Making Peace with Your Midlife, Mid-career Self

AI is transforming the world, and it starts with the right compute. ARM is the AI compute platform trusted by global leaders, proudly NASDAQ listed, Built for the future. Visit arm.com discover. Welcome to the hbr ideacast from harvard business review. I'm alison beard. Let me be real with everyone out there for a minute. Middle age isn't very fun. Why? Well, as I recently wrote in hbr, your face wrinkles, your body deteriorates, your career tends to plateau, even the best romantic relationships settle, your cute little kids become aloof teenagers and then leave home. Your elders decline and then pass away. Research has actually proven that people around my age are decidedly less happy than their younger and older counterparts. That's because we've lost the exuberance of youth, are saddled with sometimes overwhelming family and work responsibilities, and haven't yet found the joyful appreciation for life that supposedly comes with old age. As our guest today wrote in his recent book, midlife is when we begin to worry that life isn't turning out the way we expected. But he also argues that it doesn't have to be this way. Middle age shouldn't get us down. Instead, we need to see it as a period of positive transition in which we hone or make peace with our physical, emotional, mental, vocational, and spiritual selves. Chip Conley is a former hospitality industry CEO, advisor to Airbnb, and the founder of the Modern Elder Academy, and he wrote the book Learning to Love Midlife. Chip, thanks so much for coming on the show.

It's great to be here.

You initially struggled in midlife. I'm clearly not happy with it entirely. So what is it about midlife that makes so many of us pretty miserable?

Yeah, I wrote a book a few years ago called Emotional Equations, and there's an equation in that book that totally describes midlife. Disappointment equals expectations minus reality. We sort of feed ourselves on hopes and dreams which turn into expectations. And then it's often in our 40s that we start to see the future and say, oh man, I'm not going to be president of the United States and my kids aren't going to an Ivy League school and I didn't marry my soulmate. I don't love the work I'm doing. I'm actually living off somebody else's success script. All of that comes to roost in our 40s. And Brene Brown, the famous sociologist, has said that's when the midlife unraveling happens. And unraveling sounds terrible, but in her way of looking at it, it's actually a good thing because to be raveled means to be very tightly wound, like in a bundle that you cannot unbundle. And to unravel means you start to actually look at your life with some reflection on what's not working and what is working. And then you make the right choices to say, I'm ready to edit some things, and I'm going to start focusing on other things that mean a lot more to me. And so midlife doesn't have to be a crisis. It can be a chrysalis, this era, you know, between the caterpillar and the butterfly, when it's dark and gooey and liminal. But it's also the place where a metamorphosis can happen.

So how did you personally go from feeling not great about approaching middle age to learning to embrace it?

Well, it was in my mid-40s that everything that could go wrong was going wrong. There's a guy named Bruce Filer who's a great writer, and he calls this a life quake. And I was having a life quake. My personal life, romantic life, was falling apart. I had an African American foster son who was going to prison as an adult. Wrongfully. I mean, he ended up getting out, but it was, you know, it was a lot of work getting him out. I had friends taking their own lives. I had a company that I had been running for 22 years that I didn't want to run anymore at the start of the Great Recession and we were running out of cash. What I felt was this deep sense that I was getting the game of life wrong and that, you know, I was at fault for a bunch of things that were sort of standard. You know, my body was breaking down. I wasn't in good shape anymore. So I think what I came to realize, I had a flatline experience, and that was due to an allergic reaction to an antibiotic. But that was my hotelier wake up call that said to me, okay, at 47, which is ironically, the low point on the U curve of happiness, although your mileage may vary, it doesn't have to mean that 47 is a bad time. But what I came to realize is I have more options than I thought I had. And I had a bit of a seize the day moment where I said, like, gosh, I can consciously curate my life differently if I choose to. And it meant I had to really say goodbye to some identities and some roles and some of how I was living my life. I now call that the great midlife edit, because the first half of your life's about accumulating and the Second half of your life is about editing. It was really helpful for me because what it allowed me to do in my 50s is to have a little bit more of a blank slate and say, okay, so now that I've, now that I have junked all these things, you know, how do I want to live my life? What is going to give me meaning in my life? I think as we get older, it's not about being youthful, it's about being useful. And how do we actually help find the right habitat where we can be useful.

So what are some of the big internal mental blocks that we have to thinking more positively about this period of life, embracing the transition instead of resisting it?

Well, number one is the definition of how we look at ourselves is we look at ourselves on the playing field of the body. So we don't have the brawn or the beauty we used to have, and therefore we don't feel as good about ourselves. And there are other playing fields in our life. There's the emotional playing field, the psychological one, the spiritual one, the intellectual one, the relational one. If you get really fixated on the body one, you will do everything you can to keep trying to keep that six pack. But as you get older, that six pack is more expensive. And what I mean by that, it takes more work and more time. And if you choose to devote that, good for you. But that means you're not spending time on other things. So one issue is the physical body defines how we see ourselves and how the world sees us because we age externally and we have a relatively ageist society. If you want to know how ageist we are, go to the greeting card shop and look at the birthday cards for 40, 50 and 60 milestone birthdays. And they're pretty negative.

And so tell me more about the Modern Elder Academy. What do you all try to do there to help people shift their mindset about middle age and put all these strengths to work?

Yeah, so I started MEA at Modern Elder Academy after my full time period at Airbnb. I was four years full time as the in house mentor, the modern elder. And when they first said modern Elder, I was like, I don't want to be a modern elder. You're making fun of my age because I'm twice the age of everybody else here. But then they said, someone who's as curious as they are wise. And I was like, I like that. So that was an amazing experience. And I decided to write a book called Wisdom at the Making of a Modern Elder. And I was writing down here that book. I Had a beachfront home here in Baja that I owned. Baja being in Mexico. And what happened was I had a Baja. Aha. I had an epiphany one day when I was going for a run on the beach. Why don't we have midlife wisdom schools? Why don't we have a place where people can reimagine and repurpose themselves? Because, you know, if you're age 54 and you're going to live till age 90, 54 is exactly halfway between 18 and 90. So many of us don't have that longevity. Literacy to understand just how. What. How you could curate your life differently if you actually realized just how much life you still have ahead. So I started learning how to surf, and I learned Spanish at age 57, because I asked myself the question, 10 years from now, what will I regret if I don't learn it or do it now? Which is a great question. It basically creates some anticipated regret 10 years from now, which is a form of wisdom. So some of the things that we teach at MEA are everything from how to navigate midlife transitions to how to cultivate purpose, how to own your own wisdom, how to actually help a person understand the gifts and mastery that they've developed in their life, and then how to make it available out there in the world. Emotional intelligence gets better with age. Our ability to be emotionally moderate, to moderate our emotions so not react as much, gets better with age. Our ability to think systemically and holistically gets better with age. Our spiritual curiosity gets better with age. Our relational ability to invest in and feel the value of relationships gets better with age. Our ability to understand our life purpose and the through line of our life, the themes of our life. You know, when you're reading a novel and you're only a quarter of the way through the novel, you don't exactly know where it's going. But by halfway through the novel or halfway through your life, you sort of understand the through line, the patterns, and therefore you understand yourself better and you're better able to make decisions.

Yeah.

When it comes to teams, one of the things that gets better with age is psychological safety. Having a team with some older people on the team, partly because of emotional moderation, partly because as we get older, we are a little bit less egocentric. And I'm not saying that to beat up on young people. I'm just saying that that is what social science has shown us. There's a lot. There's a lot that gets better with age, but so little of what I've just said is actually out there in the popular media or mainstream.

And I want to go back to what you just said about sort of being halfway through the novel of your life, because I think this is one big reason why people do feel discontent, particularly in their jobs or careers. At middle age, you know, there is that tension between reality and what you expected when you started. I personally actually feel very fulfilled in my work because I have responsibility, but also flexibility, and I've been able to experiment with new things. But I also never wanted to be the CEO of a company. What about those people who did want that big job and realized they aren't going to get it, or they did get it and it wasn't as great as they thought it would be, or they get it and fail? You know, the story that they expected for their life didn't play out. How do they get past those types of disappointments?

The most common way that's suggested is to reframe. To reframe means to take a look at something that on its face may look one way, but if you actually look a little deeper at it or look at what might be an upside of it, you can see something better. So if you got divorced or you never became CEO, you know, the reframe could be okay. I wanted to be a CEO, but, man, maybe I'm going to start my own business. So I never made it to CEO of, you know, of Procter and Gamble, but I started my own company and I'm CEO of that company. And that's a reframe. If you're divorced and feeling lonely and feeling like I'm never going to meet someone, you know, the reframe could be, I am so much better able to be in a marriage now than I was when I got married at 24. And I'm more clear about what I'm looking for. There's another quality that grows with age, and it's called environmental mastery. And it is based upon the idea that as we get older, we are more clear about what habitats we're going to flourish in. And that could be everything from what community you want to live in to, you know, who your friends are, to what cultures at work work for you. Reframing is essential because if you don't reframe and you don't look for the upside, you will probably, instead of reframe, regret. And regret is a tough thing. But here's another thing to know about social science research on this. The regret of the thing you did that didn't go well feels bad, but the Regret of the thing that you didn't do but wish you'd done and can no longer do is twice as painful as the regret of the thing that you did, but it didn't go well.

You also talk in the book about sort of the reframe about what it means to be successful. You know, many people in their careers think that that means power, status, image in the eyes of others, money, material wealth. And so how have you worked with people, high flying executives or executives who wish they had been higher flyers than they were to think differently?

So this is the part of the book that talks about the success script. And so we are all, whether we know it or not, we were handed a success script in our teen years that sort of defined for us what success was. And we either, you know, sort of tried to emulate that and live up to it, or we in some cases rebelled against it. But in one way or the other, we reacted to it. We reacted to the success script that our community, our family, our friends, whomever gave us. Often it's in our 40s, and sometimes it's 50s, sometimes it's 30s. It can happen at any age, but it particularly happens in the 40s is you wake up and you say, this is not my definition of success. I don't want to live in. I mean, I'm not going to beat up in the suburbs. I'm just using an example. But I don't want to live in the suburbs and I don't want to live a comfortable life. I've been living my parents life and I've woken up to that now. You know, when people feel like they have more agency or choice in their decisions, they'll have less frustration or even anger later. So for many people in midlife, it's the time to actually take the deep dive to understand what is no longer serving you in terms of how you define success. It's a really important piece of midlife because you may be on the hedonic treadmill, a social science term that speaks to, we are pursuing something. And then once you actually get it, you look at it in the palm of your hand and it's not nearly as valuable as you thought it was going to be. And so you find the new shining object to pursue.

I think another challenge in the workplace, even if you say, yes, I want to be active, I want to stay working, I don't want to just give up. The pace of change today can be very challenging. So how do you help people think about reskilling or learning new technologies so that they can stay relevant in middle age and beyond.

Yeah, there's no doubt. So if a modern elder is someone who's as curious as they are wise, curiosity is the thing that actually we need to never let go of. That is the fountain of youth. The fountain of youth is the. The reason curiosity is the fountain of youth is because to be curious and to be open to new experiences are two of the most correlated variables to living a longer, healthier, happier life. But I would say even before doing the reskilling and learning about AI and all of that is you need to take a step back and say, not like, here's the 10 professions that in the next 10 years are going to have the fastest growth trajectory and I better jump on that treadmill. No, it's taking a step back first and reevaluating, reimagining what's important to you. We have an MEA alum who's a litigation attorney and she, you know, she needed, like, listen, any attorney today needs to learn AI, but she's so burned out being a litigation attorney and she doesn't like the person it's made her become. That while she was at MEA in one of our workshops, one of these exercises we did with her was to say, like, what makes you agitated or excited or curious or feels like it's rooted in your childhood? Those are four paths to purpose. And she said, okay, the thing that feels most salient here is the fact that I loved cooking pies with my grandmother when I was a teenager, and she says, I love entertaining people and having people over and I always want to get to dessert. So she decided over the course of her week long workshop with us that she had enough money in the bank that she could actually, over the course of a year, wind down her practice as an, as a litigation attorney and instead actually become a pastry chef and then actually create a bakery. And that's what she's doing. So the reskilling doesn't necessarily have to be, as a lawyer learning some new part of the, of the legal trade. You may be actually at a place in your life where you're ready to do something different.

Do you have examples of people who haven't made such drastic changes and still found happiness or comfort in middle age? You know, they didn't start their own company, they didn't change from being an attorney to a pastry chef, but sort of found greater satisfaction in the path that they were, are already on.

So I call this same seed, different soil. So same seed, different soil means okay. In my life, I'VE built a seed. And that seed is my wisdom. It's what I've learned. It's what I can bring to any, you know, to any company or any, any career that I'm in. And that seed can be planted somewhere else. In my case, I was a Boutique Hotelier for 24 years and ran and built a big company. And the idea of me being at Airbnb two years after I sold my company was unfathomable. Because Airbnb is a tech company. Yes, they're in the hospitality space. But the founders approached me and said, chip, we would like to be a hospitality company when we grow up. And we're a tech company and we're small right now, but we want to become a global hospitality brand. And so I joined them, but it was really uncomfortable in some ways because I was not in my normal habitat, but they valued what I had. So let me use another example. There's a tech engineer. So once you're after age 35 as a software engineer, you're over the hill in a lot of, in a lot of environments. And so he was a great programmer and he was constantly trying to educate himself as a software engineer to get better and better at that. But he was feeling like it was a bit like he was competing with the new collection of people who were just smarter than he was. And so in his late 30s and early 40s, he felt like his career path was starting to stunt. And so he decided to, you know, on his own to like, start learning how to coach. He always enjoyed the idea of coaching. He had a coach at one point and he really liked what he learned from her. So on the side he, he got certified as a coach and he started picking up some clients. But then what happened in his company is he realized that what the company desperately needed was someone who could coach the young entre, the young entrepreneurial engineers who were coming in, especially coaching them on some of the emotional intelligence skills. How do you microwave their eq, their emotional intelligence, and how do you help them think strategically and how do you help them lead a meeting? And so he was able to elevate in the company to a role where he's the in house coach in the company for younger engineers. It was a slight shift of his role, but it was one that was very meaningful for him.

So I love that example, and particularly the microwave your eq. I've never heard that term before for sort of cooking something fast. I like it. In the book, you talk about making 10 commitments to yourself to make sure that you're going to be sort of living into all these great reasons why middle aged people have something to bring to the table. My very favorite, I have to tell you, is show up so people notice my energy, not my wrinkles. As soon as I read that, I said, I'm going to start doing that. But what has proved to be the most valuable for you in terms of living the life that you want to lead into old age, the exercise is.

Really to say, these are commitments that you can make to yourself in midlife and beyond and live the rest of your life this way is very important. And any kind of commitment that speaks to the idea that, don't worry about what other people say about you. Focus on what you can do, not what things that you have no control over. Yeah. One of the 10 commitments on the list comes from David Brooks and his book the Road to Character. And it's based upon the premise that we sort of live our lives based upon our resume and what would our life be like if we lived it based upon the eulogy that people will be giving at our funeral. And this is really important in midlife and beyond because saying that I had the best resume around is not what you care about. What you care about is your social relations and your reputation and the love, care, and joy you had in your life. So I very much focus on my eulogy today much more than my resume, and, man, do I. I'm so much happier, but also I'm such a better person for that. Erik Erickson, the famous developmental psychologist, says said something to the effect of, I am what survives me. You know, in our 20s, 30s, 40s, it was, I am my business card, or I am what I own, or I am what others say about me, or I am what I control. But I think after 50, it starts to become, I am what survives me. And in my case, it is, I am how I serve, how I serve. How am I serving in the world.

Yeah, it reminds me a lot of the famous Clay Christensen article, how will you measure your life? Where he talks about, you know, when I meet my maker, we're not going to talk about the things I did. We're going to talk about the people that I had an impact on. And so he very much prioritized mentorship and collaboration and helping others, really. So for people who are younger, earlier in their careers right now, what advice do you give to them about how to better prepare for this phase or even start to be thinking in this way, sort of more long term, more holistically right now?

Let Me talk. Let me about a tool that I've used for 35 years now, and it was one I created myself. So I was 28 years old at the time. I had been running my boutique hotel company for two years, and we were struggling for a variety of reasons. And I sort of limped into the weekend and like, oh, God, how am I, you know, this? I'm. I'm not doing well here. I feel like, like I'm. I'm not very good at this as the 28 year old CEO. And long story short is I took a journal off the bookshelf in my home and I wrote on the COVID of it my wisdom book. And then that weekend, I spent about 30 minutes making a series of bullet points of what I had learned that week. What were my life lessons that week, whether it's personally or professionally? So this was not a journal. This was not like talking about my emotions or anything like that. It was more like, what were my lessons? And then how will that lesson serve me in the future? And so in doing that, what I was doing was I was metabolizing my experience. I was really, in some ways, accelerating my wisdom. We know people in their 70s who are not wise, and it's because they've never really learned anything about their life lessons. And then we know people in their 30s who are very wise. And so a lot of that, you know, some of that may be what we're born with, you know, but I think a lot of it has to do with how are we metabolizing our experience. And so one of my recommendations to younger people is to use this as an exercise if they choose to. You don't have to do it every weekend like I've been doing for 35 years now. You could do it once a month. What? I do it with leaders, both at all three of the companies that I've been helping to run, which was Joie de Vivre and Airbnb and Mea, is we do a quarterly leadership and team meeting. And the whole meeting is dedicated to each of the people on the team. And let's say there's 10 people on the team, each person coming to the meeting with their biggest lesson of the quarter, what it was, and how it will serve them moving forward. And then we, as a group of 10 of us, then we actually say, what was our biggest team lesson for the quarter? And we talk that one through. What's beautiful about this exercise is it allows us to be a little bit vulnerable and candid. It allows us to share. Wisdom is not taught, it's shared. So the fact that someone else in the room just talked about their lesson may serve me. I may not have to go through what they went through because I learned their lesson. And most importantly, it creates this sense that we are improving. I'm a big fan of Carol Dweck's work at Stanford. The idea of fixed versus growth mindsets and a growth mindset suggests that we're improving and getting better and learning. And that's what this exercise does. And I think more and more companies are going to develop not just knowledge practices and knowledge management, which is a big thing. It's been a big thing for 50 years now. But we're going to focus on wisdom management and wisdom practices because in the era of AI, where, you know, knowledge is commoditized, what becomes more valuable is wisdom. And wisdom is not based upon something you find in an encyclopedia or in ChatGPT. Wisdom is what you've learned yourself and maybe with other people. So I think the wisdom economy is ahead.

And are there any other ways that you would point to for people from other generations or entire organizations to better use and benefit from, you know, that long list of strengths that people in middle age have that you enumerated?

Well, one of the things we set up at Airbnb that I deeply believe in for any company is mutual mentorship. You know, by 2025, the US Department of Labor says that the majority of Americans will have a younger boss. We have never seen this before. How do we create a workplace in which intergenerational collaboration is par for the course? It's standard. And how do we have age diversity as just as important of a diversity as gender and race and sexual orientation? How do we look at a co generated set of solutions and an intergenerational potluck so everybody brings to the table that which they do best at Airbnb? Over the course of my seven and a half years between full time and part time, I had over 100 mentees. And I would say that in 80 of them, in 80 of the cases, I was a mentee of their. I was a mentor. I was a mentor and an intern at the same time. I learned as much from them, often about digital intelligence, dq, and they learned a lot from me on eq emotional intelligence as well as a bunch of other things. And I think the more we can create matchmaking in organizations where we can match a yin with a yang in terms of like, one person knows this but wants to learn that the other person's the exact opposite, let's match them within a company because Deloitte has shown that when Millennials have an in house mentor within the company, they are more than twice as likely to stay at least five years as somebody who doesn't have a mentor. So this kind of knowledge or wisdom transfer is great, but it's also a retention tool.

Chip, thank you so much for talking with me today.

Yeah, I feel honored and I look forward to meeting in person someday.

That's Chip Conley, founder of the Modern Elder Academy and author of Learn, Learning to Love, 12 Reasons why Life Gets Better With Age. And we have more episodes and more podcasts to help you manage your team, your organization, and your career. Find them at hbr.org podcasts or search HBR on Apple Podcasts, Spotify or wherever you listen. Thanks to our team, Senior Producer Mary Dew, Associate Producer Hannah Bates, Audio Product Manager Ian Fox, and Senior Production Specialist Rob Eckhart. And and thanks to you for listening to the HBR IdeaCast. We'll be back with a new episode on Tuesday. I'm Alison Beard.