In an age where meaningful leadership and authentic connection are more crucial than ever, Jerry Colonna, coach, entrepreneur, and author of the transformative books Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong.

Jerry has worked with CEOs and change-makers from across the world. His company offers a complete foundation for what it means to emerge as a leader through coaching, 360-degree performance reviews, bootcamps, peer groups, internal training and organisational change management, along with plenty of rich resources for entrepreneurs, including their podcast.

This two-part conversation looks at the internal barriers and personal histories we need to face to unlock our true leadership potential. And it continues into the subject matter of "Reunion", extending this journey outwards, exploring how leaders can foster a sense of belonging in a fractured society through authenticity and shared stories.

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This is the Friday fireside brought to you by the Happy Startup School.

Uh, for those of you who are listening to the podcast, uh, you haven't been subjected to the mayhem and the madness us by the universe.

Um, and so this is gonna sound all calm and very, uh, swan like in its delivery.

today we are joined by, I feel embarrassed to say that.

What a hero for me.

I discovered Jerry many years ago on the Startup podcast by Gimlet Media.

I heard about, you know, he was the CEO whisperer, the man who made cEOs cry, which intrigued me because very much, it was a contrast to the idea of what it meant to be in business and in Startup and to be a leader.

And this whole I, and something Laurence and I have been thinking we were alone in, in terms of what, what's the human side of this stuff, stuff of business?

And Jerry was writing about the stuff, talking about the stuff, working with CEOs, really digging deep.

And so for me it was a revelation to know that within this world of big business Startup world, there are people who are thinking about leadership and, and humanity in this way and vulnerability.

And so I'm very grateful to have Jerry with us today.

For those of you who don't know him, he is an author, a coach, a founder, a business person.

Devastatingly handsome.

Supremely wise,

Great

Amazingly knowledgeable.

All praise to the Jerry.

And recently he's written a book called Reunion.

The previous book was reboot, both books I found very fascinating and it's a really interesting journey that I think I'd like to take us on by understanding some of the background to this book.

That's my little potted history of my view of Jerry from the outside of Jerry.

Jerry, how would you like to describe what you do now and maybe a, a brief sojourn from the beginning to now?

I think the thing to understand about everything that I have done, everything that I do, is that I am, organized around trigger warning, I'm about to talk about Buddhism, organized around what I would call is my Bodhisattva vow.

And for those who don't know, Bodhisattvas are folks who have achieved enlightenment, but regardless have chosen to take rebirth until all beings are free of suffering.

So when we take a Bodhisattva vow, which is a thing that one does, you work towards the liberation of from suffering of everybody.

And my particular karma is to live in this bizarre realm between business and Buddhism and psychology and with a particular intent to making life easier for other people.

Sometimes I succeed, sometimes I fail, but that's what I try to do.

It's what I try to do when I write books.

It's what I try to do when I'm engaging in a podcast conversation.

It's what I try to do as a coach.

It's, it's the thing that gives me ground and a center and purpose.

The calming energy and presence is I think something that I have admired from afar in the way you present and you have conversations with people.

I think is one of the main reasons I was attracted to your work, because of the contrast that it has against what it sometimes well, a lot of us perceive it means to run a business and be particularly in a startup, in a hustle culture and where it feels like a dog eat doc world.

You talk about Buddhism and you talk about psychology as, as drivers or I think there's anchors or pillars of the, in the way that you approach things.

What is it from your experience that makes.

This idea of launching something new, trying to grow it, trying to keep hold of it, so effortful for leaders?

Carlos, the experience that you were having just a few minutes ago is a good example.

There's a conscious experience for you that I will liken to our efforts to create the magical unicorn of a startup.

I have this plan and it's going to unfold in this way.

But behind that all of what you call this, what you referred to as the second arrow, which is the arrow that comes at us after we've already been shot by an arrow, which contains all the stories that we tell ourselves, including, for example, all the negative self-talk.

If we look at the experience that we just had a few minutes ago as a microcosm of the entire experience of leadership in a startup, we have this idea, we have this plan, and the challenge seems to arise from the plan not unfolding as anticipated.

The real source of suffering, the real source of challenge.

Is to use a Buddhist notion, our attachment to the way things are supposed to be.

This is a life hack, 'cause it's not just about startups.

Mm-hmm.

But one of the phenomena about being in a Startup is we very early on, because of the meaningfulness of the work that we're trying to do, we very, very quickly attach our sense of self-worth and identity to the goal.

And then the plan doesn't unfold the way we anticipate, and so we suffer, just like you, just like a few minutes ago, there was a whole bunch of weight that you put onto this experience.

This is Jerry.

He's my hero.

Maybe someday I can be like him.

Whatever the story that's running, and that's the source of suffering.

That, to use your terminology, that's the source of effort that makes the challenge so difficult.

So we work with a lot of, founders, professionals, mainly in transition.

They're either exiting one business, going into another, or they're stopping a career in corporate trying to do something more purposeful and meaningful.

I was struck by the analogy that a guy called David Spinx, he wrote a book called the Business of Belonging, and he talked about the trapeze, where you're on one trapeze, the other trapeze is just outta reach and you have to let go of one to reach to the other, and there's a chance of being in free fall or even falling to the abyss.

And that's an experience for that person in transition, starting something new.

When you look at people who we perceive as successful, who are doing all the things, we think they're impervious.

They don't have these feelings.

It isn't something that, well normal only for the mortals.

While those who are like leaders of industry, they don't have this stuff.

I'm curious from your perspective of working with some, I assume quite influential or more established, bigger scale founders, I'm wondering what your story of that is and how you've seen that.

What I saw were two sources of suffering, which is confusing.

You described many of the folks who participate in your program as trying to move towards a more purposeful, or meaningful life, especially as it relates to work.

And what a mind fuck that can be.

Because let's imagine ourselves approaching midlife.

And I can imagine it 'cause I was there, right?

Working at JP Morgan, feeling the disconnect from meaning and purpose in my life, and feeling a kind of anxious energy that says, am I gonna die never having felt purpose and meaning?

And so we move.

And we create these conditions and we start to, okay, I'm gonna do this startup.

And we start to attach a sense of our beliefs about our own wellbeing to an accomplishment of this goal.

And then we struggle.

And part of what fuels that.

Is that we look back and we look at the world around us and we see our heroes, and we perceive them.

We project into them a whole story.

And the story oftentimes has at its base how inadequate I am.

If only I was like, fill in the blank, then I could be bulletproof as one client once said to me, in speaking about an admired person, they're bulletproof, right?

The mind fuckery is that the energy that fuels our movement towards creating say an experience that is impactful for other people, which is a gorgeous energy can also be a challenge.

Let me tell you, give you a specific example from my own life.

I have wanted, since I was a little boy, to be an author.

And to be clear, there is the someone who aspires to be a writer who doesn't write.

Then there's the someone who aspires to be a writer who writes.

And then there's this magical golden land where someone who writes gets published.

Oh, okay.

And so I endeavor, in writing reunion, one of the things I took on was this, larger than life task.

What can I do to help heal the world?

No big task.

Just trying to kill the world and stop us from trying to kill each other.

That's all.

And it's my Bodhisattva vow.

And I lay awake at night after a weekend of trying to write and not getting the words right, and the story starts flowing.

Who are you?

You're not a writer.

You're never gonna be an author.

Because the desired impact is so existentially important to me, because it feels wonderful.

When you wrote to me, Carlos, and you said your book reboot was so impactful to me, a little part of my heart just settled down.

Ah, I have lived a life of meaning.

Hmm.

Our task is to balance all these forces, and there's no simple little five point checklist.

Do these exercises and then you're free.

Our task is to every day.

Lift up and acknowledge what was going on.

At the very, very start, I slowed us down and stopped to acknowledge and give some relief to Carlos's anxiety, which not only made Carlos feel better, but I warrant made Laurence feel better, certainly made me feel better, and probably made some of the folks in the audience feel better.

Totally unexpected.

The right thing to do in that moment.

That particular last piece about slowing down, I think is quite pertinent to this.

And I'm aware of this in myself that I am.

I've been addicted to speed to just, and not the drug, but to this real need to get somewhere to move really quickly.

And how that adds to, I think, not only the frantic energy, but the amount of input that's coming in.

Like, I've gotta do this, could do this.

It's always moving to the next thing.

Okay.

I'm gonna interrupt you, coach.

Okay.

Okay, so remember my famous question how have I been complicit in creating the conditions I say I don't want, I wish to have, and I trademarked that 'cause I would've made millions from that.

The important thing to understand about that question is the psychological concept of secondary gain.

We do something, even if it hurts us, because it produces a benefit.

So I want to Go back to something you said.

You said, I think you said I've been addicted to speed.

What does it feel like when you go slow?

And what is the story you tell yourself?

Remember before when you were talking about being anxious and you were worried about, what does Jerry think of me?

What is the story you tell yourself when you are going slow and feeling anxious?

Not being productive, not doing.

And what What will happen to Carlos if he's not productive?

Oh, he'll be rejected.

By whom?

Oh.

Now we're going deep.

My dad comes in and says what are you doing?

You're wasting your time.

Right, right.

That's baked in.

Alright, so stay right there.

So we're gonna turn a little bit to Reunion.

and by saying, turn in your reunion, folks, those who haven't read the book, I spent a lot of time talking about our relationship to our ancestors.

What was at risk?

He was from being in a small village in Sardinia, kind of scraping a living, to wanting to.

Basically build a life for himself, build a new life for himself.

And so he is always valued learning and using every single day to improve himself, to move forward.

So Sardinia was his home.

What did his parents do?

Farmers

Okay.

So they had a lot of money.

Not at all.

So great grandparents.

Great grandparents.

They did well.

Okay, so what happened?

Oh, now we're going into family history.

What we're doing, Carlos, is unpacking why Carlos feels anxious when he's not productive.

Hmm hmm.

Okay.

So without going too much, there was a moment in the family lineage where people were relatively comfortable, then they were not comfortable.

Hmm, yeah.

And nothing can produce anxiety quite like having it taken away.

Hmm.

Okay, so back to Carlos is on the floor watching television.

Dad comes in.

Carlos, what are you doing?

Don't you have homework to do?

Yep.

You better get busy getting busy.

Don't waste your time.

Don't waste your time.

Time is precious.

Because the moment it can be all taken away from you.

Because guess what?

We have family lineage history that proves it.

I heard many stories of that time.

During the war.

During the war.

That's when it was really hard.

And that was basically, yeah, things got really bad.

Really bad.

I don't think that you were as addicted to speed as you were trying to make sure that what happened in the past doesn't ever happen again.

There is an element of trying to create security.

Trying to make sure you're on top of everything, making sure you're ahead of what might happen

You want to hear a mind fucking concept?

Go for it.

Right outta Silicon Valley?

If I move fast and break things, things won't get broken.

Hmm.

That is not the logic of a fully actualized adult.

That is the logic of a child carrying the burdens of parents and grandparents.

and great grandparents.

And great-Great-great-great, great grandparent.

Makes perfect sense until you examine it.

Hmm.

See, if I move really, really, really, really fast, then I won't be unhappy.

And being still then invites all the feelings and that doesn't feel great.

It invites in the challenging feelings.

And it introduces the risk.

And everybody's story is slightly different, but many of the stories have echoes that are the same.

One of the phrases that sticks with me from your writing is this idea of longing for belonging.

IAnd I'm wondering if this is the core of it because I, I definitely recognize in myself part of this need to be productive, need to work, need to move, need to always be doing things is this need for acceptance, this need for, you've done well you're good, pat on the head.

Keep on going.

We're impressed by your productivity.

And whose voice is that?

Oh, that's dad.

That's dad's voice, of course.

So, I'm gonna read a quick quote.

And this is actually not my words, but it comes from, the opening epigraph to the new book, reunion.

And, um, this is written by Frederick Biner.

Biner was a theologian, an American theologian, and he wrote their lies, the longing to know and be known by another fully and humanly.

And that beneath that, there lies a longing closer to the heart of the matter still.

Which is the longing to be at long last, where you fully belong.

It's from his book, the Longing for Home.

Carlos, I think you did something very, very sophisticated right now in which you saw that the way you're carrying forth that multi-generational transpersonal experience.

That then manifests in the very thing that might drive you crazy as a startup leader, if I don't move fast and break things, then I'm not gonna be happy.

This is the framing.

And the sophisticated statement was that I think that you realize that if you take on the burden of that belief system, what I refer to in Reboot as a sub routine, if you take that on, you know where you'll fully belong, you'll belong to your family.

And that's really powerful.

And not everyone belonging to belong, which is a universal feeling as beaker points out manifests in the way yours does.

But there is a universal longing to belong that you can lift up and use to connect with Laurence when he drives you crazy.

Because Laurence has a sub-routine that's running every one of your co-founders, every one of your employees, every one of your romantic partners, every one of your children, every one of your parents has that universal longing to belong, as I wrote in Reboot, the Wish for Love, safety, and Belonging.

And when we see that.

We apply the radical self-inquiry to know what is my sub routine.

You know, Laurence, I haven't put you on the spot, but if we, we know that Carlos needs to move fast and break things, right?

Mm-Hmm.

Or let's say he moves fast, even if it breaks things.

But now we have a clearer understanding that when he's doing that, he's saving not only his father but his grandparents.

What would it be like, Carlos, if you could enjoy the craft and the magic of creating.

The improbable startup that has beauty and impact and is able to bring in, what is it, 56 people on a Friday who patiently waited while we got our shit together on technology?

What would it be like if you could enjoy that?

for what it is and not for what it has to do.

How would that feel?

Oh, it would feel a lot less effortful.

It would feel a lot more connecting, peaceful, light.

Hopeful, even.

Just a sense of, particularly with the idea of being with others and sharing an experience with others.

It creates a real sense of possibility for me when I think I'm with others.

How does that feel in your body as you name all those things?

It's kind of like a, a rush from the chest to the throat.

It's like a flowing, a warm tingly rush from chest to throat.

And those who are listening, check in with yourself.

Imagine the subroutines that are driving you.

Yes, someone wrote, Dennis wrote, driven or driven mad.

Imagine those belief systems.

And imagine us reframing the relationship with the assignment, with that core, your core longing to belong.

Where it's motivated by the.

That wish for connection and the craft and the beauty of trying to create something out of nothing, which is the art of startups.

Hey kids, let's put on a show.

This speaks very much to our experience of taking people through a learning journey.

So we run a coaching program and on one level you could look at it as I got all of these lessons, all of these challenges, I need to complete them all, and once I've done them all, I'm good.

But the most powerful part that we found of this is, and I think I speak that you, I'm trying to speak to what you said, is when we slow down and we see each other in the group, and we learn about these stories, maybe not go to the level of the subroutines, but just the motivations,

the drivers, maybe the drivers that drove us mad, but seeing what's behind the behaviors of the various people that we coach as a group.

And what I'm hearing is the importance of when we slow down and we see, and I'm gonna quote you from your Reunion, this idea of your story is my story to be able to like you just did then is like connecting this story, my story for moving, always moving, being always in movement.

But then maybe Laurence being able to connect to ah, that's behind that story.

It connected to something else that maybe he can connect to in his own sub routine.

Let's imagine a world where everyone that we endeavored to really know each other and see our own stories and their stories, let's imagine the effects of that world.

It's kind of hard to dehumanize, push to the margins systemically, press or systemically other, those whose stories we actually know.

So one of the things that we do, we have, we run a little coaching program, It's just kicked off.

And every Friday we have a check-in and we just get them to say, one thing, um, to celebrate one thing that's been a challenge and one thing they've learned, which is a nice way to just reflect on the week.

And I was thinking, checking in with that actually.

'cause a challenge has been herding cats trying to get a group of people to agree, a time to meet and talk.

Success was to actually find a time.

And it's one of those things where, oh my God, is it gonna work?

Is it gonna work?

And it finally works.

And the thing I learned, which I was really curious about this week, was the relationship between emotions and feelings.

I always got them interchanged.

And one of the things I learned was emotions are these sensations in the body and the feelings are the stories we tell about the emotions.

And that for me is like, oh, mm-Hmm.

And how you can have, well, as I understand it, similar feelings in different people's bodies, but ,Oh, similar emotions in different people's bodies, but different stories and so different feelings.

it's like the difference between weather and climate.

There are labels, you used the phrase stories we might say, this feeling of my heart racing is, excitement, or this feeling of my heart racing might be fear.

But what is known is that my heart is racing.

I think being able to hold on to the distinction is really important.

Of course, I'm always fascinated by the stories we tell ourselves and what is the raw material of that story making?

And this is just a real random reaction, sometimes we use the phrase, the story I'm telling myself, as a kind of bit of curiosity.

And sometimes it can have a little bit of an edge, like a self-critical edge to it.

And in my experience, one of the things human beings are really good at is trying to make sense of the world through stories.

So one of the ways I would react to what you've just said is that rather than if you, if you have this proclivity of seeing feelings as through a negative lens, just simply see it as a way of trying to make sense of the world, trying to make sense of the inner weather, if you will, or the inner climate.

And allow the curiosity to really drive that.

Why do I see my heart racing as fear?

What prevents me from seeing it as excitement about potential?

For me, it touches well, this is element of curiosity that I'm hearing about this.

It's trying to, rather than fix this into this saying, all right, I'm like this and this is the way it is.

It's like, what is it that's happening here that makes me react and respond this way?

I remember I was listening to a podcast that you were doing, I think it was the Evolving Leaders podcast.

And there was, you were having, you were talking about the idea or I think someone was talking about the idea of making the unconscious conscious.

And I wanted to mention that because I don't think we had a chance to really cover much is the kind of stuff that I understand that you talk about in Reboot, about leadership, and what it means not to be a terrible leader as opposed to what it means to be a great leader.

' Cause I think a lot of us can resonate with having bad bosses, leaders who aren't particularly skillful.

And maybe just blaming them and saying that they're idiots but there's something else there.

As I understand from your work.

That's a symptom of something else.

And I was curious how you would talk to that in terms of what is it that might make a terrible leader?

First, on the reference to making the unconscious conscious, in fairness and giving credit, that is, there's a quote from Carl Jung that is particularly useful in this moment and speak to that.

And what Carl Jung said was until you make the unconscious conscious, it will direct your life and you'll call it fate.

Now, that's one of those incredibly simple, yet powerfully wise statements that just sort of unpacks a whole bunch of things.

And to your point, when we experience someone whom to use your phrasing is a quote, terrible leader, and notice I'm a little uncomfortable saying that because I do not want to label as bad, bad behavior, right?

I don't wanna label the person.

What is often at play are unconscious or barely unconscious, what I would call our subroutines belief systems that drive that person to behave in a particular way.

A very important subroutine that many people who hold power have is that, unless I'm perceived to be as infallible or right, then my, power is going to be threatened.

And so they exacerbate the power over construct by, in a sense, wiping out everybody and saying that they are just fundamentally wrong.

You can immediately envision what it's like to be in that environment where you're constantly put down because someone else has this unconscious need to always be right.

Because really what they're doing is battling a demon that probably goes back to their childhood or even their parents' childhood that says if you're anything other than right or perfect or correct all the time, then you're less than and you are in danger of being wiped out.

There's a corollary to this, which is how we are as individuals.

And I think it's equally important to ask ourselves what are the belief systems that are driving us?

What are the unconscious pieces of us that we are calling simply fate?

And that's where my infamous question, how have I been complicit in creating the conditions I say I don't want is particularly useful.

Because in both instances, whether we're looking outward at someone else or looking inward at ourself, the key intellectual process is radical self-inquiry.

The key intellectual process is curiosity.

Perfect journey you're taking us, Jerry, because this is, how I wanted to bring us to this idea of our own.

And like you said, how we complicit in circumstances we find ourselves, or creating circumstances we find ourselves.

I like the way that you said is like trying not to label this person as bad.

It's just the behavior.

This idea of trying to show these people who we might create uncomfortable emotions in us, treating them with compassion in order so that we can treat ourselves with compassion.

They're our human beings, so are we.

And for our community, a lot of people who either join our program, join our community, come to our events, they're on this journey of a transition to do something different with the way they work and how they create impact in the world.

And they struggle many with, I'm not an entrepreneur, I'm not a salesperson, I'm not necessarily a leader.

But there's still this need to become more, in a sense, or just to, to not settle for where they are at the moment.

They, they, they're working, they're making the money, it's fine, but it's, the question is, is this it?

And so they want to go beyond what this is, but then to go beyond what this is, they have to maybe battle some demons.

Mm-Hmm.

In your parlance.

And so, uh, uh, yeah, I just wanted to sort of like get your thoughts, because there's a lot of stuff out there about how to start a business, how to do a career pivot and the tactics and strategies.

But my belief and Laurence's as, as well, and our experiences, there's, there's also other stuff that gets in the way.

There's probably more important to tackle than just to learn how to do marketing.

So from your experiences as someone who's worked with, with leaders and startups and entrepreneurs, what kind of advice would you give someone who feels like they're pushing against a glass ceiling or a invisible barrier and, and what, what things to think about maybe?

So let's recognize that, there are some transitions that we go through that are acute and present, we're feeling it directly.

And then of course, there are transitions that occur chronically over time because we're all in a process of becoming.

We're not really sure what we're becoming, but we're always in a process of becoming.

We're always in this transitory state.

And it's kind of a trick of the mind.

And now I just wanna honor my Buddhist teachers here.

It's kind of a trick of the mind to think that permanence is something that's achievable, right?

I've become this and that's it, and I'm done.

And best I can tell, the only permanent state that human beings exist, experience is death.

So we don't want that.

We want life, which means we are choosing transition, we are choosing impermanence.

And that a big source of our frustration and our struggle is to see transitions as kind of like step function.

I'm going from this step to this step, to this step, as opposed to, oh, this is actually the normal state where things are always in flux and things are always changing.

So that's an important concept to hold onto.

But you also mentioned, you know, thinking about, I think what you said was sort of marketing skills and that sort of thing.

So I want to give you a bit of a framework, and I see from a little bit of the chat that there was a, that I used a phrase that folks may not have been familiar with.

I used the phrase radical self-inquiry.

So I wanna go back to that and I'm going to give you a framework for thinking about this, which will be familiar to both of you and Laurence 'cause you've read my books.

And that is that practical skills, so if you could visualize this practical skills plus what I refer to as radical self-inquiry, plus something that I think you all do quite well, shared experiences, actually talking about the experiences, those three equal enhance leadership and most importantly, greater resilience.

And resilience in the face of the emotional challenges, not only of being a leader, but simply being an adult, being a human being.

One of the challenges that I have seen over my now 20, 25 year career as a coach is that those who hold leadership positions in organizations fixate on what we would call the practical skills.

How do I fundraise?

How do I launch this?

Or if we're talking about folks in transition, what is the next job?

What is the next manifestation?

Now I wanna be clear.

Those are really important questions, but those questions undertaken without the other pieces will lead to one, just using one's unconscious to make choices for ourselves.

And we end up in positions where we might five years in say, how the hell did I end up here?

That's not what I wanted.

And so it's critically important to develop the other two components.

Radical self-inquiry and shared experiences.

Now I'm gonna jump to shared experiences.

Shared experiences is what we're doing right now.

We're being honest, we're talking, we're checking in.

It's like trying to live life without bullshitting ourselves.

Radical self-inquiry is the skillset that we're least likely to have developed as children, and it's arguably the most important, which is having the non-judgmental curiosity to strip away the performative mask that we start to wear so that with loving curiosity we start to ask questions like, how have I been complicit in creating the conditions I say I don't want?

Or some of the other questions I'm famous for, what am I not saying that I need to say even to myself?

Like, I don't really like my job and I can't say that to myself because fill in the blank, all these other rules like, oh my God, what am I gonna do for a living?

And the important notion is by looking at each one of those components, we end up not only being better leaders, but leaders and adults who are more likely to withstand the naturally occurring vagaries and challenges of this really difficult journey called being a human being.

I think that that formula, which I first wrote on a whiteboard at some talk I was doing in answer to the question, well what is it, this thing that you're doing, Jerry?

This weird combination of Buddhism and psychology and business leadership?

And it's like, I thought about it, it's like, well, what is it that I'm trying to say?

And in some ways that formula has been a guiding principle, not only to my work as a coach, to what Reboot the company does, but really at the basis of everything that I write.

I was trained as a physicist.

And one of the things I appreciated through that training is elegance.

When you can find that simple leveraged pivot point that actually tackle that and everything else just seems to fall into place.

Mm-Hmm.

That for me is, yeah.

That's, an example of elegance outside of a mathematical formula.

Well, it's slightly mathematical, but outside of the lab, it feels so clear.

So simple.

I appreciate that because, to go back to what we were talking about before, I see us as human beings, as sensemaking beings, right?

We experience to use the language from before the climate, and we try to label it in terms of weather.

We experience the emotions and we try to label it with feelings.

We are trying to make sense of it.

And what I was trying to do is simply to make sense of what it was that I was being a proponent of, but also what I had experienced myself.

So that once I had, and thank you for giving me this term, an elegant understanding of the world, as subjective as that is, I could then make sense of what was happening to me.

It, it's not that dissimilar, for example, to one of the theses that I put forth in my first book Reboot, which is that if we go back to the unconscious, what we're really looking for are love, safety, and belonging.

We want to love and be loved.

We want to do both.

We wanna receive it and we wanna give it.

We want to feel safe physically, existentially, emotionally, spiritually, and we want to know down to our bones that we belong.

We go all the way back to another point you made, bad leaders.

It starts to shift the conversation that when we see toxic behavior through the lens that might occur when we say, well that's just a five-year-old kid trying to seek love, safety, and belonging.

It doesn't excuse the behavior, but it makes sense of what the activities are.

When we are selves fail to live up to our aspirational values, when we are selves fail to be the leaders that we want to be.

If we look with curiosity and that radical self-inquiry at our own behavior and say, oh, I was just trying to keep myself safe.

Mm-Hmm.

Boy, that's a knuckleheaded way of doing it, but that's what it was.

I'm not a bad person.

I'm just trapped in a five-year-old's body trying to make sense of the world.

The one thing that I was curious about was how important you see the shared experiences part to that formula, because I think of people can go on a self-help journey to do some self-inquiry, but it's lonely.

Or maybe it's with one person, maybe it's with a coach or a therapist, and they go on that road.

I'm just curious how important you see community to breaking through some of those barriers.

What I often say about radical self-inquiry is that it's radical because we so rarely do it.

What makes the shared experience radical is also because we so rarely do it.

A question for everybody, and we'll treat it rhetorically, is what was it like in your childhood?

How free were you able to say, I am scared, I am hurt.

In my experience, I do a lot of public talks around the world, and invariably people will explain to me that in their culture, German culture, British culture, Chinese culture, it was unacceptable to talk about what was actually really going on.

And then I point out that this happens in every single culture I go,

So we see it through the lens of the culture in which we grew up, or through the family in which we grew up.

But the truth is, we are not encouraged, Laurence, to share.

In fact, you know, it's really through things like what you guys are doing that that culture can start to change.

Think about how often in social media, the experience is look at me, I'm living the high life, and we all know it's bullshit, right?

We have lots and lots of language and mantras where we say, you know, don't judge a person's inside by what's happening on the outside.

Don't compare your inside to their outside.

And yet, so much of our culture makes it incredibly difficult to even identify what we're experiencing, the climate behind the weather, let alone be brave enough to call a fellow CEO and say, I don't have the fucking foggiest clue as to what I should be doing.

When I first started doing this work, I used to stand up in front of people and say nobody's crushing it.

People would say, how's it?

How's it going?

How's your startup going?

Oh, we're crushing it,

right?

You both laugh 'cause you know it's bullshit, right?

And yet there's still this culture that persists, ' cause we're trying to make sense of like, well, why do I do it if it's so hard?

Why do I throw myself into this ring?

Why do I go through what I'm going through?

So I would argue it's both the most radical and perhaps the most transformative part of that entire formula is the ability to share in community a true story of what we're experiencing.

And with that, it feels this sense of community less and less these days.

Particularly in the world of work, from my own experience.

And there's something about shared, well there's, we can have many types of shared experience, but, you know, the word vulnerability was coming up for me when you're talking Jerry.

And to be, that process of radical self-inquiry, the way I hear it, it requires honesty, real honesty with yourself, which then opens you up.

If you are gonna be honest with yourself, and then you wanna be honest with other people, you're then going to, people are gonna see, like you said, our insides that isn't always received in the best way with others.

And the kind of examples I'm saying is like, people jump into fix to tell you what to do, or to say, oh, this is what happened to me.

Mm.

My understanding of your work is you create these shared experiences where I'm imagining lots of crushing at people come, but I'm assuming you, you create a space where vulnerability is how was, uh?

Encouraged?

Not only encouraged, feels allowed, allows people to be vulnerable.

I don't know.

Curious about how do you engineer a space so that people can do that inquiry in companionship with others.

I would argue that vulnerability is the feeling.

I feel vulnerable.

And the emotion behind it is honesty.

And I typically prefer the word honesty or authenticity to the word vulnerable because vulnerable does describe how I feel.

I feel at risk, like something bad is gonna happen.

So I want to tease it out so that we can again see more clearly and perhaps a little bit more elegantly what's going on.

If I'm honest, I feel at risk.

I just wanna let that statement land for a moment.

If I'm honest, I feel at risk.

What a fucked up notion, right?

We project all this power onto people against a backdrop of, if I am honest, I am at risk.

And then we sit there and go, why do we have such terribly dishonest leaders?

Carlos, you asked the second question which was in effect, how do we create conditions?

How do we create containers?

And you hit upon one of the more important ones, which is really hard for entrepreneurs, really hard for, for a lot of folks.

And that is to not fix, ' cause as you know, and you're skillful enough to know this, that when we fix, we turn other people into problems.

And people aren't problems.

They're human beings having experiences often labeled as feelings, right?

And so one of the most important, skills to develop, which many of us did not experience as children, is compassion.

Compassion, etymologically breaks down into two words.

Com, passion.

Okay?

That's the Latin.

Com means to be with.

Passion refers to feelings.

It does not break down into fixing feelings.

It literally means to witness someone else's experience labeled as a feeling.

So a core rule, if you will, of safe community is compassion.

Now this is a little bit of a real challenge.

I remember when we first started doing our bootcamps 11 years ago, I had this rule that if somebody started to cry, do not leap across the room and hand them a tissue.

And that really messed with people, because we're wired to try to fix the tears.

And we evolved away from that.

Now, I'm less of a hard ass than I used to be, but, my point would be, do you remember when we were children and we would cry and there were typically two kinds of annihilating responses we would get?

The first was, oh, you're crying.

I'll give you something to cry about, right?

And a whole bunch of people just went into a PTSD state having said that.

But the second experience, which was well intended, was, sh don't cry.

I would argue that the compassionate response is you must really be in pain.

You must be sad.

Especially for children who struggle to have language to name those feelings and just experience the emotions to be able to say yes, sad, that's the word behind the tears.

Or la you know, as labeling the tears.

To witness someone crying and to allow the full experience of that is to allow them to be fully human.

That sometimes rushing across the room and shoving a tissue in their face interrupts.

So my less hard ass rule right now is give it a minute, you know, slow down.

Or bring your own tissues.

Own tissue.

But give it, let it sit a little bit.

Yeah.

Don't be so quick to make it better so that we all can practice the art of self-soothing.

' Cause then this other thing starts to happen.

Oh, I'm crying, I'm having emotions now I see you reacting.

Now I gotta take care of you because you're trying to take care of me.

Oh my God.

Stop.

Easy.

Just be together.

I, I actually just little penny dropped when you talked about let's self-soothe together.

'Cause the scenario I'm thinking about is being in a group.

Someone starts to cry and that creates discomfort in me.

And so to get rid discomfort in me, I'm gonna stop you crying.

But I need to learn to soothe myself while you're soothing yourself.

Yes, you got it, Carlos, go to the head of the class.

In fact, Parker Palmer in his book A Hidden Wholeness, which is a great book, half of the book is a sort of a guidepost to running, shared experience peer groups, which he called circles of trust.

And there's actually a list of things that he talks about and he very eloquently explains that phenomena that you just identified, Carlos, which is the helplessness that I might feel when you are having an overwhelming emotional state, which by the way is probably why people would say to you when you were a kid, don't cry.

Because I don't know how else to make it better.

So please don't make me feel terrible about not being able to help you.

So, shh, don't cry.

Right?

He also lists a bunch of rules, like don't, no fixing, no setting straight.

Hey, the problem with you is There's a wonderful line in there, which is when the going gets tough, turn to wonder.

So if I'm having a difficult experience because you are having a difficult experience, hello, radical self-inquiry time.

Why is it so difficult for me?

What is it triggering in me?

So that I can stay empathetically connected to you.

Because you're not a problem that needs to be fixed.

You're human having an experience just like me.

This is why I love your work.

And I feel like it's, it's the kind of work that we are trying to do because it's not just about the ideas and the concepts and the plans and the strategies.

It's the fact that if we don't have a relationship with that and ourselves in the process, we are less able to make decisions that benefit us

And we start to allow our unconscious to drive us rather than to become adult drivers of our own life.

Yeah.

Which is really, that's the wish that I have,

That was the point I was thinking of, and I was thinking about a Parker Palmer book that I can't remember.

It's something to know as you known, I think, along those lines.

Yes, yes.

And this idea, there's the relationship with the content in, in the area of teaching, there's a relationship with the content, there's the relationship with the teacher, the teacher's relationship with the student, and there's just the relationship with the space.

And for me, this is the missing element, I think, and myself and Laurence, I'd say experience in the world of learning about business.

It was very much, that's the plan, these are the strategies, these are the models, these are the case studies you can look at, but never addressed what's my lived experience of this?

Yeah, very much chalk and talk.

Sitting in a conference listening to someone telling you the answers.

I think that's a symptom of education in general.

It feels

Well, I'm glad you brought Parker back into the room in this way, to recall.

In addition to his career as a writer, he is an educator and, really a master at teaching what it is that teaching is about.

Even if you're not an educator, I would encourage you to read The Courage to Teach, which was his central book on teaching.

The book that I first read of his, that changed my life was Let Your Life Speak.

We now have a 20 year friendship, that is deep and profound.

I just saw him a few weeks ago in Madison for his 85th birthday.

There are a few things in life that are more delightful than just sitting in a sunroom with your teacher and mentor, and just sit for hours and have questions and be together.

But I think that the essence of what Parker's work is all about, whether it's in A Hidden Wholeness or To Know as We Are Known or Let Your Life Speak, or the Courage to Teach is to recognize the human being in yourself and in the other.

In the early books, which are primarily focused on education, he's really speaking about, the human to human connection that exists in the teacher-student relationship.

He's overcoming that notion of tabular rasa, right?

You're a blank slate and the teacher's job is to write on the blank slate and give you the information.

You know, we can look back with jaundiced eyes on our own education experience and, and realize the falsity of that as a model, right?

Our greatest teachers were the ones who taught us how to ask questions, how to seek knowledge, how do we integrate knowledge?

What is often lost in leadership is it's exactly the same challenge in leadership.

You know, probably the greatest leadership writer of the 20th century, Peter Drucker, used to say that a CEO's job is to ask questions.

Just think about how profound that statement is . And think about how it goes against the type that we carry, which is that a leader's job is supposed to have the answers.

And then what ends up happening is, of course we don't have the answers, but we have power and we rise within an organization, and we have a little whispery voice in our head that says, you don't know what you're talking about.

You don't have the answers, but you better pretend that you have the answers or else they're going to be anxious.

And so that whole basis of trust and learning within an organization, honesty gets tossed out the window.

So just like the teacher and student relationship, our relationships at work are fundamentally between human beings.

Of course they are, but we don't think of it that way.

Another penny dropped for me there.

And it reminded me of the Maya Angelou quote.

You know, I've learned that people will forget what you did, but they'll never forget how you made them feel.

And when you're talking about teachers, you know, the kinds of teachers I remember, teachers I remember created an experience for me.

They didn't just read out of a book.

They showed, they demonstrated, they got us involved.

And I'm particularly thinking about Mr.

Young, Laurence, my physics teacher, But he was the teacher of my school.

He was the person who switched the light of physics on in my head because it was an experience.

It was an, it is something I remember his lessons.

And I think there's something here about a skill of creating shared experiences, creating experiences that connect, that I don't think has been.

Enough priority in, in school and in work.

You know what I often recommend, you know, client will often say to me, how do I measure my effectiveness as a leader?

Because the impulse, of course, is to look at the outcome of the organization.

And one metric, which reminds me of the conversation we're having about students and teachers.

One metric I would ask is, how many leaders have you helped create?

What are the conditions in your organization such that those innate leadership skills and the people with whom you work start to rise?

What would happen if everyone within an organization felt enough love, enough safety, enough belonging that they could overcome the subroutines that hold them back, so that they can be their greatest, most actualized human self?

Now, I can't guarantee that it's gonna create the best financial return on investment, but what an extraordinary organization it would be.

What if that was the role of, schools?

What if that was the role of our communities?

I love that idea that that definition of a leader, their role is to help others rise.

What goes through my mind is those leaders who love to micromanage and be in everything and do everything and make sure everyone's doing the right thing and the way they wanted to do it.

And that's just so draining and energizing.

I remember when we ran our agency, Laurence, it's like feeling a little bit of that, oh, want to control the output.

As opposed to let go of the work but spend more of my time helping them get better as opposed to me trying to push them down.

That would've been so tapped into what I think Laurence and I enjoy most, which is helping others sort of find their thing.

But then it would give them the freedom, like you said, to find their own leadership or the way they can lead.

And that feels like a nice, nicer place to work.

I only where I wanna work.

I'm also curious how many bad leaders have led to leaders that they've, been in charge of going, I can do this better than you ever did.

Almost to spite you, I'm gonna prove, I mean, we know a few, I think maybe we are those people who've been in organizations where thinking, okay, I'm gonna start my own business 'cause I don't wanna be a boss or have a boss.

Well, it's like the 20-year-old who decides that they're gonna be anything but their parents.

And so they grow in the shadow of a negative example, and uh.

Yeah.

You know, there can be growth in that way.

There's no question about that.

But, I do find, I liked your word, Carlos, energizing, I find it energizing to model myself after someone I admire versus to reject someone I don't admire.

And so I am as lucky as I am to have found mentors like Parker, in my life.

I literally will say to myself at times, well, what would Parker say in this moment?

And, that's really a powerful guide.

In Reunion I talk about our ancestors and turning our ancestors into elders as part of the process of creating systemic belonging within an organization.

And what I just did there, even though he's not technically my ancestor, it's really responding to Parker as my elder.

He, by the way, insists that I'm the older brother, not him.

That's just his delusional state.

So,

And this, for me, touches and this idea of leadership, for instance, you know, this, where we're trying to help our colleagues rise rather than control them.

It speaks to, not just standing by.

How can you participate in the world in a way where you are, I think contributing to more belonging.

And that's, for me, is a really powerful message in the book, because it Connects to our work and I think what people in our community want to do.

'Cause it isn't just about self awareness and self-improvement.

It's about how can I do something purposeful in this world?

You know?

Well there's so many things that could be addressed, what's my work to do?

And then how do I become complicit in making that environment better in this world?

So maybe we can just, yeah, move towards the end with some thoughts on that.

Yeah.

Well, thank you for making that connection.

You know, iIn Reunion, what I'm trying to do is presume a level of self-awareness or presume a level of radical self-inquiry as a foundation to go beyond looking inward, to looking outward.

Because I think that there's a core question, which is, what is my responsibility to the world outside of the meat sack of me?

Now you have a responsibility to the meat sack of you do not hurt people, period.

Take care of your own stuff so you don't hurt people.

But beyond that, what is beyond that?

What is beyond that is to look at how I have been complicit in and benefited from a world where others are oppressed, for others who don't fit.

A heteronormative binary structure where people like me, white, cisgender, straight male, seem unassailable and dominant, especially in Western Europe, United States, north America, that kind of an experience.

What is my responsibility and equally important, what am I willing to give up that I love, including my own love, safety, and belonging, so that someone else can feel those things?

I think that there's a moral responsibility to ask those questions, to strive for those answers.

That's what reunion's about.

More important than having the right pathway, it's encouraging the question.

I experienced that as quite a confronting question because it makes you really think about what is mine that I'm willing to let go of?

And that's uncomfortable.

And then having to sit that discomfort.

And then who can I be around to sit in that discomfort with?

That's right.

And if it's uncomfortable, imagine who has been bearing the emotional load of systemic oppression, and imagine how uncomfortable it is for those folks.

Nice soft light ending for everyone.

I was on a podcast the other day and someone said, boy, this is really deep.

I said, I've never been accused of being shallow.

And I think it's important.

I believe it's fundamentally important to be able to have these questions and this awareness, particularly if we wanna give this idea of business, of being a force for good.

Not just as a label, but actually something that people can, I love this word, operationalize.

As always, really appreciate your wisdom, your time and yes.

Your presence and energy and, and well, all the work you do.

Very inspirational for us.

And yeah, just looking forward to seeing what the new book is going to be like.

Yes.

We'll see.

Alright.

Back to me in about two years.

Yeah, exactly.