When Life Doesn't Look Like You Thought It Would

“Life doesn't look like I thought it would.”

If you're a millennial woman reading this, chances are that sentence just hit you right in the chest. You're not alone if you find yourself looking around at your life—maybe it's good, maybe it's even objectively successful—and still feeling like something's off. Like you're somehow behind where you thought you'd be by now.

Maybe you recognize yourself in some of these experiences:

• You're single while it feels like everyone around you is coupling up, moving in together, getting engaged, or married—and you're tired of being asked about your dating life at every gathering

• You're struggling with fertility or have decided not to have children, yet your social media feels like a constant stream of pregnancy announcements and baby photos that leave you feeling isolated and alone

• Your career feels stagnant or unclear while others seem to be climbing ladders, getting promotions, or confidently pivoting to dream jobs—and you're not even sure what your dream job would be

• You're still in your small apartment while friends are buying homes or upgrading to bigger spaces, and the math of NYC real estate feels increasingly impossible

• You gave up creative pursuits for financial stability, but watching others succeed in the fields you left behind brings up a complicated mix of longing, envy, and regret

• You achieved what you thought you wanted but feel surprisingly empty or anxious about what comes next

If any of these resonate, please know: you're not failing at life. You're not behind. And you're definitely not alone in feeling this way.

The Comparison Trap We Can't Escape

Living as a millennial woman in New York City means existing in a constant state of comparison. Social media shows us curated highlights of other people's lives. The city itself puts success on display everywhere we look. Even well-meaning conversations with family and friends can leave us feeling measured against invisible benchmarks.

The challenge isn't just that we're comparing ourselves to others—it's that we're often comparing our inner reality to other people's external presentations. You see your friend's engagement photos but don't see the relationship work they're doing in therapy. You hear about a colleague's promotion but don't know about their anxiety attacks or sleepless nights. You watch someone launch their creative business but don't see the financial stress or family pressure they're navigating.

This constant comparison can create a painful loop: you work harder to achieve what looks successful from the outside, but when you get there, it doesn't feel as satisfying as you expected. So you set new goals, work harder, achieve more—and the cycle continues.

When Working Hard Isn't Enough

Many millennial women I work with are incredibly driven and hardworking. You're not sitting around waiting for life to happen to you. You've likely worked your ass off to get where you are. You've made sacrifices, taken risks, put in long hours, invested in yourself.

And that's exactly why it can feel so disorienting when life doesn't unfold according to plan.

When you've done everything "right"—gotten the education, worked hard, made responsible choices—and life still doesn't look like what you imagined, it can shake your sense of how the world works. It can leave you questioning not just your choices, but your worth, your judgment, and your ability to create the life you want.

This is where perfectionism shows up—not necessarily as needing everything to be flawless, but as this deep belief that if you just work hard enough, want something enough, or do enough research and planning, you should be able to make it happen. When reality doesn't match that formula, it can feel like a fundamental failure rather than just life being unpredictable.

The Myth of the Life Timeline

We grew up with certain assumptions about how life would unfold. Graduate college, start a career, find a partner, maybe buy a home, perhaps have children—all following some general timeline that felt achievable and normal. But the economic and social realities we're living in are vastly different from the ones our parents navigated.

The cost of living in cities like New York makes traditional milestones like homeownership feel increasingly out of reach. The job market requires constant adaptation and reinvention. Dating has been fundamentally changed by technology. The pressure to optimize every aspect of our lives—from our careers to our relationships to our wellness routines—can be exhausting.

Meanwhile, we're also the first generation to have such intimate access to everyone else's lives through social media. We can see not just our immediate circle, but hundreds of acquaintances and strangers living lives that might look more successful, more fulfilling, or more aligned with what we thought we wanted.

What's Really Underneath the Disappointment

When I sit with millennial women who are struggling with how their lives have unfolded, what emerges often goes deeper than just unmet goals or delayed timelines. What I notice is that underneath the anxiety about the future or disappointment about the present, there's often something that looks a lot like grief.

“Underneath the anxiety about the future or disappointment about the present, there’s often something that looks a lot like grief.”

This might sound surprising. We typically think of grief as what happens when someone dies. But grief is actually our natural response to any significant loss—and when life doesn't match our expectations, we experience multiple losses simultaneously.

You might be grieving the version of yourself you thought you'd be by now—more confident, more settled, more clear about what you want. You might be mourning relationships that didn't work out the way you hoped, or career paths that led somewhere different than you imagined. You could be grieving time that feels lost, dreams that feel out of reach, or the sense of security you thought you'd have by this point in your life.

Here's what's important to understand: this grief often doesn't look like sadness. It can show up as anxiety about the future, as feeling stuck or restless, as difficulty making decisions, or as a general sense that something's missing even when your life looks good on paper.

The Weight of Unprocessed Disappointment

When we don't acknowledge or process these losses, they tend to accumulate. That anxiety about your career might be connected to grief over the creative path you didn't take. The pressure you feel about relationships might be tied to mourning the family relationships that didn't give you what you needed. The restlessness you feel in your current life might be grief over dreams that feel increasingly impossible.

The challenge is that our culture doesn't really give us space to grieve these kinds of losses. We're encouraged to focus on gratitude, set new goals, or find ways to reframe our disappointment as growth opportunities. While there's value in all of these approaches, they can also prevent us from actually processing what we're feeling.

Why Traditional Therapy Approaches Sometimes Fall Short

If you've tried therapy before and felt like it didn't quite address what you were experiencing, this might be part of why. Many therapeutic approaches focus on managing anxiety about the future or developing coping skills for disappointment. These can be helpful, but they often miss the deeper work of actually processing loss.

You might have been encouraged to practice gratitude, set SMART goals, or develop better work-life balance. Again, these aren't bad suggestions—but if there's unprocessed grief underneath your anxiety and restlessness, you might find yourself feeling stuck in the same patterns despite implementing new strategies.

Therapy that honors the complexity of what you're experiencing creates space to actually feel what you're mourning, rather than immediately trying to fix it or move past it. It recognizes that your disappointment makes sense given what you've been through, and that processing these feelings—rather than managing them—often creates the foundation for genuine change.

What This Looks Like in Real Life

Let's say you come to therapy feeling anxious about your career and frustrated that you're not where you thought you'd be professionally. Instead of immediately jumping into goal-setting, career planning, or anxiety management techniques, we might explore what's really underneath that frustration, such as:

• What messages you received growing up about success and worth

• What you're really grieving about your career path so far

• How your perfectionism might be protecting you from deeper disappointment

• What would feel meaningful to you now, separate from external expectations

• How to build compassion for the choices you made with the information you had at the time

This kind of work requires time and trust. It involves building a therapeutic relationship where you can explore these feelings without judgment or pressure to feel differently. It's not about staying stuck in disappointment, but about moving through it rather than around it.

The NYC Context

Living in New York City adds particular intensity to these challenges. This is a city where ambition and success are highly valued, where the cost of living makes it harder to take risks, and where you're constantly surrounded by reminders of what achievement looks like.

Many of us moved to New York with specific dreams about who we'd become here. When those dreams don't materialize as expected—or when they do but don't feel as fulfilling as we hoped—the disappointment can feel especially acute in a place where success feels so visible and urgent.

Moving Through, Not Around

The path forward isn't about convincing yourself to be satisfied with less or forcing gratitude for what you have. It's about creating space to honestly acknowledge what you're experiencing, including the losses and disappointments that might be driving your anxiety or sense of being stuck.

This doesn't mean wallowing or giving up on what you want. It means recognizing that your feelings about how your life has unfolded make complete sense, and that honoring those feelings often creates the foundation for clearer decision-making about what comes next.

When we try to skip over disappointment and loss, they tend to show up as anxiety, depression, or feeling stuck. When we create space to actually process these experiences, we often find that our energy naturally begins to shift toward what feels meaningful now—not what we thought we should want years ago.

You're Not Behind

Here's what I want you to know: you're not behind in life. You're not failing because your life doesn't look like what you imagined at 22. You're not broken because you're struggling with disappointment or feeling lost.

You're a thoughtful person navigating a world that's more complex and unpredictable than anyone prepared you for. Your feelings about how your life has unfolded make complete sense, and they deserve to be honored rather than immediately fixed or reframed.

The goal isn't to stop wanting things or to lower your standards. It's to build a different kind of relationship with uncertainty and disappointment—one that doesn't require you to have everything figured out in order to feel okay about yourself.

Ready to explore what's really underneath your disappointment and anxiety about the future? Therapy for millennial women navigating unmet expectations isn't about fixing what's wrong with you—it's about understanding what you're actually experiencing and creating space for who you're becoming now. Schedule your free 15-minute consultation to explore whether this approach might be what you've been looking for.