Grieving the Life You Imagined: Coping With the Pain of Unmet Expectations

Odile McKenzie, LCSW
Jul 24
3 min read

As teenagers, many of us mapped out the blueprint for our dream life. We imagined when we’d land our perfect career, get married, start a family, buy the brownstone, build generational wealth, and maybe take that dreamy Bali trip once a year. We expected milestones to unfold in a tidy, linear timeline.

Fast-forward to adulthood, and for a lot of us… things didn’t quite pan out that way.

Some of us are still waiting for the right job to come, still searching for the right partner, still trying to afford a vacation, let alone a mortgage. Others might have checked all the boxes and still find themselves staring at the ceiling at 2 a.m., wondering, Why doesn’t this feel better?

There’s a name for that ache that doesn’t go away: grief.

But not the kind of grief we usually talk about.

This is the grief of unmet expectations. It's the quiet sorrow for the life we imagined but didn’t get. And unlike acute grief, which is easier to validate and understand, this one lingers in the background like a dull hum. It’s often mistaken for laziness, bitterness, or failure. But at its core, it’s very human.

Let’s Get Honest: Are You Holding On Because It Feels Safe?

Before we talk about how to cope, it’s worth asking a deeper question:

What are you gaining from staying stuck in this space?

It’s a tough one. But sometimes, the fantasies we grieve are also the same ones we cling to because they offer something comforting—certainty, identity, validation. And if we're honest, the sadness might also be serving a function: protecting us from disappointment, failure, or vulnerability.

So, ask yourself gently:

Is there something I’m still hoping will magically happen if I wait right here?
Is staying in this grief giving me an excuse to not try again?
Is this sadness giving me connection, even if it’s just to my past self?

There’s no shame in your answer. But once you know it, you can decide whether it’s time to meet that need in a more life-giving way.

How to Cope: Tools From ACT, Buddhism, and Stoicism

Let’s talk about how to move forward. Not by pretending the pain isn’t there, but by learning how to hold it and still live.

1. Accept What Is (ACT Therapy)

Acceptance and Commitment Therapy (ACT) teaches that suffering often comes from fighting reality. You don’t have to love it, but resisting what is keeps you in a loop of pain. Try saying:

“This hurts. And it’s okay that it hurts. I can still choose how to live today.”

You don’t need to wait for the grief to pass before building a life that matters. You just need to make space for it while reaching for something more meaningful.

2. Drop the Illusion of Control (Buddhism)

Buddhist teachings remind us that attachment to outcomes is one of the roots of suffering. When we tie our worth or peace to things going a certain way, we set ourselves up for disappointment.

Try practicing non-attachment:

Write down what you dreamed of, and honor it.
Then ask: Can I still find meaning if this never happens?
Choose to water the seeds of what is blooming, instead of only mourning what didn’t.

3. Focus on What You Can Control (Stoicism)

The Stoics were big on this. You can’t control what happened, what others do, or the timing of things. But you can control your attitude, values, and actions.

A few Stoic-inspired questions to ground you:

What is within my control right now?
How do I want to show up, regardless of circumstance?
What kind of life can I build starting from here, not from the dream I lost?

Final Thoughts: Grief and Growth Can Coexist

Grieving the life you imagined doesn’t make you weak or ungrateful. It makes you human. You get to honor your disappointment without being defined by it.

You get to rewrite the story.

You get to move forward, not because everything is perfect, but because you are worthy of living fully, even in the “after.”