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When the Life You Built Is No Longer Enough | Caroline Myss artwork

When the Life You Built Is No Longer Enough | Caroline Myss

The Midlife Chrysalis

October 9, 2026

Midlife can feel like the life you built suddenly stops fitting. Caroline Myss believes there’s a deeper reason: this is when the soul begins asking something different of you.

Speakers Caroline Myss, Chip Conley

TopicsSelf-ImprovementEducation

Caroline Myss (0:00)

And at some point in that, as you are on your career walkabout, creating hotels, doing whatever, you will stop and say, this isn't enough. This is, and that's programmed into it too. This is how contracts work. It's programmed so that one point you will lose the appetite for the road you're on. Because, and it's not, you're bored with the scenery in your soul.

You're bored with the thoughts that life has given you. You're bored because now it's time for your calling.

SPEAKER_2 (0:30)

Welcome to the Midlife Chrysalis Podcast with Chip Conley, where we explore how midlife isn't a crisis, but a Chrysalis, a time of profound transformation that can lead to the most meaningful chapter of your life.

Chip Conley (0:46)

Welcome to the Midlife Chrysalis, this is Chip Conley. And wow, this conversation goes all over me and Carolyn Mace. Carolyn's pretty famous because guess what? Oprah has had her on her show so many times that, frankly, Carolyn became best known as the medical intuitive for Oprah. Carolyn wrote a book called The Anatomy of the Spirit and nine other books, co-published The Creation of Health, and has a background that really speaks to the idea of mysticism and wellness mixed together. But this conversation goes from everything from talking about career advice and calling advice to astrology, to sacred contracts, to why wisdom schools are necessary right now, to at the end, she gives me some health advice for me with my cancer journey. Some people will love this one, some people won't be your cup of tea. But I'll tell you, I think you should stick to the end because this is a woman who has a lot of wisdom to be shared and she gave me some, that's for sure. So wait till the end and you get to hear my three key lessons of listening to Carolyn. And it was listening.

I didn't get into a lot of questions because she has a lot of thoughts.

Hope you enjoy it. I'll talk to you at the end. Carolyn, welcome to the Midlife Chrysalis.

Caroline Myss (2:10)

What a pleasure to be with you. Really, what a pleasure.

Chip Conley (2:14)

When we first connected, you were just intrigued by this idea of a Midlife Wisdom School.

Caroline Myss (2:19)

Oh, I still am.

Chip Conley (2:22)

Tell me, why does that resonate with you?

Caroline Myss (2:25)

Well, we have all day to talk about this and it would take me that big because it is such a perfect idea for the perfect time.

First of all, let's talk, what are the years that we call midlife? So let's say.

Chip Conley (2:38)

I say, based upon sociologist point of view on where longevity is going, 35 to 75, so you'd still be in midlife.

Caroline Myss (2:47)

Yes, and don't I look good for midlife?

Chip Conley (2:49)

You do.

Caroline Myss (2:50)

Yeah. But we're the generation, the first generation actually, that has dismantled all the major pillars that have held together society for thousands and thousands of years.

I'll get to those pillars in a minute. While simultaneously being the first generation since the nuclear age, to have our inner sensory system animated in order to accommodate the fact that we've entered the energetic era and our five senses are no longer adequate to help us negotiate life. Now, what have we dismantled? In the process of it, we've dismantled the collective allegiance societies have had to morals, to ethics, to religious tenets. Now, this is important to understand. It's not about what you believe. It's the fact that you had a psyche that accepted that there was something greater than yourself. We've taken that down. We do not have a world anymore in which anyone living can assume they'll make it to the end without a destructive war.

We now have the capacity to destroy all life and we celebrate that. We've become inverted in a way that has never existed before. We celebrate our own demise thinking that we can nuke them but they'll never nuke us.

We, our species are dying out at incredible levels and for the first time we have problems that are planetary in size from pandemics to climate change to a to the challenge of artificial intelligence which is something we've never had before and we've never had to deal with perhaps the intelligence of species coming to the table.

So the challenges that face us are so gargantuan that we haven't even recognized them and we have never, we have yet to adapt to a understanding of how we work as a bio-spiritual, intellectual, ecological center that is our body. And it is a bio-spiritual, ecological center from which we run our universe. We are each individual cells of a very vibrant universe. The way we have understood life is obsolete in terms of how we now have to understand life. And along with what's becoming outdated are all the traditional religious mythologies that simply don't work. There is no off-planet god. There is no off-planet god that looks like us, behaves like us and operates an illegal system. It is time that we evolve to an understanding of the divine that is as more according to its nature, that it is the creative force of love, light and law. And it is in all matter. And that the purpose of life is not to turn this into a giant shopping center and a shopping cart and accumulate all this stuff thinking as people do. That the more wealthy they get, they eventually think they can actually take on the power of life and death. And they cross the Rubicon of Madness, Chip, and they decide, well, I will build something underground to survive. You'll die, but I won't. Or I'll get in my little rocket ship and I'll go to Mars. You'll die, but I won't. We've destroyed this planet, but what the hell? There's a whole universe out there. The madness that exists now is in cosmic proportions. As is, and it's a madness that comes from having determined that you are your own God. That there is nothing, no source to which we are held accountable. And that the purpose of life is to make the physical form live as long as it can, while lying about age so that you look younger.

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