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Dare to Lead: Brave Work. Tough Conversations. Whole Hearts.

Compiled by Chuck Olson

Title: Dare To Lead: Brave Work. Tough Conversations. Whole Hearts. 

Author: Brene Brown

Copyright: 2018

Having been challenged by her book Daring Greatly, when I learned that Brene Brown had written a book on leadership, I quickly downloaded it on my Kindle. I was not disappointed. In Dare to Lead: Brave Work. Tough Conversations. Whole Hearts, Brown consistently uploads leadership insights about trust, vulnerability, courage, and more.

Here’s one: From corporations, nonprofits, and public sector organizations to governments, activist groups, schools, and faith communities, we desperately need more leaders who are committed to courageous, wholehearted leadership and who are self-aware enough to lead from their hearts, rather than unevolved leaders who lead from hurt and fear.

Can you even begin to imagine what our world would look like with that type of person leading our institutions? Check out these Book Notes to see if this book needs to find its way on to your ‘next-up’ reading list.

Signature Chuck


Book Description:

Leadership is not about titles, status, and wielding power. A leader is anyone who takes responsibility for recognizing the potential in people and ideas, and has the courage to develop that potential.

When we dare to lead, we don’t pretend to have the right answers; we stay curious and ask the right questions. We don’t see power as finite and hoard it; we know that power becomes infinite when we share it with others. We don’t avoid difficult conversations and situations; we lean into vulnerability when it’s necessary to do good work.

But daring leadership in a culture defined by scarcity, fear, and uncertainty requires skill-building around traits that are deeply and uniquely human. The irony is that we’re choosing not to invest in developing the hearts and minds of leaders at the exact same time as we’re scrambling to figure out what we have to offer that machines and AI can’t do better and faster. What can we do better? Empathy, connection, and courage, to start.

Four-time #1 New York Times bestselling author Brené Brown has spent the past two decades studying the emotions and experiences that give meaning to our lives, and the past seven years working with transformative leaders and teams spanning the globe. She found that leaders in organizations ranging from small entrepreneurial startups and family-owned businesses to nonprofits, civic organizations, and Fortune 50 companies all ask the same question:

How do you cultivate braver, more daring leaders, and how do you embed the value of courage in your culture? 

In this new book, Brown uses research, stories, and examples to answer these questions in the no-BS style that millions of readers have come to expect and love.

Brown writes, “One of the most important findings of my career is that daring leadership is a collection of four skill sets that are 100 percent teachable, observable, and measurable. It’s learning and unlearning that requires brave work, tough conversations, and showing up with your whole heart. Easy? No. Because choosing courage over comfort is not always our default. Worth it? Always. We want to be brave with our lives and our work. It’s why we’re here.”

Whether you’ve read Daring Greatly and Rising Strong or you’re new to Brené Brown’s work, this book is for anyone who wants to step up and into brave leadership.

Book Quotes:

The courage to be vulnerable is not about winning or losing, it’s about the courage to show up when you can’t predict or control the outcome. LOCATION: 157

I define a leader as anyone who takes responsibility for finding the potential in people and processes, and who has the courage to develop that potential. From corporations, nonprofits, and public sector organizations to governments, activist groups, schools, and faith communities, we desperately need more leaders who are committed to courageous, wholehearted leadership and who are self-aware enough to lead from their hearts, rather than unevolved leaders who lead from hurt and fear. LOCATION: 195

We started our interviews with senior leaders with one question: What, if anything, about the way people are leading today needs to change in order for leaders to be successful in a complex, rapidly changing environment where we’re faced with seemingly intractable challenges and an insatiable demand for innovation? There was one answer across the interviews: We need braver leaders and more courageous cultures. LOCATION: 220

We get stuck and defined by setbacks, disappointments, and failures, so instead of spending resources on clean-up to ensure that consumers, stakeholders, or internal processes are made whole, we are spending too much time and energy reassuring team members who are questioning their contribution and value. Too much shame and blame, not enough accountability and learning. LOCATION: 252

When something goes wrong, individuals and teams are rushing into ineffective or unsustainable solutions rather than staying with problem identification and solving. LOCATION: 259

The Heart of Daring Leadership:

  1. You can’t get to courage without rumbling with vulnerability. Embrace the suck. LOCATION: 272

At the heart of daring leadership is a deeply human truth that is rarely acknowledged, especially at work: Courage and fear are not mutually exclusive. Most of us feel brave and afraid at the exact same time. LOCATION: 273

A rumble is a discussion, conversation, or meeting defined by a commitment to lean into vulnerability, to stay curious and generous, to stick with the messy middle of problem identification and solving, to take a break and circle back when necessary, to be fearless in owning our parts, and, as psychologist Harriet Lerner teaches, to listen with the same passion with which we want to be heard. LOCATION: 278

Our research led to a very clear, very hopeful finding: Courage is a collection of four skill sets that can be taught, observed, and measured. The four skill sets are: Rumbling with Vulnerability, Living into Our Values, Braving Trust, and Learning to Rise. LOCATION: 282

Consider this carefully: Our ability to be daring leaders will never be greater than our capacity for vulnerability. LOCATION: 288

  1. Self-awareness and self-love matter. Who we are is how we lead. LOCATION: 295

The true underlying obstacle to brave leadership is how we respond to our fear. The real barrier to daring leadership is our armor—the thoughts, emotions, and behaviors that we use to protect ourselves when we aren’t willing and able to rumble with vulnerability. LOCATION: 299

  1. Courage is contagious. To scale daring leadership and build courage in teams and organizations, we have to cultivate a culture in which brave work, tough conversations, and whole hearts are the expectation, and armor is not necessary or rewarded. LOCATION: 304

Daring leaders must care for and be connected to the people they lead. LOCATION: 308

If the culture in our school, organization, place of worship, or even family requires armor because of issues like racism, classism, sexism, or any manifestation of fear-based leadership, we can’t expect wholehearted engagement. Likewise, when our organization rewards armoring behaviors like blaming, shaming, cynicism, perfectionism, and emotional stoicism, we can’t expect innovative work. You can’t fully grow and contribute behind armor. It takes a massive amount of energy just to carry it around—sometimes it takes all of our energy. LOCATION: 324

The definition of vulnerability is the emotion that we experience during times of uncertainty, risk, and emotional exposure. LOCATION: 350

Vulnerability is not winning or losing. It’s having the courage to show up when you can’t control the outcome. LOCATION: 352

The third thing I learned has turned into a mandate by which I live: If you are not in the arena getting your ass kicked on occasion, I’m not interested in or open to your feedback. There are a million cheap seats in the world today filled with people who will never be brave with their lives but who will spend every ounce of energy they have hurling advice and judgment at those who dare greatly. Their only contributions are criticism, cynicism, and fearmongering. If you’re criticizing from a place where you’re not also putting yourself on the line, I’m not interested in what you have to say. LOCATION: 361

No one captures the consequences of choosing that level of self-protection over love better than C. S. Lewis: To love at all is to be vulnerable. Love anything, and your heart will certainly be wrung and possibly be broken. If you want to make sure of keeping it intact, you must give your heart to no one, not even to an animal. Wrap it carefully round with hobbies and little luxuries; avoid all entanglements; lock it up safe in the casket or coffin of your selfishness. But in that casket—safe, dark, motionless, airless—it will change. It will not be broken; it will become unbreakable, impenetrable, irredeemable. LOCATION: 380

Our daily lives are defined by experiences of uncertainty, risk, and emotional exposure. There is no opting out, but there are two options: You can do vulnerability, or it can do you. Choosing to own our vulnerability and do it consciously means learning how to rumble with this emotion and understand how it drives our thinking and behavior so we can stay aligned with our values and live in our integrity. Pretending that we don’t do vulnerability means letting fear drive our thinking and behavior without our input or even awareness, which almost always leads to acting out or shutting down. LOCATION: 414

Trust and vulnerability grow together, and to betray one is to destroy both. LOCATION: 561

What most of us fail to understand, and what took me a decade of research to learn, is that vulnerability is the cradle of the emotions and experiences that we crave. Vulnerability is the birthplace of love, belonging, and joy. LOCATION: 681

Adaptability to change, hard conversations, feedback, problem solving, ethical decision making, recognition, resilience, and all of the other skills that underpin daring leadership are born of vulnerability. LOCATION: 690

Over our years of researching and working together, we’ve learned something about clarity that has changed everything from the way we talk to each other to the way we negotiate with external partners. It’s simple but transformative: Clear is kind. Unclear is unkind. LOCATION: 736

When we’re in tough rumbles with people, we can’t take responsibility for their emotions. They’re allowed to be pissed or sad or surprised or elated. But if their behaviors are not okay, we set the boundaries: I know this is a tough conversation. Being angry is okay. Yelling is not okay. I know we’re tired and stressed. This has been a long meeting. Being frustrated is okay. Interrupting people and rolling your eyes is not okay. I appreciate the passion around these different opinions and ideas. The emotion is okay. Passive-aggressive comments and put-downs are not okay. LOCATION: 1023

At the center of all our elaborate personal security measures and protection schemes lies the most precious treasure of the human experience: the heart. In addition to serving as the life-giving muscle that keeps blood pumping through our body, it’s the universal metaphor for our capacity to love and be loved, and it’s the symbolic gateway to our emotional lives. LOCATION: 1051

Wholeheartedness captures the essence of a fully examined emotional life and a liberated heart, one that is free and vulnerable enough to love and be loved. And a heart that is equally free and vulnerable to be broken and hurt. LOCATION: 1058

Shame is the feeling that washes over us and makes us feel so flawed that we question whether we’re worthy of love, belonging, and connection. LOCATION: 1096

As a shame researcher, I’ve learned that wherever perfectionism is driving us, shame is riding shotgun. LOCATION: 1124

Perfectionism is, at its core, about trying to earn approval. Most perfectionists grew up being praised for achievement and performance (grades, manners, rule following, people pleasing, appearance, sports). Somewhere along the way, they adopted this dangerous and debilitating belief system: I am what I accomplish and how well I accomplish it. Please. Perform. Perfect. Prove. Healthy striving is self-focused: How can I improve? Perfectionism is other-focused: What will people think? Perfectionism is a hustle. LOCATION: 1131

Perfectionism is a self-destructive and addictive belief system that fuels this primary thought: If I look perfect and do everything perfectly, I can avoid or minimize the painful feelings of blame, judgment, and shame. LOCATION: 1139

What is the one thing that people who can fully lean into joy have in common? Gratitude. They practice gratitude. It’s not an “attitude of gratitude”—it’s an actual practice. They keep a journal, or make a note of what they’re grateful for on their phones, or share it with family members. LOCATION: 1182

Embodying and practicing gratitude changes everything. It is not a personal construct, it’s a human construct—a unifying part of our existence—and it’s the antidote to foreboding joy, plain and simple. It’s allowing yourself the pleasure of accomplishment, or love, or joy—of really feeling it, of basking in it—by conjuring up gratitude for the moment and for the opportunity. LOCATION: 1187

We all numb. We all have different numbing agents of choice—food, work, social media, shopping, television, video games, porn, booze (from beer in a brown paper bag to the socially acceptable but equally dangerous “fine wine” hobby)—but we all do it. And when we chronically and compulsively turn to these numbing agents, it’s addiction, not just taking the edge off. LOCATION: 1207

There is no us and them when it comes to numbing—we all do it. The question is to what degree. And, when we’re talking about the pain surrounding addiction, it’s never a self-contained storm, it’s a tornado. LOCATION: 1213

Winner or loser, survive or die, kill or be killed, strong or weak, leaders or followers, success or failure, crush or be crushed. Sound familiar? This is the philosophy of people who subscribe to the paradigm of Victim or Viking. In this binary world of paired opposites, you’re either a sucker/loser who always gets the short end of the stick, or you’re a Viking who refuses to be victimized. You’ll do whatever is required—control, dominate, exert power, shut down emotion—to ensure that you’re never vulnerable. LOCATION: 1278

Cynicism and sarcasm are first cousins who hang out in the cheap seats. But don’t underestimate them—they often leave a trail of hurt feelings, anger, confusion, and resentment in their wake. LOCATION: 1322

Open, honest discussion, in which everyone feels free to offer suggestions and contribute, stimulates creativity. LOCATION: 1349

Voicing and owning our concern is brave. Pretending that we represent a lot of folks when we don’t is cheap-seat behavior. LOCATION: 1355

At the end of the day, at the end of the week, at the end of my life, I want to say I contributed more than I criticized. LOCATION: 1360

We used to utilize the Apple DRI model, appointing someone as the “directly responsible individual” for a specific task and recording their duty in the meeting minutes. But what we learned is that despite the team member’s willingness to own it and be held accountable for executing, they didn’t always have the authority to be successful. We’re currently switching to a TASC approach: the Accountability and Success Checklist: T—Who owns the task? A—Do they have the authority to be held accountable? S—Do we agree that they are set up for success (time, resources, clarity)? C—Do we have a checklist of what needs to happen to accomplish the task? LOCATION: 1434

In times of uncertainty, it is common for leaders to leverage fear and then weaponize it to their advantage. Unfortunately, it’s been an easy formula throughout history—in politics, religion, and business—that if you can keep people afraid, and give them an enemy who is responsible for their fear, you can get people to do just about anything. This is the playbook for authoritarian leaders here and around the globe. LOCATION: 1506

In our desperate search for joy in our lives, we missed the memo: If we want to live a life of meaning and contribution, we have to become intentional about cultivating sleep and play. LOCATION: 1536

True belonging is the spiritual practice of believing in and belonging to yourself so deeply that you can share your most authentic self with the world and find sacredness in both being a part of something and standing alone in the wilderness. True belonging doesn’t require you to change who you are; it requires you to be who you are. LOCATION: 1548

Daring leaders fight for the inclusion of all people, opinions, and perspectives because that makes us all better and stronger. That means having the courage to acknowledge our own privilege, and staying open to learning about our biases and blind spots. LOCATION: 1557

One of the patterns that I’ve observed in working with leaders is that many people lead from a place of hurt and smallness, and they use their position of power to try to fill that self-worth gap. LOCATION: 1616

As daring leaders, we have to stay curious about our own blind spots and how to pull those issues into view, and we need to commit to helping the people we serve find their blind spots in a way that’s safe and supportive. LOCATION: 1634

When we deny our stories of struggle, they own us. They own us, and they drive our behavior, emotions, thinking, and leading. Daring leadership is leading from heart, not hurt. LOCATION: 1648

The credit goes to the person in the arena—and the greatest arena in a world overrun with fear, criticism, and cynicism is vulnerability. LOCATION: 1654

Shame, which is often referred to as “the master emotion” by researchers, is the never good enough emotion. It can stalk us over time or wash over us in a second—either way, its power to make us feel we’re not worthy of connection, belonging, or even love is unmatched in the realm of emotion. LOCATION: 1698

Shame is the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love, belonging, and connection. LOCATION: 1791

The majority of shame researchers and clinicians agree that the difference between shame and guilt is best understood as the difference between “I am bad” and “I did something bad.” Guilt = I did something bad. Shame = I am bad. LOCATION: 1822

Ultimately, shame resilience is about moving from shame to empathy—the real antidote to shame. LOCATION: 1939

One of the signature mistakes with empathy is that we believe we can take our lenses off and look through the lenses of someone else. We can’t. Our lenses are soldered to who we are. What we can do, however, is honor people’s perspectives as truth even when they’re different from ours. LOCATION: 2046

Based on research, there are two ways to predict when we are going to judge: We judge in areas where we’re most susceptible to shame, and we judge people who are doing worse than we are in those areas. So if you find yourself feeling incredibly judgmental about appearance, and you can’t figure out why, that’s a clue that it’s a hard issue for you. LOCATION: 2074

Empathy is feeling with people. Sympathy is feeling for them. Empathy fuels connection. Sympathy drives disconnection. LOCATION: 2180

Again, the difference between empathy and sympathy: feeling with and feeling for. The empathic response: I get it, I feel with you, and I’ve been there. The sympathetic response: I feel sorry for you. LOCATION: 2196

Vulnerability is the greatest casualty of trauma. When we’re raised in unsafe environments, confronted with racism, violence, poverty, sexism, homophobia, and pervasive shaming, vulnerability can be life-threatening and armor is safety. LOCATION: 2359

Curiosity says: No worries. I love a wild ride. I’m up for wherever this goes. And I’m in for however long it takes to get to the heart of the problem. I don’t have to know the answers or say the right thing, I just have to keep listening and keep questioning. LOCATION: 2450

A value is a way of being or believing that we hold most important. LOCATION: 2601

Living into our values means that we do more than profess our values, we practice them. We walk our talk—we are clear about what we believe and hold important, and we take care that our intentions, words, thoughts, and behaviors align with those beliefs. LOCATION: 2603

If you say something to me, or in front of me, that I find racist, or sexist, or homophobic, even if other people are laughing, I’m not going to laugh. I’m going to ask you not to say that stuff around me. I don’t do this out of self-righteousness or being “better than”—trust me, there are times when I’d rather just shoot you a dirty look and walk away. I say something because courage is one of my key values, and for me to feel physically, emotionally, and spiritually okay, courage insists that I honor it by choosing my voice over my comfort. LOCATION: 2656

To opt out of conversations about privilege and oppression because they make you uncomfortable is the epitome of privilege. LOCATION: 2718

I know I’m living outside my values when I am…drum roll…this is a huge issue for me…resentful. Resentment is my barometer and my early warning system. It’s the canary in the coal mine. LOCATION: 2745

  1. I know I’m ready to give feedback when I’m ready to sit next to you rather than across from you.
  2. I know I’m ready to give feedback when I’m willing to put the problem in front of us rather than between us (or sliding it toward you).
  3. I know I’m ready to give feedback when I’m ready to listen, ask questions, and accept that I may not fully understand the issue.
  4. I know I’m ready to give feedback when I’m ready to acknowledge what you do well instead of just picking apart your mistakes.
  5. I know I’m ready to give feedback when I recognize your strengths and how you can use them to address your challenges.
  6. I know I’m ready to give feedback when I can hold you accountable without shaming or blaming.
  7. I know I’m ready to give feedback when I’m open to owning my part.
  8. I know I’m ready to give feedback when I can genuinely thank someone for their efforts rather than just criticizing them for their failings.
  9. I know I’m ready to give feedback when I can talk about how resolving these challenges will lead to growth and opportunity.
  10. I know I’m ready to give feedback when I can model the vulnerability and openness that I expect to see from you. LOCATION: 2767-2811

Integrity is choosing courage over comfort; it’s choosing what’s right over what’s fun, fast, or easy; and it’s practicing your values, not just professing them. LOCATION: 3122

There’s a terrible pattern in organizations in which leaders turn to their teams, or their investors, or their board, and say “You need to trust me.” Typically, that happens in a moment of crisis, when it is far too late. Trust is the stacking of small moments over time, something that cannot be summoned with a command—there are either marbles in the jar or there are not. LOCATION: 3188

When we have the courage to walk into our story and own it, we get to write the ending. And when we don’t own our stories of failure, setbacks, and hurt—they own us. LOCATION: 3404

The challenge is that very few of us were raised to get emotionally curious about what we are feeling. Whether it is a failure, a sideways comment from a colleague, a meeting that is full of disconnection and frustration, or a feeling of rising resentment when asked to do more than someone else, we’re hooked, and we weren’t taught the skill that the most resilient among us share: Slow down, take a deep breath, and get curious about what’s happening. Instead, we bust out the armor. LOCATION: 3424

In the absence of data, we will always make up stories. It’s how we are wired. Meaning-making is in our biology, and when we’re in the struggle, our default is often to come up with a story that makes sense of what’s happening and gives our brain information on how best to self-protect. And it happens a hundred times a day at work. Our organizations are littered with stories that people make up because they don’t have access to information. If you’ve ever led a team through change, you know how much time, money, energy, and engagement bad stories cost. LOCATION: 3535

Note: should you wish to find any quote in its original context, the Kindle “location” is provided after each entry.  

Chuck Olson

As founder and president of Lead With Your Life, Dr. Chuck Olson is passionate about inspiring, resourcing and equipping Kingdom leaders to lead from the inside out.  To lead, not with the external shell of positions, achievements or titles, but from an internal commitment to a deep, abiding and transparent relationship with Jesus. Serving as a pastor and leadership coach for over forty years, Chuck has a track record of building these truths deep into the lives of both ministry and marketplace leaders.

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