Let Your Life Speak by Parker Palmer | with guest Jerry Colonna

0:01Welcome to Business Book Club, the show where top entrepreneurs break down the most powerful insights from the world's best business books. I'm your host, Sam Brown, and today we're diving into Let Your Life Speak by Parker Palmer. This book has guided CEOs, teachers and activists alike selling hundreds of thousands of copies and becoming a modern touchstone for authentic leadership. Parker Palmer is a celebrated educator and founder of the Center for Courage and Renewal. Named one of the 25 most influential leaders in higher education, his life's work centers on helping people align their inner truth with their outer lives, even in high stakes leadership roles.

0:40In this episode, we explore how entrepreneurs can find clarity, not through hustle, but through honesty, and why true leadership starts with listening to the quiet voice within. And joining me today is Jerry Colonna. He's the CEO and co-founder of Reboot.io and the author of the books Reboot and Reunion. A former venture capitalist turned executive coach, Jerry is known for guiding leaders through radical self-inquiry. His work blends psychology, mindfulness, and leadership experience to help people lead with integrity and heart. Thanks for joining, Jerry. Why did you choose Let Your Life Speak?

1:19Well, Let Your Life Speak changed my life, actually saved my life for two very important reasons. The first, it was one of the first books I've ever read written by someone I admired who spoke with honesty and integrity about their own struggles with depression. And that was really critical for me because it gave me permission to speak openly and honestly about my own struggles with depression. But relevant to this podcast, relevant to this conversation, I would argue that the entirety of my approach to leadership development is really embedded in this book. And in particular, this notion of leading from within.

2:02This notion that true leadership begins with an inner understanding and an inner awareness of that which really troubles us as individuals. Even though it's not positioned as a classic business book, I think it is one of the most important leadership books ever written. What is lesson number one? Leadership begins within. What's important about that and what Parker is really saying, and specifically he writes about this in chapter five of the book, which is called Leading from Within. What's most important is that we as leaders, those of us who hold power, are often socialized to look at the output, to look at the outcome.

2:48So if you walk through a bookstore's business section, for example, you're going to see a lot of books about return on investment. You're going to see a lot of books about creating good business plans. What you're not going to actually see is a lot of books that teach us how to be good leaders. And I don't know how you can build a good business without first learning how to be a good leader. And the non-intuitive lesson around that is that one has to actually become familiar with one's own inner demons. You, in the introduction to me, talked about my phrasing radical self-inquiry. Well, radical self-inquiry is my version of what Parker is saying when he talks about leading from within.

3:36One of the most important insights that Parker shares in this book is that we all have, what Carl Jung would say, a shadow side to what we're doing. We all have, say, a fear of failure that can drive us to be overly urgent, overly toxic in some ways, and ironically destroy the very business that we're trying to create by being so terrified of failing. In his parlance, this notion of connecting with that which is driving us within is the best way to actually manifest the leadership that we want to have. When you said some information around this book across, one of the quotes that you sent was that The power for authentic leadership is not found in external arrangements, but in the human heart.

4:26Could you unpack what you mean by human heart? Well, you've just launched a new business, right? Why is it so important for you to do a podcast about business books? The main reason was because I miss speaking to entrepreneurs, VCs. I used to run a podcast production company, and in that podcast production company, all my clients were founders. And I loved speaking to them on a daily basis. What did it do for you? Made me feel great. Made me love the role that I had in helping them with their journey. And so when you have a great conversation, how does it make you feel about you? I suppose valuable.

5:02So you just asked me about this notion of leading from the heart. And everything that you just said were feelings. I love it. It makes me feel valuable. It makes me feel perhaps connected. It makes me feel alive. Okay. There is literally no business reason that you just described. There's no like, I'm going to create this like monster hit and I'm going to be a big, rich person. The truth is, just like everyone else, all of those entrepreneurs, all of those founders that you admire, they're motivated by an inner desire. The problem, though, is that when we become intellectually disconnected from that inner desire.

5:47What ends up happening is we drive and we drive and we drive, but we're disconnected from what motivates us. And this notion of leading from within is about reconnecting with the most powerful motivations that we have. That's the thing that will compel you to work nights and weekends on this business. That's the thing that if you're not careful can compel you to drive your colleagues crazy because you're working so hard. Does this make sense? It does. A lot of what you do when you're in the sort of weeds of running a business is you're trying to optimize things. You're trying to set up systems and processes.

6:26You're trying to track in the metrics. You're making sure that your customer acquisition cost is going down, this sort of thing. Lesson number two is the inner journey is the hardest because we live in a social environment where we train children not to stay connected to their heart. When you were in school, no one talked to you about your heart. They talked to you about your grades. They talked to you about the outcome on your tests, but they didn't make the connection that it would feel really good to learn because that's not what we value in our society. And as a result, that inner journey is actually incredibly hard.

7:05You introduced me as an executive coach, and I said that this book not only saved my life, but shaped everything that I do. You know what the secret of being a good executive coach is? It's helping people connect back to their motivations, back to their heart, so that they understand why do they do what they do, positively and negatively. Let's dig into how you might do that then. So how does this affect you in your work? What are the frameworks, or what does a typical session look like when you're trying to do this? I was coaching you just a few minutes ago when I asked you why you launched the business in the first place.

7:41Let's imagine in this scenario, you came to me and you said, I'm having trouble with my colleagues. They're not working as hard as I'm working. I can't get them to feel the importance of what needs to happen, right? Really, really common problem. And I'd say, well, tell me about why you started the business in the first place. You asked me a question at the start of this, which was, why did I agree to come on the show? And I said to you, because I love talking about books, books have saved my life. My own writing and the writing of others have saved my life. It's the way I battled my depression.

8:18Now, let's just pause. How do you feel about me as I revealed inner workings of my heart? How do you feel about me? I suppose it's refreshing to hear someone speak honestly and a bit openly. How would you like to come work for me? Yeah. I mean, yeah, I trust you. Yeah, right. So yeah, it builds the connection very quickly, doesn't it? I trust you. I feel compelled. I feel drawn in because I'm showing up as real and authentic. Now, let's just put that in a framework for a moment. What is it that we're trying to do when we're business leaders? We're trying to do the impossible. We're trying to create something out of nothing.

8:57And imagine creating a situation where a group of individuals can come together and use their best intelligence, their best creativity to create magic in the world. That's compelling. Yeah, it's a great song. This is what good coaching does. It helps the individual cut through the noise and the clutter. Think about the things that you struggle with. How am I going to pay the bills? How am I going to hire people? Is there going to be anybody who listens to this podcast? What if nobody listens? Have I been worth anything? But what if I'm facing all of those fears with a group of individuals who are committed to doing something magical?

9:36That's pretty powerful. Yeah, really instilling that magical feeling in a group of people, I think, is still a difficult thing to do, though. It's made more difficult when we are disconnected from our own heart. When we show up and we bullshit our way through leadership. But when we show up and we're real and we're honest with the things that we're excited about and the things that we're terrified about, all of a sudden we create a sense of community, create a sense of teamwork, and that becomes the source ground for all the magic. I think I've mentioned on this podcast before that one of the things that I look for when I hire people is some experience of acting in a high-functioning team and for example I played rugby a lot growing up and I happen to know that like if you're in a rugby team an easy one for me is you can be the best player in the world in a team that doesn't work together and you will lose every match so it's a breeding ground for people who understand how to work as a team as most team sports are you mentioned fear earlier on some of the other things that you kind of need to confront ego, insecurity.

10:46How do you balance confronting fear or being open with your fears, ego, and insecurities with your team? The reason why I'm asking about it is because a lot of people, myself included, would have a bit of hesitation to open up too much or fear that you've done it in the wrong way. Right. So let's talk about that for a moment because you're right. This is the biggest impediment, not only for us as business leaders, but frankly, us as adults. Somewhere along the line, we got socialized that if we reveal the authentic nature of ourselves, we are either going to be perceived as weak or perceived as less than ideal, less than perfect.

11:26And in fact, this can get really twisted up in the thinking that somehow as a business leader, we're supposed to have all the answers. Otherwise, why would people follow us? But here's the truth, Sam. People don't follow us because we have all the answers. People follow us because they believe in us. In fact, there's something quite powerful in giving people an inspiration, a reason to believe, even if we don't have the answers. Because the truth is, we don't know what the future is going to bring. Nobody knows. But imagine being a team together. Imagine being drawn in and doing something because of the love of the game, not because of the love of the outcome, right?

12:13You loved playing rugby, and some of your best games were the games you lost, and some of the worst games were the games you won. That's confusing. Logic would say the only time you had a good time was when you won. Because that's the goal. but you didn't win every game, but you loved your players. You loved your teammates. You loved being on the field and giving your all and trying, even if you were defeated. I've got a one-year-old and I've now served a lot of content on Instagram on how to bring up emotionally healthy kids. And I saw this Instagram video the other day with a woman saying that she's actively not teaching her kids to succeed.

12:52She's teaching her kids to struggle well. So not succeed well, but struggle well because they'll figure out how to succeed well. but she's teaching them to stick at difficult things, knowing that when they get through them, it's going to be like the best feeling in the world. What she's pushing up against is a society-wide training to attach our sense of self-worth to success. And the reason that that's so important is that it actually undermines resilience. We are going to fail. That is just a truth. And when we attach our sense of self-esteem and self-worth to an accomplishment of a goal, we are setting ourselves up to feel terrible because not every endeavor is going to succeed.

13:36It's just a fact. But what we really want is the capacity to withstand regardless of success or failure. Then when we succeed, it's even sweeter. We get to have this experience of doing it in community, on a team, with others that we really care about. Lesson number three, community heals. Community, the experience of being together, the experience of having a kind of band that you riff with and you make incredible music and you do something extraordinary. Parker has another concept. He talks about individual work that can only be done in community. Our work is to grow up. Our work is to confront the parts of ourselves that we do not want to deal with.

14:28Because if we don't and we develop power, we will spread toxicity around those that we lead. But if we do our work and we are surrounded by people who have our back, who are just as committed as we are to doing their individual work, then we can hold each other accountable. I can say to you, Sam, you're doing that thing again that you said you never want to do. Come on, you're better than that, dude. Come on, let's go out there and do it together. People don't think of businesses as an opportunity to build community, but those are the best businesses. I asked you before about why you wanted to do this podcast.

15:09Those founders, those entrepreneurs you hung out with, they're your community. They're your gang. They're your friends. The power of community is huge. I'm always struck by how lonely people are nowadays. especially in cities, how few people they've got to really turn to, to talk to. I learned something about Quakers reading this book. When Palmer was making a really important decision, because he's a Quaker, when he went to sit in front of a group of, I'm not sure if you call them elders, or well-respected people in the community, and they didn't give opinions, they asked questions, which is something that you only get from a community when people really care about you and have the time to dedicate and give to you.

15:51And even then, even if you have a community that really cares about you and will dedicate some time to you, it's hard to find people who won't tell you what they think and will help you just make a decision by asking questions. You asked before, what's a coaching session like? A great coaching session is predominantly the coach asking clients questions. Open, honest questions, just the way the Quakers might in a clearness committee. Questions that are not designed to make you feel small or to tell you how smart I am, but questions that are designed to help you find your way to your own answer.

16:28questions that are designed to help each of us to grow up and into the best version of ourselves. Now, that's what I mean when I say community heals. When you sent over this lesson, you said community heals, but only when it respects the soul. What do you mean by respect the soul? Well, if I tell you what you should do, or if I ask a question that behind which is an agenda, Like, have you ever considered therapy, Sam? That's not an open, honest question, right? That's actually an attack. If I ask a question that's respectful of you as a person, of your soul, what ends up happening is you find your way to the right answer, which may or may not be the thing I had in mind, but that's not relevant, what I had in mind, because you're the focus person in that moment.

17:22My job isn't to clear the way for you. My job isn't to stand in front of you and shovel the snow out of the way so you can walk unimpeded on the path. My job is to stand next to you, shoulder to shoulder, and say, oh, that looks like a big struggle there. When you're doing these coaching sessions, because you're just asking them questions, you're trying to help them figure it out themselves. Do you ever come across a time where what they've taken away from it isn't what you thought that it would be and that you think that they might be back with having regretted what they're taking away? Well, two things.

17:55One is, yes, oftentimes the person walks away with something I didn't expect. And that can be a very, very good thing. Because by respecting the souls, the phrase respecting the soul, one of the things I've I'm respecting is your inner wisdom. You know your life better than I do. You know what motivates you better than I do. The best I can do is I can say, hey, dude, you got a little smudge of ketchup on your nose. I can point out things you can't see, but I can't tell you whether or not you like hamburgers. That's for you to decide. So yes, there's a lot of unexpected stuff. And I'll confess, a lot of times there's just frustration.

18:35Sometimes I just want to tell clients what to do. I have a famous story I tell. I once had a client who for years, years, years, struggled about whether or not he was going to commit to moving in with his girlfriend. And he would come in and he would talk about how he was allergic to her cats and it was impossible and they were never going to live together. And the truth is he was just terrified of making a commitment. And finally, in exasperation, I just yelled out, get a Dyson animal vacuum. Get a vacuum to clean up the cat hair. And he looked at me, he was like, what? It's like, you're just avoiding the commitment.

19:13It's not about the cat hair. So sometimes you get a little frustrated and sometimes you fix. But for the most part, what you're really trying to do is help people come to their own conclusion. The best coaching relationship ends with the client no longer needing the coach. That's brilliant. And in your experience, how long does that typically take? It depends on the situation. It could be weeks. It could be years. I've had clients that I've worked with for 15 years. Either I'm a lousy coach or they're really an impossible client, right? And I've had clients who come for a few sessions and then they move on.

19:51They come to the decision that they needed to come to and then they move on. Both are perfectly fine. I love this approach to coaching. I've often heard that the difference between coaching and mentorship is that mentorship gives you the answers. coaching helps lead you to the answers. And I've never really understood until this conversation how that kind of works. Coaching presumes you already have the answer. You're just blocked from it. Like the client I was telling you about, the answer was he was terrified and he needed to actually confront his fear of commitment. It wasn't about the cat hair.

20:23It wasn't about his allergies. I want to draw things to a close by kind of going through a few of the bigger takeaways. Near the top, we spoke about that children are not really taught to listen to the heart anymore. Through school, you're taught that winning matters. We've got a systemic societal problem that outcomes is what you should be focused on and not what's internal to you. You touched on a problem that a lot of CEOs face, which is getting their employees to be more invested in their work and in your business. And the solution to that is cultivating a place where people can feel a sense of community and a sense of teamwork.

20:58And following from that, that people don't follow you because you have the answers, that they follow you because they believe in you. When I spoke about sport for a little while, you spoke about loving the game and not loving the outcome. It doesn't just apply to sport. We should take that into everything that we do, like fall in love with the process. A lot of people end up disappointed when they get to the end, when they get to the outcome that they've been striving for without loving the journey and find out that they've just got now a new task, a new next thing, when it doesn't feel as good as they thought it would be.

21:30And then a quote of yours here, we have to detach our self-worth from success because we will fail and it's a normal part of life to fail. And what we need is the capacity to struggle through. And then I've just written here, confront your fear. I think there was confront your fear, ego, insecurities, but this is something that we kind of need to do more a little bit of as a society. And then we moved on to community and it's really hard to find a really good community. But the way that I found it anyway is that I decided I was going to be an entrepreneur. I attracted people who also were on that journey.

22:03It kind of happens. I think that's the same with how you act in general. So if you act in a way that you want your community around you to act, you mentioned asking agenda-less questions without attacking and questions you ask people around you should help them find their way. They're going to be the sort of people who you end up around as well. So you'll be able to cultivate that community a little bit. And your philosophy is kind of grounded in that you trust that each person contains their own answers, which is another thing that I really love and didn't really understand before this conversation.

22:33I just wanted to give you the chance to speak about Reboot a little bit. And I know that you run leadership boot camps. Can you just tell us about those before we wrap up? Reboot is 11 years old this year. It grew out of my individual practice as an executive coach. We have 12 different coaches and we do a variety of things, including our leadership boot camps. And the leadership boot camps relevant to this conversation, the leadership boot camps are an attempt to create an immersive experience where people can really explore the parts of themselves that hold them back from being the leader that they really want to be.

23:10If you think of leading from within as a sort of call to action, this is a framework for creating community that allows the leading from within. In the camps, we use a lot of the material that Parker has put forth in his books, including clearness committees and learning how to ask questions that really support somebody in their own journey. That's what we do. So who would be the ideal person to join you on these leadership boot camps? First-time leaders, first-time CEOs. But really, at this point, what we have found is young entrepreneurs like yourself to old farts like me. Everybody's at a different point in their journey.

23:53So it's really kind of quite open. I think these sorts of things, like in-person events where you get to meet other people, they're probably like-minded people. We've been speaking a lot about how community is so great. So if anyone wants to join Jerry on this camp, there'll be a link in the show notes. If you want to buy Let Your Life Speak by Parker Palmer, there'll be a link in the show notes as well. Thank you so much for listening and I'll see you on the next one.