and loneliness to caregiving responsibilities and the pain of realizing that some dreams may not arrive on the timeline you expected (or at all).

“We just want to validate this sort of everybody’s in the same bucket in terms of, like, this is evaluation time, and am I where I want to be?” Greenberg says.

To be clear, the episode isn’t about giving up. If anything, it’s about rewriting the definition of what a meaningful life can look like. Grief and gratitude can coexist, and you can mourn the life you thought you’d have while still making room for joy in the life that’s unfolding in front of you.

If you’re questioning everything right now, you’re probably in very good company.

Millennial Midlife Crisis: Grieving the Life You Imagined

You can grieve the life you imagined

There’s a specific kind of heartbreak that comes from missing something you never actually had. You assumed you’d be married with kids by now or have that thriving career you’ve been planning since high school. For a lot of us, we grew up with the idea that if you work hard and make good choices, eventually the pieces will fall into place. But life rarely follows a set timeline.

Hesseltine mentions friends who envisioned motherhood and partnership as part of their future and are now navigating different realities. “I think you can mourn the life that you didn’t get to have,” she says. “That is some people’s greatest dream in the entire world.”

Permitting yourself to acknowledge that grief matters. And no, it doesn’t make you pessimistic or incapable of appreciating what you do have. Two things can be true at once. You can deeply love the life you’re building and still feel sadness over the version of it that never materialized. “There’s no finish line. The goalpost is always moving,” Greenberg says.

There is no perfect life waiting on the other side

It’s easy to fall into the trap of thinking happiness lives just beyond the next milestone. We convince ourselves there’s a version of life waiting ahead where everything feels settled and secure.

And comparison is the thing that often fuels these feelings. It’s easy to look around and assume someone else has the life you should have had. But Hesseltine and Greenberg repeatedly return to the same truth: everyone is carrying something.

Hesseltine shares the story of a friend who attended her 20-year reunion feeling self-conscious about not having the family she’d always envisioned. Instead, she found people envying her freedom and lifestyle. Sometimes, the things we see as shortcomings are often the exact things someone else wishes they had.

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And, look, the dream job doesn’t magically eliminate stress. The marriage doesn’t solve every problem, and that nice house eventually needs repairs. Even the milestones we spend years chasing don’t magically erase uncertainty.

That’s what makes the idea of a “perfect life” so elusive. You have to learn to find joy in the life that’s actually happening right now, instead of constantly measuring it against the one you imagined.

You can still pivot—even now

Letting go of one version of your future doesn’t mean you’re out of possibilities. If anything, it creates room for new ones. Reinvention doesn’t have an expiration date.

Greenberg started doing stand-up comedy when she turned 40. Hesseltine got married. Listeners wrote in about changing careers, moving to new cities, picking up hobbies they’d never considered before, and finally prioritizing the things that make them happy. “If you are really at the rock bottom, you really feel like you have nothing to lose, no better time to take a big swing, no better time to pivot, f**k it,” Greenberg says.

You don’t have to blow up your entire life. You can start small, like taking the class you’ve been putting off, applying for the job you don’t think you’re qualified for, joining a new club, or booking the solo trip. If something no longer fits, you’re allowed to change course. Even now.

To hear the full conversation, listen to Girls Gotta Eat wherever you get your podcasts.