Time is our most coveted, most unrenewable resource

If being on the receiving end of one of life’s most valuable gifts fails to leave you with a lump in your throat or butterflies in your stomach, then you’re not paying attention

Effective speaking is about the unpredictable and uncomfortable art of connection

People. People. People

“It’s not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again... who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.” - Theodore Roosevelt

If you’re going to dare greatly, you’re going to get your ass kicked at some point

If you choose courage, you will absolutely know failure, disappointment, setback, even heartbreak. That’s why we call it courage. That’s why it’s so rare

The courage to belong to ourselves is a prerequisite for true belonging

You can’t get to courage without rumbling with vulnerability

Embrace the suck

A leader is anyone who takes responsibility for finding the potential in people and processes, and who has the courage to develop that potential

The way to move information from your head to your heart is through your hands

“What stands in the way becomes the way.” - Marcus Aurelius

We avoid tough conversations, including giving honest, productive feedback

People are opting out of viral conversations about diversity and inclusivity because they fear looking wrong, saying something wrong, or being wrong. Choosing our own comfort over hard conversations is the epitome of privilege, and it corrodes trust and moves us away from meaningful and lasting change

When something goes wrong, individuals and teams are rushing into ineffective or unsustainable solutions rather than staying with the problem identification and solving. When we fix the wrong thing for the wrong reason, the same problems continue to surface. It’s costly and demoralizing

Organizational values are gauzy and assessed in terms of aspirations rather than actual behaviors that can be taught, measured, and evaluated

Perfectionism and fear are keeping people from learning and growing

4 skill sets of courage:

Rumbling with vulnerability

Living into our values

Braving trust

Learning to rise

Self-awareness and self-love matter. Who we are is how we lead

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

Daring leaders must care for and be connected to the people they lead

Daring is saying “I know I will eventually fail, and I’m still all in.”

Vulnerability is the emotion we experience during times of uncertainty, risk, and emotional exposure

Vulnerability is the courage to show up when you can’t control the outcome

If you’re not in the arena getting your ass kicked on occasion, I’m not interested in or open to your feedback

Let what’s unproductive and hurtful drop at your feet of your unarmored self

To love at all is to be vulnerable. Love anything, and your heart will certainly be wrung and possibly be broken

When we define ourselves by what everyone else thinks, it’s hard to be brave. When we stop caring about what anyone thinks, we’re too armored for authentic connection

Make a list of the people whose opinions of you matter. The on your list should be the people who love you not despite your vulnerability and imperfection, but because of them

How do I act when I’m feeling vulnerable?

“When we were children, we used to think that when we were grown-up we would no longer be vulnerable. But to grow up is to accept vulnerability.” - Madeleine L’Engle

Needing no one pushing against everything we know about human neurobiology. We are hardwired for connection

We don’t derive strength from our rugged individualism, but rather from our collective ability to plan, communicate, and work together

“To grow to adulthood as a social species, including humans, is not to become autonomous and solitaryC its to become the one on whom others can depend.” - John Cacioppo

We need to trust to be vulnerable, and we need to be vulnerable in order to build trust

Trust is earned through paying attention, listening, and gestures of genuine care and connection

“Seek first to understand, then be understood.” - Stephen Covey

“It’s very hard to have ideas. It’s very hard to put yourself out there, it’s very hard to be vulnerable, but those people who do that are the dreamers, the thinkers, and the creators. They are the magic people of the world.” - Amy Poehler

Clear is kind. Unclear is unkind

Most of us avoid clarity because we tell ourselves that we’re being king, when what we’re actually doing is being unkind and unfair

“The cave you fear to enter holds the treasure you seek.” - Joseph Campbell

“You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.” - Jim Stockdale

You face your fears to find the power and wisdom to serve others

Other people’s emotions are not our jobs. We can’t both serve people and try to control their feelings

Daring leadership is ultimately about serving other people, not ourselves. That’s why we choose courage

“In the past, jobs were about muscles, now they’re about brains, but in the future they’ll be about the heart.” - Minouche Shafik

Wholeheartedness: engaging in our lives from a place of worthiness. It means cultivating the courage, compassion, and connection to wake up in the morning and thing, no matter what gets done and how much is left undone, I am enough. It’s going to bed at night thinking, yes, I am imperfect and vulnerable and sometimes afraid, but that doesn’t change the truth that I am brave, and worthy of love and belonging

Our ego drives pretending, performing, pleasing, and perfecting

Our ego will do almost anything to avoid or minimize the discomfort associated with feeling vulnerable or even being curios, because it’s too risky

“We’re not here to fit in, be well balanced, or provide exemplary for others. We’re here to be eccentric, different, perhaps strange, merely to add our small piece, our little clunky, chunky selves, to the great mosaic of being. As the gods intended, we are here to become more and more ourselves.” - Jim Hollis

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

Healthy striving is self-focused: how can I improve? Perfectionism is other-focused: what will people think? Perfectionism is a hustle

Perfectionism is not the key to success. Perfectionism hampers achievement. Perfectionism is correlated with depression, anxiety, addiction, and life paralysis, or missed opportunities. The fear of failing, making mistakes, not netting people’s expectations, and being criticized keeps us outside the arena where healthy competition and striving unfolds

Wherever you go, there you are

You’re only as sick as your secrets

Easy does it

One day at a time

Live and let live

To think own self be true

HALT: don’t get too hungry, angry, lonely, or tired

Let go and let God

It’s not what you do; it’s why you do it that makes the difference

Agency is belief in our ability to stay on the path until we’ve arrived

Criticism often arises from fear of feelings of unworthiness. Criticism shifts the spotlight off us and onto someone or something else. Suddenly we feel safer. And better than

Daring leaders tell their team members the unique contributions they make so that everyone knows where they’re strong

The less people understand how their hard work adds value to bigger goals, the less engaged they are

Take the time to explain the why behind strategies, and how tasks link to ongoing priorities and mission work

In scarcity we invent worst-case scenarios

There is incredible relief and power in naming and normalizing fear and uncertainty

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

The greatest barrier to true belonging is fitting in or changing who we are so we can be accepted

Rewarding others rather than seeking to be rewarded is the only way to continue to grow within an organization, and to fully embody the mantle of daring leadership

We love truth because it is increasingly rare

“You can never get enough of what you don’t need”

When we own our hard stories and rumble with them, we can write a new ending—an ending that includes how we’re going to use what we’ve survived to be more compassionate and empathetic. 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

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

The broken-hearted are the bravest among us because they got past their egos and busted their hearts out of that prison so they could love

Empathy is connecting to the emotions that underpin an experience

Shame is the fear of disconnection

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

Shame drives two tapes:

Never good enough

Who do you think you are?

Guilt = I did something bad

Shame = I am bad

We feel guilty when we hold up something we’ve done or failed to do against our values and find they don’t match up. It’s a psychologically uncomfortable feeling, but one that is helpful. The discomfort of cognitive dissonance is what drives meaningful change. Shame, however, corrodes the very part of us that believes we can change and do better

“People believe they deserve their shame; they do not believe they deserve their humiliation.” - Donald Klein

The hallmark of embarrassment is that when we do something embarrassing, we don’t feel alone. We know other folks have done the same thing and, like a blush, the feeling will pass rather than define us

Using comparison as a management tool stifles both creativity and innovation

School leaders have enormous power and influence, and how they use that power and influence changes people. For better or worse

Always give people a “way out with dignity”

When you’re delivering the news, be kind. Be clear. Be respectful. Be generous. Can you let the person resign rather than be fired? Can you provide severance pay? Ask the person how they want to let colleagues know about their departure and follow their lead on that if possible

Empathy is the real antidote to shame

Empathy is not connecting to an experience, it’s connecting to the emotions that underpin an experience

A response can rarely make something better. Connection is what heals

We can honor people’s perspectives as truth even when they’re different from ours

It’s only when diverse perspectives are included, respected, and valued that we can start to get a full picture of the world, who we serve, what they need, and how to successfully meet people where they are

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

We don’t judge in areas where we feel a strong sense of self-worth and grounded confidence, so the more of that we build, the more we let go of judgment

When we can’t name and articulate what’s happening to us emotionally, we can’t move through it

Engage, stay curious, stay connected. Let go of the fear of saying the wrong thing, the need to fix it, and the desire to offer the perfect response that cures everything. You don’t have to do it perfectly. Just do it

Empathy is feeling with people. Sympathy is feeling for them. Empathy girls connection. Sympathy drives disconnection

Talk to yourself the way you’d talk to someone you love

Developing fundamental skills through disciplined practice is what gives players the grounded confidence to dare greatly

You have to have complete confidence about your mastery of a skill so you can focus on other things

Leaders need grounded confidence to stay tethered to their values, respond rather than react emotionally, and operate from self-awareness, not self-protection

Easy learning doesn’t build strong skills

To be effective, learning needs to be effortful

Curiosity is uncomfortable because it involves uncertainty and vulnerability

“If I had an hour to solve a problem, I’d spend fifty-five minutes thinking about the problem and five minutes thinking about solutions.” - Albert Einstein

“It’s not that I’m so smart, it’s just that I stay with problems longer.” - Albert Einstein

What did we set out to do, what happened, what did we learn, and how fast can we improve on it?

“People don’t care how much you know until they know how much you care”

People, people, people are just people, people, people

A value is a way of being or believing that we hold most important

Pick two values you hold most important

“If you have more than three priorities, you have no priorities.” - Jim Collins

Have faith if you do what’s right for you, there will be other opportunities

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

Love and growth

If we can’t cheer ourselves on, we shouldn’t expect others to do it

“Spirituality is the deep human longing to experience the extraordinary in the ordinary, the miraculous in the mundane, and the sacred camouflaged in the profane.” - Pittman McGehee

I’m ready to give feedback when:

I’m ready to sit next to you rather than across from you

I’m willing to put the problem in front of us rather than between us (or sliding it toward you)

I’m ready to listen, ask questions, and accept that I may not fully understand the issue

I’m ready to acknowledge what you do well instead of just picking apart your mistakes

I recognize your strengths and how you can use them to address your challenges

I can hold you accountable without shaming or blaming

I’m open to owning my part

I can genuinely thank someone for their efforts rather than just criticizing them for their failungs

I can talk about how resolving these challenges will lead to growth and opportunity

I can model the vulnerability and openness that I expect to see you from

Mastery requires feedback

Be brave enough to listen

Be calm, respectful, listen, don’t get discouraged, keep asking questions

We don’t fully see people until we know their values

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 processing them

Slow down, take a deep breath, and get curious about what’s happening

We call emotions feelings because we feel then in our bodies—we have physiological response to emotions

Box breathing

Inhale through your nose for a count of four

Hold in that breath for a count of four

Slowly exhale all the air through your mouth for a count of four

Hold the empt breath for a count of four

When you are in the middle of a story, it isn’t a story at all, but only a confusion; a dark roaring, a blindness, a wreckage of shattered glass and splintered wood; like a house in a whirlwind, or else a boat crushed by the icebergs or swept over the rapids, and all aboard are powerless to stop it. It’s only afterwards that it becomes anything like a story at all. When you are telling it, to yourself or to someone else

The power of “the story I’m telling myself” is that it reflects a very real part of what it means to be a meaning-making human. It’s disarming because it’s honest. We all do it. This is why it works across diverse environments and with all people

Own the story and you get to write the ending. Deny the story and it owns you

The level of collective courage in an organization is the best predictor of that organizations ability to be successful in terms of its culture, to develop leaders, and to meet its mission

We fail the minute we let someone else define success for us

“The cave you fear to enter holds the treasure you seek.” - Joseph Campbell

Write a new ending for yourself, for the people you’re meant to serve and support, and for your culture

Choose courage over comfort. Choose whole hearts over armor. And choose the great adventure of being brave and afraid. At the exact same time