If you had asked me ten or twenty years ago what my life would look like by now,
I had a picture.

I thought I would be finishing up my career as a public school music teacher, living on Long Island (my first home), and married with a few kids. I imagined serving in a church, singing, and leading worship. I pictured friends, a vibrant community, and a built‑in pool for backyard parties.

I would be utterly content.

But there is a gap between expectation and reality that often doesn’t get spoken about. We sit in that gap, looking back at what we thought would be and forward into what is. No one prepared me for sitting in that gap, and the grief of realizing that life didn’t turn out the way I thought it would.

The Framing of Grief.

When we think of grief, we often picture funerals or obvious losses. Yet grief can also settle in quietly over dreams that never took shape, ministries that never found their footing, or bodies that do not work as we hoped. We grieve fragile homes and financial lives when we were promised “The American Dream” and security if we just played by the rules. And we grieve the version of ourselves we thought we’d be by now.

This is not about feeling sorry for ourselves.
We aren’t playing the victim or pulling out that tiny violin to worship our sob-stories.

Instead, this is an honest lament—a recognition of the possibilities that have faded and the dreams that have not come to pass. We do not only grieve people. We grieve the stories we believed we were living, and the moments we hoped would be ours by now.

Self‑pity? No.
Grief and pain? Yes.

In Romans 15:4, Paul wrote,

“For everything that was written in the past was written to teach us, so that through the endurance taught in the Scriptures and the encouragement they provide we might have hope.” (NIV)

Scripture is full of people whose lives did not go as they planned. Their stories teach us that disappointment is not the end of God’s work. Often, it is the very place where God begins something new. Their stories offer us encouragement so that we might have hope.

Consider Moses.

Moses was born a Hebrew, yet he grew up in Pharaoh’s palace, surrounded by the wisdom and privilege of Egypt. If you had looked at his life from the outside, you might have thought his story was set in stone.

But sometimes, the story we expect is not the story God writes.
For Moses, the first forty years seemed like a perpetual unraveling.

After Moses acted in anger and killed an Egyptian who was beating a Hebrew slave, he ran for his life into the wilderness of Midian. The prince of Egypt became a shepherd, far from the life he once knew.
There he married Zipporah, started a family, and spent forty years tending sheep on the far side of the desert. When his first son was born, Moses named him Gershom, saying, “I have become a foreigner in a foreign land” (Exodus 2:22).
That name, Gershom, has always stayed with me. There is something haunting about it. Isn’t there?
- It tells us that even after building a home, marrying, and raising children, something inside Moses still felt displaced. Midian was where he lived, but it wasn’t where he imagined his story would unfold.

Moses was not just grieving Egypt.
He was grieving the life he thought he would live.

Yet it was there, in the quiet and ordinary rhythms of an unexpected life, that God met Moses in a burning bush. Those years in Midian looked nothing like the life Moses might have imagined as a young man in Pharaoh’s palace. But it was from that hidden place, far from the spotlight, that God called him to lead His people out of slavery.

Friend, sometimes the wilderness is not where our story ends, but where God begins something new.

Consider Naomi.

When the book of Ruth begins, Naomi is living in Bethlehem with her husband and two sons. Her name means “pleasant.” That’s important. The author of Ruth is trying to show us what her personality was like in those early days.
Famine forces the family to leave Bethlehem for Moab. There, Naomi’s husband dies, and later, both of her sons die as well. She leaves Bethlehem with a family and returns without them.
When she arrives home, she tells the women of Bethlehem, “Do not call me Naomi; call me Mara, for the Almighty has dealt very bitterly with me” (Ruth 1:20).
- Naomi means pleasant.
  Mara means bitter.
- When Naomi asks to be called by a new name, she is giving voice to how grief has shaped her. The life she returns to is not the life she imagined. Her home is now filled with memories of those she has lost.

Think about the disciples after Jesus died. They went back to fishing, back to the life they knew before their hope was shattered. Or Jeremiah and Isaiah, who followed God’s call even when almost no one listened. Or the exiles in Babylon, grieving the loss of a home and a way of life they would never get back.

The Bible doesn’t shame people for grieving the life they thought they’d have; it shows God meeting them in that in‑between.

Grateful and Grieving

If you had asked me ten or twenty years ago what my life would look like by now, I had a picture. But instead of living in my hometown on Long Island, I live in a little community on the eastern shore of North Carolina. And much like Moses, I still feel like a stranger here.

I thought I would be finishing up my career as a public school music teacher; instead, I run a non‑profit community theater completely voluntarily. While I have the greatest son on earth, I have also had more miscarriages than I can count and have mourned babies I never got to hold.

We do not have the backyard pool or the lively gatherings I once imagined. My body feels the weight of years and weariness, and contentment does not always come easily.

The “American Dream” we were promised as ’80s and ’90s kids never did come true for most of us, did it?

But here is what I know to be true.

A God who walked with me and is walking with me still.
The promise of a life on the other side of this one that is greater than anything my mind could imagine.
A God who can handle my lament, my complaints, my grief, and my fear.
A God who is still writing my story and a Savior who is my hope.
Rainbows in the middle of the rain.
Good days in the midst of some really bad ones.
Weeping and dancing go hand-in-hand.

That is all true.

So if you find yourself some days walking through the ruins of the life you thought you would have, grieving dreams that never came to be and yet still finding gratitude for what is, know that this tension is both normal and healthy.

Uncomfortable to sit in? Absolutely.

But that tension is where we find the saints of Scripture, time and time again. You can be grateful and grieve at the same time. Scripture shows us both in the same breath:

“I well remember them, and my soul is downcast within me.
Yet this I call to mind and therefore I have hope:
Because of the LORD’s great love we are not consumed, for his compassions never fail.
They are new every morning; great is your faithfulness.
I say to myself, “The LORD is my portion; therefore I will wait for him.”
The LORD is good to those whose hope is in him, to the one who seeks him;
it is good to wait quietly for the salvation of the LORD.”

Lamentations 3:20-26 NIV

An Invitation.

I don’t know if this journal entry will make you “feel better.” I suppose that isn’t the point. The point is to let you know that you are not alone if you are grieving the life you thought you’d have.

Perhaps try this short exercise:

Name one “life you thought you’d have” (a sentence or phrase).
Choose a passage (Psalm 13, Psalm 73, Lamentations 3, or Matthew 6:25–34).
Write that passage by hand.
Underneath, write one sentence of lament related to that lost life and give it to God as a prayer.

Friend, some losses will not be “fixed” in this life, and yet there will still be hope. Hope is not “you’ll get everything you wanted later.” Hope is “God is with you in what is, and He will not waste what you’ve walked through.”

May you have permission to grieve the life you thought you’d have, and may you discover, slowly, that Jesus does not roll His eyes at that grief.

He walks it with you.