In this episode, Chip Conley defines a midlife makeover and how to redefine success and happiness after 40. He shares how the most difficult stretches of his life ended up being the start of something completely new. Chip also explains the pull of the ego, the search for identity and how letting go of traditional success can open the door for something more meaningful. If you’re in a season of life where things feel uncertain, or if you’re wondering what this phase of life is really for, this episode will help you feel a little more hopeful.
Key Takeaways:
- Personal experiences and challenges faced during midlife, including burnout and loss.
- The importance of perspective on aging and reframing societal perceptions of midlife.
- The concept of a growth mindset versus a fixed mindset in personal development.
- The relationship between time management and personal autonomy in midlife.
- The physical and emotional changes associated with aging, particularly for men.
- The role of purpose in maintaining energy and engagement in life.
- The significance of gratitude and specificity in practicing gratitude.
- The idea of positive commitments versus commandments in guiding life choices.
- Navigating disappointment and expectations during midlife transitions.
Chip Conley is on a mission. After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, Conley co-founded MEA (Modern Elder Academy) in January 2018. Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, MEA is the world’s first ‘midlife wisdom school.’ Dedicated to reframing the concept of aging, MEA supports students to navigate midlife with a renewed sense of purpose and possibility. A New York Times bestselling author, Conley’s 7th book Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age is about rebranding midlife to help people understand the upside of this often-misunderstood life stage and he was asked to give a 2023 TED talk on the “midlife chrysalis.”
Connect with Chip Conley: Website | Instagram | LinkedIn
If you enjoyed this conversation with Chip Conley, check out these other episodes:
Life Transitions with Bruce Feiler
Successful Aging with Alan Castel
The Happiness Curve with Jonathan Rauch
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Episode Transcript:
Eric Zimmer 00:02:18 Midlife has a way of sneaking up on you. I know because I’m in it, and it’s not without its challenges. But talking with Chip Conley shifted something in me. In this conversation, he shares how the hardest stretch of his life. Burnout, personal loss, and near-death experience ended up being the start of something completely new. We talk about the pull of ego, the search for identity, and how letting go of traditional success opened the door to something more meaningful. His idea of moving from return on investment to ripples of impact especially struck me. If you’re in a season where things feel uncertain, or if you’re wondering what this phase of life is really for. I think you’ll hear something in this episode that helps you feel a little more hopeful. I’m Eric Zimmer and this is the one you feed. Hi, Chip, welcome to the show.
Chip Conley 00:03:14 It’s great to be here, Eric.
Eric Zimmer 00:03:15 I’m really excited to talk with you. Your book is called Learning to Love Midlife 12 Reasons Why Life Gets Better With Age.
Eric Zimmer 00:03:24 And what a great topic. And is somebody who’s squarely in the middle of midlife. I’m your target audience. We’ll get to the book, though, in a minute after we start in the way that we always do, which is with the parable. And in the parable, there’s a grandparent who’s talking with their grandchild, and they say, in life there are two wolves inside of us that are always at battle. One is a good wolf, which represents things like kindness and bravery and love, and the other is a bad wolf, which represents things like greed and hatred and fear. And the grandchild stops and they think about it for a second, and they look up at their grandparent and they say, well, which one wins? And the grandparent says, the one you feed. So I’d like to start off by asking you what that parable means to you in your life and in the work that you do.
Chip Conley 00:04:09 As is true for so many things in life. I’m not sure it’s binary. There’s nothing that says we can’t feed both, and it doesn’t necessarily mean you want to feed both, but it does mean that we do possibly feed both.
Chip Conley 00:04:21 And there’s certain parts of our life. In my life, I’ll just speak for myself. Certain parts of my life are that have a voracious appetite. So there’s certain times in your life where your ego wants to be fed incessantly and frankly, as is true with the hedonic treadmill, the psychology theory that just when you thought the thing you wanted was good enough. Once you get it, you want something more. Yeah, I think that that is very true of the ego, as is true for many things. The ego in moderation is wonderful. Feeding your sense of accomplishment, feeding your sense of having an identity in the world that differentiates you is very important. But it’s when it gets out of balance and you realize that there’s never enough. That’s when you got to be very careful with, with with feeding that wolf. The other wolf, you know, often isn’t asking for anything. It can get along on a steady, small diet. It’s quieter. It’s not demanding. And that, wolf, though in the long run, is what nourishes you the most.
Chip Conley 00:05:32 And so for me, in my life, just to sum up, I was very, very focused on ROI, the return on investment as an entrepreneur for much of my life. But I have come to see that the ROI that I really appreciate these days is ripples of impact and the return on investment mindset I had sometimes meant that I was feeding the ego and feeding the greed. Greed. I’ve never been very greedy, but. But certainly feeding the desire for accomplishment. And today, what I want to feed is that part of me that really is giving back and having a profound impact on other humans as my primary way of feeling success in life.
Eric Zimmer 00:06:17 Wonderful. Let’s start with maybe setting up how you got to the place where you wrote a book about midlife. You have the Modern Elders Academy. Let’s talk about how you got there, and you describe it in the book as the tale of two midwives, one very bad, followed by one very good. Talk to me about that.
Chip Conley 00:06:38 Yeah, I went to college and graduate school at Stanford a couple of years out of Stanford Business School.
Chip Conley 00:06:44 I started a boutique hotel company at age 26 called joie de vivre Vive joy of life! And French ran that company for 24 years, based in San Francisco. We had 52 boutique hotels around California, became the second largest boutique hotelier in the US. But I really was struggling in my late 40s. At the time, I had never heard of the You Curve of Happiness, which shows that the low point on the U curve is around 45 to 50. And yes, that was the era I was in, but I didn’t know anything about that. What I thought was, oh man, I’ve hit my midlife and I’m having my crisis. But it was not just the internal feeling like something wasn’t right, but it was also externally I had I had friends committing suicide. I had an adult foster son going to prison wrongfully. I had a long term relationship ending. I was running out of cash during the Great Recession with my boutique hotel company, so it was both internal and external. And then I had an NDE near-death experience due to an allergic reaction to an antibiotic.
Chip Conley 00:07:40 And that was the hotelier wake up call. That was when I finally said, like, I’ve got to make a transition in my life, but I just don’t know how to do it. You know, I felt now a deep sense of a catalyst from that NDE over the next two years, with some help from one of my best friends who was a coach, I, between age 47 and 50, pretty much changed everything in my life. Some of it was not at all easy. It was in fact very difficult. But by age 50, I sort of hit the reset button and I was ready for something new. And then my 50s were spectacular. So the tale of two midlife were late 40s was rough. My 50s were spectacular. And, you know, I spent from age 52 to 59 helping the founders of Airbnb take their little tech startup and turn it into the world’s most valuable hospitality company, which is where I earned the title Modern Elder. I didn’t like it at first, but then they said, Chip, you’re as curious as you are wise, and that’s a modern elder.
Chip Conley 00:08:40 And I was like, okay, I like that. And next thing I knew, I was ready to create the Modern Elder Academy, the world’s first midlife wisdom school. So I would just say midlife is a complex time. It’s a time that hasn’t been given a lot of attention. Part of what I’ve been doing as a midlife activist now is to help to demystify and elevate and and maybe operationalize. How do you go through midlife differently? And what are the tools that are available to you. And the key themes that are often going on in people’s lives during this time? And that’s why we have 7000 graduates from 60 countries who are part of the MBA alumni crew.
Eric Zimmer 00:09:16 So let’s define midlife real quick. Like, what are we talking about here? What years, what characteristics? How do you think about determining yep, somebody’s in midlife or they’re not in midlife.
Chip Conley 00:09:28 Well, technically, midlife is the life stage. That is a bridge. So think of it as a bridge between early adulthood and later adulthood.
Chip Conley 00:09:36 Make sense? Right? I mean, the middle age is between early and late. So early adulthood was originally conceived as 18 to 30 and now 18 to 35 by some sociologists. So you could say that maybe midlife early midlife starts around mid 30s. Let me be clear that my definition of midlife, which is defined by a lot of sociologists, is at odds with the historical definition, which has been 40 to 60 or 45 to 65. But I’m saying maybe mid 30s, it starts to creep up on you, and then you have this very long bridge, because later adulthood, if you’re going to live till 90 or 100 later, it might start around 75. It’s when at that point probably retired. Although a lot of people are still working in their late 70s still. So it’s possible that the bridge of midlife lasts 40 years, from 35 to 75, with three stages in it early midlife, 35 to 50, the core of midlife 50 to 60, and then later midlife 60 to 75. And each of those three stages has a different flavor to it.
Chip Conley 00:10:39 But we didn’t have this worry in the year 1900 because the life expectancy in 1900 was 47. So midlife really didn’t exist.
Eric Zimmer 00:10:48 That’s amazing when we think about that. Let’s first talk about what our perspective on aging is and why it’s important. You know, you referenced just a second ago, 1900 age of 47, right. And I think many of us of my age, I’ve noticed recently we’re looking at pictures of our parents at our age or even more, our grandparents at our age. And we’re like, goodness gracious, I seem very different than that. And I think some of that is we’ve begun to have a different perspective on what it is to age. But talk to me about why our beliefs about aging are so important.
Chip Conley 00:11:31 Well, our beliefs about aging are in the US. Culture’s just pretty toxic. Let’s just be honest. If there was a bumper sticker that defined our belief of aging, it would be just don’t do it. And yet, if you don’t age, you’re probably dying or dead.
Chip Conley 00:11:45 So long story short, is because US culture has defined aging, often by the physical side of aging, which does over the course of your life, you show physical deterioration. People are scared of it. And yet our emotional aging process, we actually get better at emotional intelligence as we age. We get better at social relationships as we age. So the social side of aging can be better culturally. Not everybody, but a lot of people actually get more interested in culture as they age. They get more interested in spirituality in certain pursuits. Intellectually, they are more adept as they age because of crystallized intelligence as opposed to fluid intelligence. So, long story short, is the society perspective on aging is pretty negative. And yet the U curve of happiness research shows that, you know, after age 50, people get happier with time. And Becca Levys work from Yale has shown that when you shift your mindset on aging from a negative to a positive. Around midlife, you you add seven and a half years of extended longevity.
Chip Conley 00:12:49 So part of my role, part and part of MEAs mission is to help people own their age, feel good about the upside of aging and what gets better with age. And then look at how you can not just be youthful, but useful as you get older.
Eric Zimmer 00:13:06 Well, being useful is one of my favorite ideas and core values. Have you ever read The Cider House Rules by John? Oh yeah. Of course. Yeah. Doctor Wilbur Larch and, you know, always be useful. Very influential on me when I was a teenager. So as we look at people aging, I think many of us will see people who have become what you’re describing as wiser, kinder, better people as they’ve gotten old. And then there’s the stereotype of the grumpy old man who doesn’t want a kid on his lawn. And hardens and ossifies in some way. What to you shapes the trajectory from one of those outcomes to the other?
Chip Conley 00:13:51 It’s really the difference between a fixed and a growth mindset. So Carol Dweck at Stanford popularized this idea of mindset.
Chip Conley 00:13:59 So mindset is the way you see yourself and the world. And if you have a fixed mindset, you tend to think you have a fixed amount of luck or money or time, and you optimize that and you define success as winning and you’re trying to prove yourself. But if you have a growth mindset, you’re open to something growing with time. But that’s time or money or luck or knowledge or skill. And so your job is to actually not win and optimize, but it’s to actually learn and get better at something. And therefore it’s not about proving yourself, it’s about improving yourself. Often when someone only wants to play games that they can win, their sandbox gets smaller and smaller and they get more bored. And when you get bored, you can get cranky. And the reason you get cranky is because the world is passing you by and you don’t understand things anymore because you haven’t really been open to learning something new. There are a lot of people who fit this profile. I mean, let’s be just honest.
Chip Conley 00:14:58 It’s a profile that defines a lot of people who are older. So the growth mindset is really important because it helps you to realize you’re open to learning something new. When I joined Airbnb at 52 years old, average age in the company was 26. I had never been in a tech company before, and I was supposed to be the modern elder. I was supposed to be the one who’s, like, helping the founders figure out what to do with this business, this little growing tech startup. And yet at times, it felt like I was the dumbest person in the room. So I had to be open to not just being the oldest, but being the most clueless. And that wasn’t easy. But that required me to have a growth mindset, say, you know what? I’m going to get better. I’m going to learn about tech. I’m going to learn about, you know, DSCC, digital intelligence. I had a lot of EQ to offer, but I had to learn some DCPS. So long story short, is the people who tend to get ossified and calcified and get cranky are often people who have gotten very fixed in their perspective of the world and themselves.
Eric Zimmer 00:15:55 Yeah, it’s so interesting because I observe this in myself, the desire to become more certain that I know the way things are, you know, a certain skepticism of the way things are being done today versus when they were done before, a certain amount of less openness to new experiences. Like, I feel some of that happen and I’m very committed to actively countering those things. Yeah. You know, actively making myself take on new things, new challenges. I found myself really trying to anytime my brain is like, well, it was better back when. Is to really take that as like a chance to stop and pause and go hang on a second. Like that’s a reactionary way of thinking. Yeah. Not that it may not be true in certain cases, but it’s also true that some other things are better. Like you said, it’s this openness.
Chip Conley 00:16:55 Well, I think there’s a couple things. Number one is in our 40s in particular, we are so busy that it’s really hard sometimes to have the time and space to be curious. Curiosity is the opposite side of judgment. And so in many ways, learning how to judge things quickly. It’s a super skill because when you’re really busy, being able to make a quick judgment on something allows you to sort of say no to something or to edit your life accordingly. You know, that’s a coping skill during a busy time. So let’s know that there’s an upside to that. The other thing is you could say, well, gosh, you know, as I get older, I’m more discerning, I have more wisdom. And that’s probably true as well. Yeah, but wisdom is not about just what you can say no to. It’s also what you can say yes to. It’s also what you can learn. Wisdom is not about knowing everything. It’s about learning everything. Back to Socrates times. He laughed when people said, you know everything. It’s like, no, I’m still learning. And it’s that learning perspective that really makes the most difference. Being willing to become a beginner at something in your life at every time of your life.
Eric Zimmer 00:18:08 Yeah. Like you, I have taken up surfing later in life. Unlike you, I don’t live anywhere near where that’s a reasonable hobby. It’s a stupid hobby for me.
Chip Conley 00:18:18 Where do you live, Eric?
Eric Zimmer 00:18:19 Ohio.
Chip Conley 00:18:20 Oh.
Eric Zimmer 00:18:21 It’s a dumb place to take up surfing. I mean, it just doesn’t make sense, but, you know, I do it as often as I’m able. But I’ve also taken up, like, rock climbing and just different things that keep me a little bit more limber. You say in the book, you’ve got a line that I really like. You say time can be a dictator, but it can also be a liberator. Say more about that.
Chip Conley 00:18:41 How we look at our calendar has a lot to do with how we live our life. I mean, it makes sense. How we spend our days is how we spend our life. That’s a wonderful quote. And so for me, it’s a really interesting part of my life. I am very focused on my calendar.
Chip Conley 00:18:59 And so in some ways it dictates my life. It dictates, you know, how I’m spending my time with you today. You know, I got ten minutes extra time at the start of what was supposed to be our meeting, which was nice because I needed it. And I appreciated the fact that you needed to start ten minutes later. And that was. But when I say that, it’s like, oh my God, time defines and dictates my life. Similarly, during Covid, when my life got really spacious because, you know, I spent most of my time running MBA, teaching classes, etc. and all of a sudden we were closed for a period of time because of the pandemic. I put on my calendar three hours a day on Monday and Wednesday and Friday afternoons spying on the divine, and that was my opportunity to go into nature with my dog, Jamie, and to just be offline, not listening to a podcast, which is what I usually do when I hike, and just noticing things, being curious.
Chip Conley 00:19:54 I was doing what’s called an hour walk or what sometimes people call forest bathing and it was just really beautiful. So in that way, my calendar could be a liberation. Yesterday I thought I was going to go spend three hours with somebody who’s who’s a healer here in Santa Fe just for fun, not necessarily even healing session, but it didn’t turn out that I did, but I blocked four hours of my afternoon yesterday for that. And the reality was I wasn’t feeling very well yesterday. So that was fine ultimately. And I got to spend that time just relaxing, taking a bath and taking a nap and that’s what I needed. So we have more control and volition over our calendar than we think we do. But the language we use around time and counter is like, it’s almost as if we’re in prison.
Eric Zimmer 00:20:59 I think it’s some version of what you just said, which is like, I’m just so busy. I’m overwhelmed. I have no free time. I, you know, there’s there’s different ways of talking about it.
Eric Zimmer 00:21:09 I think it’s an interesting concept of time being potentially a liberator. You mentioned like being really busy in your 40s and then maybe in your 50s, a little bit less busy. And as time goes on, and I think time can be a liberator if we learn to use little bits of it better. I can say I don’t have time to do x, Y, or Z, but if I examine my life, then I’m like, but I spent an hour doing that and 35 minutes doing that, and there are little chunks there. Even in a very busy, dynamic life for me, there are places that without making radical changes, I can begin to claim some more autonomy.
Chip Conley 00:21:52 No doubt about it. Just being able to sit for a moment, maybe even five minutes and close your eyes and meditate and lose track of time is really valuable. I mean, there’s lots of social science research that shows that. I think, you know, one of the things that I find interesting is when you can get into a flow state.
Chip Conley 00:22:10 I was lucky enough to spend some good quality time with Mihaly Csikszentmihalyi, who popularized the idea of flow. And what’s interesting about being in a flow state when you’re doing something that has timeless awareness, meaning you’re so engaged in it that you lose track of time. There’s starting to be some research that shows that when you lose track of time in a state of flow, it is possible that you’re not aging during that time. So finding time in your life where you can lose track of time is not just joyful and make you feel nourished, but it also may extend your longevity.
Eric Zimmer 00:22:48 I want to change directions here for a second, and talk about one of the things that we all know about aging is that your body changes in often ways that are less than desirable. And you say men are not spared the bodily indignities of aging and that women talk a lot more about it. We talk about menopause, we talk about perimenopause, and we could argue whether we talk about it enough, I don’t know. I’m not I’m not a woman. I’m not going to weigh in on that. But I certainly hear people talk about that way. More than I ever hear people talking about men and aging. Outside the context of, you know, an ED commercial, right? Like outside of that, it never gets mentioned.
Chip Conley 00:23:33 Bob Dole selling Viagra.
Eric Zimmer 00:23:36 Talk to me about this. And how might we as men better support each other in this?
Chip Conley 00:23:42 Yes. You know, it’s beauty or brawn when it comes to women. It’s beauty and the fear that you lose your beauty with time. Just as you get comfortable in your own skin, it starts to sag with men can be brawn. You know, the physical virality, the feeling virile. There’s a word to describe the men’s version of menopause, and it’s called andropause. What’s different versus menopause is menopause obviously has a huge fertility element to it. In terms of you no longer having menstruation and therefore no longer able to have children. and it’s huge. I mean, it’s a very important part of a woman’s life.
Chip Conley 00:24:23 For men that you don’t have that kind of sort of functional change, but you have a lot of things that are happening. One of them is the gut. You are actually gaining a fat in your gut. That can be actually very dangerous and remarkably stubborn. It is. It’s really hard to do. It’s very hard to get rid of. I gained a bunch of pounds when I was doing some cancer treatments the last two years, and, cannot get rid of that gut. You know, my gut is not huge, but it’s it’s something. So there’s that there’s the reduction in testosterone that really starts in your 30s, and it actually declines over time. And it can really accelerate for many men in their 50s and be more noticeable in terms of the lack of both appetite for being sexual or even capacity. So that’s happening. Obviously, you’re losing your hair, maybe losing your energy. There’s a lot of elements to this. Many of them sort of relate to men feeling a little bit less masculine.
Chip Conley 00:25:25 And that can be interesting. That’s a some of the crankiness that some men get into in their 50s and beyond is just trying to mask the lack of masculinity that they’re feeling internally. My father’s an interesting example of this. My father is 87 years old. Both my parents are 87, and my dad was a marine captain and a real hardcore, you know, masculine dude. And when he got into his 50s, 60s and 70s, he all of a sudden started to soften a little bit. And I don’t know how much of it was really the physical or hormonal side, but emotionally he started to, you know, read poetry occasionally or just be open to having an emotional conversation. And so I do think, you know, there’s a real beauty in seeing men start to become a little bit more soft, seeing women become a little bit more vocal and strong willed in their opinions, as opposed to just a people pleaser. This is one of the reasons why I say that as we’re growing old, we’re also growing whole.
Chip Conley 00:26:25 And what that means is we’re learning the alchemy, the polarities inside of ourselves, you know, whether it’s wisdom and curiosity. Introvert. Extrovert. Masculine. Feminine. Gravitas. Depth and levity. Humor. I think that one of the things that I really admire about an 85 year old person is when I spend time with them. They are so present. They’re not compartmentalized in any way. They have alchemised their polarities into this sort of integrated whole. And I think that’s really what we maybe should aspire to.
Eric Zimmer 00:26:59 I’m going to take a moment and ask a more personal type question here of my own interest, which is you mention energy dropping in people as they age. And one of the things I’ve talked to a number of men in their 40s and 50s about this, and it is a drop in energy and trying to figure out what is it? Is it, you know, lack of engagement with something that you’re doing? Is it diet or is it this? And one of the questions I sort of ask myself is like, what is a reasonable amount of energy for a 55 year old person? How have you thought about that question? You know, have you noticed an energy decrease and how have you thought about it and contextualized it?
Chip Conley 00:27:43 Well, I mean, just on a personal level, for two years I had to take hormone depletion therapy because I was dealing with prostate cancer.
Chip Conley 00:27:52 Okay. That went from stage one to stage two to stage three. And so to actually, in essence, inhibit my testosterone so that it was running around 8 or 10 instead of 500 meant that I was struggling with not a lot of energy at a time. When I had a book tour and I was launching our second MBA campus and all kinds of stuff. So dark chocolate. I was feeding on that. I think that you can feel the lack of energy inside you, and you need to respect that. And look at what are some of the root causes. Are you getting enough sleep? Are you eating well? Are you drinking too much alcohol? for a lot of people. A lot of men, they’re drinking more in their 50s and 60s than they did when they were younger. And the truth is that, you know, alcohol is problematic. And actually, it’s even more problematic for older women in terms of how you metabolize it. It can mess with your sleep as well. So some of the reason that there’s a lack of energy could be just physical issues, but sometimes it’s also not feeling the sense of purpose.
Chip Conley 00:28:56 And when you have a sense of purpose, it’s like a North Star that you are aspiring to get to. And, you know, you keep walking in the desert to see that North Star. You’re never going to catch the North Star because it’s just like a rainbow. You’re never going to catch the rainbow. But it is what drives you forward. So I think for some men there’s that. I actually think the physical side also of when you start getting some weight and you’re not exercising as much, there’s that going on as well. You’re carrying around a little bit more of a load. You don’t have the cardiovascular program that you used to have. I mean, I think it’s multifaceted. I will also say that as someone who is running on a treadmill in my career, that actually getting off the treadmill allowed me to slow down a little bit and realize how completely fatigued I was. And sometimes you just need that, that space to get some sleep and to just and slow down a little bit. And that’s okay.
Chip Conley 00:29:55 As long as in the long run you feel like you’re regenerating yourself. There’ll be a renewal as a result of that. Yesterday I was not feeling well. Last night I went to bed early. I had no alcohol, and the night before I had had small alcohol. I fasted last night, I didn’t have dinner, and I took a bath last night and I just felt so good when I got up this morning. I felt very different than I did yesterday and I have a lot more energy. So I just on a personal level, I can say like that is just two days for me of very different feelings.
Eric Zimmer 00:30:30 Yeah. Let’s talk for a moment about gratitude or being grateful for our lives. And you have a line in the book that I think is really interesting, and I don’t remember who you were talking to or who said this to you, but here’s the line that you wrote. It was the particular ness of his gratitude that shielded him from either envy or pride. Talk to me about gratitude and particular ness of it.
Eric Zimmer 00:30:55 What does that mean?
Chip Conley 00:30:56 I mean, there’s a lot of social science evidence showing that gratitude and happiness have a lot. They’re like kissing cousins. If you’re struggling, the best thing you can do is to find gratitude. If you want to feel happy, go write a gratitude list. But what’s been found is that just a generic gratitude list is not necessarily as helpful as being quite specific about what you’re feeling gratitude toward. And so the specificity, if someone wants to do a gratitude journal or a daily gratitude list. The specificity is what’s important, you know. And because what it does is from a neurological perspective, it’s like there’s a precision that you’re sort of saying, honing in on. That’s what I want to feed, you know, is back to, you know, the one you feed. I want to feed that. If you said, you know, like, I’m feeling gratitude because I feel, you know, love for my family. Well that’s great. Okay. what’s specific about that today? Yeah.
Chip Conley 00:31:51 Could you say I feel love for my family? Because my daughter today just told me how much she loved me, and I could see a twinkle in her eye. That’s much better than just saying I feel love for my family. Because the love for your family could be generic across any day, But actually when you say, because my daughter said she loved me and I could see that twinkle in her eye, it’s almost you can visualize it and your brain is sort of saying like, oh, more of that, please. And when something’s generic, it has less visceral impact on you. And I think when it comes to gratitude, feeling the gratitude and visualizing it is really important.
Eric Zimmer 00:32:31 That makes a lot of sense. I know for me, if you’re just listing the things that you intellectually know, you should be grateful for my family, my health. Those things tend to. If you’re doing gratitude as a regular practice becomes the the gratitude version of the hedonic treadmill, right? It no longer does anything but the specificity that you’re talking about does.
Eric Zimmer 00:32:58 I also think it tunes us into the granularity of our experience more, which is a really positive thing. For a while I used to do a gratitude list and have a couple pictures with it, and my dogs were always on it. Like when I looked back, I was like, well, I appear to be ten times more grateful for my dogs than any other person in the world, which seems funny in retrospect, but taking a picture of what they were doing that I found so adorable was a way of getting that specificity.
Chip Conley 00:33:30 Yeah, I think that makes a ton of sense. And you don’t want to get bored with a gratitude list. Yeah, let’s just be really blunt. Yeah, it will be boring if it’s generic.
Eric Zimmer 00:33:39 So a lot of people talk about here are the things I’m not going to do and is a recovering alcoholic and drug addict. I think that there have been some very clear things for me that it’s like, I’m not doing that, I’m not doing that. But you talk about creating something you called the Ten Commitments, which is a play on the Ten Commandments.
Eric Zimmer 00:33:57 Tell me about that.
Chip Conley 00:33:58 Yeah. You know, I grew up learning the Ten Commandments. And I remember saying to my parents, you know, like, it’s all about do not, do not, do not. I think eight of the ten are do nots. And so for me in my life today, and while I do have a spiritual practice and belief system, it’s not so much the Ten Commandments, which I do feel are helpful, but it’s really more about what are my proactive, positive commitments I can make in my life. And those are not going to be hard and fast and say like, okay, those are the only ten I’ll ever have. But you know, having ten that makes sense to me and are working for me, you know, today are important. And they become sort of the guardrails of my life. And so that’s, that’s a that’s a good thing.
Eric Zimmer 00:34:44 What are a couple of them. Can you share a couple of your commitments?
Speaker 4 00:34:47 I, I.
Chip Conley 00:34:48 I don’t have them in front of me right now.
Chip Conley 00:34:52 They changed. So I like in the book I had my ten. And I think one would be just being less focused on my resume and more focused on my eulogy. And how do I show up and create the conditions in my life such that I am, after age 50, more focused on my eulogy than on my resume? And I think that’s one that has lots of catalytic effect in terms of what? What does that mean? It means less egocentric. It means I’m less focused on my accomplishments. It means I’m more focused on the small things I do in life that are impacting other people. That’s an example of a commitment as opposed to a commandment.
Eric Zimmer 00:35:50 That’s back to the the ROI, the ripples of impact, which I absolutely love. I think that is such a a great phrase in a way of thinking of it. And I love the idea of ripple. Right. Because I think that’s the way our impact generally is. Sometimes we get to see it directly, but most of the time I don’t think we actually see the good that we put into the world.
Eric Zimmer 00:36:15 It ripples out in this very gentle way, and it takes a certain amount of faith and belief that indeed, that is happening.
Chip Conley 00:36:24 Yeah, there’s Kip Tindall, who I always thought of as a role model for me. He started the Container Store Company a long, long time ago, and he talked about your wake, you know, in the context of your life, sometimes you don’t know what the wake is that you’re like in a boat. There’s there’s a wake behind you as you’re focusing forward on the boat, especially if you’re driving it. You don’t necessarily know your wake behind you. Yeah. And the truth is, the bigger you are in an organization, the higher you are an organization. The more power you have, the larger your wake. And as a water skier who knows what it’s like to ski across the lake, I know that, you know, having a huge wake can be hard. It can be very disruptive. So the ripples are sort of a form of wake. There’s a wake also.
Chip Conley 00:37:12 What you really want to do in life is to have a really positive wake and recognize that the more senior you are, the more contagious your emotions, the more contagious your character, in essence, the bigger your wake. I think metaphors are often very helpful for people to sort of visualize how the world works.
Eric Zimmer 00:37:31 You have a question in the book that you say to ask, am I frustrated or disappointed? What’s the difference and why does it matter?
Chip Conley 00:37:40 So when you’re frustrated, there’s still the opportunity to change something. And so frustration can relate to anger. It can relate to a lot of sort of combustible emotions that can propel you forward, to take action, to make it different. Disappointment, which some people could say they’re the same, but they’re not. Disappointment is an energy that actually is a shrinking. Frustration is a growing. Disappointment is a shrinking. Partly because you’re beyond frustration. Disappointment is when you come to realize that there’s not much you can do to change something. Yeah, now. And regret is one step further, which is a sense of responsibility about that disappointment.
Chip Conley 00:38:23 So, you know, a regret is actually more painful than disappointment because you actually feel like you had some fault in leading to the disappointment. But disappointment could happen in all kinds of ways, and often it’s outside of your control. Therefore, there can be a sense of like, okay, oh, well, I’m gonna have to live with that. When someone has too much frustration in their life, it can lead to anxiety and high blood pressure and a deep sense of urgency and stress. When someone has a lot of disappointment in their life. It can lead to learned helplessness and depression and a sense that, you know, oh, woe is me, or there’s nothing I can do. So they’re very, very different in terms of emotional affect. And yet sometimes people talk about saying I’m frustrated and disappointed. It’s like, well, which one is it?
Eric Zimmer 00:39:14 Yeah. Well, it’s another version of the Serenity Prayer, right? The things I can change, the things I can’t change, and the wisdom to know the difference and wisdom is a big word with you.
Eric Zimmer 00:39:27 And I think that’s a really important thing to know. Right. Because the response is very different. You talk about expectation in the book. So you say, you know, when you’re faced with disappointment, you can either improve your reality or lower your expectations. So improving my reality would sort of throw me back over on the maybe not frustrated side of the court, but that energy, right? The energy of change. If, on the other hand, I’m on the disappointment sighed. Then lowering my expectations. Talk about how we do that in a wise way.
Chip Conley 00:40:00 So one of the reasons that people often feel not great about age 45 to 50 is because of disappointment equals expectations minus reality. In your teens, your 20s or 30s, you build these expectations. They sort of propel you forward. And then by the time you’re getting starting to flirt with 50, you’re at an age where like, yeah, I don’t know if that’s ever going to happen. Yep. You could believe it’s going to happen in your 30s still.
Chip Conley 00:40:25 But by the time you get closer to 50, maybe not. And that’s really hard. And, Brené Brown calls it the midlife unraveling. And the midlife unraveling is unraveling your expectations in such a way that you are no longer feeling so wrapped up in something that there’s no space for anything else. So the key, the wise way to deal with that is to rejigger your expectations and get clear on what’s important to you. For a lot of people around 45 to 50, they are in a stage in their life where they they are running on a treadmill that was defined by their parents or their spouse or their community, but not themselves. And so it’s around that era of life that sometimes people wake up and say, like, I want to be a firefighter. I don’t I don’t want to be an accountant. We see those people come to me or, you know, a woman recently who was like, I don’t want to be a litigator. I want to be a pastry chef. It’s like, okay, you can do that.
Chip Conley 00:41:25 You know, at 20, it was hard for you to do that because your parents were sort of saying, you got to go to college, you got to make money, and then you end up getting on the treadmill and you say like, oh, I’m getting married. And now I have kids. It’s like, oh, and for some people, they wake up around 45 to 50 and say, like that David Byrne song Is This My Wonderful Life? And it’s not their wonderful life, it’s the life that you know. Somebody else wrote the script for. So finding the agency, and then the autonomy and the clarity of vision is part of what we help people with. At me.
Eric Zimmer 00:41:57 People coming to me, is there a guiding idea of what’s bringing them? There are people coming there largely because they are feeling unmoored in middle age, and they’re not quite sure what to do.
Chip Conley 00:42:12 For some people it’s something abstract like that. It’s like, okay, I feel sort of a little lost in middle age, and I’m feeling not good about aging and I want to improve on that.
Chip Conley 00:42:22 And sometimes it’s like, I feel like I’ve got to get clear on what my purpose is or what my wisdom is I’ve built, and that’s also important. But the number one reason people come to me is because they’re going through some kind of transition in their life. Maybe they’re in the sandwich generation, but they’re about to lose a parent, or they’re becoming an empty nester. The kids are leaving or they’re getting divorced. They’re selling their business. They’re changing their career. They have a cancer diagnosis. They’ve stopped drinking. They have decided that they’re going to move to a new place. They have a new spiritual curiosity that’s leading them back to Catholicism. There’s lots of things that are happening for people in midlife, and there’s menopause. There’s so much going on and so little in the way of social infrastructure to help support people during this time. So that’s the number one reason people come.
Eric Zimmer 00:43:14 That makes a lot of sense. I mean, we we tend to seek out extra support and help when we are facing something that feels acute.
Eric Zimmer 00:43:22 You mentioned in the book, Bruce Feiler, who’s been a guest for us, you know, a couple times and wonderful guy who talks all about that sort of life quake idea.
Chip Conley 00:43:31 Bruce has taught in our online programs, and I have a lot of respect for his work and his writing. In his book, life Is in the transitions, he talks about when you’re having multiple transitions at once. Yeah. He calls that a life quake. And I think the thing that’s really helpful to know about transitions is you can go through multiple of them at once, but each transition sort of has this anatomy or a framework, and it’s usually the ending of something is the first stage. The second stage is the messy middle, and then the third stage is the beginning of something new. And there’s coping mechanisms for each. And once you understand that three steps ending, messy, middle, beginning, you can realize that in one part of your life you’re having a transition, but you’re at the ending of something and another one. You’re in a transition where you’re at the beginning of something and another one, you’re at the messy middle. And so there’s a different coping mechanism for each. And once you have that sense, it really helps.
Eric Zimmer 00:44:24 Wonderful. Well, I think that is a great place for us to wrap up. Chip, I’ve really enjoyed this conversation. You and I are going to continue for a little bit longer in the post-show conversation, because I want to talk about something that you write about, which is this idea of basically wanting what we have, you know, how do we get to that because that’s a you know, what I have is all I need. So, listeners, if you’d like access to the post-show conversation to hear Chip and I continue, as well as ad free episodes, a special episode I do for you each week called Teaching Song and a poem and Other Benefits. We’d love to have you as part of the community. And that’s at one you feed. Join Chip. Thank you so much.
Eric Zimmer 00:45:07 Oh thank you Eric, it’s been a pleasure. Thank you so much for listening to the show. If you found this conversation helpful, inspiring, or thought provoking, I’d love for you to share it with a friend. Sharing from one person to another is the lifeblood of what we do. We don’t have a big budget, and I’m certainly not a celebrity, but we have something even better. And that’s you just hit the share button on your podcast app, or send a quick text with the episode link to someone who might enjoy it. Your support means the world, and together we can spread wisdom. One episode at a time. Thank you for being part of the one You Feed community.
In this inspiring and deeply human conversation, Eric sits down with bestselling author and Modern Elder Academy founder Chip Conley to explore the wisdom, challenges, and surprising gifts of midlife. From redefining success and navigating transitions to embracing aging with purpose and curiosity, Chip shares raw personal stories—including a near-death experience—that reshaped his entire approach to life.
They dive into the “U Curve of Happiness,” the liberating power of a well-used calendar, and why “ripples of impact” might matter more than ROI. Whether you’re in the midst of a midlife reset or simply wondering what’s next, this episode offers profound insights and practical tools to help you feel more hopeful, useful, and whole.
Midlife has a way of sneaking up on you. I know because I’m in it, and it’s not without its challenges. But talking with Chip Conley shifted something in me. In this conversation, he shares how the hardest stretch of his life. Burnout, personal loss, and near-death experience ended up being the start of something completely new. We talk about the pull of ego, the search for identity, and how letting go of traditional success opened the door to something more meaningful. His idea of moving from return on investment to ripples of impact especially struck me.
In this episode, Chip Conley defines a midlife makeover to redefine success and happiness after 40. He shares how the most difficult stretches of his life ended up being the start of something completely new. Chip also explains the pull of the ego, the search for identity and how letting go of traditional success can open the door for something more meaningful. If you’re in a season of life where things feel uncertain, or if you’re wondering what this phase of life is really for, this episode will help you feel a little more hopeful.
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