The Gold of Midlife (Chip Conley)

Listen now (38 mins) | “The midlife crisis is not a dark night of the soul. It’s a dark night of the ego.”

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Chip Conley is the founder of the Modern Elder Academy (MEA). They have a series of workshops and programs designed to help people navigate midlife transitions, and really tap into the wisdom that’s available to us at this point in our lives.

Chip is also the author of Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age. And a lot of his work focuses on dispelling the myths that we’re led to believe about midlife. We talk about a few of those today, and some pretty interesting—and optimistic—data on what actually happens in midlife.

We talk about how, in midlife, we have an opportunity to move from constant knowledge gathering into transforming all that knowledge into something more useful: wisdom. We talk about how we’re both a little allergic to the word “purpose,” and why Chip prefers to think of it in verb tense, as being purposeful.

Chip shares the MEA theory that we have three vaults in which we can speak and communicate from. And how part of our process of growing up is moving from fact to story to essence.

MORE FROM CHIP CONLEY:

Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age

Modern Elder Academy (MEA)

EPISODE TRANSCRIPTION:

ELISE:

Let's talk about midlife. Let's talk from role to soul. I thought there were some, and I know this is obviously contending with midlife. Maybe contending with midlife is not the right way to talk about it actually, because you present a more optimistic frame. Let's start there with the specter of midlife and how it's been presented to us and how we're thinking about it entirely incorrectly.

CHIP:

Yeah. Midlife is a modern creation. So in the year 1900, the average longevity in the US is 47. By the year 2000, it was 77. So in that century, we had in 30 years to life, which really led to a midlife period that also during that same century, adolescents got created as a word 1904 and retirement did too. Adolescents, retirement and midlife are the three sort of modern creations of life stages. The first two have gotten a lot of love and attention. Midlife. On the other hand, all it got was a bad brand. The midlife crisis in 1965 and midlife has not been well studied, but what we know about midlife is that it's an era that's full of transitions, and so adolescence is full of transitions, and so is middle essence. Middle essence is another word to describe midlife. So we tend to, as a society, create rites of passage and rituals to help people through their natural transitions, and we have all kinds of them for early in life, but in midlife, not much in the way of rituals or rites of passage.

So as I started to explore this further, I started to wonder what would it be like to create a midlife wisdom school and to create a place where people can reimagine and repurpose themselves in midlife and see midlife not as a crisis, but as a chrysalis. The idea based upon the U curve of happiness research, which is global research, has shown that in fact people get happier. Their life satisfaction grows starting around age 50 and just continues to grow as they get older. Now, that is really at odds with the societal definition of midlife, which is if you can survive it, you have disease, decrepitude and death. And in some, I would just say that midlife is a natural process for anybody who's getting older. It is a life stage that may last 40 years based upon some academics who say it lasts from 35 to 75 because it's such a long period of her life. It's a life stage that deserves to be demystified and elevated.

ELISE:

Yeah, I thought too, it was interesting when you were discussing the U curve in your book, how people's expectations come down as their happiness begins to rise. And then also I thought this was a really brilliant query, which is middle essence actually the end of the ego in the beginning of the soul, or to go to Father Richard Rohr. And the way that he describes it as container building or tower building sometimes uses that language too in the first half of life, and then the second half of life is when you fill the container or move out of the tower and find the meaning. But that's the rub, right? Stability and meaning and how do you find that balance throughout your life or transition into it. But I think it is the end of the ego, maybe not the end of the ego because we need our egos the

CHIP:

End. No, no, it's definitely not the end. Richard's on our faculty at MEA and just a good friend, and he says that it's around age 50, that the primary operating system moves from the ego to the soul, but nobody gave us any operating instructions for this new system that shows up. I like to think of it the following way. When I was in sixth grade, I went to ballroom dancing school and I learned how to ballroom dance as the boy and the boy leads the girl, and the girls learn how to go backwards in heels and guess what they have to learn and deal with for a very long time. And I think that early in life, the ego's, the boy, the soul's, the girl, and it's around midlife that the roles switch and all of a sudden the soul is leading the dance and the ego is going backwards and heels.

So the ego better have a sense of humor if that's going to happen. Otherwise, there's this intense struggle, and quite often that is what happens. That can be the midlife crisis. The midlife crisis is not a dark night of the soul. It's a dark night of the ego, and it's because something is meant to be molting. When a snake gets bigger, it molts its skin, and as a human gets bigger, it outgrows its shoes. What happens is we get into adulthood, we outgrow our roles, our identities, our mindsets, our thinking, and there's meant to be something new and fresh there. So yeah, I laugh at my ego now. I'm 64 next week, and I laugh at my ego because it doesn't do a great job of going backwards in heels, and that's okay. That's okay.

ELISE:

Yeah, I always butcher quotes, but Carl Jung has a great quote too about how most of us are walking around with shoes that are too small. I'm sure most people listening to this conversation have that feeling of too a soul that wants to be bigger than its current constraints or to expand and grow. I also like that you asked this question, I hadn't ever thought of it in this frame, which is why are we so comfortable talking about growing up and then we transition to aging, growing versus aging when really they're essentially the same function?

CHIP:

Well, we're fixated on the physical, but the truth is that we actually grow as humans, emotionally, spiritually, culturally, relationally, intellectually as we get older. But if we obsess purely on aging as being the physical side of things, then yeah, there's some deterioration as we get older. But what I tried point out in this book was how might we give some attention to the other parts of our life where we do get better with age? We actually do grow,

ELISE:

And we went through it really quickly, but at the beginning we were talking about the longevity data and this massive span between of midlife, right? That starts at 35 or potentially older. I know you like Connie's Wag as well, but I love that she essentially talks about how Elderhood is theoretically available to almost anyone. It doesn't necessarily. You don't get your elder card with your A RP membership, but it's a long period and it's often the most fruitful or the most wisdom laid in time of our life. And also, this was a stunning statistic. You write for many boomers, the sunset of their career is when they become an entrepreneur. According to a recent Census Bureau's annual business survey, 30% of American business owners are between 55 and 64, and another 20% are over 65. Wow. Who knew that half of American entrepreneurs are 55 plus? I did not know that. That's for

CHIP:

Sure. The data from the Kaufman Institute, which or Kaufman Foundation, which has studied this even more than the US census has slightly different numbers than that, but they're pretty comparable. And what they've also shown is that a 50-year-old starting a business is more than twice as likely to succeed as compared to someone in their twenties. So the Hollywood trope about the Mark Zuckerbergs of the world with their hoodies doesn't really match the data. And it's partly because sometimes the companies that older people are starting are not as risk seeking. They're more conservative businesses, but even in the tech world, the data on this, someone in their fifties starting a tech company, someone in their twenties still, the person in their fifties is more likely to succeed. So really interesting data, and part of what I've tried to do is to help dispel some of the myth around what does it mean to get older, and in this case, what does it mean to be an entrepreneur at any age?

ELISE:

A lot of my work is about exploring unconscious stories that we live and abide by without really knowing what's driving us. And then the moment where we decide, wait, whoa, whoa, I need to choose something else instead. And I have my own unconscious stories about aging, and I was a good corporate citizen for the first 40 years of my life. I've never had a big financial event that would set me up. I don't know that that would actually change my scarcity minded personality to be fair chip. But I've been working for myself for the past four plus years, and I write books and have a podcast. I have many, many, many lines in terms of what I do. And I was talking to my financial planner and we were looking at revenue and where I'm at, and I'm the primary breadwinner and I grind. I am not an Enneagram three, I'm a six, but I have a lot of three. And I was saying to him, I'm so breathless, truly, and I don't know that I can maintain this pace of output. I'm going to die. And he was like, well, wait. We haven't done a retirement. Let's look at this. So are you retiring in five years? I'm like, as if, no, I think I will work happily until I die. And he was like, this is a totally different plan, but I have been pursuing my thirties and my forties as though I'm going to age out of my

Industry and this is it. This is it, chip. This is my moment. But it was interesting to recognize, oh, I could calm down a little bit and maybe be more present for my small children and acknowledge that actually my work might get better as I gain more wisdom or convert more knowledge into wisdom. But I'm sure I'm not alone in this being completely subscribed to this idea that in a few years, nobody will hire me. I'll be irrelevant. I'll age out. I'm screwed. This is it. It's insistent. Yeah.

CHIP:

Thank you for that rant. I loved it. What I heard there was a combination of institutional, societal, ageism

With the personal, maybe a little bit of ego attached to what defines success, and along with some of the financial fears that could actually come with this. So all of them not great. What I will just say is if we could see life as a little more like a game and you define the rules of the game and you define what define success in the game, so that's very unusual. This is not the game of life that we grew up with on the board game where the rules were very set. You had to get married, you had to have kids, you had to have a good job, buy a home. It was very much American propaganda. I think if there's one thing that I heard you say just now that I want to just really elevate as an important difference in mindset is we are going to be working into our sixties, seventies, and eighties.

It's either by choice or necessity. Only 11% of people in their fifties say that they are going to retire and not work again. So that's incredibly different than 50 years ago. People would retire on a Friday, on a Monday, they'd have no work. And quite frankly, it led to the acceleration of mortality by two years because people lose purpose, community and wellness without a job. So we see people working longer. The question is, what will you do? How will you make money? How will you have a sense of purpose? I'm a big fan of Arthur Brook's book From Strength to Strength, and he really talked about the idea that we move from fluid intelligence to crystallized intelligence. And there are a bunch of careers that are well suited for people in their sixties, seventies, and eighties, being a coach, being a therapist, being a professor or teacher, being a mentor, being a strategist, all the things that address the crystallized intelligence, which is being more focused on systemic, holistic and connecting the dots kind of thinking. So I guess what I would say is there are lots of opportunities. It does require that we evolve over time and constantly learn something new, but I have no doubt you wear a lot of hats.

Some of those hats will fit better as you get older and some won't.

ELISE:

Yeah, no, it's true. And it's not entrenched, but it is just an unconscious program that I was running and convincing myself that this is what I needed to do. And the reality is I'm also in probably the most expensive part of my life. So anyway, but it was a moment where I was like, wait, wait, this is actually, I don't think I need to do this. Do I actually need to do this at this pace? And he was very kindly like, absolutely not. You do not need to do this. Calm down.

CHIP:

That's your six Enneagram six. For those who don't know it, there's something called the Enneagram, and we're typing each other here, but there are personality type characteristics of the three, which is where I am in the six, which is where Elise is that have a tendency sometimes when we're most full of fear to actually show themselves.

ELISE:

Yeah, sixes, that's our vice. I wrote a book about the sins and they share the same fathers, the Enneagram of Evagrius Ponticus. And so for people who are familiar with the sins, they're each aligned with an Enneagram point, which is nine point and plus fear and vanity, which is three, right?

CHIP:

Yeah. The vanity. So the six is sort of ruled by fear, and if six can either be phobic or counterphobic, the phobic tends to be the victim of the fear. The counterphobic leaps tall buildings and tends to be a big risk taker, but there's a fear underneath that that's leading to that behavior. For three, it's about performance, it's about how it looks to others and being successful. America is very much a three culture. The idea of, oh, whether I'm in Hollywood or on Wall Street, my job is to be successful in the traditional status oriented way that we look at success. I was lucky enough in my early twenties, 40 years ago to learn that I was a three, which was really helpful because an unconscious three can be incredibly superficial and very focused on how things look very image conscious,

ELISE:

Statusy,

CHIP:

Right? And that's why vanity, you mentioned the vanity thing, and it's not to suggest that I don't have those issues still I do, but the fact that they're conscious and I can see them and laugh at them.

ELISE:

I'm assuming you wing four.

CHIP:

I wing four in a big way, and the four is the aesthetic original, someone who likes to go deep. And so a three with a four wing could be a really interesting combo because the four is sort of the artist melancholy, the person who a little bit of an introvert, but is a true original.

ELISE:

Yeah, no, and we're in a big four, I can't remember. I might've read this, but was saying that they feel like culture moves the Enneagram too, and that we're moving from three to four, which is very sort of the me story, and how is everyone not feeling everything that's present? And this is all very traumatizing, which it is. I'm not suggesting it's not, but that's a very four. Once you know the Enneagram, I love it. Every time I do a panel, I'm like, oh, that's it. There's our eight and there's the seven. Who just wants to, it's like, where are the cocktails? And no, I love the Enneagram. I find it helps me depersonalize almost every interaction once I know what I'm working with and to really, even though you're categorizing and typing to have a little bit more humanity for people,

CHIP:

You understand that people wear different pairs of glasses, and depending upon the pair of glasses you're wearing, you're going to see things a little bit differently and it's much deeper than say, Myers-Briggs or some of the other personality typing tools that we have in the corporate world. And that's why I like it as well. It gets down to the root of who you are and what are the biases you have in life based upon that. So

ELISE:

Yeah, I'm a fan. Well, I'm a six who wings five, so I just want all the information. I want all the knowledge to my own deficit. I don't know when to stop. Vibes can be wonderful and insufferable, but so much of your book is about that transition right where you stop, not that the quest for knowledge ceases, but that you are actually metabolizing it, you're transforming it into something that's usable for other people. That's wisdom. Can we talk a bit about that and the difference between the two?

CHIP:

Between knowledge and wisdom?

ELISE:

Yeah.

CHIP:

Yeah. So knowledge is something you accumulate, and so if you think of it in a arithmetic kind of way, it's a plus sign. And part of what we want to do in life is accumulate more knowledge, being knowledge driven. There's nothing wrong with that. But we live in an era today where we are awash in knowledge. All the world's knowledge is on this little phone in my pocket through chat GBT or Google or whatever app I'm using. And wisdom is different than that. Wisdom is a division sign. It is taking a lot of information and taking it down to the square root. We accumulate knowledge, we distill wisdom. Now, the other thing that's interesting is when we're distilling wisdom, yes, it could be understanding a lot of knowledge out there and distilling it down to what's truly important. But what's a big piece of wisdom is personal experience.

And I like to say our painful life lessons are often the raw material for our future wisdom. And what I mean by that is that it is the experiences we have in life that helps us to have our wisdom fingerprints. And so just like fingerprints are not the same for anybody, our life experiences are not the same for everybody. And it creates a wisdom fingerprint. And the wisdom fingerprint speaks to your point of view and perspective based upon those life experiences, metabolization of those life experiences. So in an era in which knowledge is commoditized, wisdom becomes more important and more valuable. Peter Drucker coined the term knowledge worker in 1959, and nobody had any idea what he was talking about because most people had never seen a computer. But here we are, what, 65 years later. And I do think it's almost time for us to start talking about wisdom workers, not knowledge workers, because knowledge workers frankly are in trouble in the AI world because knowledge is so plentiful already. And so wisdom workers are really valuable because they are the ones who can help a team, an individual, a leader, or even a company make sense of what they've learned along the way

ELISE:

I love this line from Seneca that you have, no one was ever wise by chance. Wisdom requires a very active engagement with life in part to extract the meaning from what's happening and to look for the pattern, understand the story, maybe tell a different story going forward or recognize that your life is going to change and your story will change with it. I know you work with a lot of people. The friction point that I observe, and this is mostly in the company of women, is an acknowledgement that the story that they're holding onto might need to change or that they don't like the story, but yet an unwillingness to let it go and choose something else instead. And we get stuck and story is identity and story is how we make sense of our worlds. But I'm sure you see this too where it's like, do you want to put that down? But no, sometimes people don't.

CHIP:

One of the things we talked about at Modern Elder Academy MEA is the three vaults in which we can speak and communicate from. The first vault being our facts of life, often in our brain, the second vault being the stories of our life often in our heart, and the third vault being the essence of who we are. Unscripted often in our gut. For a lot of us moving from fact to story to essence is part of our process of getting older and maturing and getting wiser. And so stories can actually be an incredibly distracting, you're driving from this place to that place, and in order to get there, there's this traffic circle. And the traffic circle is your story. If you don't make sense of the story, the narrative in a way that's productive, you get stuck in that circle. You never get to wisdom. You never get to the essence of who you are because you get so stuck in the story and the narrative. And in the book, I go into some depth about the hero's journey, which I like to call a human journey, understanding these three stages of any transition in life and being able to see the narrative without getting caught up in it. This is why we hire coaches, why we hire a therapist. It's why you have a spouse or a best friend, they can see your blind spots.

ELISE:

Yes, a hundred percent. And help you interrogate those stories, particularly when you are in a loop de loop. Either you're revisiting the same exact same story or recreating the story. And I love that you do facts, stories, essence. I write a lot about the CLG conscious leadership group facts versus stories because so often we conflate the two and really a story is an interpretation of events always doesn't mean that doesn't feel true or that it's not somewhat accurate, but to even be able to question that story, is that true? Can I spin out on this whole narrative based on my experience of this event, or should I actually go back to the event and imagine that maybe something else is present. So MEA, do most people who come to you, are they in some sort of crisis? Obviously I love Bruce. I think on your too. Are they in a life quake?

CHIP:

Yeah. So life quake is Bruce ER's term for having maybe multiple transitions happening at once. And Bruce wrote a book called Life is in the Transition. He's on our online faculty. I would say almost everybody who's coming is either considering a transition in the middle of a transition or finishing a transition and maybe more than one, so

Getting divorced while becoming an empty nester, et cetera. And so I don't think people are typically in crisis. If they are in the application process, we'll figure that out and say like, okay, gosh, we are not meant to be a place where we're going to lock you up for two months and you're going to be in therapy. We are a midlife wisdom school dedicated to helping people navigate their transitions, cultivate purpose, own their wisdom, and reassess their relationship with aging. Because Becca Le Yale has shown that when you shift your mindset on aging from a negative to a positive, you get seven and a half years of additional life. So people are usually in low grade transition mode and often a little bit scared or bewildered by it. The name Modern Elder comes from my time at Airbnb when for seven and a half years I was the in-house mentor to the three young founders taking a tiny little tech startup into becoming the world's most valuable hospitality company.

And they called me the modern elder, someone who is as curious as they're wise, that term stuck in, but we mostly call it MEA these days, and we are the world's first midlife wisdom school dedicated to helping people to make sense of their wisdom. And so we're sort of new to this, but it's really exciting how many people are coming to our public workshops as well as our private retreats. Yeah, and we have two campuses, one in Baja on the beach in Mexico, and the second one, a 2,600 acre regenerative horse ranch in Santa Fe, New Mexico.

ELISE:

Fun horses say no more. It's probably hard. This might be an impossible question, but are most people coming because they want to commune, they want to be in community with other people who are experiencing the same things, or are they looking to do deep personal work, or is it some combination?

CHIP:

It's really a combination. I would say those who want to do deep personal work, sometimes people come for that and then they end up realizing what they really needed. In addition was the community. So it's both. The number one reason people come to is they're in transition in some way coming to try to pursue your purpose is secondary. And then wisdom is usually third. Although the thing that people I think get the most out of the program is the fact that they didn't even know they had any wisdom. And so our part of our job is to help them to unlock that wisdom.

ELISE:

Yeah, you said purpose. I have somewhat of an allergy to that word.

CHIP:

Yeah, I probably,

ELISE:

Because yeah, I like using contribution just because all of your work explores it evolves and changes and will

CHIP:

Change. We tend to look at purpose as a possession, a noun, and if you don't feel like you have one and everybody else has one, you feel like somehow you didn't get your Christmas present or your holiday present or whatever. And the bottom line is it's not a noun, it's a verb being purposeful. And there is something to be said for being purposeful, and yet there's a big purpose and there's a small P purpose. And the big P purpose maybe what would be on your LinkedIn profile, the small P purpose is what they'll say at your eulogy, and it's the way you impact other people. It's the way you have shown up in the world in ways that people really admire. They're both important, but we in the US tend to get a little bit possessed by the possession of purpose

ELISE:

Or just as you said, the noun and not the verb. And we think of our life as a series of stage gates and then don't really get the coaching or have the imagination to go beyond that. So many women I know had this conversation of, I didn't really have any imagination for my life after I had kids because I was so focused on achieving these life stages that I didn't think about it. But life as a process, there's no other way around it. It's not an end state, even though these things feel so fixed to us in time.

What are you doing next? I read your hero's journey. So what's happening? Are you at the top of your circle?

CHIP:

Yeah, I feel like a little bit that way. Just meaning in top of circles you've been through the three stages of the default mode into the adventure mode, which is often complicated and scary. And then coming back into society, a little bit of a changed person. I do feel that way. I just announced that I am moving into an executive chair role of MEA instead of being CEO. And that feels good. That's a shift for me. I do have a second campus in Santa Fe that's actually in town. It'll probably be a campus dedicated to longevity. And so that's certainly something we're going to be doing. We have a lot of colleges and universities approaching us about how we can collaborate. That's an encouraging sign. I want to be a good dad. I have sons who are 12 and nine with a lesbian couple. I happen to be gay, and I am doing my best to spend more time with them because one of the most important questions I think we need to ask in midlife and beyond is 10 years from now, what will we regret if we don't learn it or do it now?

And so my biggest regret moving forward would be at this point at age almost 64 would be I didn't spend 10 years of my boys with them enough.

ELISE:

No, that hits and that part of your book, I have a nine-year-old and an 11-year-old, and the part about being too busy for them when they're young, and then when you finally have the time the way that we would imagine our conceiving our lives, they're too busy for you. That's a cute, and I recognize more than ever, I really just want to be home and engaged in parallel play. Sometimes I do work while they do homework, but yeah, I feel that acutely and would be very sad if I miss this.

CHIP:

Yeah, agreed. Agreed.

ELISE:

Well, thank you, chip. Thanks for everything you do for all of us. Here's to accelerating wisdom and thank you reframing aging here for it. Thank you.

CHIP:

Well, we're on this team together. We're on the same team, so look forward to seeing you at MEA. Look forward to connecting to you in the future.

ELISE:

Oh, I hope so. Just wanted to read a brief bit to you from Chip's book. He writes, knowledge is local, wisdom is global and portable. It can take you places you never imagined. Well outside your usual sphere of influence and expertise. Yes, knowledge may be power, but wisdom is wealth mentally and spiritually. Knowledge is static and risks obsolescence with time. Meanwhile, wisdom becomes more potent in your life, the longer it ferments. Knowledge is simple. Interest wisdom is compounding interest. Now, if that is not an advertisement for wisdom and cultivating it in our lives, then I don't know what is.

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