the gates of grief
“No one ever told me that grief felt so like fear.”
C.S. Lewis
“A man of sorrows, acquainted with grief”
Isaiah 53
I am a cup-half-full kind of man.
I am a cup-overflows kind of man.
But there have been a few moments lately where my cup was bone dry.
These were moments of grief.
We don’t talk about grief in men’s spaces that often. We talk about men’s discipleship, men’s ministry, men’s wounds, addictions, porn, ambition, anger, and loneliness, but we often skip over grief.
Maybe it’s worth bringing grief back into the conversation.
The Bible uses over twenty words to describe grief, from loud wailing at death to quiet cries for help. Grief was not a stranger in redemptive history. There was liturgy and ritual, space and place to let the pain of the heart breathe. In modern society, where we have sentimentalized death and have no patience for ongoing pain; we hurriedly demand that grief be quiet and quick.
We're subtly taught to bypass our sorrow, to move efficiently into acceptance without fully acknowledging what we've lost. But this can have catastrophic consequences for the heart. When we neglect grief, we risk numbing our hearts, breeding bitterness, fostering addictions, and even dismantling our faith through disappointment and deconstruction. According to a study from Harvard Medical School in 2020, unprocessed grief can lead to high blood pressure, heart disease, insomnia, and a weakened immune system.
The reason grief hits at a visceral level is because it’s about loss—soul-level loss. Grief, at its core, is love without a home. As Nicholas Wolterstorff notes, “Every lament is a love song.” To mourn openly and honestly is to affirm the depth of our love and the pain of its loss. Or as Stephen Wilson Jr puts it, “Grief is only love that’s got no place to go.” (Grief Is Only Love by Stephen Wilson Jr)
THE GATES OF GRIEF
Part of the pain of grief is that it seems to sabotage our lives and intrude without permission. Knowing where grief gets in can slightly soften its blow. That’s why I was grateful that a friend recommended The Wild Edge of Sorrow by Francis Weller to me. I listened to it driving home from doing my father-in-law's funeral. It’s a book you must filter through, but one that contains incredible explanatory power for the grief we experience in our lives.
Weller identifies five gates through which grief enters our lives:
Gate 1: Everything we love, we will lose
Inevitable losses, such as family, friends, health, and dreams.
Gate 2: The places within us that haven't known love
Neglect, emotional wounds, and unfulfilled needs.
Gate 3: The sorrows of the world
Grief over injustice, violence, societal brokenness, sin, and alienation.
Gate 4: What we expected but didn't receive
Dreams that didn't materialize, careers, relationships, and achievements.
Gate 5: Generational and collective grief
Pain passed down generations, family trauma, and historical wounds.
I have since spent real time examining these gates of grief. They have helped me understand and categorize much of what I have experienced. If you are facing things you are struggling to name and identify, these could help. Perhaps your grief is hidden behind unfulfilled dreams or family wounds that silently shape your reactions and decisions. Maybe it's a childhood ache that you carry, a burden you bear quietly, isolated from those around you.
Research shows that being able to name and identify the source of our grief (affective labeling) is a step towards healing. In a conversation with my wife recently, where I was angry, this happened for me. She graciously said. “It may not be anger you are feeling, it may be grief. You may want to go on a grief journey with this to see if you are confusing the symptom with the cause.” That naming and framing transformed how I walked through the confusion and pain I was feeling.
GRIEVING WITH HOPE
Christians are not exempt from walking through grief. Even after a personal encounter with Jesus, a trip to heaven, and raising the dead, Paul still wrote, “We were under great pressure, far beyond our ability to endure, so that we despaired of life itself.”
Jesus wept, even though He knew He would raise Lazareth from the dead. He sweat drops of blood at the cost of the cross, even though He knew He would rise from the dead. To bypass grief, even though we know we will live in a future without “mourning, crying, or pain,” is not helpful. Grief gets us ready for the glory to be revealed.
That’s why Walter Brueggemann’s insights on the Psalms are so helpful. He suggests that the Psalms describe life through three movements.
1) Orientation (when all feels right and stable)
These psalms reflect stability, gratitude, and trust in God’s Word. They’re rooted in creation, Torah, and covenant faithfulness.
“Like a tree planted by streams of water…”(Psalm 1)
“What is man that you are mindful of him?”(Psalm 8)
“The heavens declare the glory of God…”(Psalm 19)
“Bless the Lord, O my soul…” (Psalm 103)
2) Disorientation (when grief and chaos upend our world)
These psalms are honest cries from the pit. They include lament, rage, grief, betrayal, sickness, and loss. Brueggemann argues that these are the most underused and urgently needed psalms in modern faith.
“How long, O Lord? Will you forget me forever?” (Psalm 13)
“My God, my God, why have you forsaken me?” (Psalm 22)
“Darkness is my closest friend.” (Psalm 88)
“Save me, O God, for the waters have come up to my neck.” (Psalm 69)
3) Reorientation (when we discover new depths of faith and gratitude through God’s restoration)
These psalms emerge after disorientation, not a return to naïveté, but a deeper, tested gratitude. They reflect a hard-won joy, often after deliverance.
“You turned my mourning into dancing.”(Psalm 30)
“He lifted me out of the slimy pit.” (Psalm 40)
“I love the Lord, for he heard my voice.”(Psalm 116)
“Those who sow in tears will reap with songs of joy.” (Psalm 126)
The Psalms teach us to lament without reserve, to wrestle honestly with God, and to wait patiently for renewal. If we dismiss the disorientation, we end up as shallow, scrambling, self-sufficient men. Paul wrote that the reason we encounter hardship is so that “…we might not rely on ourselves but on God, who raises the dead.”
It is God raising us, not our own self-effort or spiritual bypassing, that lets us grieve with hope.
___________________________________
DISORIENTING DISCIPLESHIP
We so often talk about orientation and reorientation in the church, The goodness of God and the redemption of God. But if we want to live from whole hearts, and go deep with each other, we must do discipleship in the place of disorientation.
We must meet each other in the grief, pain, and heartache of life. When we “weep with those who weep,” we build a trust and depth, a communitas that can journey through the valley of the shadow of the table of death to a table in the presence of our enemies.
It is there we learn the participation with His sufferings, not just the power of His resurrection. A participation then enables us to genuinely become wounded healers, not just teachers of the Bible but bystanders to the pain of life.
I am learning to grieve well. I may be a slow learner, but I look behind me and see grace and progress in my life. I am learning to mourn loss, embrace disorientation, and trust that God will reorient me in His own time and way.
I pray the same for you. As C.S. Lewis wrote in A Grief Observed, “No one ever told me that grief felt so like fear.”
May God give us the grace to have the courage to walk forward, even as we grieve along the way.
Thanks for reading.
Cheers.
Jon.
___________________________________
Discussion Questions:
C.S. Lewis said grief feels a lot like fear. Can you remember a time you reacted with anger or anxiety but were actually grieving? What were you grieving?
Which of the Five Gates of Grief feels closest to your experience right now? What loss or pain does this bring up for you?
Life often moves between feeling stable, feeling overwhelmed, and then finding hope again. Which stage are you in right now? Are you honestly facing what you’re feeling?
When you experience loss, do you usually slow down to feel it, or do you rush past it to get on with life? How might your life change if you paused and really faced your grief?
Jesus is called "a man of sorrows, acquainted with grief." How does knowing that Jesus felt deep sadness help you deal with your own grief?
___________________________________