How To Work Through Grief—A Journey Worth Taking

Every year when the NFL playoffs come around, I’m reminded of a dream that slipped through my fingers.

It’s a familiar ache. Watching the games takes me back to a version of myself that was so close to a life I imagined—a life I worked for, poured everything into, but didn’t live.

For a long time, I saw that grief as something to push down, something I needed to “get over” if I wanted to move forward. But grief isn’t something you move past; it’s something you work through.

And working through it? It starts with courage.

The Courage to Be Seen

Grief is a deeply personal experience, but it isn’t meant to be survived alone. One of the most powerful lessons I’ve learned is that grief needs to be witnessed.

For years, I kept my grief locked inside, thinking it was mine to carry and mine alone. But the weight became too much. I realized I couldn’t make sense of it by myself, nor could I heal in isolation.

It takes a willingness to be authentic—to invite someone into your grief story. To say, This hurts. I don’t have it all figured out, but I need to let it out.

Francis Weller, in his book The Wild Edge of Sorrow, writes about how grief is a communal process. He calls grief a doorway, one that opens us up not just to our own pain but to a shared humanity.

When I first opened up about the grief I carry, it didn’t fix everything. But it changed something. Being seen in my sorrow reminded me that I wasn’t alone. It gave me the courage to keep going.

Creating Space for Grief

Working through grief doesn’t mean rushing to “get over it.” Grief has its own timeline, and it moves in waves. Some days it feels like a dull ache, and other days it crashes over you like a storm.

To work through grief, you have to create space for it—space to feel what’s there without judgment or distraction.

This is part of the work that we do in The Deepening.

For me, this has looked like sitting with my feelings instead of avoiding them. Whether through journaling, quiet reflection, or even going for long walks, I’ve learned to hold the discomfort instead of running from it.

Francis Weller describes this as welcoming grief into the house of our being. He reminds us that grief isn’t here to harm us; it’s here to teach us. It reminds us of what mattered, of what we loved and lost, and of what still remains.

It’s not easy. But creating space for grief allows it to move through us, rather than getting stuck inside.

Finding Meaning Through Ritual

Another practice I’ve embraced is creating rituals around grief. Weller speaks to the importance of rituals in honoring our losses, both big and small.

This doesn’t have to be complicated. For me, it can be as simple as lighting a candle during the playoffs and taking a moment to reflect—not just on the dream that didn’t happen, but on the person I’ve become because of it.

Rituals help us mark the significance of our grief. They remind us that our sorrow has a place and that our pain is worthy of acknowledgment.

The Gift of Grief

What I’ve come to understand is that grief isn’t just about pain—it’s about love.

The depth of our grief reflects the depth of our connection to what we’ve lost. And when we allow ourselves to fully feel it, grief can stretch us, creating space for greater joy, connection, and meaning.

My grief for what could have been has taught me to love more fully what is now. It’s shown me that while some doors close, others open—if we’re willing to let them.

Your Journey Through Grief

If you’re carrying grief today, I want you to know this: you don’t have to do it alone. Invite someone into your story. Let them witness it. Create space for your grief, and don’t rush the process.

And when you’re ready, find small rituals that honor what you’ve lost.

Grief isn’t here to ruin you. It’s here to shape you. To teach you. To expand your capacity for life.

It takes courage to face grief head-on, but it’s a journey worth taking.

Because on the other side of grief is something unexpected: a deeper connection to yourself, to others, and to the life you have right now.

With you in this,
Caleb