You Can’t Rush Grief: Learning to Feel What We’ve Lost
The Midlife Chrysalis
September 9, 2026
Some losses hit harder than we ever expect, and grief doesn’t follow our timeline. In this deeply personal episode of Midlife Chrysalis, Chip Conley opens up about the unexpected death of his beloved dog Jamie and what the experience has taught him about grief, love, and loss.
Speakers Chip Conley, Derek Gale
TopicsSelf-ImprovementEducation
Chip Conley (0:00)
Grief is a natural thing. I think the thing about grief is it helps you to see what you really care about. If you don't have grief, you don't have love. Grief is the natural result of having something that you love not go the way you wanted it to go. So you could have grief about a relationship ending. Doesn't have to be just death.
SPEAKER_2 (0:18)
This is The Midlife Chrysalis. Welcome to Wisdom Wednesdays with Chip Conley and Derek Gale, your weekly conversation about thriving in midlife. Together, we explore the questions, insights, and practices that help you live this chapter with more purpose, vitality, and joy.
Derek Gale (0:35)
Welcome to The Midlife Chrysalis podcast. This is another Wisdom Wednesday episode. My name is Derek Gale. I'm the CEO here at MEA and I'm with our founder, Mr. Chip Conley. Chip, how are you doing?
Chip Conley (0:46)
Howdy. I'm good.
Derek Gale (0:47)
It's September.
Chip Conley (0:49)
It's gorgeous.
Derek Gale (0:50)
Yeah.
Chip Conley (0:50)
We're having some beautiful weather here in Santa Fe, and it's still warmish during the day, but cooling down a little bit at nighttime, and really good hiking weather, walking weather.
Derek Gale (1:01)
Good walking weather. Yeah. It was a warm summer, I think. I think we can say it was a warm summer for most of the continent.
Chip Conley (1:10)
Yeah, mostly most of the world, and yeah, especially Europe. Europe is actually getting punished by climate change more than anywhere else in the world so far in terms of the-
at the end of the day, there are a lot of parts of the world that are going to, you know, small islands that are going to disappear and places in the world that are going to have famine and, okay, that's not what we're talking about today though.
Derek Gale (1:32)
No, that's not what we're talking about today. But yeah, it's September.
September always feels like to me like it's like the middle of the year New Year's, you know, it's summer's over. It's like a reset. It was a big reset for me. My son's off to university.
Chip Conley (1:47)
Yeah. Congratulations. University of British Columbia.
Derek Gale (1:51)
UBC.
Chip Conley (1:52)
So he's not too far from you.
Derek Gale (1:54)
No, it's funny. From my bathroom window, I can see UBC, but it's still like 45-minute drive to get there.
Chip Conley (2:02)
Yeah.
Derek Gale (2:04)
But yeah, yeah, no. So big, big changes, big changes. But what I want to talk today about, I want to talk about Jamie.
Chip Conley (2:13)
Jamie, my dog.
Derek Gale (2:13)
Jamie, your dog. And let's take it as far as you want to take it. She passed away in July down in Baja.
And you wrote a substack article on your substack on Wisdom Well when she passed. And then you wrote one, God, probably about seven weeks later. You called her.
Chip Conley (2:30)
I keep writing them.
Derek Gale (2:31)
What's that?
Chip Conley (2:32)
I keep writing them, yes.
Derek Gale (2:34)
You keep writing them. And so let's start with who was she to you?
Where did Jamie come from?
Chip Conley (2:41)
Well, she went from riffraff to royalty. That's the story of Jamie. She showed up on the construction site at the MEA campus in Baja. We were open already, but we were adding the Desiarto home, which is a new build, and she was just sniffing around for food. She was a street dog, about a year old, and Oren, my partner, who trained dogs, he used to train the guide dogs for the blind, is really, really good with dogs and took Jamie on as a project, moved Jamie into our home there. We were, at that time, living on campus, and basically gave her all the love and discipline needed to turn her into a really amazing dog. What was interesting over time, and Oren and I have had dogs before, is in this case, over time, Jamie became even more my dog than Oren, partly because Oren was in Israel a lot, which is his homeland. Jamie during COVID was going out with me on, spying on the divine three-hour hikes three days a week, and honestly, she became my therapist.
She was the kind of dog, like any dog, but of course, your own dog is so much better at being able to listen to you and hear you. Dogs are so sensitive to emotions, and Jamie knew when I was coming home and I needed some love and care, and then she would give me that love and care and then say, it's time for a walk, Chip.
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