Chip Conley, 63: Midlife Chrysalis

This week, we check in with my friend, my teacher, and my fellow traveler, Chip Conley. It was almost 8 years ago when Chip, who at the time was head of Global Hospitality and Strategy at Airbnb, reached out as he was in the process of writing Wisdom at Work: The Making of a Modern Elder. AGEIST was in its infancy, and to get a call from Chip was a big deal, and we were very much not. It began a friendship with a man I can always count on to return my calls, to offer advice, and encourage me to keep pushing. I think I read a lot, but Chip is a walking resource library, an oracle on all things midlife, on which he can speak with deep and generous authority. One of the things I learned from my career photographing the well-known was that there were very few truly good people, and equally few bad people. Chip is one of those rare truly good ones.

Chip has a new book, available for pre-order now, coming out in January called Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age. My bet is it will be another much discussed bestseller.

Below is an edited version of our recent conversation.

Why did you write a new book?
For the past six years, we’ve been running MEA (Modern Elder Academy) and I have had the opportunity to witness 4000 people from 44 countries come down here to Baja to experience the opportunity to have a midlife atrium, a place to reflect upon. How do you want to live the second half of your adult life?

Based on my own personal experiences, I felt like it was time to give midlife a new brand. Maybe it’s not a crisis, maybe it’s a chrysalis. I have a TED Talk coming out on November 13th that’s on that same topic about the idea of the midlife chrysalis. I’m trying to help give a new perspective on what midlife’s purpose in our life is.

“A lot of people in midlife are going through a lot of transitions”

Both of us, we’ve seen some people have roadblocks. They have difficulties. Some people  get stuck. Talk to me about these blocks that you’ve seen and how people overcome them.
We have three key pillars of our curriculum, and that’s navigating transitions, cultivating purpose, and owning wisdom. A lot of people in midlife are going through a lot of transitions. You’re changing your job, selling your company, getting divorced, empty nesters, parents passing away, or menopause.

Yet, we don’t really have much in the way of education during the transitions. People who are going through a transition often get stuck in one of the three stages of a transition. The first stage is the ending of something. The second stage is the messy middle. The third stage is the beginning of something new. Think of a caterpillar, a chrysalis, butterfly. 

About a quarter of people get stuck at the ending of something. You have to ritualize something when you’re ending something. That really helps. We help people to ritualize what we call the great midlife edit. What is it? The mindsets, the identities, the archetypes, the ways of thinking and being that aren’t serving you anymore as well as the people in your life who aren’t serving you anymore.

About 50% of the people get stuck in the messy middle. That’s when you’re in the chrysalis and it’s dark, gooey, and solitary. But it’s also where the transformation happens. Why do people get stuck in that stage? Because, frankly, it’s really confusing. It’s awkward.

It’s sort of like being not on solid ground and that’s when it helps to have a coach, have good friends, to see the throughline of your life, to understand the theme in your life and how to get to the other side. When you’re in the messy middle, you have to be able to see how you can get to the other side.

“You have to learn how to become a beginner again and have a growth mindset”

The third stage of a transition is the beginning of something new. And 25% of people actually have a hard time with that. That is the butterfly coming out of the chrysalis and realizing that before it can flap its wings, it ends up on the ground often because it doesn’t know how to do this and its wings are maybe a little too wet from being inside the chrysalis. You have to learn how to become a beginner again and have a growth mindset.

I often use the phrase “poverty of imagination” – we lack an imagination of what we can be generally because we’re barraged by media that says that we can’t be. How do you deal with that? How do you expand someone’s imagination of what’s possible?
That’s a great point, David, because, for a lot of people, the problem they have in midlife is a sense that their options are closing down as opposed to opening up. And one of the truisms of midlife and one of the chapters in my book is about time affluence. It is true from about age 55 and beyond we actually have more space in our life.

Now, that’s not true for all of us. But on average, that is true. If you have more space in your life, you actually have more space for options and to become a beginner again. One of my favorite questions to ask someone who’s feeling stuck is: “What is it that you know now or have done now that you wish you’d known ten years ago?”

Once you have that thought in your head, ten years from now, what will you regret if you don’t do it or learn it now? What that does is it creates anticipated regret. Anticipated regret is a form of wisdom, and it also gets you off your ass. 

“Anticipated regret is a form of wisdom, and it also gets you off your ass”

I’d like to help people see, “Wow, not only do I have more options, but I have more time and I don’t want to have that regret.” It helps to have a supportive community of people who are there for you. 

What I’ve seen is there tends to be a mismatch between people’s actual capacity and their perceived capacity. We tend to feel that we’re less capable than we are. And how do you address that?
There’s the imposter syndrome and then there’s the growth mindset. The imposter syndrome is like, “I don’t know what the hell I’m doing and when are they going to figure that out?“ “They” meaning the world. And you get very caught up in social comparison. 

And then there’s a growth mindset, which is, “I don’t know what the hell I’m doing yet.” Figuring it out is the growth mindset. Allowing yourself to try something that is new is something we’ve done our whole lives. Why should we starve ourselves of curiosity and an openness to new experiences when those two qualities, curiosity and openness to new experiences, are two of the top five qualities for people who are happier and healthier later in life. If you’re willing to be curious, then that may lead to you thinking, “Oh, I’d like to try to serve, or I’d like to learn Spanish, or I’d like to learn pickleball.” This is the time of your life when you shouldn’t be reducing your options, you should be expanding your options. Yes, you’re going to be awful at certain things, but you’re going to surprise yourself with how good you’ll be at many other things. 

The other thing that people have to look back to is: when you were under the age of 18, what did you love doing? We had a litigation attorney here recently, she was 60 years old and she was so weathered. Being a litigation attorney means you’re just arguing all the time. And when she was in her teens, she loved cooking pies with her grandmother. And so while she was here at MEA, she came to the conclusion that, “In the next year, I am going to retire from being a litigation attorney and I’m going to become a pastry chef.”

That’s what she’s doing now. Helping people with their dreams is part of what we do, because sometimes these dreams have been papered over, concreted over by decades of life experience doing whatever everybody else expected you to do.

“Helping people with their dreams is part of what we do”

Let’s investigate the intersection of a growth mindset and becoming comfortable. One of the things that happens is people get older, they get this idea that they should be comfortable, as in, I want the softest chair, I want the cushy ride, how can I be most comfortable? Is that in complete opposition to a growth mindset?
Yeah, it is, because a growth mindset suggests that there’s a wide berth here. The wider the berth in terms of what you’re going through, the more of a growth mindset you have. What it does for you is it creates a bigger space; instead of a balancing beam, it’s a sidewalk — it’s wider so you can walk it. You’re not going to fall off. What a growth mindset helps a person do is to give themselves the space to actually not volley between anxiety and boredom, which is how a lot of people live their lives.

“Oh my God, I tried that. And it made me so anxious. And so, I’m not going to do that again. And instead I’m going to watch 47 hours of TV, like the average retiree in the United States, and get bored.” It’s silly. A lot of people who are willing to try a little bit get anxious and then they go say “no more” and then they get bored.

It’s partly because they’re on this very narrow balancing beam between anxiety and boredom. If you give yourself the space to actually learn how to get better at something, you’re going to get better at it. If you don’t like it, you don’t have to keep doing it. But then go try to find something else. My number one question I ask now at cocktail parties is: “What in your life are you a beginner at right now?” Most people can’t answer. They aren’t beginners at anything right now. 

What? That’s your opportunity.

“If you give yourself the space to actually learn how to get better at something, you’re going to get better at it”

Brilliant. My experience is this stuff varies dramatically based on gender, right?
Yeah. First of all, our research and research from social sciences have shown that the number one feeling that men tend to have in their fifties and sixties is irrelevance. And for women, it’s invisibility. What this means for women is that sometimes you have to have a bigger voice because you feel people aren’t hearing you or not seeing you. 

For the men, if you are irrelevant, how are you going to make yourself relevant again? Men: you are valuable, you will not be irrelevant. You will be very relevant. There’s a lot of constraints we put ourselves under; as Shakespeare said, there’s nothing worse than the prison that you didn’t know you were in. 

My experience at Airbnb — where I joined at 52 and was at a tech company for the first time and was pretty much helping to run the company — as someone who didn’t understand tech, that meant that I had to be a mentor and an intern at the same time. How do we learn how to become a mentor and an intern at the same time? We are the perfect alchemy of wisdom, and curiosity is wisdom because curiosity opens up possibilities and wisdom distills down what’s essential.

You can be a mentor, you can be a role model. There’s all kinds of ways that we can have an influence on others. Erick Erickson famously said that, after age 45 or 50, the mantra in our life should be: I am what survives me. And the question is, what’s going to survive you?

And it doesn’t have to be a building with your name on it or a book that you’ve written. It literally could be the mentee who will read your eulogy at your funeral, or it could be the little community garden that you help to get built. Or it could be being a great grandfather. There are things that actually have a huge long term effect on other people.

Men’s Challenges in Midlife

I want to talk a little bit more about the men because the women are kick-ass in this age group, they’re starting the companies and starting the organizations — yet they feel invisible. They are very, very not invisible. But the men, they’re a problem. What do you feel are the particular challenges men in this age group have?
So, there are a few. Number one is women have dealt with sexism their whole lives. And men, especially men in their fifties or sixties, especially if they’re straight white men, have never dealt with an ism. It’s the very first time in their life that they actually are dealing with a societal bias against them, and they’re not prepared for that. That’s one thing. 

Number two is, for a lot of men, their definition of who they are is their business card. So if they are not at the top of their game in terms of their career or if they’re actually retiring, they have not prepared themselves for the identity replacement.

Thirdly, they don’t know what’s going on with their body. And they think of it as their own problem. There’s a bunch of things that are happening biologically to them that they don’t understand. 

“For a lot of men, their definition of who they are is their business card”

Women are much more socialized to talk about their vulnerabilities and look for support when it comes to going through challenges or transitions. Men, on the other hand, don’t do that as well. You get these men in that state of quiet desperation where in some cases their life narrows and it doesn’t expand. Whereas for a lot of women the opportunities expand.

I’m thinking that one of the sort of delusions that men in this group have is that they feel they have a lack of strength, a lack of capacity. Thoughts on that?
First of all, there are lots of forms of strength and they are not just physical, they’re emotional, they’re spiritual, they’re intellectual, they’re relational. Whether it’s men or women, as our brawn or our beauty starts to fade in conventional terms, it’s understandable that we feel we’re not strong anymore. But there are all kinds of forms of strength and I’ve got to tell you that the older man or woman who shows me their character, which they have forged over the course of many decades and reveals to me their wisdom as well as their generosity, that is a form of strength that I want.

I think some of this is really a function of a society that defines beauty or brawn based upon some old-school ways of looking at it. But let me also say, and this is very relevant to you and to AGEIST, look at all the people who get better with age when it comes to our bodies. One of the things I talk about in the book is the six pack. And as we get older, the six packs are more expensive, it takes more work and more time and more discipline to have a six pack.

And so, if that is true and you want to have a six pack at 85, it’s going to take so much of your life to do that or even 55 relative to 25. And so then the question becomes, How expensive in terms of your time and attention is that six pack? 

Let’s also recognize that women have been better at being multitaskers throughout their whole life. Therefore, when they’re at this stage, they have multiple things going on. Whereas men, we’re doing that less. So it’s easier for men to stagnate because they have one role, they have one identity, and they’re not doing it anymore and they’re not sure how to go find something else to do. Whereas women have a lot on their plate always. 

What do you want your legacy to be?
Oh, kindness. I would love someone to come to my funeral and say he was a great mensch. I would love to be known as a mensch. My legacy beyond that personal anecdote or personal perspective is I would like my legacy to be a person who helped to rebrand Midlife as a time of opportunity when our best years may be ahead of us.

You and I are both doing that and we both have a lot of societal messages working against us. But I actually think both of us are making some progress.

What are the three non-negotiables in your life today?
I have a really good sleep pattern and I want to be in bed by 830 or nine; that’s a non-negotiable. 

Another non-negotiable is the idea that, you know, I’m walking at minimum 10,000 steps a day in a month, but preferably 15,000 on average in a month, per day.

And then another non-negotiable is I won’t work with people I don’t respect or don’t enjoy being with.

Connect with Chip:
Website 
Modern Elder Academy
His blog
Preorder Chip’s book coming out 1/16/24