The Hardest Leadership Lesson: Let Someone Else Be the Hero
The Midlife Chrysalis
September 30, 2026
Being the person who saves the day feels good. But letting someone else do it can make you a better leader. MEA founder Chip Conley joins Derek Gehl to talk about one of the hardest changes in his career: moving from hero to coach.
Speakers Chip Conley, Derek Gehl
TopicsSelf-ImprovementEducation
Chip Conley (0:00)
So, a young leader thinks they know it all. An older leader knows they don't know it all, hopefully.
That's wisdom. Wisdom is absolutely about knowing you don't know it all.
SPEAKER_2 (0:09)
This is The Midlife Chrysalis. Welcome to Wisdom Wednesdays with Chip Conley and Derek Gehl, 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 Gehl (0:26)
Welcome to Wisdom Wednesday here at The Midlife Chrysalis podcast. My name is Derek Gehl. I'm the CEO here at MEA. I'm with our founder, Chip Conley. Chip, how are you?
Chip Conley (0:33)
Hello, Derek. I'm good. It's a little soggy here.
Derek Gehl (0:36)
It is. It is. Yeah.
Chip Conley (0:38)
It's very interesting. Santa Fe has monsoon rains in the summer that are amazing. Then you have rainbows and double rainbows afterwards. It lasts about an hour.
Then within six hours, it's dry again. But we're having just an ongoing rainstorm here. For sure. For about two weeks.
Derek Gehl (0:56)
Yeah.
This is Pacific Northwest. This is what I'm used to.
Chip Conley (0:59)
It's actually gorgeous. I think for those of you who are coming in October or November, you may get wildflowers, which we don't usually get in the fall. We usually get them in the summer. You may get some wildflowers here because we're getting a really good soaking right now.
Derek Gehl (1:13)
Yeah. I imagine the Arroyo is just ripping right now.
Chip Conley (1:16)
I know. I wish it was out there. Yeah.
Derek Gehl (1:19)
It may not be safe, but I totally want to go check it out.
Chip Conley (1:23)
The creek goes underground most of the time. Then we go to Galisteo, the village next door near us.
The creek's above ground. It's very interesting.
Derek Gehl (1:32)
Interesting.
Chip Conley (1:33)
The creek can go below ground.
Then all year round, it's above ground there. Yeah. But when we have rains or snowmobiles or things like that, we have a nice little creek running.
Derek Gehl (1:44)
Yeah. Look, it's fascinating. I've learned a lot about water rights and how water works out under this desert and it is fascinating.
Chip Conley (1:51)
Yeah. Water is such an essential part of life. Yeah. It also brings life together. Yeah. Water sources, you see animals near water sources. It's part of the reason actually why we are a migratory bird sanctuary on some level, this ranch is. We have a lot of birds that migrate through here.
Because it's relative to the rest of the desert, it's a little bit wetter here because the Rapparian corridor, which is basically the area around the creek.
SPEAKER_2 (2:21)
Yeah.
Derek Gehl (2:21)
But I mean, just the landscape from Albuquerque to here is so much more barren in Albuquerque. It's so much greener and lusher here.
SPEAKER_2 (2:29)
Yeah, it's true.
Chip Conley (2:29)
Yeah.
Derek Gehl (2:30)
Fascinating. All right. Let's dig in. We're going to talk about leadership today.
There's a chapter, the new book you're working on. We'll talk about that later in another episode, but there's a chapter.
Chip Conley (2:43)
Here's the name of the book. It's called The Art of the Reframe.
Derek Gehl (2:46)
The Art of the Reframe.
Chip Conley (2:47)
Comes out in January.
Derek Gehl (2:48)
Pre-order, so it should probably be ready in October.
Chip Conley (2:50)
Yeah, pre-orders will be ready in October. We should definitely get you to pre-order because that will help us with any lists that we potentially could be on.
Derek Gehl (2:57)
We want to be on all the lists.
Chip Conley (2:59)
So, that's not the only metric. It's not the only metric.
Derek Gehl (3:04)
There's a chapter in this book, and I'm in it. I made a debut. You wrote that the hardest shift you've made in the last few years is going from hero to coach.
Chip Conley (3:12)
Yeah.
Derek Gehl (3:14)
I'm sitting right here. Let's talk about that.
What's been the hardest part for you? Handing this over.
Chip Conley (3:19)
Well, I think when you're a leader, first of all, leaders are role models.
Derek Gehl (3:22)
Yeah.
Chip Conley (3:23)
Let's start with that. If we were to replace the word leader or manager for a month, and just said, whenever you're going to say leader or manager, save role model, it will remind us what our role is. Because the higher you are in an organization, the more contagious your character skills or challenges. When you're a founder and also CEO, which I did for 24 years in a boutique hotel company, never had a succession plan. So when I really did need to have a successor, we didn't have one. Now, we have one.
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