“The hardest thing in life is to accept that life is not the way you imagined it would be. The hardest thing in life is to mourn not what is, but what could have been.”
—Rabbi Harold Kushner

There are two kinds of grief we don’t often name.

One is the sadness over what never happened: the life you imagined, the dreams that never took off, the relationships that didn’t become what you hoped.

The other is the ache of intention. When you look back and realize you meant to do something good but didn’t. You meant to love well, to show up more, to make the ask, to say the words. But life moved on, and the window quietly closed.

Rabbi Harold Kushner, an insightful and compassionate teacher best known for his book Why Do Bad Things Happen to Good People, helps us name this grief. It is not the grief of what is, but of what could have been—a life not lived, a hope not realized, a version of your story that stayed locked in the pages of intention.

And Jesus understands this grief.

Jesus Wept Over What Could Have Been

In Luke 19:41–42, we see a rare and tender moment:

“As he approached Jerusalem and saw the city, he wept over it and said, ‘If you, even you, had only known on this day what would bring you peace—but now it is hidden from your eyes.’”

Jesus stands over the city he loves and weeps. Not for what is, but for what could have been—the peace his people could have embraced, the healing they could have experienced.

This is not a God who is detached or unmoved by our choices. This is a Saviour who grieves the missed moments and the paths not taken. Jesus joins us in the sorrow of unrealized intention.

He doesn’t scold. He weeps.

And that changes everything.

Naming the Quiet Losses

When Kushner speaks of “the grief of unrealized intention,” he gives voice to a kind of sorrow many of us carry silently. These aren’t the losses others can see. They don’t show up in obituaries or farewell parties. But they are heavy nonetheless.
• The career path you never pursued
• The child you hoped to raise
• The person you wanted to become but didn’t
• The friendship that faded before you could say the truth
• The calling you felt but couldn’t quite follow

These are sacred losses, not because they were ever fully real, but because they were real to you. They mattered. And that’s enough to grieve them.

Why It Hurts So Much

This kind of grief is hard because it has no ceremony. We don’t get closure for things that didn’t happen. There’s no funeral for an unlived life. No ritual to honour the version of ourselves we didn’t become.

Yet the ache is real. And like Jesus, we are allowed to feel it.

In fact, naming that sorrow might be one of the holiest things you can do. It honours the fact that you cared. You had hopes. You were reaching for something good.

Jesus didn’t just weep for what was lost. He wept because it could have been beautiful.

So can we.

What Now?

Grief doesn’t always resolve, especially not this kind. But it can be held.

Instead of pushing away the pain, we might sit with it long enough to say:
• “That mattered to me.”
• “I hoped for more.”
• “That version of my life was worth imagining.”

And then we can begin to ask new questions:
• “What still matters now?”
• “Who am I becoming in light of what I’ve lost?”
• “How can I live with deeper awareness and compassion?”

Jesus’ tears don’t erase the pain of what could have been. But they do affirm that your grief is not foolish or weak. It’s part of being deeply human. Part of being created in the image of a God who also grieves.

An Invitation to Grace

If you’re mourning something that never happened, you’re not alone. And you’re not behind.

You are a person who dreamed.

Let that tenderness stay with you. Not to trap you in regret, but to remind you: you still care, and you still have time.

Because although some chapters closed before they began, there is still a story unfolding. 

So today, even in your sorrow, whisper the brave question:

What is still possible?

You are not behind. You are becoming.

David Simpson is the Community Care Pastor at Parliament Community Church in Regina, SK, located near Harbour Landing. As a church, we offer programs for all ages, from children to youth, young adults to Seniors who are part of our Heritage groups. We are also diverse in cultural backgrounds but share a desire to grow as disciples of Christ together.