#171 - The Great Midlife Edit - with Chip Conley & Jerry Colonna

Chip Conley
Midlife has a terrible brand. The first word attached to it is crisis. And the fact is, it's more of a chrysalis than a crisis. It's dark and gooey and solitary, but it's also where the transformation happens. And so it is a time, I would say, in midlife, when much of what got us here is not what's going to get us there.

And much of what we valued may no longer be important. And it's time for us to actually start looking at the world with a new pair of glasses.

Jerry Colonna
Welcome to the reboot podcast. We are so glad you're here.

As a 42 year old man, feeling very much in my own midlife transition, feeling more father than boy, this episode feels particularly relevant and timely for me in this conversation. We welcome renowned author, entrepreneur, and speaker Chip Conley to the podcast. In a conversation with Jerry, they discuss the challenges of midlife transitions, how society views aging, and the benefits of accepting uncertainty. This engaging discussion provides valuable perspectives on how life changes and the impact of the legacies we create. Enjoy this conversation with Jerry and Chip Conley.

Are you interested in coaching but unsure where to start? At reboot, we know finding the right coach can feel daunting. If you'd like to explore coaching with reboot, our engagement team will work closely with you to find the coach to best match your goals so that you can learn to unlock what's in your way, leverage your talents as a leader, and live and lead a more aligned life. To learn more about reboot's approach to coaching or to connect with our engagement team, head to reboot IO coaching. Well, welcome, Chip.

Jerry Colonna
Welcome to the Reboot podcast. Thank you for coming on the show. It's great to be here with you. I look forward to our conversation. Yeah, you know, when we plotted this out, the spark, if you will, is your wonderful, brilliant new book, learning to love Midlife.

And it sparked a whole bunch of conversation and thoughts for me. But as we were preparing for today, I was on LinkedIn. We were both on LinkedIn, and I saw you post something on LinkedIn. So I do want to go back to that in a way. But let's take a step back and talk about learning to love midlife.

Chip Conley
Yep. Why do we have a hard time with midlife? Well, it's a great question. Let me give you an answer in two parts. I'll talk about my own side of this and then maybe the societal one.

Personally, it was like midlife sort of was lurker in a back alley, and one day it jumped on me and just said, hey, I'm here, notice me, and I'm dangerous. And, you know, that was my late forties. My late forties were rough. Everything that could go wrong was going wrong. And not just circumstantially.

Yes, that's true. Things circumstantially were not going well, but also just internally. And I actually think that's a lot of what's going on with what's happening in midlife, the internal process and evolution. And if disappointment equals expectations minus reality, let me say that again. If disappointment equals expectations by naturality, it is often around our mid forties to later forties we can see the future.

And some of the expectations we had in our life may not be coming to pass. And so we have to do something that my friend Brene Brown calls the midlife unraveling. We have to actually unravel ourselves from our emotions and expectations and not from our emotions. We have to face the emotions, but we have to unravel our expectations. And that's what I had to do in my late forties.

And thank God I had an NDe. You don't hear that very often, do you? I had a near death experience. You need to describe what an NDE is. Yeah, NDE is a near death experience.

I was in the midst of all this bad stuff happening and losing five male friends to suicide during the great Recession. Ages 42 to 52. I had an allergic reaction to an antibiotic because I had a broken ankle and a septic leg. I ended up dying nine times in 90 minutes and obviously came back each time. And sometimes it's because the paramedics had paddles and paddled did the electric paddles to my chest.

But that was a wake up call for a hotelier because that's my background, was a boutique hotelier, one of the first in the US, and created one of the largest boutique hotel companies in the world. And long story short is I didn't want to do it anymore. I didn't want to have this life. The wake up call forced me to say, you know what? How might I change this?

And I did what we now at MEA, the modern elder academy, called. I did a great midlife edit. I edited what wasn't working. I really, using discernment, tried to decide, like, what do I need to change? That gave me space in my early fifties, to have a midlife atrium space, to imagine how I want to consciously curate the second half of my adult life because I sold the company at the bottom of the great Recession and I ended up being introduced to Brian, Brian Chesky, who in early 2013 reached out to me and said, listen, how would you like to help us democratize hospitality?

I'd like you to be my in house mentor and the head of global hospitality and strategy. And within a couple months, he and his two co founders were calling me the modern elder, which I didn't like at first because I thought they were making fun of my age. But they said, chip, you're twice the age of the average person here. You're 52. And they said, a modern elder is someone who's as curious as they are wise.

And this opened up my next seven and a half years, four years full time, three and a half years part time, helping them steer that rocket ship that led to Airbnb going IPO as the most valuable hospitality company in the world. During that time, I had my fifties, which I loved, so I had my late forties, which I hated. My fifties I loved on many levels, not just my career side of things. And that's what led me to starting to be very curious about midlife and ultimately creating the world's first midlife wisdom school, the modern elder academy mea. And what I can say to just summarize, and then we'll go to the next question or your observation, midlife has a terrible brand.

Let's start with that. The first word attached to it is crisis. And the fact is, it's more of a chrysalis than a crisis. It is a period of time, if you look at the, you know, famous biological journey of the caterpillar to the butterfly, the midlife is the chrysalis. It's dark and gooey and solitary, but it's also where the transformation happens.

And so it is a time, I would say, in midlife, when much of what got us here is not what's gonna get us there. And much of what we valued may no longer be important. And it's time for us to actually start looking at the world with a new pair of glasses. It's also when our ego starts to maybe evaporate a little bit at least, and our soulful spirituality and interest in meaning and purpose and something beyond ourselves really grows. And so, for all those reasons, I think midlife is extremely misunderstood and understudied.

And that's why I decided to write, learning to love midlife, because we've had over 4000 alumni from 47 countries come to Meas campus. And I've been able to study people in midlife to understand what they were going through as well as what I was going through. Well, I appreciate all of that, and I have a bunch of things to react to. One is, I really feel your journey. I really felt your journey.

Jerry Colonna
And as many folks know, my midlife Chrysalis transformation really began at age 38, because I'm precocious as fuck. You are precocious. I am so precocious. And it was a time period, and it was marked by, and I think of your friends, the five friends who died by suicide. It was really marked by a profound depression that caused me to do what you would call as a midlife edit to re examine things.

I often will advise people that pruning shears are the best tool for you in that time, or even more, the bonsai snips, which actually strengthen that core. Beautiful plant that's, in its own way, an elder. And so I really related to that. And if we go back to the question, I have my own theory. As an interviewer, you want to ask questions to which you have an answer, but you also want to stay curious, is to hear the guest answer.

I think that part of the reason that we fear or that we have difficulty loving midlife is it's kind of the shadow of death, isn't it? Oh, totally. Thank you for, this is why I love collaborating with you. That's what I didn't talk about yet. It is two key things here.

Chip Conley
Number one is as a society, we're an ageist society. Ageism is the last socially acceptable bias. And Hallmark Cart, Hallmark cards is even in on the game. They're going to make you feel bad about turning 40, 50, 60, 70 or more. So we have an age of society, and there's a lot of reasons for that, and that's more true in the US than any other country in the world.

And. But part of what's going on also is this fear of death and the fear of the body disintegrating. And that's partly because we come face to face with our parents passing, our friends passing. We see our own body start to not look as good as it used to. I mean, I think of our body as a rental vehicle that we were, we were issued at birth.

And by the time you get to 40, 50, 60, 70, that rental vehicle doesn't look so good on the exterior, or it doesn't look as good as it used to. It's all a matter of the beauty is in the eye of the beholder. But what we really need to look at is like, okay, why do we have this fear of death? And why do we have this, this infatuation? Not infatuation, but obsession with loss.

And that midlife and later is about loss. And that's why the subtitle of my book, Learning to love Midlife, is twelve reasons why life gets better with age. Because as a society, we're really good at reminding us about what gets worse with age, but we're not very good about talking about what gets better with age. And there's a lot of things that do. And so I really spent a lot of time talking to social scientists and academics and some of our faculty numbers at MEA and to compile this list that is, you know, that's got some social science backing it up.

Jerry Colonna
You know, I want to go back to this fear that I see it. And, you know, to be fair, and I agree with you about the ageism and our inability as a society to come to grips with, you know, okay, trigger warning. I'm about to speak about Buddhism, the impermanence of aging. Right? Yeah.

I am fascinated by the first line of the Donald justice poem, men at 40, which is quite gendered, so I want to acknowledge that.

So the first line of men at 40 is, men at 40 learn to close softly doors to rooms they will not be going back to. Ooh, I love that. And when I think back to my own transformation process, it was the realization partially because of physicality, as you write so eloquently in the book, and partially because of the impermanence of aging, but partially because of the loss of. In a sense, it felt like I was entering a period of grieving dreams. Yeah, grieving.

That which, as I often joke, people at midlife learn to close softly doors to rooms that will not be coming back to. I will not do the things that I had hoped to do when I was 7810, 1215 years old. And I think that there's a correlation, too. If we go back to the experience, you mention your friends and their suicide.

Terry Real has done a fabulous job examining this question of mostly men of the species, but not exclusively men of the species. Our difficulty of speaking of depression, say, from 35 to 65, what that is like. And I think that there's a correlation between our fear of midlife, our perceiving it as a crisis, and our inability to sort of make sense and sort through these powerful feelings of loss. And the implication at the end of the line of death, does that make any sense, having become so much of an expert in midlife? Well, I think what makes sense is that, yes, it makes a ton of sense, Jerry.

Chip Conley
And I think there are a couple things going on that are gender specific. So around age 50, if you were to survey, and we have, but if you look at social science surveys on this, generally, the thing that women are fearful at 50 is invisibility, and men, its irrelevance. And it's very interesting. It's pretty gender specific. Women are less worried about irrelevance because at times, actually, frankly, from a career perspective, they're on the incline.

Women's confidence and career paths tend to be actually getting better with each decade, whereas men are plateauing and maybe actually coming down. And men, especially, if you're a straight white man, you've actually never been face to face with any ism. You haven't had to deal with racism, sexism, or homophobia. And all of a sudden, if you're white, right? If you're white, that's what I said.

If a white, straight white man, all of a sudden you're in your fifties and people are looking at you a little differently now, in certain industries, you're still. If you're president of the United States, you're still rocking the we want you in your fifties. In fact, we like people in their fifties as opposed to maybe in their seventies or eighties. And the reality is that in many industries, though, especially industries that are very tech focused, gosh, being in your fifties is like being a dinosaur, unless you are a modern elder and you're as curious as you are wise, because you have to be with both of those things. If you're just trying to be the wise one, you're gonna try to dispense your wisdom, and no one wants to hear it.

They're gonna say, okay, boomer, because of the fact that you are not coming from a place of curiosity, you need to have context to be able to actually offer your wisdom. If you just offer it to a willy nilly to anybody and say, here's the way the world works, people will tune you out. So for men, this idea of being a pipe, you know, a previously important person as opposed to a vip, is really painful, made harder by the fact that men don't talk about these things. Women are so much better and socialized to have an emotional insurance policy. Other women often, sometimes other men, but other women that they can talk to about the things that aren't working in their lives.

Men don't do this as much. And this is part of the reason why peer to peer networks have become so popular, because it is a way to socialize through YPO, vistage EO, and other programs like that. The opportunity to create the safe crucible to have a confidential conversation about things that aren't working. Thank God. Because one of the things we have living a life of quiet desperation is, I think it was maybe Thoreau who said that a very 1950s perspective was like, okay, you're the organization man.

You have a path to live your life. It is the game of life. There's only one pathway in the game of life. There's not multiple choices. No.

You get tokens along the way in your little plastic car for getting married, having children, getting a promotion, buying your first home, etcetera. And we are, in essence, inflicted by successism, just like consumerism, where it is this societal definition of how success is meant to be carried out. And your job is to execute on that. Yeah, you're making me see something that I hadn't seen before, and I appreciate that. It's this tension between loss and a belief system that success and a meaningful life means accumulation.

Jerry Colonna
Right. So, you know, when I've internalized the game of life, that game that we played as children, if you remember, at the very end, there's a split where you go into millionaire acres or their retirement. Right? That's right. The corollary game, which I played way too often as a child, was monopoly.

And so I think the message that we internalized early on is that a meaningful life is measured by that which we have accumulated. Yes, yes. And I think that you have this lovely construct in the book citing the difference between aging and growing. And I think part of what you're talking about in growing is growing towards a life where meaning is not derived by accumulation. Yes.

Meaning is not derived by accomplishment or status. Cause there's that previously important person struggle. And in a sense, it points us to that which Brian and I guess Joe and the others at Airbnb sort of dubbed you this modern elder. It points us to what is an elder. So let's go back to that.

What is an elder? Well, if we look back historically, first of all, elder is a relative term. It is not the same thing as elderly because elderly is often the last five or ten years of your life. It's a time when you need interdependence and support to be an elder can be. Tom Brady in the NFL was an elder at 42.

Chip Conley
As an NFL quarterback. If you're a software engineer at 32, you might be an elder on your team because everybody else is ten years younger. A fashion model is an elder at 26. So long story short is elder is a relative term, and it's a term that bestows a certain level of experience, maybe wisdom, and often power, historically. So if you look at the founding fathers of the United States, they wore wigs, gray wigs that make them look older because they were young.

So that's not the only reason they wore them. But that was a part of the reason, is to actually connote that they were more mature and wise than their years. We don't do that anymore. Of course, we do quite the opposite with Botox and things. But bottom line is, historically, the elders have been, from an indigenous perspective, those that passed on the spoken word, lineage and traditions and wisdom, maybe a lot of it, land wisdom, that was very relevant to the next generation.

And so they were the meaning makers in many ways. And so that was a very important role. And then we went from the agricultural era and the hunting gathering era to agricultural era, to the industrial era over 100 years ago. And like, oh, well, the elders are not as important when you're talking about factory floors and assembly lines. So that was the start of the diminishment of the value of an elder.

But still, frankly, you paid your dues in an organizational way. The older you were in the organization, the more power you had. And then we went into the tech era starting 50 years ago, and it was, frankly, 65 years ago that Peter Drucker said, knowledge workers will rule the world. And in fact, that's true. Seven of the ten most valuable companies in the world today are tech companies.

So knowledge workers became the thing. And not only did elders not matter, because it was like, during the industrial era, it was more like, okay, we need people who've got physical bodies to do things. Now it's all about brains, and it's about the most recent knowledge you have around digital intelligence. DQ and EQ became less important, emotional intelligence. The truth is, the best organizations that are tech focused are a combination of DQ and EQ.

And that's what I tried to have us embrace at Airbnb. Long story short, though, is elders today. It's a word that people are scared of. The reason we called the first midlife wisdom school modern elder academy is because to me, once I owned the idea of being a modern elder, someone as curious as I was wise, I thought it was an aspiration that we should make in society. So I think the idea of being a modern elder was aspirational.

And yet still, we now call ourselves mea, partly because there's a lot of baggage attached to the word elder, even if you give modern right before it.

But I think that at the end of the day, I think the most important thing is to see the symbiotic relationship across the generations. That's the big difference. It is no longer about respecting your elders. Yeah, I think that one of the things I'm taking away from your work and our conversations and quite frankly, my own experience, I turned 60 in December. And one of the things that's been going on for the last couple years for me has been a sometimes conscious, sometimes unconscious embrace of my own eldering, my own movement towards that.

Jerry Colonna
And when you reached out and we connected live, I was partially excited to really learn more about this phase of my life that I was going into. And one of the things that I have been kind of internalizing is one of the elders in my life. One of the many elders in my life is the american buddhist nun pema Choden. And I've had the great good fortune of being her student for almost 20 years now. And we're pen pals.

We write letters to each other. And this past fall, she sent me a copy of her latest book, which I highly recommend, and I want to read just a little bit of it to you and come back to it. And her latest book is how we live is how we die. And she's speaking about aging, and she's speaking about what we've been talking about, although she doesn't use the word midlife and the Chrysalis transformation, but she is talking about transition and change. And she says, we don't enjoy uncertainty, insecurity and groundlessness.

We don't seek out vulnerability and rawness. These feelings make us uncomfortable, and we do whatever we can to avoid them. But these states of mind are always with us, if not blatantly. And I'll add, as they might be in midlife, then at least subtly in the background to some degree, we always sense that we're on a plank 40 stories up. This is the all pervasive suffering the Buddha described.

Now, I read learning to love midlife, and I kept thinking about Pema's teachings in this book, partially because at one point in the book, you talk about your own experience with ndes and your experience of your friends. And so implicitly, I think you and Pema are saying very similar things. How we live is how we die, and it matters how we live. And I'm going to argue that I think part of my definition of elder is learning to be comfortable with uncertainty. Yes.

Yes. Yeah. I think it's learning to be comfortable with uncertainty. It's learning to not be stuck in the ghetto of your mind and ego. It's learning to get comfortable with liminality.

Chip Conley
Liminality, for those who don't know that word, it's a spectacular word. It is the idea of transition, and life is just one constant, evolving transition. And yet we, as Dan Gilbert from Harvard in his TED talk, speaks to people, vastly underestimate how much change they have coming ahead of them. They overestimate how much is coming in the next year and underestimate how much is going to happen in the next ten years. So if it's true that we're in constant, evolving, an evolving state, why is it that no one taught us how to get a master's in transitional intelligence, TQ, and to be able to understand how do you navigate liminality?

And that's really part of what we teach at mea. That's a big piece of it, because, quite frankly, we go through a lot of liminality in adolescence in our teen years, and we have so much love, support and guidance during that time, and peer to peer connection, because you're going through it with the same group of people and you're talking about it, but you go to, from adolescence to middle essence, middle essence being midlife, when you're going through the same kind of hormonal, emotional, physical and identity transitions. But we have no roadmap. We have very little in the way of support and frankly, not a structure that helps you to understand, you know, what are the important questions to be asking and how do you execute on a liminal journey during that time? And so, you know, that's part of the reason why mea exists.

Part of the reason we're very popular is because there's so little out there for people to understand that what Pema's talking about is life. And is life. That's right. Yeah. It is just life.

Jerry Colonna
The fear of transition, the loneliness that one can fear in transition gets labeled as a fear of death. But I think it's actually a fear of life. I think back to Pema's teachings and when things fall apart, that the grip that we want to hold onto to things as they are is actually antithetical to the way life actually unfolds, which is constant change and constant impermanence. I want to go back to the definition of elder, and I want to play with this a little bit because I think one of the challenges, in a corollary word to elder is the word wise.

And I think it's a challenge for this reason. Chip, I think that there is a misunderstanding of what that word wise means. I think it implies you have all the answers and you laugh because, I mean, think about it from our own experience, Brian and others might look to you and say, well, what should we do? How should we live our lives? Think of the great Clay Christiansen's book, how shall I live my life?

Chip Conley
Yeah. How shall I measure my life? How shall I measure my life? Right? And I think the thing that's uncomfortable that I'm coming to grips with is that part of the task of being an elder is being okay with all of this uncertainty, impermanence and change, but also letting go of the need to not only know it, but to be right, to have the answers.

Jerry Colonna
And if we go all the way back to the challenge, to our ego, that says, well, who am I if I don't have the answers? Yeah. So I wrote a book called Wisdom at the making of a modern elder. And it was a book chronicling my time at Airbnb. And what I really believe is that the process of becoming an elder, or a modern elder starts with being.

Chip Conley
There are four steps, being willing to evolve. And I had to evolve at 52, joining Airbnb, whereas two years earlier I'd been CEO of my own company for 24 years, grew it to 3500 people and 52 hotels, and all of a sudden, now I'm going over to Airbnb and I'm not the CEO. I'm like you. Someone called me the CEO whisperer, and you have been called that before. My role was not to be the sage on the stage, I was to be the guide on the side.

My job, I had to right size my ego and get really clear that I am evolving my archetype, my identity in the workplace. And so that was the first step. And the second step was to learn. So instead of being the elder who comes in and teaches, I had to come in and learn because at 52, I never worked in a tech company before. And I was in charge of, yes, all the hosts in the world.

That made sense because I was a hospitality guy, but I was in charge of strategy for the company. I was in charge of strategy for a tech company. I didn't even understand what the word product meant. So, long story short is I'd never been involved with Ux, Ui, etcetera, but I had to learn and I had to be willing to turn my fear into curiosity, and I had to be great at packaging questions. You know, Jimi Hendrix famously said, knowledge speaks and wisdom listens.

And I had to be a great listener and I had to be not a motivational speaker, but a motivational listener. And to really understand things and maybe before I opened my mouth, I would, you know, I'd try to grok what I was hearing, and I was mostly looking for what wasn't being said. And so that's the second phase. So evolves first listen. Third is to collaborate as an elder.

It's not about us being the hero to sort of, like, dispense wisdom. You know, as we get older, we get better. One of the twelve things that gets better with age is we're smarter emotionally. We have greater emotional intelligence, more emotional moderation. We know how to collaborate well.

And that's not everybody. I mean, for those of you, like, oh, my God, of course, my uncle is, like, awful at that. These are averages. But the reality is, collaborate is the third step. And the fourth step is the thing that some people think is the first step is to learn how to counsel, how to be the confidant, the person who gives confidence to people younger than them in the role of the elder.

But you've earned that. If you've done evolve, learn, and collaborate first, then you will have people leaning into you. And over the course of my seven and a half years at Airbnb, I had over 100 mentees, but many of them were not deep, long term mentees. It was more like I was the librarian, and my job was to have the know how and know who, and say, like, point people in the right direction, have three meetings with them. And that was as much as the mentor relationship worked.

So it really was less of a mentor and more of a scarecrow pointing directions, as well as the librarian knowing, hey, have you read this? Have you talked to this person? Etcetera. But people will lean into you if you do those first three things first. And so if people find that interesting, read wisdom at work, which is really a testament to what does it mean to be a midlifer in the land of millennials?

For me, back then, when I was twice the age of the average employee. There, I'm going to pull some things. Together, which is the way I'm learning from you in this moment. You know, I opened up by bringing our attention back to death. I opened up by bringing our attention back to the sense of loss and the grief, to doors, to rooms that we will not be going back to, and in some ways, the avoidance of the pain of that loss morphing into a kind of low, pervasive depression, and what I have found from my own life.

Jerry Colonna
And I wonder if this relates back to the experience that you've had being an elder to those emerging elders, if you will. Is that an embrace of not knowing? An embrace of that uncertainty, an embrace of this guide on the side role where you ask more questions and provide answers for me has been an extraordinary uplift in my emotional well being. Yes. I spend so much of my time bemused by the world when I'm not outraged at the way we hurt each other.

I look at the world and I want to be clear. It's with empathy and it's with compassion. But it's. I find myself less likely to be riled up and more likely to respond with empathy to what I see and therefore to bring it back. I'm less likely to be depressed.

Chip Conley
Yeah, well, I think part of that. First of all, this is really deep. I can't wait to go for a long hike with you here in Santa Fe as you're going to be teaching with me here in Santa Fe later this year on our campus.

To take off the cape of the hero is incredibly liberating. And to go into a place, a state of curiosity and bemusement to see what is happening there and to become a first class noticer. In the movie the intern with Robert de Niro and Anne Hathaway, he was twice her age. And she said at first that she didn't want him to become her senior intern because he was a little too observant. Don't we all wish we could be a little more and too observant?

Because it just means we're observing the world. We're becoming a first class noticer. And I think the process of becoming a first class noticer takes us to that classic Victor Frankl statement, which is between stimulus and response. There's a space. In that space is our power to choose our response, and in our response lies our growth and our freedom.

And so to be able to take away the reaction and instead to be able to respond to life. But in order to respond to life, you have to observe it. You have to be open to the fact that you're not there to fix it in a moment's notice, which is how I've lived my life. Oh, and it's how you were rewarded by life. That's true.

How is rewarded as well. And so to be the can do it here. I can do it. I can do it. There was a year, a few years ago when I, in my hotel company, I gave away 3500 copies of the book the little engine that could, that little engine that says I think I can, I think I can, I think I can.

Because the number one variable for our loyal guests in the hotel business was the can do it attitude of our employees. So I wanted them to all feel like, I can do it. I can do it, you know, sort of like the Obama thing, you know? Si, se puede. We can do it.

You know, there's a sense of like, okay, we can. Yes, we can. So I've tried to move from being the canduate hero to the conduit, from canduate to conduit, because conduit is something that comes through you, but you have to make the space for it to come through you. If you are in constant motion and trying for your ego benefit to actually be the one solving the problems, there's not a space for something to come through you. That's a big change for me in the last ten years.

Jerry Colonna
I'm going to give you an image that comes to mind, and it's one of my favorite images. It comes from Pema Chodron. And she writes about this in her book, comfortable with uncertainty. And she talks about how all around us, the world and its emotions are like the weather, and it's storming all around us. And oftentimes that weather just sort of flows into us, and we storm and we ebb and flow, and we feel these things.

And her elder advice, that wise advice, is to sit like a mountain in the midst of a hurricane. And when I think about my movement, my movement from in my thirties, being an investor and really living with a kind of hollowness and an emptiness inside of me that was just painful into where I am now, in my sixties, I think more and more, I sit like a mountain in the midst of a hurricane. I still internalize the rage and the weather. I still internalize the fear of impermanence. Will my children continue to love me as I age?

Will I be abandoned? Will I be alone? Those feelings come up for me. But more and more, I internalize that notion of this sort of rooted rock of ages that has a core that goes down miles into the earth and is immovable, but not obstinate, and is the thing. This is what I wish more than anything, the thing upon which others may rest and seek shelter.

So even as I sit there and bemused, it's not without empathy, but it's the ability to sort of reach down and say, as one elder, my psychoanalyst of 30 years used to say to me, this too shall pass. Of course. Yeah, well, weather's a fascinating metaphor for our emotions. I mean, I'm a big fan of the roomy poem about the guest house. Of course I love that particular one because I was a hotelier, a hospitality person for all my life, all my career.

Chip Conley
And so the idea that we are a guest house and these emotions come rushing in like a guest who's just lost their luggage at the airport and they're checking into your house, your hotel of emotions, but they're not there forever. So the idea that the external weather, right now, as we're talking, there's a major thunderstorm, not just a thunderstorm, but there's a craziness in southern California with weather, and it will end. It will end subside. It will move on. The problem for us with our emotions, because there's external weather, and then there's our internal weather.

The problem with our internal weather is we hold onto a resentment, or we hold onto a feeling of being irrelevant, or we hold onto a sense of guilt or shame, as if we're trying to control the weather. As if we're saying that weather system that has come in in the form of an emotion is something that I'm not going to let go of. And therefore, we are trying to be God of our emotions. And if we can actually learn how to be that roomy guest house of those emotions coming through us over time, being less affected by them. Because the thing about the roomy quote, those of you who haven't heard it, go google it.

The guest house by Rumi. It can be frightening to have all these emotions coming and then going. But if you actually, if you show up as the gracious hotelier or host, recognizing that they're not staying, they are checking out. Your job is to actually just help to be the Sherpa and the hotelier of these emotions so that they actually don't overstay their welcome. And even the good ones.

Jerry Colonna
Yeah, I think that we've hit upon something. You've certainly given me something more of the definition of what I'm striving towards, more of that definition of what I'm becoming in this discussion. You said it will end. Now I'm going to lift that up and highlight that, because I think that is perhaps one of the most profound pieces of wisdom out there. It's not just, as doctor Sayers used to say to me, this too shall pass, but I'm going to expand upon it.

It will end. The weather will end, the storm that you're dealing with will end. Your life will end. And here's the corollary. Good news.

And that's okay. Yeah. And that's okay. You know, in a sense, that honoring of the endings which I think so much. I certainly think about my own transition, but the liminal space between my thirties and forties which so terrified me.

Doors closing and rooms that I will no longer enter that space, understanding that that end is not this greater end, but this interesting new space of a beginning. Yeah, well, the three stages of a transition are really the ending, the messy middle and the beginning. And trying to use that frame at the MEA website, which is meowisdom.com. Comma. There's a free resource in the footer which is called the anatomy of the transition that goes through those three stages, the ending, messy middle, the beginning.

Chip Conley
And how do you cope through each of those three phases? Because frankly, for a lot of us, when we're going through a really difficult transition, we feel like we're stuck in the chrysalis in that messy metal and it's never going to change. And that's okay. And that's okay. And that may be partly because we're trying to control the weather.

Jerry Colonna
That's right. That's right. That the suffering comes from thinking that that transition is wrong, is bad, is negative, when the liminal space is a necessary part of life. And, you know, if we can approach all of it in that way, I think we end up transition, we end up passing along to. I'm fascinated with this notion of ancestors and descendants.

I write about them a lot in my new book, reunion. As I think about. I spend a lot of time thinking about descendants and not just my children, but their children and their children and their children. What does that mean? Can I be a mountain of an ancestor?

That my descendants two or three generations forward can look back and say there was a wise elder? Yeah. Well, Eric Erickson, the developmental psychologist, says that in the later stages of our life, the question we need to ask ourselves, or actually the statement we need to own, is I am what survives me, beautiful survives me. And, you know, I am not my stuff that I own. I am not the books I write.

Chip Conley
I am not, you know, some of those things will survive. I'm not even the trauma that happened to me. I am not the trauma that happened to me. I am not my successes or my failures. Right?

I am what survives me. And to really ponder that question is, what do you want that to be and how will it show up? And what in a 7th generation kind of way? What seeds are you planting today that will survive you? And to me, at the end of the day, mentorship is a big piece of that.

Because if I help someone to be a better human, I hope that they will continue that legacy. Well, Chip, my friend, my deep new friend, God bless you for the work that you've done. Thank you. God bless for who you are becoming and you've helped me and I know the thousands of people that you have helped. Thank you.

Jerry Colonna
If you enjoyed this episode and want to hear more, go to reboot IO podcasts to listen to all past and present seasons of our show and leave us a review at Apple Podcasts or Spotify. That's the best way for other people to find and enjoy the show, just as you have done. And don't forget to join our mailing list at reboot IO signup so you never miss an episode. Thank you again for listening.

How long till my soul gets it right? In any human being ever reach that kind of light? I call on the resting soul of Galileo, king of night vision, king of insight.

We often talk about the work of rebooting your leadership as individual work you can't do alone. If each member of your leadership team is pursuing the work of self inquiry and actualization, that's wonderful. But to create the company that you'd all like to work for, you must also create the opportunity for the collective to grow. Experiences like facilitated leadership groups, offsite retreats, organizational change explorations, and immersive leadership trainings move the organization closer to its fullest expression of the inherent values. At Reboot, we're here to support you and your team members in bringing forth the best that you have, using everything that emerges from organizational life, both the challenges and successes, as opportunities to grow head to reboot IO team experiences to learn more and more about reboot's virtual and in person.

#171 - The Great Midlife Edit - with Chip Conley & Jerry Colonna

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1. Introduction

2. Personal Stories of Midlife

3. Societal Impact

4. Redefining Roles

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