Chip Conley: How To Infuse Your Life With Generosity, Adventure and Love [EP033]

New York Times bestselling author, brilliant leader at the forefront of the world’s sharing economy, Chip Conley is an expert in bringing wisdom to life’s deepest challenges. And, as you’ll hear, he has lived those challenges! In this episode, Chip will teach you how to infuse your life with generosity, love and deep insight–at exactly the point you’re at right now. You’ll thank yourself for listening!

Episode Table of Contents

Episode Introduction: Life With Generosity

Transcript Notes

Living our lives with gusto and goodness. Chip Conley is a brilliantly successful thought leader, humanitarian and entrepreneur. But the heart of what has brought him his success and his vision of the world is committing to a life with generosity, adventure, kindness and curiosity. In this episode, Chip is going to teach us how we can infuse those qualities into our lives right here, right now at exactly the point we’re at. So stay tuned to the deeper dating podcast.

Hello, everyone, and welcome to the Deeper Dating podcast. I’m Ken Page, and today I’m going to be interviewing Chip Conley who’s going to teach us how to infuse gusto and goodness, adventure and kindness into our lives. Every week I’m going to be sharing the greatest tools and the greatest resources I know to help you find love and keep it flourishing in your life because the skills of dating are nothing more than the skills of love, and the skills of love are the greatest skills of all for a happy life.

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You can also find the whole transcript of this interview at And if you go there, you can also receive my free ebook and learn a lot more about integrating these ideas into your own search for love.

I also want to say that everything I share in this podcast is educational in nature. It’s not medical or psychiatric advice, and if you’re experiencing any serious psychological conditions, please seek professional help. Also, if you like what you’re learning here I would be so appreciative if you could subscribe on Apple Podcast and leave me a review, so thank you so much for that.

Let’s Hear About Chip

For those of you who don’t know about Chip’s work, and for those who only know a little about his work, let me tell you about this man. Chip’s a rebel hospitality entrepreneur and a New York Times best selling author and a leader at the forefront of the sharing economy. At age 26, he founded Joie de Vivre Hospitality, which is the second-largest boutique hotel brand in America, and after running the company as CEO for 24 years, he then served as Airbnb‘s Head of Global Hospitality and Strategy.

Chip has five books out, and they include Peak and Emotional Equations, and they’re inspired by the theories of famed psychologists, Abraham Maslow and Viktor Frankl. And in his new book Wisdom at Work: The Making of a Modern Elder, which I also highly recommend, Chip shares his experiences as a mentor and an unexpected intern at Airbnb and why he believes that the intergenerational exchange of wisdom is critical to our society.

Chip’s a recipient of hospitality’s highest honor the Pioneer Award, and he serves on the boards of the Burning Man Project and the Esalen Institute, which is also the home of the Conley Library. So, without further ado, I’m thrilled to welcome Chip Conley.

Ken: Chip, welcome to the Deeper Dating Podcast. I am just so delighted to have you here.

Chip: Thank you. I’m grateful that you have this message out in the world, Ken. I’m honored to join you.

Ken: Thank you, Chip. Knowing you for many years, and having watched you go through a number of different incarnations, and I’ve only been here for the last few. But witnessing these, the reason I most wanted to bring you on this show is because you are a magician in a certain kind of way.

A Life of Magic

A Life of Magic
Photographer: Keila Hötzel | Source: Unsplash

Ken: It’s not just pyrotechnical kind of non-replicable magic; it’s a magic that anybody could learn and capture. I’m here to capture and help bottle for my listeners. I’m here with you to capture some of those things that you have done that I have seen through the years.

You have been through profound hardships and vast learning curves, and not only created success, but, again and again, created a life filled with richness, love and meaning. How you do that, on top of your successes, your wisdom and your insights, the life that you create, is, to me, one of your greatest kind of magics.

Chip: One of the things that’s true in life is that we’re all role models for each other. I appreciate everything you just said, because it means that, I guess, I can be a role model for others, just like others have been role models for me.

Ken: I think that’s such a key piece of your teaching, and that’s the piece of being a learner and a teacher. We are going to get to that just a little bit down the road. But I want to start further back, and start with your creation of the company, Joie de Vivre. You created many incredibly successful boutique hotels. In fact, in your area, you were probably the greatest creator of boutique hotels in the country, if I have that correct.

Not only was there the success that you created financially, the beauty that you created aesthetically, but you taught lessons of kindness. Somehow, in creating the company, kindness was paramount to you in how staff were treated, how guests were treated, even how housekeepers were treated.

Joie de Vivre

Ken: I’d love you to talk about what led you to become a person who placed kindness so far to the front of the line.

Chip: Well, it’s been proven by social scientists that our emotions are contagious, and, truly, frankly, the higher you are in an organization or in a leadership or high-profile role, the more contagious your emotions. So when you create a company called Joie de Vivre, which means joy of life, you’re, in essence, trying to provide a contagious kindness or joy in the world, and emulate that for your staff, then allow our staff and team to provide that to our customers.

I think one of the things that leaders forget is that they’re the emotional thermostats of those that they lead, which basically means you sort of set the climate control in the room or in the organization. Was I joyful and kind every day? Of course not. Was it where I kept trying to move my climate control, even on a bad day? Yes. The place I tried go because I knew that the contagious nature of our emotions meant, if I moved a little closer to kindness or joy, I was influencing other people as well.

Ken: So you are now articulating something exquisite. You’re describing a life practice that applies at work and everywhere else. Am I moving my needle toward my joy? Am I moving my needle toward kindness? That’s what I call, which I think is just so essentially you, gusto and goodness. So this is a rich practice that you’re describing.

Chip: And I didn’t learn it from anyone. I guess I just learned it along the way. I think the thing I did learn is the contagious nature of our emotions.

Mastering Your Emotions

Chip: I kept reading about that since college. I ultimately wrote a book called Emotional Equations, which was a deep dive into creating an operating manual for my emotions. It’s a funny thing that we’re not taught how to address our emotions in school, and, in many cases, our parents aren’t necessarily the best teachers for these things.

You actually have to start developing a relationship with your emotions over time. That allows you to become a master. When I say a master, it doesn’t mean you control them. It just means that they don’t control you.

Ken: I guess, those times when we do feel overwhelmed by our emotions, we still find a way to hold them with some degree of compassion, until the storm passes.

Chip: I think that’s true. More than anything, I wish that I could go back to some times where I didn’t have that kind of emotional moderation. There’s a beautiful quote from Viktor Frankl in Man’s Search for Meaning, that book about being in the concentration camp in World War II, a psychologist. He says,

“Between stimulus and response, there is a space. In that space is your power to choose your response. And in your response lies your growth and your freedom.”

To me, no three sentences have ever been written that are more relevant to the question of can you be emotionally responsive as opposed to emotionally reactive. Creating that space is a critical piece of it.

Ken: So much in what you just said, and I’m going to kind of scroll through some of those points I know about your life that you’ve written about, one being your company having a really difficult time during the financial crash and what that was like for you.

A Life with Generosity, Humility and Gratitude

A Life with Generosity, Humility and Gratitude
Photographer: Ullash Borah | Source: Unsplash

Ken: Another one was having your heart flat line. Another one was entering into a company where you were nobody’s age. You were older than everybody at Airbnb. Those experiences of confronting a stimulus that was incredibly challenging and somehow finding your way.

We’re going to come back to that. I want to say that you’re a guy who has been humbled by a lot of stuff. It’s these qualities that helped you find a way to respond, and that way informed who you were and what you taught.

Chip: Wow, you brought back a lot of memories and some PTSD as well. I think one of the things that’s been clear to me along the way is I don’t have to do it alone. We can look at people like me in the context of this podcast and potentially make me sound heroic because of a variety of things that I’ve gotten through, yet, in each one of those circumstances, I didn’t do it alone.

In some cases it was my father who was by my side. I had a difficult upbringing with my dad. But as adults, especially as we’ve gotten older, we’ve become closer. In other cases, it was a good friend, Vanda Marlow, who you’ve met and know. She’s a leadership coach, a life coach. She was very supportive. In other cases, it’s been just good friends.

I think, more than anything, one of the things that’s been really interesting in studying happiness literature, went to Bhutan to study the Gross National Happiness index there 10 years ago, is two key consistent facts around happiness research.

Facts About Happiness

Chip: Number one is …

The fastest way to get to happiness is through gratitude.

Gratitude gets you to happiness faster than just about anything else.

Number two is the consistency at every age in people’s lives of connection, social connection. Social connection has an enormous impact on people’s sense of well being and contentment and satisfaction with life. You don’t save that connection only for the good times. Part of what is the beautiful thing about having the connection during the difficult times is not only does it support you foundationally, but, frankly, more than anything, you have a moment you can go back to with a friend where you can say, God, we were in that together.

That friend was there for you at that time. Having that kind of authenticity and candor in a friendship is what creates the richness of a friendship. If you only had a friend when you were going to DisneyLand, excuse the childhood thing, but if you only had a friend when you were doing the good stuff, the depth of that relationship would be lacking.

Ken: I think that’s so huge and true. This is something I teach people all the time, that if you’re trying to make a change in yourself and you can’t do it and you can’t do it again, the way to do it is to do it with support. If you can’t do it yourself, the key, the magic key, that is breathtakingly powerful is to connect with someone else, when there’s a hurdle, when there’s a hill you can’t climb. You’ve done that. When I go to thinking about you. And I’m moving ahead. I want to move back too.

That Thing Called Ego

Ken: But when I think of you at Airbnb, realizing that you were from such a different generation and that the community of people that you were working with and surrounded by was just of a different world, you didn’t just go outside for help. You said these people are going to be my people too. How can I teach? Even more importantly, how can I learn? I’d like to you talk about that approach to challenges and life.

Chip: It’s an interesting thing what an ego can do for us or against us. When I was asked to join Airbnb six and a half years ago by the three young founders, because I was a long-time hospitality executive and here’s this little startup trying to disrupt the hospitality business, I initially thought, okay, my role is to be the mentor to the CEO, Brian, who is 21 years younger than me, and to dispense wisdom somehow. After the first week, I realized, oh, my God, I’m 52 years old. I’m twice the age of the average person here.

I don’t understand the lingo they’re talking, mostly tech but sometimes Millennial talk. I felt like I was Margaret Mead amongst the Millennials. I felt like I was a cultural anthropologist in a very foreign place. What was interesting about my ego at that time is I thought I was supposed to come in and sort of be the wise one. What became clear very quickly was, yes, I probably had some wisdom to offer, but, actually, I had curiosity also. So I was as much the intern as I was the mentor.

Now that, the ego, had to get stretched, or shrunk. I don’t really know. It just had to be different than it had been.

Wearing Different Garments

Chip: Having been the CEO of my own company for 24 years with 3,500 employees, I was used to having deferential treatment and sort of being the sage on the stage. But to actually now be the person who’s the guide on the side and sort of behind the scenes helping these three young Millennial founders was a complete change of identity.

For those of us in mid life, one of the most important things we need to do is occasionally take off all our garments.

I’m not talking literally, although wise to do that occasionally, especially before a shower. But the thing is we wear a lot of identities. Each of these identities are almost like a garment. These uniforms we wear, get almost stuck to our skin, and therefore we actually have a hard time being someone other than what we’ve always been.

If we do that, we end up with way too many garments. It gets steamy and hot. So, in some ways, what I had to do was basically take off some of the garments I was used to, and go from being the one who was always interesting to being the one who is interested. I had to be the one who was interested in these young people about supporting them. I think it’s part of what we learn when we have kids. It’s part of what we learn as we move from the early part of our life to the later part of our life.

More than anything, what it helped me to see a modern elder, which is a relatively new term, not regarded with reverence of a traditional elder of the past. A modern elder is appreciated for their relevance. It’s not reverence; it’s relevance.

Hall of Mirrors

Hall of Mirrors
Photographer: Ludomił | Source: Unsplash

Chip: In order to have relevance, better be as curious as you are wise, because the world is changing so much. If you have wisdom but you don’t have context for how to apply the wisdom to modern day problems, people won’t listen to you.

Ken: That’s beautiful and true. There’s a way that you are kind of cocked for curiosity in your life, and I’ve seen that about you. That curiosity is such a deeply important thing too. I think there is a gusto in curiosity. There’s an aliveness. There’s an adventure, and all that leads to a willingness to be changed.

For me, being a dad and now being a dad of a teenager, I’ve always believed that the blueprint of the way things were is that our kids demand that we turn ourselves inside out, in order to be the kind of parents we need to be.

That’s our job, to be willing to be turned inside out, which is a grueling process, but it’s what we need to become who we need to be.

My workaholism, my irritability, my judgmentalism are all qualities that, again and again, my son has called me out and said stop. God, has that been humbling, but it’s helped.

Chip: It’s sort of the hall of mirrors. Certain kinds of situations and relationships are there to reflect back on you so you can see yourself. Sometimes we see ourselves through other people. For so many of us, often the person we’re most judgmental towards is the person who reminds us a little bit of some of our shadow qualities. So why is that helpful? It’s helpful because having that kind of reflection allows you to do some deep reflection.

How Evolution Manifest the Relationships We Create

Chip: Having that mirror allows you to go a little bit deeper. And, going deeper allows you to potentially make the change necessary to shift out of that way of being. Part of our lifetime is really to just evolve our consciousness on this planet. That is not a bad way to look at the game of life, is that we are constantly curious about so many things, including how we show up and how people are influenced by us.

Ken: In looking at that, what would you say the greatest area of learning, the greatest see and the greatest revelation for your own growth has been in relation to intimacy and your relationships with other people? What’s been the greatest seeing for you, the most important one?

Chip: I think what’s been interesting in my life, and you know this pretty well because we’ve talked about it a bit. I’ve been able to, in my career life and my life in the world, manifest things relatively easily. When its come to romantic relationships, I’ve felt really lacking in intuition at times and a little bit lost. So I have really appreciated friends and advisers as people I bounce things off of.

I don’t feel the need to do that quite as much in my work life, which is surprising, because for some people that’s exactly the opposite. But being able to talk about things and reflect on it is helpful, and, yes, being in relationship. I’ve had two long relationships, one 11 years, one 8 years, both with men, in both of them, I would say, I came out of those relationships a lot more aware of who I was. Both relationships ended not well.

Breaking Away From Traditional Partnership

Chip: The first one ended relatively well, and I’m now closest with that. My closest friend in the world is Oren, my Israeli boyfriend. We live together. We’re basically best friends. In many ways, we’re living a very intimate relationship, without it necessarily being a traditional partnership people are used to.

So I think that one of things I’ve learned is also that we all change with time. The kinds of changes that Oren and I have made over the course of knowing each other for more than 30 years have made it such that I think we actually understand each other really well. I think, more than anything, you want to be with someone in life, whether that’s a friend or an intimate partner, who really understands you well, appreciates your eccentricities, but also is open to giving you candid, loving feedback when you need it. Oren does that with me, and so I would say, if I had to say one person, Oren intuitively gets me. I feel very lucky having him in my life.

Ken: Thank you so much for being so vulnerable. Chip, I really appreciate that, because the intimacy journey is a really, really challenging one. It’s the most deeply challenging in so many ways. You’ve been so phenomenally successful, not just in your profession, but in building this rich, rich world and life for yourself. So thanks too for sharing kind of a cutting edge of growth.

Chip: Thank you. Helen Keller said it long ago,

“Life is a daring adventure, or it’s nothing at all.”

I sort of believe that.

Ken: I think you do. I think you do, and that brings me to Fest300.

The Magic of Travel

Ken: I’d like to talk about travel a little bit, about the magic of travel, how travel connects to romance, but how it connects to Eros. I don’t just mean typical romantic relationship romance, and I don’t just mean sex Eros. I mean the richness of the world, the magic, the kind of romance of life and the world. I know, for me, travel has been such a piece of that.

As a therapist who works with people who are looking for relationships, something I’ve seen again and again is, when you go to places with people who share your values and there’s an immersion experience, that’s probably one of the most absolute pieces there are, most likely places there are, that you’re going to find romantic love, as well as deep friendship. So I would just love you to talk a little bit about Fest300 and about your love of travel, connection and adventure.

Chip: With what you just said, let me sort of build on that. There’s a French sociologist from more than a century ago named Émile Durkheim. He coined a phrase, “collective effervescence.” He was studying religious pilgrimages, and what he saw was that, when people have a similar sense of purpose and intention, they actually have to go and have a devotion to something.

Back then, we didn’t have cars, and so people had to sometimes walk 100 miles to go to some kind of festival or pilgrimage. When people actually have that kind of intention that leads to this sense of connection with everybody, people’s sense of ego separation starts to melt or evaporate. What comes in its place is communal joy. It’s almost like they’re just sort of diametrically opposed to each other.

Connecting With People

Chip: As ego starts to melt, what comes in its place is this communal sense of joy, and Durkheim coined this collective effervescence. I was intrigued, having been a 20-year Burning Man veteran and being a founding board member of the non-profit for the last almost a decade, I was intrigued by how, at a time where we are more and more connected online, the more digital we get, the more ritual we seem to need.

That ritual often shows up in festival, and it’s all kinds of festivals. In the year 2012 and ’13, I went to, over about a 12-month period, 36 festivals in 20 countries, all kinds; music festivals, transformational festivals, religious pilgrimages. I went to Kumbh Mela, which is the largest festival in the world, 100 million people at the Ganges River. It’s a Hindu devotional pilgrimage.

What I experienced from all of that, yes, you can feel a strong sense of intimacy in a large group with 100 million people. I absolutely felt a sense of intimacy with the two people I was traveling there with. It was partly because we were experiencing something so unusual together. What that felt like was we were more connected on a level that was beyond the surface. I loved that.

I created Fest300, a website dedicated to having an annual list of the 300 best festivals of the world. I still love Fest300. It’s now part of Everfest. But the challenge was, to be honest with you, right as I was finishing that and launching it, the Airbnb founders asked me to join them. So I didn’t have a whole lot of time to put into it after that, but I appreciated it, and I still have an appreciation for collective effervescence.

A Shedding of Self-consciousness

A Shedding of Self-consciousness
Photographer: Toa Heftiba | Source: Unsplash

Ken: I love that phrase. For many people, there’s a shedding of self-consciousness. I’ve thought a lot about self-consciousness, because I’ve felt crippled by it many times in my life, in so many different ways. My capacity to reflect, evaluate and notice things has hampered me like the centipede was asked, “So which leg do you put first?” Then he couldn’t walk anymore. That’s often been my experience of such a huge amount of noticing that kind of paralyzed me.

I noticed that, when I travel, that lightens. It’s almost like I’ve described it as those fun house mirrors, that kind of self-scrutiny voice. These fun house mirrors that are you, but they’re just a little bit kind of creepy, not extreme. But there’s an ugly twist that they put to you, and kind of pain of seeing that. Much more sinister than fun house mirrors are the fact that this inner voice tells you that it’s reality.

That holds us back from our generosity of spirit. I don’t know if you agree with this, but kind of in our day-to-day lives. Maybe this doesn’t happen for you, but I know it happens for a lot of us. It’s so easy to get stuck in those micro-cripplings of our self-consciousness and our limited ways of being.

Chip: I completely understand and appreciate that. I have felt that way. We had a good chance to get to spend some time, a week together in Mexico. I believe that the Modern Elder Academy, which is the world’s first mid-life wisdom school that we created about a year and a half ago, and you were in the first beta group. I think part of what goes on there is collective effervescence.

The Modern Elder Academy

Chip: Part of what goes on is this self-consciousness, especially being awkward with people you don’t know. You start to realize as that self starts to melt, what comes together is a sense of oneness with other people who are very different than us.

Since the time you were there, Ken, you were in the first cohort during the beta time, now the content we do is about 80% different. We now have 35 cohorts with people from 17 different countries and 500 alums. What I’ve learned from that experience is this deep sense of desire for play and connection in mid-life.

People want that. We take ourselves too seriously. We’re too self-conscious, too self-oriented. All of that gets to a place where you just want to lay it down and play with others in a way that makes you feel like, wow, I have such a connection with these other people.

Ken: So true. I was there in the first cohort, but to this day, the ripples of that experience are with me. They’re with me in a visceral way. I can’t describe the beauty of this space that you created, right on the edge of the ocean. The warmth and sweetness of the community and the sense of ease and relaxation. I went with my husband, Greg, and as I said, it’s still with me like the beautiful, quiet waves of the ocean are still with me.

It was just rich and wonderful. I want to encourage everybody. Chip, I’ll ask you how people can learn more about your work, but I encourage everybody to learn more about the Modern Elder Academy and consider going there. It’s one of the most healing and exquisite experiences. I gained so much from that experience.

Life That’s Rich with Love

Chip: Well, I’m glad you were courageous enough to be a guinea pig in the first cohort.

Ken: It was really fun. I want to talk about some of the things that you’ve described. Tell me if you would agree with this, that these are things that have helped you truly gestate and create a life that’s rich with meaning and love. You’ve talked about generosity, a kind of generosity of being, a kindness, a collaboration, the importance of not doing it alone, curiosity, so many factors, and willingness to turn yourself inside out and see life and the challenges of life as an adventure.

Chip: Yes. It’s a lot to digest just listening to all of that.

Ken: It’s a lot to digest. I want to ask you, if you were bottling this recipe for everyone listening, what would you have to say about what’s most important to create a life that’s rich with love?

Chip: I think Oscar Wilde long ago said,

“Be yourself. Everyone else is taken.”

Chip: I think the process of learning what it means to be yourself and who you are is a lifelong exercise. I think what’s helpful for some of us is, when we struggle with something early in life, it forces us to take stock and say I am different than other people, which then can lead to the courage to say, that’s just who I am. Whether that’s in my case or yours, as gay people, or whether that’s a person of color. There’s a variety of other ways a person could actually feel like the extreme introvert in a very extroverted environment, or an artist, or just a total science geek.

Saying Yes to Being Yourself

Chip: All these elements of saying yes to something when it’s actually a little bit aberrant and a little bit different are the starting steps of people actually learning to say yes to being yourself.

Ken: Gorgeous.

Chip: I think that saying yes to being yourself, again, with the mirror neurons in our brain and the contagious nature of who we are, the more you do that and have that authenticity, you are putting out a welcome mat for other people to do the same.

Ken: I think that’s so exquisitely true. Because it’s a polarity, also, that the more we do that, there is also a risk of us becoming what they say in 12-step programs, becoming terminally unique. In other words, in the honoring and the cherishing and the valuing and the protecting of our uniqueness, forgetting the collaborative nature too, not that that is something that at all has to happen. In fact, I really think it’s true that the more we embrace who we are, just the more generous we become to the world and in the world.

Still, in holding that uniqueness and difference, the act of saying, what about the people around me? What are they experiencing? What are they doing? What are they needing? I have noted in you a capacity to de-center from Chip and look at the people around you. I wonder if you have any thoughts that you want to share about that.

Chip: I think it’s really interesting.

One of the risks of not doing your own personal work early in life is you end up doing it later in life

Chip: which is really the time, in some ways, as life stages go, we’re most suitable to actually be there for other people.

A Legacy Effect

A Legacy Effect
Photographer: Laura Fuhrman | Source: Unsplash

There’s something to be said for learning about yourself in your teen years and your 20s. It’s part of the reasons why, in terms of life stages, we often look at people in their 20s as narcissists and self-absorbed, etcetera. That’s the stage of life when that happens. If you’re doing that in your 70s, 60s or 50s, something went wrong. But, in 12-step, there’s also the possibility that you just live your life constantly self-absorbed in your reflection that you’re not really available for other people. It’s like reading the same fucking book, excuse me, reading the same darn book over and over. You may get really good at understanding all your lines in the book, but at some point you get bored with that.

Chip: The nice thing about starting to notice those around you and moving from being interesting to being interested is the process of actually seeing how you can have a legacy effect on others. That’s a really important part of it. If you’re only just doing the best to create this impeccable person that you are, but without any effect on the people around you, guess what? At some point you’re going to die. We all die. What have you actually accomplished in the process?

So my friend Marc Freedman has a book out right now called How to Live Forever, and his whole premise is not that we’re going to live forever, but it’s that the legacy you have is the impact you have in a bigger way in the world, but also absolutely one-on-one with people. That kind of legacy effect is the thing that allows us to start noticing the people around us.

The Big, Archetypal Question

Chip: I do believe that modern elders, as we get into our mid life and beyond, we are first-class noticers. We start to really understand and notice ourselves, the people around us, and even just the overall energy in a room.

Ken: This is another ingredient that goes into this bottle, the word noticing.

I’m going to ask you another hard question, but you’re good at this. For everyone who’s listening now who’s looking at their life and thinking how can I make it richer, how can I make it more adventurous, how can I make it more love-filled, which all of us ask. Those are great questions. I’d like to ask you to formulate a few questions that people who are listening and thinking about these things can ask themselves. Wherever they’re planted at the moment, what is some kind of big and important archetypal questions that, wherever you are, you can ask yourself to help move yourself in that direction?

Chip: I think that it’s a great question. I think the subject that initially comes up for me is regret. Regret’s a really painful emotion.

You feel more regret for the things you didn’t do than for the things you did badly.

I think one of the things I would ask myself, 10 years from now, what will I regret about today? When I say today, I mean this stage of my life. What will I regret not having learned now? What would I regret not having done now? What would I regret not having said or shown up for people in my life now? So I think sometimes looking out in the future and then looking back and then using regret as the lens is one way to consider this.

The Box of Unlived Life

Ken: Wait, are you going to move on to your next thing? Because I just want to really highlight this before you do.

Chip: Sure.

Ken: Oh, my God. I love that. I want a drum roll. I want a little marching band surrounding that. That’s just fucking gorgeous. So what a rich question, and I really encourage everyone to do that now, to think, right now, what later will you regret? I didn’t eat that part of life. I didn’t give that love. I didn’t go for that thing. I mean, you just bottled a life-changer question, so I’d just like us all to stay with this for a moment. Thank you.

Chip: There you go. So a second question that’s sort of related to the first one, there’s an element of the Modern Elder Academy where we talk about the box of unlived life. It’s really unlived and unloved. There’s certain parts of your life that you have really mastered, and then there’s other parts of your life that have atrophied, because you haven’t given them love. That sort of relates to the regret, but let me use that as a bridge over to this next question.

David Brooks from The New York Times has written quite a bit. His recent book was The Second Mountain, and he has quite a famous New York Times op-ed article that he wrote about resume versus eulogy. I think one of the things that’s interesting, he in essence said we’ve sort of created a culture that is more focused on a resume than we are on the eulogy that will be given for us years from now. I think one of the questions that I would open with for people to consider …

Living Life for A Eulogy

Chip: Because the resume’s obvious. We have a LinkedIn. We have career paths we’re on. We have accomplishments. All these things show up on a resume. Yet the eulogy features of our life are more intangible, and maybe even more valuable, and yet we don’t have constant rewards associated with them.

So I think the question I would ask is, if you were to live your life more for a eulogy than a resume, what are the changes you would make in your life to do that? Similar to that, I would say what is it that, if you had to tweet your obituary, 280 characters, that’s it, and someone was going to write a 280-character, which is very short, obituary for you, what would it say?

Ken: What would it say? Then what would you want it to say?

Beautiful, so powerful. Let’s all just take a minute and just think about that. I mean, that’s so rich. What would you want your eulogy to say? Well, these are world-changing questions. They’re life-changing questions, and they’re questions that are rich with love. The nature of those questions touches a dimension of love and meaning and adventure, which is everything that we’ve been talking about in this episode, so I adore those questions. Were there more?

Chip: That’s it for now.

Ken: Yeah, those are fabulous. They’re wonderful. I want to ask you, in thinking of this theme and in this conversation that we’ve been having, this theme of kind of building a life that’s rich with meaning and love, with gusto and goodness, are there any last thoughts that you want to share with the listeners?

A Broad Marathon Length of Identities

A Broad Marathon Length of Identities
Photographer: Matúš Kovačovský | Source: Unsplash

Chip: My last thought is something I’ve learned about mid life, especially with the Modern Elder Academy. The first half of our lives is really about accumulating all kinds of things, stuffs, relationships, career paths, responsibilities, identities. The second half of our life is about editing, getting clear on what it is that is most important to us. Your listeners may be in mid life. I define mid life as 35 to 75. Mid life is a broad marathon length of identities, the people in our lives, or habits that we have. We just continually accumulate, and we wonder why we feel so weighted down. That would be my last thought.

Ken: I love that thought. Now I’m going to ask you once last question. Chip, what’s next for you on your horizon? What’s your cutting edge of growth, adventure, gusto and goodness?

Chip: First of all, I just love the Modern Elder Academy and learning about this period of our life, mid life, so I continue on that. On my dating and romance journey, I really appreciate that I’m approaching. I did a 27-page document, a Google doc understanding all of the people I’ve dated in the last 9 years and trying to making sense of it, about a year ago. It really helped me come to the conclusion that I have certainly had enough choice. I’ve had a lot of choices. I’ve had a lot of opportunities, but I can see my patterns. So I think what’s interesting to me in my life is my box of unlived life feels very much in the romantic and intimate world.

Ideal Conditions vs Ideal Partner

Chip: Building a connection with Oren after 30 years of knowing him, after almost 20 years of not being in a relationship that‘s what it is now. What it’s maybe going to go into, is feeling like, wow, this is really juicy. This is an awkward part of my life. This is a part of my life that doesn’t feel perfect.

I think what’s really helped me to have an awareness of what is important on this level is

I’m no longer looking for the ideal partner as if there is a checklist that someone has to satisfy.

Chip: I don’t want a checklist to satisfy someone else’s perfect partner. What I’m looking for is the ideal conditions of my life. The difference between ideal conditions versus ideal partner is the holistic perspective on how I want my life to be lived. When I think of things that way, it actually is a really great editing function. I sort of know where I want to live, how I want to live, what kind of people I want to have in my life.

Partly because I live in a relatively remote part of Mexico, it means that the choices I have, if I was looking at life from an ideal partner perspective, would be quite limited. So looking at my life as the ideal conditions allows me to move away from the checklists of life. I don’t want to necessarily be on someone else’s checklist and helps me to see, having a wonderful, intimate partner in life is part of the gestalt, the full package of life. So, I think, learning that the ideal conditions in my life, and I have so much influence over those, means that I feel a lot more, I don’t know.

Influencing the Conditions to Unknot The Love You Want

Chip: I have the capacity to create great life. A lot of times, when people are focused on finding the ideal partner, there’s a sense that their life is failing them somehow. When you say, okay, I want the ideal conditions, well, you can influence those conditions. Then within those conditions, maybe someone will show up who’s the right person. So I just like that framing. It gives me more of a sense of the potential for success.

Ken: I love that framing too, and I just also want to articulate what you did with a challenge in your life. Because you’ve just talked about a challenge in your life, which is finding a partner. The way I watched you hold that is the way I’ve watched you and read about you holding so many challenges in your life.

You don’t grab it too tightly to get your way. You hold it with a sense of curiosity and openness, and you say, where’s the learning? Just like a really complicated knot that you’re not going to be able to completely undo, but here’s a piece that you can unknot.

You’re going to follow that and go with it. So the quality of curiosity and compassion and kind of going with the wisps of wisdom and the streams of wisdom that come to you at the moment in a really complex challenge, we are witnessing you doing that kind of gentle healing and exploration work that you’ve done so many times before and that we all are doing in our own lives, hopefully with that kind of grace and curiosity.

Chip: Thank you, Ken. I don’t know what to say other than that. You’ve said it all.

Connect with Chip

Ken: Well, in closing, Chip, I would love it if you could just share with people how they can learn more about you and your work.

Chip: So it’s Chip Conley. The last name’s spelled C-O-N-L-E-Y, six letters, You can learn about me on Facebook. I write articles for LinkedIn, so you see a bunch of my articles there, Twitter, even a little bit of Instagram. Then the Modern Elder Academy, that’s or .org – either way, and you’ll learn more about our campus in Baja, Mexico. So feel free to reach out to me.

Ken: Chip Conley, someone to follow, someone to learn from, someone to relish. His books are just wonderful too, so I want to acknowledge that as well. Chip, it’s been an honor and a joy to have you on the show.

Chip: Thank you. Thank you, Ken. Thank you for just putting all this love out in the world.

Ken: Thank you so much. Everyone, we look forward to seeing you at the next episode of the Deeper Dating Podcast. Bye for now.

More About Chip Conley

Rebel hospitality entrepreneur and New York Times bestselling author, Chip Conley is a leader at the forefront of the sharing economy. At age 26 he founded Joie de Vivre Hospitality (JdV), the second largest boutique hotel brand in America. After running his company as CEO for 24 years, Chip served as Airbnb’s Head of Global Hospitality and Strategy for four years and today acts as the company’s Strategic Advisor for Hospitality and Leadership.

Chip’s five books include PEAK and EMOTIONAL EQUATIONS and are inspired by the theories of transformation and meaning by famed psychologists Abraham Maslow and Viktor Frankl. In his new book, WISDOM@WORK: The Making of a Modern Elder (September 2018), Chip shares his experiences – as both mentor and unexpected intern – at Airbnb, and why he believes the intergenerational exchange of wisdom is critical to the modern workplace and our society.

Chip is a recipient of hospitality’s highest honor, the Pioneer Award, and holds a BA and MBA from Stanford University, and an honorary doctorate in psychology from Saybrook University. He serves on the boards of the Burning Man Project and the Esalen Institute, home of the Conley Library.