Episode 162

The midlife renaissance: navigating purpose and professional transitions

Chip Conley is the founder of the Modern Elder Academy and author of Learning to Love Midlife: How to Embrace What’s Next. In this discussion with Laurence and Carlos, he delves into the opportunities and challenges of navigating purpose and professional transitions during this pivotal stage of life.

If you’re an experienced professional or seasoned entrepreneur who’s achieved financial success but lost your sense of purpose, this conversation is for you.

Perhaps you’ve experienced “purpose drift”, or feel weighed down by the armour you’ve built to protect yourself but which no longer serves you.

Chip offers profound insights from his work and personal journey, showing how midlife is not a crisis but an opportunityto curate the rest of your life with intention, joy, and freedom.

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Transcript
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we've been following your work in different ways since we started

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our digital agency way back.

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We were very into the idea of company cultures and happy cultures, and

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there's, there's stuff about your work that we picked up on then,

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but just more recently, given.

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Lawrence and I turning 50 last year, and also our journey of entrepreneurship

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starting when we were 40 in terms of the Happy Startup School.

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Uh, and that whole process.

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We were talking before about entrepreneurship as

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a journey of self-discovery or spiritual awakening even.

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you know, I'm, I'm really loving having you on and being able to share the stuff

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that I've learned from you, hopefully with our community, and explore some

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ideas that I'd love to get your thoughts on as well, um, around transitions

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and change and, and what gets in their way and how to navigate that.

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In this case, we have Chip Cony.

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He is founder of the Modern Elders Academy.

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he started a boutique hotel at the age of 26 called Jo Aviv.

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And since then, been a, on a, a smorgasbord of adventures.

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Um, one of them, one pit stop being Airbnb, but I won't butcher his story.

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He knows it better than me, and you probably can tell it in a more apt way.

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So what I'd like for you to do, chip, if possible, is maybe for those of

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our audience who, who aren't aware of the Modern Elders Academy, maybe

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sharing a bit about what is it and, and what you're trying to do with

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it, and then any relevant bits of the story that got you to starting it.

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so I went to Stanford undergrad and Stanford Business

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School, um, in California.

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And a couple years out of business school I started, um, a boutique hotel,

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uh, called the Phoenix that was part of a, um, a brand called Jo Aviv.

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And over the course of the next 24 years, we created 52 boutique hotels around

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the state of California, and we began the second largest boutique hotelier in

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the US And I loved it till I hated it.

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So I was the founder and CEO and in my late forties, I had now been running

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the company for almost two dozen years.

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Um, I didn't wanna do it anymore, but it was the great recession, so

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I could not wa I couldn't sort of just say, okay, goodbye everybody.

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Um, we were going through a really hard time, As was true for

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everybody in the hotel business.

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Uh, and I had a bunch of other stuff going on too.

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I had, um, I was losing some, uh, friends to suicide.

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Unfortunately, I lost five male friends to suicide between 2008, 2010, ages 42

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to 52, uh, three of them entrepreneurs.

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And, um, I could see my friend Tony Shea also starting to spin outta control

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a little bit, um, in certain ways.

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Uh, and so I was, he, he wrote the Forward for two of my books.

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He was a very good friend of mine and I could see not just him, but a couple other

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of my friends, Blake McKowski, who's a amazing entrepreneur from Thomas Shoes

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also being challenged during that time.

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So and they were both younger than me.

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I could see two things going on during the Great Recession and afterwards.

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Number one is that the Great Recession was really punishing

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for a lot of entrepreneurs.

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And many entrepreneurs, defined their identity and esteem purely

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based upon their business card.

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And therefore if their business was going under or having difficulties,

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it affected their self-esteem.

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And then secondly of, especially for those who are a little older like

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me, um, I was going through at age 47, a sort of an existential crisis.

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And I had an NDEA near death experience where I had an alert, an allergic

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reaction to an antibiotic, and I died nine times over 90 minutes.

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so when you go to the other side and you sort of see, you know what

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the other side feels like and you come back, it really does give you

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the opportunity to say, okay, I can press the reset button on my life.

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And I did.

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Um, and so by the age of 50, I'd sold my company at the bottom of the market.

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I had what was called a midlife atrium for two years, where I got to really

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create the space and light and air to reflect upon how do I wanna consciously

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curate the second half of my life, uh, second half of my adult life.

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and by age 52, I was asked by the founders of Airbnb to join them.

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They had read a book of mine called Peak, how Great Companies

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Get Their Mojo from Maslow.

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So it was a psychology, A positive psychology perspective applied

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to leadership and business that I'd written, uh, in 2007.

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And so I joined Airbnb in 2012, 2013, um, and spent seven and a half years

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there taking this little tech startup and turning it into the world's

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most valuable hospitality company in concert with the three founders

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who, I was mentoring basically.

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But I was also, I was full-time in the company.

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I was the head of global hospitality and strategy.

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Much of the company was being run by me, and it was, it was an amazing experience.

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I loved it.

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Um.

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Toward the end of my full-time work there, I decided that I was going to

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write a book called Wisdom at Work, the Making of a Modern Elder, because

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at Airbnb they called me the Modern Elder, which I didn't like at first.

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It's like, oh no, you're making fun of my age.

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I was 52 when I joined, and the average age in the company was

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26, so I was older than everybody.

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But I also sort of thought that, you know, when you hear the word

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elder, it sounds like elderly.

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Um, but they said, you know, chip, uh, Brian said, chip.

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A modern elder is someone who's as curious as they're wise.

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And the reason we love you is because you have that curiosity.

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You're not just dispensing wisdom, you're learning things along the way too.

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And so, you know, I decided to write a book about it.

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Came down here to Baja, where I am right now today.

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And while I was here, I went for a run on the beach one day in front of my house.

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And I had a Baja aha, an epiphany, uh, which was, why don't we

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have midlife wisdom schools?

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Why don't we have places where people can reimagine and repurpose themselves,

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uh, whether they're going through a transition, whether it's a divorce,

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or, you know, selling a business or, you know, parents passing away or

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empty nest, kids moving away, um, or a health diagnosis that's scary.

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or, or, you know, getting fired or retiring or whatever it is.

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So we started, uh, MEA, the world's first midlife wisdom school, and we now

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have two campuses, one on the beach here in Baja, and the other a 2,600 acre.

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Uh, ranch, regenerative Ranch, horse Ranch in Santa Fe, New Mexico.

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Well, I'd like to or start off with, because one of the things

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that's close to our hearts of the moment is this idea of the wisdom

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worker and what it means to be wise.

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So I would love to get your thoughts on that.

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Um, you know, you say to be as curious as you are wise, how would

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you define wise from your perspective?

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So let's talk about the difference between knowledge and wisdom.

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I mean, they're both important, but to be quite frank, we live in an

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era in which knowledge has become commoditized between Google and.

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Chat, GBT knowledge is accessible to all of us.

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And whereas in 1959, Peter Drucker, um, coined the term knowledge worker.

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And within 20 years, knowledge management had become a, a, a discipline within

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companies, large companies today, um, I would say knowledge is like

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the, and knowing how to connect with knowledge and access, it is sort of

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like the ante to get it to the table.

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But I don't think that knowledge alone is what creates the differentiation.

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So knowledge is, let's be clear, knowledge is something you accumulate.

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Wisdom is something you distill.

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So if it's a math equation, knowledge would be a plus sign.

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And wisdom would be a division design.

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It's the essence of something.

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It is taking all of that knowledge, all of that information and distilling

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it down to what's essential.

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also, wisdom is often something you learn from personal experience.

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I like to say are painful life lessons are the raw material for our future wisdom.

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And so in many ways, wisdom comes from the school of hard knocks, meaning the

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school, you know, the, the challenges we've had, and so long story short is,

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one of the things we're very good at as a society is we've helped people

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to know how to accumulate knowledge.

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But we've done a very poor job of helping people to distill their

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wisdom, to understand from their life experience what they've learned

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and how to apply it moving forward.

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And in the series of questions you may ask going forward, I can tell

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you more about how we do that.

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But let me say that wisdom is perceived as being abstract.

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In fact, it's very much in your gut.

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You know, knowledge, knowledge is in your iPhone, and wisdom is in your gut.

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And the question is, how do we create the practices and environment,

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the habitat and the conditions for people to access that wisdom?

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Because at the end of the day, I am not going to learn a lot of wisdom from

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AI at this point, maybe in the future.

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So I will.

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Um, but today what, you know, the AI will give me is a distillation

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of knowledge out there in the world.

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And, and it does it very well.

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I, I enjoy ai, but my greatest wisdom comes from my own life experience.

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And yet there are very few practices or tools that we have created

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in society to help us understand what we've learned along the way.

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There's a couple of things that spring to mind here that.

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There's, can I and should I, and there's like, these tables can make, allow us to

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do lots of things, but whether we do them or not, I think needs to come from a place

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of discernment, which I think is what you're talking about in terms of wisdom.

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And I love that what you said about wisdom comes from the school.

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You know, you will learn wisdom from the school of hard knocks.

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And I know from a personal perspective, the school of hard

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knocks is a scary school to go to.

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You wouldn't choose to go there.

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Yeah, I'll stay at home.

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Um, I'm feeling ill today.

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and, and this is from our experience of our work, when we step into that space

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of uncertainty and when we try things that we're not sure that are gonna work.

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And like you said, you learn from that experience.

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That's where we, I'm hearing we learn wisdom.

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because, and also from what I heard from you, given having been an entrepreneur

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from an early age, it sounded quite instinctive to, to move towards stuff

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that might not have been at a certain bet.

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How do you, how would you communicate?

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What wisdom would you share to help those of us, particularly when you're

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a certain age and you think risk is you have a certain relationship to

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risk already 'cause you've already settled, but you need to change.

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How would you get someone to refrain, reframe this idea of doing something

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totally new, totally different, to overcome some of that fear and hesitation?

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There are fixed mindsets and their growth mindsets.

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This, this comes from Carol Dweck, from Stanford, uh, and her research.

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And as we get older, often there's a fixed mindset that says, I'm

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too old to fill in the blank.

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Or I, I can't take that risk because of my, my spouse and my kids.

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And, um, I, or, or for me, when I joined Airbnb at 52, oh my God, I, I don't wanna

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have my last career move be a failure because everybody in the hotel industry

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thought I was a nut for joining this little tech startup that they thought

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would like never gonna go anywhere.

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Um, and then I also was mentoring Brian Chesky, the CEO and co-founder,

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but I was also reporting to him.

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So after having been for 24 years, my own, the CEO of my own company, having

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sold it to Hyatt or pr, John Pritzker, who sold it to Hyatt, um, he's part

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of the Pritzker family owned Hyatt.

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I was not gonna report to someone who was, who's the age of my

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biological, my, um, my foster son.

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So that there are a lot of fixed mindsets that could have

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said, Nope, not gonna do that.

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But I think one of the things that I look at is, um, a question that I ask a

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lot is, 10 years from now, what will I regret if I don't learn it or do it now?

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and, and I, and when I moved to, to Mexico, for example, I started to learn

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to surf and I started learning Spanish.

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Now I, I moved here at age 56, 57 or so.

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Like, I was not at the age where people learn to surf or say, you know, welcome

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the idea of learning a foreign language.

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Um, so I had a fixed mindset, like thinking I was too old.

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But when I thought about it in the context of like, I'm living in

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Mexico part-time, I like it here.

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I wanna live here for a long time.

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I will regret at 66 or 67, 10 years from now if I don't learn

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to serve or learn Spanish.

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Now, that helped me to learn similarly, you know, anticipated

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regret is a form of wisdom.

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The idea that I will regret that when you're 20 years old, you don't have

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anticipated regret, but when you're 40, you start to have it because you

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start to have a time clock in your head, and when you're 50 and when

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you're 60, you'll have it even more.

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and so, I, I've found that that question helps catalyze someone to try

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something that they might not have done.

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Now in terms of the practice of wisdom, I have been doing something since age 28.

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So at 26 I started my boutique hotel company with a very

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unlikely success story.

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Um, I bought a motel in a bad neighborhood, a dodgy neighborhood in

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San Francisco called the Tender Line.

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It was a pay by the hour motel, so it was the kind of place people

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went on their lunch hour to have an affair, and they paid an hourly rate.

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Now it was in bankruptcy.

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When I bought it, it had had better days.

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This is the mid 1980s and age was a big deal in the US and, and in

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specifically in San Francisco.

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And you know what?

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This, this place wasn't successful anymore.

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So long story short is it turned it into a rock and roll

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hotel and it became successful.

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But in 19 89, 2 years into it, uh, we had the, uh, a big earthquake in

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San Francisco and I had no business.

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And so one day I just said like, oh my God, I have no idea how

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we're gonna get through this.

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And I took a journal or a diary that was empty, um, off of my bookshelf,

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and I took it down and I wrote my wisdom book on the cover of it.

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And I started a practice that I've been doing now for 36 years.

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Yeah, something like that, 36 years, which is to, uh, make a list.

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Each weekend I spend 20 minutes doing this of all my key lessons of the week.

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They could be personal, professional, spiritual, physical, et cetera.

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I make a list of what did I learn this week?

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Often the lessons were painful, and then I say, how will it serve me in the future?

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Um, and by doing that, and by doing that now for all these years, every

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week I now do it in Google Docs.

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what I did and what I have had the opportunity to do is to accelerate

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the cultivation and harvesting of my wisdom by understanding

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what I'm learning along the way.

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What I do in my companies is I do a practice.

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I don't require my leaders to do this, but I do require once a quarter,

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the se, the senior leadership team comes together at a nor our normal,

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you know, leadership meeting.

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Maybe it's an hour long and let's say there's six people on the team.

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Each person says, what was my biggest l lesson of the quarter?

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What am I gonna learn from it and how will it serve me in the future?

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And because the chief operating officer across the table from me

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is talking about his or her lesson, um, I'm learning their lesson.

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I, you know, their school of hard knocks is my form of learning wisdom.

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So wisdom is not taught, it's shared.

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And sharing our wisdom is really valuable.

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And then having, at the end of the meeting, that group of six

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people say, what was our biggest team lesson of the quarter and how

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will it serve us in the future?

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I have been doing that, that leadership wisdom leadership exercise, Jo Viv at

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Airbnb, we in incorporated it into the whole company and then also now at MEA.

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yeah.

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So this is, this is how do you take abstract wisdom and make it

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practical and prescriptive and make it a strategic competency and

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differentiator within the company.

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I'd like to, So explore that aspect of sharing.

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Uh, one of the things that is core to our work and what we believe in

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and what we learned is the power of community, the power of creating

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spaces where we can share challenges.

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And, and through that process of just even voicing something, something shifts.

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And I know from your book, learning to love midlife and, and there's

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an aspect about social wellness and there's a sense of community and how

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that connects us to, well, how that's important and let's put it that way.

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Uh, and so I, I'm curious about your thoughts and perspective on that.

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What, what have you seen that creates real connection with people and allows

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from, for this learning, the sharing of wisdom to be most effective?

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I.

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Well, you know, we've had 6,500 people graduate from MEA going through

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a week long program with us, uh, in person, uh, from 60 countries.

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And what, what I most notice is that when people learn to communicate

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from what we call the third vault, so the first vault in our

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communication is the facts of our life.

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And they're usually from up here in our brain, the second,

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and they're, they're fine.

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I mean, like, frankly, when you first meet someone, it's

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like, okay, where are you from?

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You know, what do you do?

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Uh, et cetera.

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It's, it's, it gives context.

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Um, but it's actually sort of boring after a while.

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You know, you've been to a cocktail party where nobody talks about anything

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but the facts and it's like, oh, that, you know, and you wanna, you, you,

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you run for the bar pretty quickly.

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Um, the, the second, uh, vault in how we communicate is

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from, usually from the heart.

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It's the stories of our life.

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And those are interesting.

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And yet they can be liberating or incarcerating in the sense

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that sometimes our stories, um.

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Are so defined by ourselves that we have not given our stories, the

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space to maybe evolve over time or to have a new lesson come from them.

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And so stories are helpful.

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They certainly are more, they build a level of, you know, emotional connection.

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Um, and you can feel really connected to someone else when they're telling

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their story and you can relate to it.

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But the problem with stories is that they often solidify and identify an identity.

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And there's, for the person giving the story, it's often not

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very pre, it's very predictable.

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And so you get bored with your own stories.

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And then the third vault of communication comes from the gut.

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And it's when you are communicating from a place of unfiltered.

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Spontaneity and you have to create the space.

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Now, it's not something you do normally at a party easily, but

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you have to create the space that you to hold space and invite grace.

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And that's what I like to say.

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And invite the environment where people are gonna go there and they're not

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gonna, they're, they're, they're not gonna plan ahead what they're gonna say.

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They're gonna say just what's going on from a place of respect, but also from a

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place of vulnerability and authenticity.

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And so that's sort of how a week works at MEA, whether we're doing a private

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retreat with a leadership team or, you know, YPO Young Presidents organization,

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or whether we're doing a public workshop, what we're really offering

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is the opportunity for people to, Allow the spiritual plumber to open up the,

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the, the plumbing pipe that goes from the head to the heart to the gut slash

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soul, because that, that heart to soul plumbing pipe is usually pretty clogged.

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And the moment you start to open that up, it's not that, it just feels liberating

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to be able to speak from your truth.

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That's been sort of stuck there in the plumbing pipe.

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But the epiphanies, we become sort of a, a midwife for midwife epiphanies

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and new ideas come up that have been sort of stuck down there.

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And that is, you know, one of the miraculous things about, you know,

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coming to an MEA workshop is people leave saying, I always had that inside of me.

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I. But it was stuck and I hadn't known how to actually access it.

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So I think of us doing a bit like an archeological dig.

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Um, and so how do we uncover that wisdom that, hmm, that intuition

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that is stored down inside of you, um, and open it up without fear that

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it's gonna sound really stupid the first time you say it, potentially.

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And, and that doesn't have to be a business idea.

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It could be a, you know, a, a personal memory.

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We do have people who have come to MEA and like, wow, they have

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some memories that have been stuck there, that they had, like, let you

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know that they had tried to ignore.

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So, long story short is it's, it, you know, I, I think our, our,

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our journey as entrepreneurs.

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Is just a human journey.

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And the more we are able to embrace every aspect of who we are as humans, the more

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we bring the full range of, of skills and intuition to the table to be an effective

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human first and entrepreneur second.

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I've got a quick question about, your background in hospitality, how much you

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see that influencing how you host or just your love of creating community?

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'cause I think that's something a lot of people we meet want to start

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communities or think they wanna start a community and actually host events and

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retreats, but doing it is another thing.

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So I guess the question's maybe more about the design and the

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experience you're creating.

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How much you think that played a part in the success of MEA in terms of

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those experiences you are creating?

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You know, I. In creating MEA, there were really four component parts.

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One was hospitality and hospitality has been my career, almost my full career.

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So that was an easy one, but it was an important one because

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generally speaking, when you go to a retreat, uh, a retreat center, the

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hospitality's not a high priority.

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Um, like the aesthetics.

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Maybe the food is sometimes, especially if it's a, a healthy place where

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they have their own garden or farm.

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But sometimes the aesthetics are not great and the, and the quality

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of the service is not great.

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And so I wanted, I wanted hospitality to be front, front and center.

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Um, and you know, when I was at Airbnb, I was in charge of all the hosts globally.

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That was one of many things I was in charge of.

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So I loved the idea of.

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Uh, Airbnb hosts being many entrepreneurs and, uh, helping them

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to understand how to be a better host.

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So, uh, hospitality is a big part of it.

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Secondly, um, a retreat center.

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So I was on the board of the Esan Institute, uh, in Big Sur, California.

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Really maybe the best known, um, retreat center in the United States.

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And I was there for 10 years on the board, and I taught there

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for 12 years, once a year.

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And I loved it, but I also learned about, you know, what, how do you run

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a retreat center in a different way?

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I, for example, Essem, which has a a great history, has no alumni program.

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Nobody like, they, they don't have regional chapters.

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We have, you know, at, at MEA, we have 58 regional chapters for our alumni.

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There just, there were a lot of things they didn't do that I wish they'd

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done, but, you know, they didn't do it.

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Um, thirdly is wellness.

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You know, the experience of of having a, building a community, especially

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in a in-person kind of thing, is we're really trying to help with wellness.

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And this idea of social wellness is really important.

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How do, how do you create the environment for people to both

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feel a sense of personal wellness, but a, a, a social wellness?

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And I, I like to say that illness starts with the letter I and

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wellness starts with the letters.

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We, and wellness is not just a personal journey.

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It can be a, a collective journey.

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Um, and, you know, I have for 28 years owned the largest spa in San Francisco.

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And so wellness has been always a, a part of my, you know,

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integrated into how I try to live.

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But also some of my businesses, I've owned them a number of spas.

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And then finally the fourth piece was the curriculum.

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I didn't wanna just be a retreat center where people come and

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have a beautiful experience with hospitality and, and, you know, great

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service and, you know, wellness.

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But I really wanted to have, I wanted to be a school, you know, an

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academy where we have a curriculum.

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And the curriculum is really based upon my book Wisdom at

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Work, the Making of Modern Elder.

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But it's based upon all these faculty members from Elizabeth Gilbert to

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Blake Kosky, to Jerry Kelowna, to um, I mean Arthur Brooks, who come and guest

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faculty with us at our, at our two centers in Santa Fe and in Ba Mexico.

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And so that's really, those are the four ingredients.

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The good news for me is like all four of those ingredients were in my.

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History that allowed me to, to do this.

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But I think building community is such an essential part of our modern

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life because, you know, I was, uh, uh, the first member, I was the

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first board member of Burning Man.

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So Burning Man had six founders, and then they asked me to come along and help

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create a, a, a board for Burning Man.

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And so, um, that was 16 years ago.

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Yeah.

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16. 16 years ago.

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And I loved it.

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And I, and I was a long time burner and burn, you know,

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burning Man has a community.

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And how do you, how do you have a, a board of directors for something that says sort

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of like, um, I don't know, uh, crazy.

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And uh, what do you call it?

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Uh, anarchist as, as Burning Man.

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Um.

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But I learned a lot about building community in that community.

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And I think in a, in an era in which we are all so online driven, that in, in real

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life, the IRL experience is so essential.

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Um, and so the craft, and it really is a craft of how you bring people together

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and host them in person when, because it's so precious, uh, because it's,

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it's, we do it less than we used to.

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I mean, before we had computers, we, that's all we did.

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Um, but in the era of computers, we're doing what we're doing right now.

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But the pro the, the craft of hosting is so essential.

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Um, and Priya Parker is a friend in her book, the Art of Gathering.

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I highly recommend to people who wanna understand how do you, how do you host

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in, in a way that, um, is magical?

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So firstly, I think you're just with MEA and how you're talking about it,

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you're describing the organization, the business, the mission that

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Lawrence and I were dreaming of when we started the Happy Startup School.

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So it just lovely to hear It is just, yeah.

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And the names, you pull out the hat go, ah, that's amazing.

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Um, and the other aspect of this is that feeling, I don't know, it's just like, I

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dunno if you've ever had this, you go on a first date and they're just talking.

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I was like, tick.

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Yep.

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Tick, yep, tick.

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Yeah.

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Oh my God, I'm in love with this business.

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This person, whoever it is in front is just like, alright.

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Music to my ears.

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What I was hearing, particularly when Lawrence was talking about hosting,

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'cause I think part of this idea for us about the way we run our business,

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'cause it's very about how we are in terms of what we talk about, building a,

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a business more aligned to who you are.

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I. And that person definition of success.

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And I think we run retreats and we run a, a festival.

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And the reason why they'd be all they have been going on for so long.

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We believe because we need it and we value it as much as we

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trying to give it to other people.

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And community is in our DNA in a sense, being connection, actually the need for

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connection is forefront as a priority in the, in our work and who we are.

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And so I'm curious from your perspective of how much you've been guided on your

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journey of entrepreneurship and work about your sense of yourself in terms

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of like tying what you do, being part of who you are, uh, and whether that was

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always there or that's been a journey.

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And then your experience with people who come onto MEA who are trying to find

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something more aligned in themselves.

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I heard a great quote last week, um, which was, if you don't know who

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you are, you'll become what you do.

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it starts with who you are, and that's the fertile ground.

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I like to say be good soil.

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Be good Soil means, um, how do you create the soil in which fertile of

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the fertility of that soil allows greatness of all kinds to, sprout.

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And so, you know, for me, I. When I was 22 years old, I was between my first

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and second year of business school.

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Uh, and at Stanford I had been a all American water polo player in high

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school and, and a little bit of college.

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I was in a fraternity.

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I was, I was sort of a jock.

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I was sort of like, you know, whatever.

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I was doing my life, but I felt like something wasn't fulfilling me.

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And I was, I felt a little lost.

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And, um, you know, I, I had to go through a dark night of the soul,

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what I now call the dark night of the ego to realize I needed to, I

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needed to go deep into who I was.

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I started learning about the EN Enneagram, which is a, a personality typing tool.

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And I, I learned a lot about that.

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I was in therapy and ultimately, I, I came out, uh, at age 22, uh, as a gay man.

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And that was not easy.

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In 1983, in the midst of the AIDS, early stages, the AIDS era, uh, AIDS crisis.

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And, you know, being at Stanford Business School and, and GA based

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upon the world I had lived in.

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So, but, you know, the, the gift of that was at a time where it was

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potentially career ending to come out and at a time where when it was,

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you know, physically, health-wise, risky, I had to have the courage to

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be able to say, this is who I am.

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And that process both opened me up to, in my twenties, doing a real deep

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dive in terms of understanding who I was and who I am still in such a way

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that it created that fertile ground.

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Good soil and what it did.

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Uh, you know, when I started my company at age 26 and was very open about being out

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as a gay man, um, it was really unusual even in San Francisco because like, you

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know, first of all, 26-year-old CEO's, not, not normal, um, especially back then.

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Today it's much more normal.

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Um, but also then the gay CEO, like it was weird.

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Yes, the hospitality interest in Pu boutique hotels was

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made it a little easier.

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But long story short is I had, I accelerated my process

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of understanding who I was.

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Mm-hmm.

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And what that allowed me to do, you know, is to tap into some skills I had that I

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might've been embarrassed about before.

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I might've been embarrassed about the fact that I have a good design eye, you

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know, straight guy, you know, queer Eye for the Straight Guy is a, a TV show.

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It's partly because like the straight guy doesn't know how to

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like design his apartment like.

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But I was pretty good at design.

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I was pretty good at empathy.

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Um, I, because I created a culture in Aviv, uh, that was very open

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about people of various diversities, not just sexual orientation.

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We attracted really talented people who felt like in their environment,

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whether they were a woman or a person of color, or someone of a, you know,

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um, someone who, uh, felt aged out.

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You know, we, we were able to attract great people because they

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felt like wow, they were welcomed in a place where, uh, the CEO had,

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you know, been open about who he is.

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So, I, I, you know, I, I, I feel like what could have been a curse was a blessing.

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Um, and yes, have I dealt with discrimination?

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Of course, I have.

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but the process of, you know, understanding who you are, is the

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most important learning lesson you're gonna have over a lifetime.

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And you get better at it over the course of a lifetime because you

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get to know who you are about a quarter of the way through a novel.

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You don't understand the characters nor the themes in the book that well.

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But by the time you're halfway through the novel or halfway through your life as

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in midlife, you understand the characters and the themes in the book a lot better,

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and you understand yourself personally.

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a lot of people that we work with, and I've experienced myself, you, you for

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a long time, you play a role because that's how you potentially can fit in.

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And what I'm hearing from your journey, the earlier you can break out that role

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that you're playing and tune into who you are and what you, what it means to be

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you in terms of playing to your strengths and doing the things that light you up.

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There's a, an effortlessness that is introduced into the work that isn't,

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that energy isn't sucked away because you're trying to be someone else.

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I'm very curious.

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You, you said you, um, you dove, dove into the Enneagram and it's

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something that I've been introduced to only in the past couple of years.

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Uh, do you, do you still, um, connect to that way of sort of understanding yourself

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and are you, are you open to sharing your, the type that you are most connect to?

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I'll share, I'll share my type.

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If you share yours.

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I have discovered, uh, that I am most connected to type three.

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And I've recognized I am a performative, well, my default is to

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perform in order to look, look good.

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Yeah.

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I am a three with a four wing.

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And so for those people who don't know the Enneagram, let's spell it for you

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because it's hard to, hard to spell if you, based upon the pronunciations.

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E-N-N-E-A-G-R-A-M.

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So I have learned about, I learned about my Enneagram type more than 40 years ago.

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I ultimately took everybody in my senior leadership team at

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Jo Aviv through learning it.

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So we, and we taught it to employees in the company if they wanted to learn it.

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Um, we teach a workshop here at, uh, MEA by a guy named Russ Hudson, who's

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maybe the most famous, Enneagram teacher he teaches at our Santa Fe campus.

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so understanding what, what the Enneagram is helpful for is, it's not like

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Myers Briggs or something like that, which sort of feels a little bit like.

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Not deeply rooted in who you are.

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The Enneagram helps you to understand what's the pair of

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glasses you're wearing that is rooted in almost a singular sentence.

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Uh, and for those who are three, like you and I are, and I'm a four with a,

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the four wing is sort of the individual artist, uh, type likes to be different.

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Um, but a three is the success achiever type.

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And you know, the sort of, the statement in our heads unconsciously

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might be, I am only as good as my last success, or something like that.

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and I, I care a lot about what people think about me and how it looks to others.

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And you, you, you, you described that Carlos, but once you

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know that about yourself.

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You are able to, as Carl Young Carl Jung was very clear about, you know,

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once you sort of understand your unconscious, you can rise above it.

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And so once you understand the sort of unconscious bias of how you see the

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world, you can sort of say like, oh God, that's me being performative right now.

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Or That's me caring too much what other people think about me.

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Or that's me being self-critical to push myself to success.

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And sometimes those are good things, but sometimes they're not.

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And to understand the dark side of your personality type

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allows you to transcend it.

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Firstly, a lot of people in our community are gonna be loving what

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you're saying now because there's a lot of fans of the Enneagram within

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our Happy Startup School community.

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Yeah.

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And secondly, that for me is the essence of wisdom.

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I. That discernment, that knowledge as I'm hearing, is when this behavior or

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this approach is serving me or not serving me and doing that without judgment.

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Yeah.

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And it, I think it connects to another, I think one of your 12 reasons is

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this idea of understanding our story.

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Yeah.

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I mean it, over the course of a lifetime, you have the opportunity to

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understand who you are, maybe you're Enneagram type and why you're here.

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You know, mark Twain wrote.

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There are two most important days in the person's life, the day you were

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born and the day you figured out why.

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And I like to say, um, the purpose of life is to discover your wisdom.

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The work of life is to develop it, and the meaning of life

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is to give your wisdom away.

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And so all of that speaks to this idea that there's a narrative that

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you know, there, there, even before the narrative, there's a, a way of

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seeing the world that defines you.

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Maybe it's the Enneagram or there may be another way of understanding

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that there's a way you've shown up and had the school of heard knocks.

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Experiences that help make you who you've been, help you to understand your wisdom,

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which is meant to be shared with others.

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And.

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As you understand who you are in the world, You are better.

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Once you understand who you are, you are better able to be, uh, an

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enlightened witness for other people.

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You're able to be a mirror and have people look at you and

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say, I want to be like you.

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or, uh, I understand myself better just by listening to you.

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There, there was a point in Jo Viv and my, you know, my boutique hotel company

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where I felt like there were a lot of my leaders in the company are leaders

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in the company who had a point of view, which was do as I say, not as I do.

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And so for one month I didn't experiment and I said, we are going

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to ban the two, the words manager and leader for the next month.

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And whenever you will use the word manager or leader, you have to

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actually replace it with role model.

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And by, by.

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So if we're having a manager's meeting today, it we're, no, we're

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actually having a role models meeting.

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Um, if you are gonna go and, and go to a, you know, a, if we're gonna

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create a leadership workshop, it's gonna be a role model workshop.

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And the reason we did that was because I, I really believed that, uh, the, the more

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senior you are in the organization, the more of a role, role model you needed to

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be, not just as a leader, but as a person.

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And it was, it was miraculous.

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What happened during that month, um, is how leaders recognize that, um,

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the more senior you are in leadership, the more contagious your emotions,

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the more contagious your habits.

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Um, your A CEO is not just a chief executive officer,

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they're the chief officer.

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Because our emotions are contagious.

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the more senior we are.

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Uh, that's part of the reason I do have some worry about what's

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happening in the United States and in many countries right now.

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Uh, you know, whether you like Trump or not in his policies, I don't think

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he's a, a, a well adjusted human.

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Um, and that worries me because he becomes the role model.

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And, and to me that's a, that's a troublesome thing

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for forgetting about policies.

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Like, I wanna put policies aside.

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and so I, I, you know, I, I, when I go and look at organizations and try to evaluate,

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you know, whether I think that company's gonna do well, I often look at that.

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When Brian, when Brian, uh, chesky at, at Airbnb, uh, soon after I joined, wanted to

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do a, a strategic partnership with Uber.

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I said like, you know what?

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You and I have sat with Travis and you know how toxic he can be and

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you know, his culture is based upon him and you know, your culture,

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you want to be very different.

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The kind of partnership we would do with them is going to be problematic for us.

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And, and we were at that time, the smaller of the two organizations, by far we

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were the two sharing economy darlings.

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But you know, if we get more affiliated with them, it will, it will hurt us.

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Similarly, when Adam Newman was wanting to do a partnership with, uh, Airbnb

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after I'd been there now three or four years, I was like, are you kidding me?

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Uh, I won't, I won't say everything that Brian used to say about

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Adam because, Brian liked Adam.

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But, I'll say it for myself.

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Adam had a mess, messianic kind of way of being, he sort of

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thought of himself as the messiah.

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And I said, you know, this is not gonna be good.

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Um, so I do believe we have to get really thoughtful, uh, that we at, as

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senior leaders in organizations are role models and contagious role models

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in terms of how we're showing up.

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So if you're thinking about going off and working in another company,

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you know, look at what, who's at the top and how contagious they are.

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If you are the happy startup leader and running the things,

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you know, how are you contagious?

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and when I ultimately needed to leave my company that I, you know, after

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24 years, I knew I needed to leave because I was sort of depressed.

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I didn't wanna do that anymore.

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I felt victimized by my company.

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Nobody had done anything to me.

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I just didn't wanna do it anymore.

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And I had that NDE and so I died and was like, okay, I can say I'm going to stop.

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And I, but I felt for the good in the, of the company, I needed to do that.

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Even if I wanted to stay, I was not, the vulnerable visionary that I used to be.

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I was the martyr.

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Um, this, this importance of authentic alignment, I think I'm hearing here

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as both as a leader, but also as, as just interacting and making,

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interacting with others and making healthy choices based on our own

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self-referencing and our own compass.

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and that what I'm hearing there is by understanding our stories, whether that's

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through frameworks like the Enneagram or any other way that you therapy or,

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or some other kind of work where you can connect with yourself that has

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a, a beneficial impact in the way we can work, is what I'm hearing here.

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So we, you know, you talk about understanding your story and I'm now

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hearing, you know, the framing in my head is like, you get to a point in life like,

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alright, this story has got me here.

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I don't wanna read the, this story has chapter's gonna close, new chapter.

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And then it's like, what is this new story?

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What is this new chapter?

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And in a sense, like, what do I actually want?

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And I'm curious from your own experience of, you know, your own life and MEA, how

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you have seen people answer that question?

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So purpose is really important in life, but I, I think especially

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in the United States, it's perceived as a noun, not a verb.

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To be purposeful, to me is more important than the noun of having a purpose.

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There are a lot of people who freak out because all their friends have a purpose,

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and I don't have a purpose as it's like a BMW in the driveway of your, of your home.

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Um, the reality is there are lots of ways to be purposeful, and there's the

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big p purpose of the things you'd see on your resume or on your LinkedIn profile.

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And then there's the small p purpose, which, uh, you know, are the things that

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people will say about you at your eulogy.

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And so I think that, you know, as we get older, we've moved from Big P purpose to

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small p purpose, realizing that When you have Big P purpose, which is important,

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it crowds out a lot of other things.

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being an entrepreneur is.

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Most often a big P purpose.

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It's the thing that defines you.

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It's the thing that you, people know you as.

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It's the thing you think about and dwell on in the shower.

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It crowds out a lot of other things.

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That's not a bad thing, except when it is.

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And when it is, is when it means you.

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It crowds out the small p purposes.

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But when you have small P purposes, whether it's being a parent or it's

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being, a political activist, or it's, you know, being a gardener, a master

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gardener, or a marathon runner, those small p purposes, or you know,

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it's being involved in a spiritual community, those small p purposes

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add to a broader tapestry of a life.

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So I would just say how a person curates their life to figure out

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what's next is a function of knowing that big P purposes are important.

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They define our lives.

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They're the way people see us, and in many ways, they can

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be sort of legacy providing.

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And yet in the course of one's life, you know, at, on your deathbed,

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it's the small p purposes that are gonna make for the full tapestry

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of a really interesting life.

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And, and so I just think understanding, you know, this

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is the kinda stuff we do at MEA.

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I mean, listen, people, if people are interested in this, like, come,

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come join us, or if, you know, most of you are in Europe, you know, we do

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have online programs as well, online courses that are in person, like,

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or in, you know, live like this.

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Um, and, and that's available to people.

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But I, I I, I, this is so important for people to understand that

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it's very easy to be the kind of person, and I am one of them.

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And Carlos, you may be as well.

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When one big P purpose is move moves on, I'm sort of now ready for

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like, what's the next Big P purpose?

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Because if I, if you're a three on the Enneagram, those big P purposes

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are the things that define me.

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And what we need to do is create interventions to help people to realize,

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oh, as I did between age 50 and 52, when I decided like, I'm gonna learn about

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emotions, I'm gonna learn about hot springs, I'm gonna learn about festivals.

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I'm just gonna be curious.

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I'm not doing anything.

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I'm gonna go find, I'm gonna start creating musical playlists

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that I'm just, just for me, not for performance in any way.

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I was able to sort of create a life that felt a little bit more full-bodied.

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Uh, and it reminds me, I think of one of the things you say is, is

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growing whole rather than just growing old, uh, and having, being curious.

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Uh, and what I'm getting here and what I'm latching onto is not being cur

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curious about the world, but also being curious about ourselves and the lenses

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that we are looking at the world through.

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So, Lawrence, was there anything that you wanted to, to ask to finish

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off or anything you wanted to share?

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Yeah, maybe something just linked to that idea of purpose and finding a

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calling or whatever you wanna call it in later life, whether it takes

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something like you experienced for people to realize what's important to them.

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So your near death experience or like a health challenge or someone

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dying close to them, like a catalyst.

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We, we find this too, like a lot of people find us at the point

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where they've hit a hard knock.

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So is there a way to accelerate that?

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Have you found it?

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What's the sequence?

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Yeah.

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Wouldn't it be nice to do it without the school of hard knocks?

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Um, you know, one of the things I like to say in on the purpose path is there

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are, um, four shortcuts to finding your purpose or finding your purposeful path.

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And there what something that excites you, something that agitates you,

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something that makes you curious or something from earlier in your

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life that you were passionate about that you, that you have neglected.

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And, if someone's really interested in that, you know, they should

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check out our Cultivating Purpose workshops in person or online.

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I. Because we go into a lot of depth on that.

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but yes, I think a, something a an external circumstance that

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that is jarring to someone, forces people to get outta their habits.

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And I think that's, you know, sometimes a good thing.

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But, you know, it's nice if you can do that on your own too, so

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you don't have to have your, the jar, the jarring circumstance.

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Yeah.

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And I, I, I kind of feel like we wish for people not to, to experience pain

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in order to find this purposeful path.

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And at the same time, it may be the only way to really commit to something

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because you really lived it or felt it.

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one last thing.

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I have a daily blog.

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It's on the MEA website, um, under the free resources section.

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It's called Wisdom Well.

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So if this is interesting to you, just uh, subscribe to my daily blog and

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um, look forward to seeing you there.

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I noticed there's Chip as well.

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Anyone wants to

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website.

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You can ask Chip GBT any question.

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And there you go.

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That's another.

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Boom, chip, GPT love, uh, because there's another aspect of this

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around understanding our story and also being good storytellers.

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And I think this is something that I have noticed about your work.

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And the, in the phrases, the words, they just capture people's imaginations.

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And that being, I think part of this, finding more purposeful paths

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is telling good stories, not about just about our, our work, but also

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ourselves, that, that motivate us.

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So thank you.

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Thank you.

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Um, we'd like to finish off with this final reflections, what we're

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taking away from this conversation.

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Um, Lawrence.

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many good, uh, insights.

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I particularly like the quote you said about if we dunno who

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we are, we'll become what we do.

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'cause that, for me is, is a great way to frame, I think the importance of

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doing this, uh, in a work really, isn't it, to understand ourselves better and

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not fall into just reacting to whatever comes our way, being more intentional.

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Um, chip, um, thank you very much.

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Is there anything you wanted to, any parting words for

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people who are listening?

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Oh, no.

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I mean, feel free.

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I, I welcome people to stay in touch, um, and, uh.

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Yeah, would love to see, see you in person one of these days.

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Uh, again, so grateful for your time, for your wisdom, for

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your energy, for your insight.

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Uh, and I'm, I, I'm someone who, who really ran away

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from the idea of role models.

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I dunno why.

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I think it's 'cause I'd like to do things myself, but actually hearing

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what you're doing and seeing what you're doing with MEA, I think I've

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found a blueprint for the business I wanna create with Lawrence now.

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So if, if we steal the idea, I'm sorry, but it's something just like

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the mission just resonates so much with what we're doing at the moment.

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Yes.

About the Podcast

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The Happy Entrepreneur