Arrrrr! 🏴☠️ Welcome to a 💎 free edition 💎 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: View the mini-book archive | Listen to another category design jam session | Enroll in the free Category Accelerator email course
Dear Friend, Subscriber, and Category Pirate,
The holidays are a paradox — a collision of joy and absence.
They celebrate what’s present as much as they magnify what’s missing.
For many of us this holiday season, there’s an empty chair where a loved one once sat. Maybe it represents a grandparent who passed. Or maybe it’s a partner, a child, a parent, or a friend.
Every empty chair is about much more than a loss.
It’s the stories that won’t be told. The laughter that won’t echo. The ache that reminds us of a permanent, painful change.
And if you’re like us, ignoring the empty chair won’t make it go away.
This holiday season, we wanted to share something deeply personal and profoundly important with you.
While we typically write about category design and business transformation, today we're exploring territory that touches every human life: grief, loss, and how we navigate through our darkest moments.
The idea for this special episode emerged from our own experiences with loss. We recognized that traditional approaches to grief often fall short. During the holidays, empty chairs at our tables speak volumes. We believe there's a need for a different framework — what we're calling "Grief Design."
Grief Design is framing, naming, and claiming your grief instead of letting it frame you.
Here's how it works:
You frame the horror instead of letting it frame you
You allow radical self-expression without violence
You build an extension in your life for grief to live
You choose your community of support carefully
It's not about "moving on."
It’s about inviting grief in, learning to live with it, and letting it deepen your humanity and courage.
Pirate Christopher calls grief an uninvited houseguest. You can’t evict it, but you can decide where it lives. You can build it a room — a place it belongs, without overtaking your life. Grief Design helps you build an extension in your house for grief, pain, and anger to live (because they're not going away), while still creating space for joy, gratitude, and even moments of lightness.
Said differently: Grief is a fire, but you decide what it burns.
There’s no shortcut through grief.
But walking through it with intention transforms it from something that consumes you into something you can shape. The first step? Frame it, name it, and claim it.
When you frame grief, instead of letting it frame you, you begin to reclaim your power to shape what comes next.
Here’s how Viktor Frankl, a psychiatrist and the author of Man’s Search for Meaning, framed the grief he experienced in Nazi death camps during World War II:
“Dostoevski said once, "There is only one thing I dread: not to be worthy of my sufferings." These words frequently came to my mind after I became acquainted with those martyrs whose behavior in camp, whose suffering and death, bore witness to the fact that the last inner freedom cannot be lost. It can be said that they were worthy of the their sufferings; the way they bore their suffering was a genuine inner achievement. It is this spiritual freedom—which cannot be taken away—that makes life meaningful and purposeful.”
Framing your grief is not about romanticizing pain but about deciding what happens after it starts to burn inside you. The fire will change you, but you get to decide how.
This is important for a few reasons.
1. Grief doesn’t disappear when you ignore it.
Radical self-expression isn’t weakness — it’s survival.
Designing your grief means you cry when the tears come. You scream when the anger rises. You pound a bag until your frustration subsides, and your arms give out. You permit yourself to feel everything. Because the more you push your emotions down, the stronger they’ll rise one day.
Expressing your emotions is a necessary step to building a place for grief to live.
2. Grief and joy can sit at the same table.
You can feel the pang of what’s missing while soaking in the magic of what’s here.
Some days, you might feel okay at 10:15 am and be in a puddle on the floor by noon. And six hours later, you’re enjoying dinner with friends. Grief doesn’t cancel joy — it coexists with it. That’s because life allows contradictions: pain and gratitude, rage and peace, grief and joy.
This isn’t about erasing the empty chair. It’s about honoring the person who’s no longer there. You let grief shape your table — not in spite of it, but because of it.
Make Room For The Empty Chair
Grief changes you in a profound, painful way.
The most beautiful gift grief gives you is the ability to help others walk through their own grieving.
This isn’t a gift we ask for, and it’s not one you should seek out. But it’s one we can accept and use to help ourselves, help others, and help the world. When you feel your grief, you give yourself the power to frame how it impacts you. That allows you to name it. And you claim grief by integrating it into your life.
Grief will forever change your future.
But you can design a new and different future that honors the empty chair.
If you'd like to hear our full conversation about Grief Design, here are key moments:
[00:25] Pirate Christopher shares his personal story of loss and the “empty chair” at the holiday table
[03:40] The concept of making "room" for grief, pain, and anger as permanent residents in our lives, rather than trying to "heal" or "move past" them
[06:48] Learn the importance of asking, “How are you?” and simply listening
[11:55] Understand the concept of “Grief Design” and its potential impact to help you frame, name, and claim your grief
[20:02] The powerful concept of being "worthy of your suffering" and choosing to design your grief rather than being victimized by it
[27:37] A profound insight about allowing yourself to experience joy alongside grief — what Pirate Christopher calls "something very punk rock"
Here’s the story Pablo Gonzalez shared about the loss of his brother that we reference in our conversation.
We're sharing this now because we know the holiday season can amplify loss in ways that feel unbearable.
If you're sitting with an empty chair this year, we want you to know you're not alone.
While we can't eliminate the pain of loss, we hope this different approach to thinking about grief might offer a new framework for living alongside it. As you gather around tables with both filled and empty chairs, remember that you have the power to design how grief lives in your life.
The empty chair will always be there, but it doesn't have to define the entire table.
With deep care and empathy,
Category Pirates 🏴☠️
P.S. - If this resonates with you, please share it with anyone needing support this season.
This might be the permission they’ve been waiting for — to feel everything this season brings. Together, we can honor the empty chair and hold space for both grief and joy.
