The Grief of Leaving Behind The Life You Built

You spent years working toward the life you're currently living. What happens when you realize that this dream life just doesn't fit you anymore?

Jul 08, 2025

The Encyclopedia of Grief is an archive where we talk about the kinds of grief that shape our lives quietly, often without anyone noticing. This season is focused on the grief that follows the broken promises of modern day life. We’re not here to fix anything. Take what you need and leave the rest

Some grief doesn’t come from failure. It comes from fulfillment.

From doing everything you were supposed to do. From building something that worked, maybe even beautifully, only to discover that you’re not at home in it anymore. Maybe you built a family. A business. A life in a city you once loved. Maybe you spent years climbing a ladder or watering a dream. And now, some quiet voice inside you keeps whispering: I can’t stay here.

On the day I realized I had to shut down my business, I remember walking through my favorite park in Brooklyn, battling myself:

“We have to shut it down. This is not sustainable.”

“But we worked so hard to get here! Look at everything we achieved.”

“I’m miserable….”

“But closing down will be so embarrassing. I can’t deal with that!”

Round and round I went, negotiating with myself on the easiest way to step away from this dream. Up until that point, all of the problems I’d had in the business were more than worth it. I’d been dreaming of going out on my own for years. Some conflict wasn’t going to stop me. My discomfort grew, and grew.

Eventually, I couldn’t keep lying to myself. It was time to shut down.

The grief that followed that decision was overwhelming. Not to mention the shame. Everyone was so proud of me! I’d started a tea company from scratch, and grown it into a nationwide brand with thousands of loyal customers. But the cracks in the foundation of the business were wearing me down. I stopped feeling excited about new customers or new branding projects. I stopped wanting to dream of the future. Every day was more of the same, and eventually I had to make the decision to let it all go.

We don’t talk enough about the grief of growth.

Modern culture rewards accumulation. Once you build something—a career, a home, a persona—you’re expected to keep it. Especially if it “works”. There is no graceful exit ramp for those who change. The storylines we’re handed say: Be grateful. Don’t mess this up. Other people would kill for what you have.

But the soul is not static. At least, mine isn’t. I’m constantly redefining what success looks like for me. Especially after I’ve accomplished a huge dream. We weren’t built to follow productivity timelines or personal brand strategies. And when we start to outgrow the container we built for ourselves, the discomfort is hard to ignore.

And eventually, just like I realized in the park that day, our bodies know what our minds refuse to accept. It’s time to go.

✾ What This Grief Looks & Feels Like

This grief often arrives after the decision has already been made. You’ve left the job, ended the relationship, packed the boxes. From the outside, it might even look like a glow-up. But on the inside, it feels like mourning.

It’s the ache of watching your old life keep moving without you. The former coworkers you still check on. The business competitors you see on the shelves, growing far beyond the success you achieved.

This grief is usually accompanied by shame and guilt. Maybe even doubt that you made the right decision. A strange kind of homesickness for the version of you that stayed. It lives in the body like a phantom life.

Sometimes it sounds like: Who am I, not that I’ve stopped pretending this fits?

Sometimes it feels like: I built all of that… for what?

✾ Mythic Mirror: Eight of Cups Tarot

In the Tarot, the Eight of Cups shows a figure walking away from the eight golden chalices stacked neatly behind them. The moon lights their path. Their cloak is dark. They don’t look back.

This is the card of sacred departure. Of leaving something that once brought you fulfillment. What makes this grief so hard is that nothing is obviously broken. The cups are still upright. The life you built might still be beautiful. But some part of you knows… staying would be a kind of self-abandonment.

This card doesn’t promise clarity. Only movement.

✾ Three Ways to Work With This Grief

Set up an altar to honor what you’re leaving behind.

You don’t have to rush into the next thing. Find a small corner of your house and fill it with photos, writing, tokens of the experience. Whenever you feel grief or shame coming on, light a candle and remember the person who once dreamed of achieving this. Let the mourning happen in layers.

Tell someone who won’t try to fix it.

Find a person who can hold space for your story without giving advice. Let yourself say it plainly: “I left something I worked hard for. I’m grieving what it meant to me.” Say it loud so that it doesn’t stay stuck in your body.

Confess your fears to the ocean.

Or really any large body of water. Go for a solo walk, and whisper your fears and guilt and shame to the water. Study the way ripples or waves come and go. Let the ocean hold your grief and share your shame.

“We carry inside us the wonders we seek outside us.”

- Rumi

There is nothing wrong with you for needing to leave.

Despite everything we’ve been conditioned to believe, we get to decide how to respond to our lives. You are not flaky or selfish or ungrateful. You are simply alive. And one of the only guarantees of being alive is change.

If this grief resonated with you and you’d like to contribute to future seasons of the project, you’re invited to take our Share Your Story of Grief Survey. The goal is turning this into a community-led project, and I’d love for you to get involved.

Thank you for spending some time with this grief. Each entry in this library is a small act of remembrance for the parts of us that were never given space to feel, question, or break apart.