Guest Post: Confronting our own Finitude (Part 2)

Why This Matters for Leaders I am writing and sharing my thoughts here for one reason, that I recognise now

Tom McCallum

May 10, 2026

Guest Post: Confronting our own Finitude (Part 2)

Guest Post: Confronting our own Finitude (Part 1)

Authentic purpose-led leadership is only fully available to a leader brave enough to confront their own finitude. This statement is

Tom McCallum

May 9, 2026

Guest Post: Confronting our own Finitude (Part 1)

Why I’m (Strangely) Less Discouraged These Days

Even writing that sentence feels surreal. And yet, in the quiet moments—lying in her bed for the first two nights

Chip Conley

April 20, 2026

Why I’m (Strangely) Less Discouraged These Days

Writing Mom’s Obituary

I’m lying in Mom’s bed. It’s 5 a.m. on Sunday morning. Exactly 48 hours earlier, I was on an early

Chip Conley

April 15, 2026

Writing Mom’s Obituary

The Month I Died

Image by Jonas Peterson Next February, I’m going to die. Not permanently, I hope. But convincingly enough that the world—and

Chip Conley

March 16, 2026

The Month I Died

Why I’m Ready to Die

A wailing siren and a soft, reassuring hand. That is all I remember from my ambulance trip in suburban St.

Chip Conley

February 3, 2026

Why I’m Ready to Die

Before Death, Depth

We don’t need to live longer. We need to live deeper. And that doesn’t require a plane ticket or a

Chip Conley

April 18, 2025

Before Death, Depth

Do You Want to Know When You’ll Die?

I was reading Deepak Ramola’s book “The 50 Toughest Questions of Life” and found this particular inquiry deeply intriguing. Somehow

Chip Conley

April 4, 2025

Do You Want to Know When You’ll Die?

Meditating on Memento Mori

As Steve Jobs suggested, “Almost everything–all external expectations, all pride, all fear of embarrassment or failure–these things just fall away

Chip Conley

January 24, 2025

Meditating on Memento Mori

“Bring it All, Give it All, Leave it All.”

(And, very important new note: my urologic oncologist called me midday yesterday to say that the data he gave me

Chip Conley

August 23, 2024

“Bring it All, Give it All, Leave it All.”

Reflections from a Modern Elder.

Most of us have heard “take what resonates” and leave the rest behind, so this I share with you to

Sue Madrid

July 27, 2024

Reflections from a Modern Elder.

What Will You Memorialize Today?

Happy Memorial Day in the U.S.! The wise human recognizes that death isn’t your own end-of-life ritual, but it’s something

Chip Conley

May 27, 2024

What Will You Memorialize Today?