Episode 22
22. Embracing Confusion, The Power of Idealism, and Cultivating a Well-Lived Life | Jennifer Garvey-Berger
Do you find yourself constantly seeking clarity and certainty, even when faced with complex challenges that don't have simple answers? What if that very pursuit of certainty – that comfortable feeling we all chase – is actually blocking your growth, your learning, and your ability to create something new?
This episode explores the counterintuitive idea that confusion isn't something to avoid, but rather something to value as a gateway to deeper learning. What's possible when we release our grip on needing to know and instead embrace the generative space of uncertainty? Together we consider how the most meaningful growth often happens precisely when we're willing to step into discomfort rather than rushing to make it disappear.
Jennifer Garvey-Berger is a thoughtful disruptor who's constantly questioning how we might do business, relationships, family, and leadership better. As CEO of Cultivating Leadership, she's spent decades helping leaders navigate complexity and uncertainty. Jennifer brings a fascinating blend of intellectual rigor and lived experience to our conversation, including her bold experiment of buying a house with twelve friends in France to deliberately create a different way of living. In this episode, you'll discover:
- How confusion serves as a necessary gateway to learning and growth
- Why certainty, despite feeling comfortable, often blocks our ability to discover new possibilities
- How good conversations create something neither person had thought of before
- Why crafting a meaningful life requires questioning default assumptions
- How deliberate disruption can lead to more authentic ways of working and living
- Why play and exploration remain essential elements of leadership at any age
- How creating intentional communities can challenge our assumptions about work/life separation
- Why our idealism is not something to outgrow but rather a strength to cultivate
Timestamps
(00:00) The Value of Confusion
(08:47) The Quest for a Better World
(14:55) Living Fully vs. To-Do Lists
(32:18) Creating a Unique Living Environment
(40:03) Growth Through Difficulties
(42:28) Giving Less Fucks
Other references:
- David Whyte: https://www.goodreads.com/quotes/9100423-what-you-can-plan-is-too-small-for-you-to
- Richard Bach: https://en.wikipedia.org/wiki/Illusions_(Bach_novel)
- Oliver Burkeman: https://en.wikipedia.org/wiki/Four_Thousand_Weeks:_Time_Management_for_Mortals
- Vito Perrone: https://www.gse.harvard.edu/ideas/news/11/09/hgse-remembers-vito-perrone
- Thomas Huebl: https://thomashuebl.com/
- Heidi Brookes: https://www.cultivatingleadership.com/team-member/heidi-brooks
- Andrew Maffett: https://player.captivate.fm/episode/8dc40ef3-104d-4a48-a38e-495ed4650abb
- Adam Cooper: https://player.captivate.fm/episode/48bf4ecf-f533-47d3-943e-2445135d473d
You can find Jennifer at:
Website: https://www.cultivatingleadership.com/
LinkedIn: https://www.linkedin.com/in/jennifer-garvey-berger-7b4a264/
Books: "Unlocking Leadership Mind Traps," "Simple Habits for Complex Times," and "Changing on the Job"
Check out my services and offerings https://www.digbyscott.com/
Subscribe to my newsletter https://www.digbyscott.com/subscribe
Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/
Transcript
Certainty is the enemy of growth, of learning, of openness, of listening, of gathering data that might suggest that you're wrong. know, certainty, feels so good, but actually it's a blocker in many ways. And so I think I've become more and more entranced, let's say, by what it takes to move us from certainty into confusion, which I think then is the gateway to learning.
Digby Scott (:What if confusion isn't something to avoid, but actually something to value? And what if certainty, that comfortable feeling that we all chase, is actually blocking our growth, our learning, and our ability to create something new?
Today I'm joined by Jennifer Garvey-Berger, a thoughtful disruptor who's constantly questioning how we might do business, relationships, family, and leadership better. Jennifer's the CEO of Cultivating Leadership, a global leadership development firm that is absolutely trailblazing in this space. Together we explore how good conversations create something neither person had thought of before, why confusion might be the gateway to learning, and the tension between our idealism and the world as it is.
Hi, I'm Digby Scott and this is Dig Deeper, a podcast where I have conversations with depth that'll change the way you lead. Let's get into it.
So Jennifer, what is lighting you up right now?
Jennifer Garvey Berger (:Of course, in this moment, what's lighting me up is a good conversation, the prospect of a really good conversation with an old friend. So that looks pretty good. Good conversations generally are kind of what I live for. Conversations with my clients, with my friends, with gorgeous people around the world. I've always been very conversation oriented and that just grows.
Digby Scott (:That's a good point, right? I've just ran a workshop on quality conversations yesterday and I was asking people, how do you know if a conversation is a good conversation? Like what's the marker? How do you define a good conversation?
Jennifer Garvey Berger (:think for me, a good conversation is where something new gets made. Something that neither of us have ever thought particularly about or we make things together, our ideas come together in some way. I think for me, that's the definition of a good conversation.
Digby Scott (:Yeah. So I wonder what we're going to make in this conversation. I love this. It might be the making is making sense, right? It might be that there's just a clarity about a wooly idea that emerges out of that. ⁓ you know, and often talk about, can have delivery, but you need discovery for life to be rich. can just be making stuff happen all the time, but
Jennifer Garvey Berger (:I don't know, it's gonna be cool.
Digby Scott (:Making stuff up, I think is kind what we're talking about, right? Like let's make stuff up.
Jennifer Garvey Berger (:think you're right that something that leads to clarity is gorgeous. think also something that leads to confusion is kind of also great. A conversation where you go in and you think you know what you think and then you have this conversation with somebody else and then at the end of the conversation you don't know what you think anymore. I think that's pretty cool as well because it kind of opens up a new possibility.
Digby Scott (:What do you love about that?
Jennifer Garvey Berger (:love
new possibilities.
Digby Scott (:Yeah. And it's interesting, right? Because a lot of people might go, I hate confusion. My whole life is about seeking clarity, not confusion. I rocked back in my chair as you said that. And I think for me, that's my first discovery. It's like, yeah, maybe this is not about seeking clarity the whole time. I reckon our narrative in Western culture is about valuing clarity. Right? We don't want confusion.
It's too noisy. It takes energy. I want clarity because I can get on with what matters. Right. Tell us about that. Why do you love confusion? Possibility to live there. Can we put a bit of meat on the bones with that one?
Jennifer Garvey Berger (:I don't think I love confusion. think I value confusion. right. Confusion itself is unsettling and destabilizing just like it is for others. But I also really have it in my mind. You know, I did a lot of research for a book a couple of books ago, Unlocking Leadership Mind Traps, about what happens to us when we believe we're right.
Digby Scott (:Right, okay, good distinction.
Jennifer Garvey Berger (:this idea of this felt sense, this emotional sense of certainty. And I really came to see that certainty is the enemy of a lot of things I care about. Certainty is the enemy of growth, of learning, of openness, of listening, of gathering data that might suggest that you're wrong. know, certainty feels so good, but actually it's a blocker in many ways.
And so I think I've become more and more entranced, let's say, by what it takes to move us from certainty into confusion, which I think then is the gateway to learning.
Digby Scott (:Yeah, it's like a step on the way, right? It's not the end point.
Jennifer Garvey Berger (:That's right. And it's not a very pleasant step on the way to be fair. This is why people avoid it like mad. Your brain doesn't like it because it's very caloric. It takes up a lot of calories to be confused, but it's going somewhere.
Digby Scott (:Yeah, I think the language of valuing rather than loving, I think is a really lovely distinction. know, and, and for me, you know, my personally just moved house and we're talking about when we, before we jumped online and I was reflecting in my journal yesterday morning that moving into the space, I feel like I'm on the other side of it now, but there was a big period between the idea of moving then actually being here in the house. There was.
a lot of confusion and I found myself warring between not liking it and wanting to make it go away. And as you say, part of my mind and heart was like, no, no, no, this is what you need to go through. And I noticed that the energy was about the warring rather than about the confusion itself.
Part of my brain is saying, no, no, no, no. Look, this is the thing you need to be experiencing and learning from. This will get you through to the other side. If you avoid this and you just go into Pollyanna land, for example, then there's a risk you'll come out the other side and there'll be maybe resentment or there might be a yearning to go back or whatever it might be. And I feel like now, even in the short time we've been in this new place, I did have some resistance.
I'm starting to see possibility as a result of sitting with the confusion perhaps. Does that make sense?
Jennifer Garvey Berger (:Oh yeah, confusion's uncomfortable. And as you say, the nicest thing in the world is to just make discomfort go away. And yet there's so much richness in there, right? Like these questions, why am I so confused? Why am I so uncomfortable? What am I longing for? Like these things get exposed to us in these moments of kind of pressure, right? This is a pressure moment where things are changing and we get exposed to ourselves in a way. I think that's when we can
feel ourselves and feel what might be growing in us. And that is uncomfortable and it is really rich.
Digby Scott (:Yeah, you can savor it is that might be a word we could use right. So I have a question. Where is confusion in your world right now? Where is it showing up for you?
Jennifer Garvey Berger (:my goodness, well, confusion's not hard to find. This is not tricky. You know, from the micro, like here I live in a house. We bought a house with 12 friends. And so I live in community with a bunch of friends, trying to figure anything out. In this new way of living is confusing. I'm parenting adult children these days, and you know, that's new.
And people don't talk about it. Trying to parent adult children is confusing. In my own business, we're trying to create something new at Cultivating Leadership. We're trying to make a new organisational form, a new kind of relatedness with ourselves among us and with our clients. That's tricky. My client's business world is entirely disrupted right now and trying to help them through not just complexity, but chaos. That's new. And then the world, know, then the world there's...
climate change, the crazy waves of politics and what they're doing to the world, the question of what's our future going to be like as humanity, AI, you know, like at every possible scale, my life is like a fractal of confusion.
Digby Scott (:Yeah. Wherever you look, it's there in some form and you can relate to it. It's interesting because as I listened to the way you described that some of those things you're responding, you know, the larger scale things, your clients, world, climate change, et cetera, and others, it seems to me that you've manifested or you've created or you've deliberately experimented or even you could say disrupted your world.
buying a house with 12 friends in France. this idea of let's experiment with this or let's create cultivating leadership as a completely different way of doing business. Now you went first with that, right? It wasn't the world. Well, you know, it's not as binary is it, but there's this deliberate disruptoriness in you. Where does that come from? Do you think this desire to create confusion in a good way? What's the genesis of that? you think?
Jennifer Garvey Berger (:Maybe I am always looking for how things could be better. How could we do business better? How could we do relationships better? How could we do aging better? How could we do parenting better? How could we do family better? How could we do organisations and leadership better? When I was 21 years old, I was getting my master's degree in teaching. I had an argument.
with one of the administrators of the program who is responsible for placement, placing us in a school. And he said, Jennifer, you are entirely too idealistic. If you believe teaching is a profession that people could enjoy, that the young people would like it, this is a ridiculous thing. You need to understand education as it is and not with your ridiculous idealism.
And so I went to the director of the program, admittedly in tears, and became one of my long-term mentors, man named Vito Perrone at Harvard. And I said, here's what happened. And Vito, I don't know how to let down my idealism, and I don't know who I would be without it. I don't know how to let go of my quest for things to be better. And Vito said, your idealism is not a childlike feature to be.
He said, your idealism is a strength to hold on to because with that idealism, you will always be questing for a better world. And it's only people who quest for a better world that actually create new things. He said, I am whatever he was, 60 years old or 74 years old or, know, some imaginably ancient age to the 21 year old I was.
He said, I treasure my idealism and it is responsible for everything great I've ever done. He said, it's also responsible for difficulty, but I welcome that difficulty. And I walked out of there. was like, this other guy had been like, grow up, Jennifer. And Vito had said, this is not what growing up looks like. You do not have to put this thing down to grow up. I like that.
Digby Scott (:That's a beautiful story. You know, it shaped you then and now it fuels you and it continues to feel you. There's something about that world would childlike to, I wrote a piece a few years ago called be a childlike grownup and made the distinction between childish and childlike because we lose all these qualities of idealism and curiosity and not all of us do. It sort of gets ground out of us by
the first person you mentioned, people like that. We need childlike, we? We need to hold those qualities and nourish them and cultivate them and champion them in others. And I think you and I both, we both value that, reckon. I reckon that's one of the things that forms our friendship, right? It's not about the intellectual thing. It's about the discovery and what else could be possible. When I think of you, I think of a
a yearning for a better world, but also an agency. And this comes to the disruptoriness. It's not necessarily, I think, enough to have idealism. It's definitely a key ingredient. Yet you've also got to go, all right, and I'm going to throw myself into uncertainty and confusion because that's the way through to this better world. That's a thesis I've got about how you think. How does that land?
Jennifer Garvey Berger (:I think you're right. It's probably got some childlike curiosity, wonder, and also probably some just dogged stubbornness that says, I do not believe humans evolved in a way that says we have to have unfair systems. Like we have to have people unhappy at work. We have to have power dynamics that are
somehow harmful to some of us. We have done those things, but like I'm like a dog with a bone with this. Like I believe there must be another way. And so I'm constantly looking for it.
Digby Scott (:Yeah. Yeah. I'm curious about other people, places, pivotal moments that either catalyzed or accelerated this quest. You know, they've got the bone in your mouth in the first place. If you go back to other times and places where you went, this is the path. I can't not do this. What comes to mind?
Jennifer Garvey Berger (:thing that stands out is I was having an early conversation with Keith Johnston, who would later become like dear friend, business partner, co-author. was having this early conversation with him very early in our relationship. We barely knew each other. And he was asking good questions because he asks great questions. I was a young professor with a young family and I was working on what would be my first book, Changing on the Job. And I was
on the tenure track and doing those kinds of things. I was like, Keith, here's my plan. He was asking, here's my plan. And he said, okay, well, it sounds to me like you're gonna accomplish those things by the time you're like 35, 36. He said, do you then die? Like what happens? What happens when you've like accomplished all of that? And I sat there and it literally took my breath away. Like I remember that moment.
like it happened to me last night. It took my breath away and I thought, small my dreams must be if we could actually point to a day when I could check them off. Like that's amazing. I somehow got my dreams and my to-do list confused and I shrank the dreams down to the size of a to-do list. And Keith called me on it.
Digby Scott (:⁓ it reminds me of that quote from David white, what you can plan is too small for you to live. And that's exactly what you're saying. If you can plan it, if you can put it again, chat with a date on it, it's too small for you.
Jennifer Garvey Berger (:Yeah, that's exactly right.
Right? It's too small. It's a to do. Yeah. It's a to do, but life can't be a to do. You don't want to have on your tombstone, like she checked off all her to do's and then she died. That is not the secret of a well lived life.
Digby Scott (:What is?
Jennifer Garvey Berger (:I think really being alive, right? I think really knowing I lived this day, I lived this day, I was really here, I was not asleep. You know, I've had, as you know, I've had cancer twice and for a ton of people, some kind of life-threatening experience, a car crash, an accident, a health condition, you know, they make you look around and think, this could be really short.
You know, if my head is down looking at my to do list, you know, it's like sometimes I find myself, I love to hike. Sometimes I find myself hiking beautiful, beautiful trails, looking at my boots. Like my head is down looking at my boots. think, what the hell? I've been climbing a mountain for five hours and what I've seen is the top of my hiking boots.
Sometimes life feels that way, right? We've been climbing a mountain for 50 years and what we see is the top of our to-do list. Sweetie, like look up.
Digby Scott (:Yeah. You know, Oliver Berkman would say, well, that's never going to end, right? You know, you get to the end of a 4,000 weeks and there's still your to-do list. That's right. You know, there's another mountain to climb, but are you actually savoring what this is actually about? Yeah. So feeling alive, it reminds me actually. So I have this dilemma at the moment. Actually I've worked through it, but let's, I'll tell you the story. So moving house is expensive.
a lot of disruption going on and sort of I've had my mind on, all right, financially probably need to be a bit sensible, you know, and working for myself, there is, you know, cashflow is always kind of there as a question to just pay attention to. And I had a friend call me. He was actually on the podcast, Andrew Maffet. He was retired. He's been sailing around with his wife on his 50 odd foot yacht around Indonesia.
Philippines for the last three years. And he said, we're closing this chapter. I'm going to come back and live back in Western Australia. Would you like to crew with me on the yacht to bring it back from Indonesia in August? And we had a chat this week and the timing of when I could do it. I was, there's three legs and he said, which one would you like to come on? And the timing of that leg is
four days after I get back from seven weeks in Europe and the US. that's like three or four days I'm jumping back on a plane to Western Australia and then up to the Northwest to jump on a yacht. And there's this head heart thing, right? There's this life is for living. Life is for grabbing these once in a lifetime moments. And you know, that is...
The sense of not looking at my boots. This is what life's about. So I've made the decision. I want to do it. And is that I'm trying to remember the quote, you until one is committed, there's always a hesitancy and you hold back. as soon as you commit, then Providence moves too. I'm trying to remember. think the Scottish Mountaineer actually, I'm trying to remember his name anyway. There's this life is for living. Let's go and live it. That's what makes life.
meaningful and there's this but don't be too reckless you know and don't be too hard in your sleeve about all this stuff just be sensible right and to me that is a common wrestle I think for a lot of people you know there's the dream that then gets squashed because sensible wins you know I bet you see this too and I'm wondering whether you even wrestle with that yourself
Jennifer Garvey Berger (:I wrestle with it all the time. All the time.
Digby Scott (:Yeah, tell me about that. How's your wrestle? What's the nature of that?
Jennifer Garvey Berger (:think this is a polarity we're constantly trying to handle. Like how do we lean into, I don't know, the practical, the sensible, and then how do we lean into the exploratory, the playful, the time wasting. You know, I know you write a lot about this and I learn a lot from you. I remember you were taking these big surfing trips way back when and I was thinking,
How does Digby have the time for that? And it was like literally years before I thought, ⁓ Digby like creates the time for that. It's not like time arrives and you think, ⁓ look at my diary. There's nothing for three weeks. I think I'll go to Western Australia and go surfing, right? You, you like have to protect and defend that possibility or else it doesn't happen. Absolutely. And so the thing I've always been good at is
leaning into, as you say, kind of this childlike wonder at where I am, at finding what's beautiful here, at looking at what's, you know, the small joys or pleasures that other people might not notice. What I'm much less good at is actually saying, I'm going to play. I'm going to take a date. I'm going to take a weekend off. Digby, I'm terrible at this. Taking a whole weekend off. I'm getting better.
But I am not good at this. I used to say to my clients who were wrestling with these kinds of issues, I to say, I can ask you good questions, but I cannot blaze a trail for you here. This is like one of these, take my advice, I'm not using it. So it can be all yours kind of moment because I struggle a lot with this question.
Digby Scott (:Yeah. And you're alone, right? Off. I think it's in the language, partly the word off, off from what? Off then has kind of like a void attached to it. It's like, and voids might be something that we go, well, I don't know how to be in a void. Right. So I might as well stay busy doing something. And I think the other part of that might be, and let's kick this around is play, but play is for kids.
And that language again, right? So it's funny because my surfing trip, my surfing, windsurfing sojourn has been 25 years almost every year now. I don't consider it play and I don't consider it off. I consider it something like generative time, which again, the language matters.
It feels like it and not just regenerative, which to me is about repair. You know, it's about growing something new out of this experience by being in a completely different place. And I value that so much. do fight for that time, yet I don't consider it frivolous or a holiday. Even though some people might look at it that way for me, it's not, it's way, way deeper than that. So there's something about the framing. Hey,
Jennifer Garvey Berger (:Yeah. And I think this is one of the things you're particularly good at is being able to move out of the binary of on and off or work and play and say, this is a different thing. People, you are too narrow in these descriptions. And usually I'm pretty good at that too, but I'm this one issue. I mean, there are a million issues I'm not good at it on, but this is one of them. This is one of them.
Digby Scott (:Yeah, I wonder what the wisest version of you would say that we're in conversation about that issue.
Jennifer Garvey Berger (:A promise I made to myself a long time ago, I have a man who's super important to me, old, old friend. His name is Michael Milano. Shout out to Michael in this moment. He's somebody that the first time I met him, it was like the world stopped, you know, for our conversation, the intensity of our conversation. And he was at that moment moving to Seattle. I was living in Washington. Then I moved to New Zealand.
I guess before I moved to New Zealand, I was in Boston getting my doctorate. We lived far away from each other. And then we found ourselves living in the same city. And this is a man I corresponded with. were pen pals and we would write long, long letters to each other. When he moved to the same city, we never saw each other. We never had time to see each other. We were both super busy.
And he would say, you know, like, ⁓ I'm coming into, he lived outside DC. I lived inside DC. I'm coming into the city on this day at this time. ⁓ I'm sorry, Michael, I'm really busy then. And I thought, what are you doing? What are you doing? What are you privileging here? And I decided that whenever Michael said, can you do it? I would just move stuff. I would just do it. Just say, yes, yes, I can.
And then I thought, well, there are other treasured relationships in my life. And so then I started to have this rule. This is like me in my early thirties, right? And I started to have this rule that, that relationships were in this space where you've put windsurfing, right? And those were the most generative spaces in my life. And I would make time for those. And then that became easy. So I think there is kind of,
framing issue. Maybe it's also I know how to do relationships. I don't know how to windsurf. I don't know how to ski. Like a lot of the things that people make time to go away and do. I didn't grow up doing those things. We didn't have any money growing up. I didn't learn how to do any of that stuff. We didn't live in nature. I grew up in a city.
Digby Scott (:It's kind of like what nourishes you, right? You know what nourishes you.
Jennifer Garvey Berger (:Yeah,
that's right. And what do you know how to do?
Digby Scott (:Yeah.
And if we, we look back full circle to the, I said, what's lining you up and you said conversations, right. And conversations make relationships. So you're great at relationships, I suspect, because you love conversations and through those conversations, relationships form and you value that for so many reasons. I, yeah, it's a superpower of yours for sure.
You know, it's interesting because underneath that, think it's probably the same thing that when I'm at this place in the remote part of Western Australia doing that, all those water sports, it's not, yeah, it's about the water sports. It's great, but it's about discovery, about what I'm capable of, where my limits are, the conversations around the campfire, what emerges from those, right? I think it's the same thing. It's the discovery and the making up.
that you mentioned earlier on, right? We just have different ways of getting there. I remember one of the most formative books I ever read was a book called Illusions by Richard Bach. He wrote Jonathan Libeson Seagull. It's a title book. And there's this part in this little chapter there, the main protagonist has got a mentor and the mentor, name's Don. He says to the protagonist, what's life about?
And they have this sort Socratic dialogue around it and they come to discern it's about fun and learning. What if life could just be about fun and learning and you know, and this is the play thing, right? That if we're poo pooing play, maybe we're missing out on an essential part of what living is about.
Jennifer Garvey Berger (:learning is about.
Digby Scott (:and it's learnings about and they come together.
Jennifer Garvey Berger (:So
much of that comes together.
Digby Scott (:Yeah, yeah. I'm fascinated about the play thing. I really want to come and visit you when I'm in Europe and yeah, and I want to play. Hey, Jennifer, we're playing. Let's go. I'll take you windsurfing.
Jennifer Garvey Berger (:You gotta do it.
out windsurfing on our river. One of the reasons this kind French experiment was so appealing to me is so that obviously we have a lot of conversations, but we also kind of hang out and goof off. In the summer, somebody wants to go to the river and go for swim and somebody else wants to go for a hike and somebody's trying to get you in the pool.
And so the odds of my playing are so much higher. realized, Michael, my husband, I have a husband, Michael, too. And Michael and I had this conversation when our youngest was like 10 years old. And I said, I am afraid that when he leaves home, I am just gonna work all the time. I'm afraid that the reason I play,
is to play with these kids, right? And because the kids made me silly and playful. They require play, right? They require you to play with
Digby Scott (:And they require you to play.
Jennifer Garvey Berger (:That's
exactly right. They don't just want you to watch them play. They want to play with. And I said, I don't know. Like, how do I learn? Eight and 10, I have whatever, nine, eight, nine years to learn how to do this thing. And so finally, this place where I live now is a piece of that, you know? We play cards after dinner so many nights, so many nights. We sit around, we play cards, we laugh, we...
were ridiculous together, I would have a harder time on my own doing those things.
Digby Scott (:Now it sounds like, know, James Clear, who wrote Atomic Habits says, if you want to change your behavior, join a community where your desired behavior is the normal behavior. That's what you've done. Cause I think you know how to play. What you need is the culture in which it's the normal thing. Right. And that brings that out of you. So what a perfect place for you to experiment with this, this wrestling thing that you've got.
That's Yeah, I love it. This place you're in, it sounds fascinating for people who don't know about where you are and how you live. Can you just give us a very quick snapshot of that? Because it is again, a bit like your business. It's quite different to the norm.
Jennifer Garvey Berger (:Cool. Yeah, it's fun, right? Yeah.
It's unusual. Yeah, during COVID. So I'll start with the business because at Cultivating Leadership, we really love to work together. We started as four friends who loved each other and who wanted to do work together. And as the firm has grown, we're almost 100 people now, but we are 100 people that I personally adore. And so
One of our litmus tests is if you're stuck in an airport, your flight is canceled, you're facilitating with this person, you're stuck in an airport and you end up having to spend like 12 hours, 24 hours stuck waiting for your next flight. How do you feel about that? And if there's a piece of you that's like, well, that's cool. That person is the right person. And if there's a piece of you that's like, then you know, that's not a great match.
So we were always a community of people who love to be together. We love to do client work together. And then COVID came and it stopped all that. We were not together anymore. And Michael and I were living in London, Zaffir moved to London, and Wendy at one point who lived in California came to London to stay with us. So we made a little bubble of us and we were hanging out in our little bubble. And we're like, this is great.
fabulous. What would the life be that would enable us to do more of them? We thought, let's buy a big house together. Like, what if we did this every day? Because who knows the next pandemic or like, who knows what's going to happen in the world? Where would we buy this house? And so we started to send each other real estate listings of castles. This is one of the most fun hobbies to invest in, by the way, is just looking at real estate listings of European castles. Because
Digby Scott (:That's a great question.
Jennifer Garvey Berger (:Unlike in our dreams, European castles, you know, many of them cost like what a one or two bedroom condo in Manhattan would cost, right, or Auckland. And then once we started to get a little bit more serious about it, I thought three of us are on the leadership team of Cultivating Leadership. All four of us belong to Cultivating Leadership. We can't just cherry pick our friends. Like the impact of that move on our collective culture would not be ideal.
So let's just invite anybody who wants to come to come. And so I sent a letter to everybody in the firm and I said, Hey, we're going to live together. You want to live together with us. And this handful of people said, yeah, I'm up for that. So we found a place. We bought the place. We agreed to the place over time. We've moved into this place. And of the 12 of us that own it, 10 of us are at cultivating leadership.
We work together, we play together, we live together, we eat dinner together every single night. And, you know, we make this life go together. It's not a Cultivating Leadership project, because people who are not Cultivating Leadership come here all the time and we would so welcome other residents who weren't part of Cultivating Leadership. It's not like the rule, but it is our genesis. It's our seedbed.
Digby Scott (:It's a fabulous story and a model, I think, for not just the concrete part of that story, but the idea of what if, right? And this is cool. What if we could have this all the time, right? Just that question. And then leaning into that, I think is a really rich idea, right? Like you see this good thing, how do we create more of that? Or under what conditions could we create that? Those kinds of questions, I reckon.
the questions I would love to see people asking more, not just the what is questions, but the what if questions, you know, and then acting on that, which is what I really admire about you. It's not just a, yeah, you know, I'll teach this stuff. You live in it. What's confusion and all, right? You're doing it.
Jennifer Garvey Berger (:I it. I've talked to so many people who say, ⁓ I would love to do something like that. ⁓ man, that is my dream. And then they say, but it would be so annoying to like have to agree about furniture and it would be so annoying to have to agree about all this stuff. And I think we so focus on barriers. We so focus on what would be.
difficult, annoying, irritating, maybe impossible about the life we want. And we don't really focus on, well, it kind of sucks making all those decisions by yourself. It kind of making dinner for yourself every night. It kind of sucks wondering about, like, I feel down today. I'm not even sure I have the energy to call a friend. So I just feel more lonely. All that sucks, but we don't do that.
Calculus so much. Yeah, we think ⁓ that would be hard This that I'm doing right now is the default the default is so, you know condiment teaches us how powerful the default is
Digby Scott (:100 % you know, and my story of the resistance to moving house, right? There was a, yeah, but life's pretty good how I've got it now. What could possibly be better or that maybe there is, but you know, is it worth the cost? Is that whole loss aversion thing too, right? And the other bit that just picking up on that, you know, oh, it'd be really hard to have to agree everything. Well, maybe it's not about agreeing. Maybe it's about the conversation, right? It's not about nailing it and having everyone in harmony around everything, right? It's about.
being with the tensions when we don't agree and working through it. I suspect, making that up, but I can imagine that's part of the experience more than here are the rules that we've all agreed to and they're static and will be ever forever more. I suspect it's not like that.
Jennifer Garvey Berger (:Yeah, we made a really, you know, we're a bunch of complexity consultants and developmentalists. So we made an agreement when we first arrived that we would actually make no rules and that we would see over time what rules needed to happen by where we rubbed up against each other in ways that were unpleasant or repetitive enough that we needed a rule about it. So yeah, we've been living our way into
Like, is this a place for a rule? No, probably that's a place for a conversation. Probably we need a conversation.
Digby Scott (:There you go. it's kind of like blank slate living, isn't it? It's like, we'll start from blank with an intent and a vision because it feels cool. Let's do more of this and let's see what we need. And I know you've had, you know, I've had conversations about your company, the size it is at the moment. It's like, how do we evolve that? What are the supporting structures we need to keep going forward? It's the same conversation really, isn't it? It's the same bumpy up against limits.
and frictions and go, all right, what are the conversations we need to have now? Very cool.
Jennifer Garvey Berger (:This is kind of, for me, we were talking about what a good life is. And maybe for me, a good life is when you bump up against something and that becomes the way you see what your next growth edge is. Thomas Hubel talks about difficulties. We experience difficulties as out there, but actually difficulties are really is something in here.
that can't hold whatever the moment requires. And if you could convert everything that looks like a difficulty out there into an opportunity to grow bigger, to hold it in here, life would be a different thing. And that's cool.
Digby Scott (:That's what I'd rather choose in my wrestle with the house moving. And I reckon what kept me moving forward was a version of what you've just described. It was like, this is an opportunity for me to grow bigger and not to shrink back just because it's hard and confusing. And so my mantra was, know there's a growth here, lean into that. Right. And the growth edge is a lovely term. Yeah, that's exactly right. I wonder how would you describe your growth edge at the moment?
Jennifer Garvey Berger (:And there are so many, you know, it's like, exactly. really think a lot about this question of conflict, right? How do I engage in conflict in a more generative way? I've kind of been working on that since the 90s, the 1990s, and really as a practice and as a thing to try to lean into. ⁓
Digby Scott (:How many facets?
Yeah
Jennifer Garvey Berger (:I'm really guided by the work of Heidi Brooks in this way, who challenges me in literally the best possible way. And I'm inspired by Carolyn Coughlin, friend, partner, co-founder of Cultivating Leadership, co-liver here, who's really also leaning into it. And I watch her do it with such incredible grace. That's a growth edge for me. Play is a growth edge for me, you know, the things we've been talking about.
Digby Scott (:think that's a good question for anyone who's listening to ask, you know, how could I grow? What's my growth edge? And I suspect maybe a good place to start is where's the confusion and what is that telling me? Yeah. And what conversations could I be having?
Jennifer Garvey Berger (:or overwhelmed. So many of us are overwhelmed right now. I mean, everybody is overwhelmed by something or another right now. And so just trying to figure out how can I grow my internal capacity to hold more. We're asked to hold way more than I think humans have ever really almost ever been asked to hold before.
Digby Scott (:Yeah, I wrote a piece after my last trip to Western Australia, the windsurfing surfing one. It's called Give Less Fucks and it went viral. I'm the youngest in this group. I'm 57. I'm the youngest in the group of guys I go with. The oldest is 70 and most of them are retired. They're at a stage, I think, maybe not just of age, but also of development.
where they give less fucks. And the conversations often center around a perspective that I seem to have, is why are people worrying about that? It's not a big deal, which I feel like comes with having lived a few years and going, you know what, actually it doesn't matter that much. And I suspect that's a way of them, they've developed a capacity to handle not overwhelmed, but the information income.
And they just go, well, I actually don't need that incoming, you know, or I don't need to worry about it. More importantly, there's a giving this fucks, which is incredibly inspiring. And it can go against the whole, how do I make the world better thing? Right. Because you and I are both like this restless go get our energy and we care, but it's like what to care about.
Jennifer Garvey Berger (:I think for me, there's a way that you can give less fucks that is self-oriented and self-centered, right? And like, don't care about the world. I'm going to trash it. don't care about the future. I'm going to buy my sixth car and, you know, I'm going to do whatever I want. There's that way. And that way is like, like an, don't care about you kind of.
way of giving less fuck.
Digby Scott (:Yeah, it's an attention in orientation.
Jennifer Garvey Berger (:That's right. And then there's ⁓ the, I'm not protecting my ego so much. This is the thing I think you're pointing to. Like I am not going to drink that poison anymore. That's it. I've decided that's not good for me. I'm still going to work for a better world, but I don't have to take in that crap from the outside. And my internal system is going to be okay.
It's going to be okay. don't, I don't need to impress you. I don't need to be perfect. I don't need to show you another thing on a website that says I'm so great. You know, like I could give less fucks about like showing you my ego in all of its glorious splendor and just be like, yeah, I don't know. I don't know. And I think I do not know as a developmentalist and a mom.
I think that's hard to get to without some years on the planet. I think you could do it faster than I've been able to do it. But I think that is a practice that if we started young people on it earlier, but not the, don't care about the world, but I don't need to polish and stroke my own ego to feel good about things. My daughter's come up with this little mantra, Naomi's 27, and she's like, they're not actually thinking about me at all.
Digby Scott (:I agree.
Jennifer Garvey Berger (:Right? Like I, I'm not on their mind. They're not doing that on purpose. They're not trying to do anything to me. Like they're not thinking about me. And there's a way that that news is insanely liberating and delightful.
Digby Scott (:Absolutely. I love that. It takes your ego right out of the picture, right? It's incredible. There's something about the word discernment here too. And that I think comes with years on the planet and the wisdom that comes with that, right? One of the practical things for me that helps me and I've really only started to develop this recently is noticing what happens in my body when I come across the piece of information. So I open it.
I subscribed to The Guardian, so I got the app on the phone. If I open that, and I'm doing it less and less now, I notice I'm acutely aware of what happens in my body when I read a headline. And if I'm more acutely aware of that and I've got the choice to go, hang on, is this good for me? Is this useful for my energy right now? Not am I accumulating more information, but is this serving?
my energy more than my knowledge. And if the answer is no, I'll shut it down. It's an intuitive thing more than a, you know, I'm running an algorithm in my head about it, but it's very useful as a way for me to give less fucks and still stay in tune and still stay useful and relevant. But I'm not in this consume for consume sake because that's what you're supposed to do to be if you're a professional or whatever, you know.
And that's really helping me, this kind of tune into, my energy lifting or is it dropping right
Jennifer Garvey Berger (:think as we are crafting a life, not just doing life, but crafting life, we have to be able to pay attention to what signals our body is telling us, right? We have to, because our body knows stuff. And this question about where's our energy, because really everything that's on your phone exists to make you addicted to it. That's how they win.
Digby Scott (:Yes.
Jennifer Garvey Berger (:Right? That's how that business model works. It's to get you as much as possible addicted to that. And they understand dopamine and serotonin. You know, they super understand that. If we don't understand that, then we are just on a track. We are not awake. We are sleepwalking through our lives. And if we want to craft our lives, we have to have some information that's cleaner.
that's less infected by our stories and the body gives us really clean information. It's not always right, of course, but it's clean.
Digby Scott (:Yeah, clean. then I think it's just, it's the best barometer that I can think of for making choices. I'm curious as we wrap this up, what have you learned or been reminded of through this conversation?
Jennifer Garvey Berger (:this idea of ⁓ like the generativity of play, which I think you really stand for Digby. I think this is one of the things you model and you call for and you call out of others. And it's why I always read your stuff because I need that. I need that reminder. And so that's super helpful to think about. You know, I am very intentional about crafting.
all kinds of pieces of my life. But your call is to also be intentional about play.
Digby Scott (:Thank you. That's really wonderful to hear. And I think I could own it more, actually. So I'm going to sit with that and play with it more. Thanks, Jennifer. We'll see you in a few weeks. Thanks for just coming along and being part of this. What a beautiful conversation. Thank you.
Jennifer Garvey Berger (:I look forward to this.
Thanks so much, Digby.
Digby Scott (:a couple of quick thoughts after that really rich conversation with Jennifer Garvey-Berger. I'm really struck by the idea of embracing confusion. As you probably heard, I've been chasing clarity and I've been always thinking that that's a really good thing. But as Jennifer puts it, there's a lot of possibility on the other side of confusion. And so maybe not loving it, but embracing it.
less because often that is the way through. And I think that's a lesson that I definitely could learn or at least be aware of. And I think for a lot of people in leadership roles where we're navigating change, trying to make confusion go away is one thing. But actually, what can we learn and what might be on the other side of this that will be really helpful, I think is a different set of conversations leaders can be having. What about you?
was the thing that grabbed you the most from this conversation. Whatever it is, I'd love it if you can go and share that thinking with someone else. Get a conversation going. You'll also likely enjoy the conversation with Andrew Maffet, which is episode four, around the ideas of really leaning into life, this idea of what makes life worthwhile is feeling alive. And Andrew is an exemplar of creating the conditions for that. I reckon you'll also enjoy
my weekly newsletter. If you like this episode, I publish a short practical, hopefully insightful newsletter each week, which just touches on an idea around the messiness of leadership. So find that at digbyscott.com forward slash subscribe. This is Dig Deeper, I'm Digby Scott. Until next time, go well.