Jerry Colonna is a coach, writer, and speaker focusing on leadership, business, and radical self-inquiry. For over two decades, he has proposed that work should be nonviolent to the self, community, and planet. He is host of the Reboot Podcast and the co-founder of Reboot.io, a company founded on the belief that work does not have to destroy us but rather how we achieve our fullest potential.

Jerry helps people lead with humanity and equanimity. His unique blend of Buddhism, Jungian therapy, and entrepreneurial expertise has resulted in working with some of the largest firms in the U.S. In his work as a coach, he draws on his experience in Venture Capital (VC) as Co-founder of Flatiron Partners, one of the most successful, early-stage investment programs in the New York City area.

Jerry is the author of two books: REBOOT: Leadership and the Art of Growing Up and, most recently, REUNION: Leadership and the Longing to Belong.

I invited Jerry into a conversation because of his thoughtful use of questions. We will discuss one of his core questions, which I have used to navigate life and witnessed the power in the lives of others. His unflinching desire to see life's reality, step into all we can become, and call us into belonging is not for the faint of heart, but it results in being fully alive.

Jerry, who focuses on leadership and radical self-inquiry, shares his journey of using questions to navigate and understand the world. Jerry elaborates on his early career as a reporter, where his curiosity and questioning skills began to take shape, transitioning into his roles as a venture capitalist and now a coach. Through sharing personal stories, Jerry delves into the impact of his childhood, his experiences with depression, and his path to becoming a reporter who asked probing questions and tackling subjects that elicited deep emotional responses from business executives. He also discusses historical contexts and systemic issues stemming from fear and curiosity. Additionally, Jerry discusses the importance of remembering and acknowledging personal and communal histories to build better futures. The conversation is rich with insights into how powerful questions foster growth, belonging, and a deeper understanding of oneself and the world.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

Episode Notes

[00:48] Meet Jerry Colonna: Coach, Writer, and Speaker

[02:37] The Power of Questions: Jerry's Journey

[05:07] Liberation Through Inquiry: Jerry's Early Career

[06:48] Curiosity in Journalism: Memorable Interviews

[09:58] The Role of Questions in Personal Growth

[23:59] Exploring Systemic Belonging and Fear

[31:53] Reflecting on Ancestry and Social Responsibility

[40:38] Embracing Difficult Questions

[41:05] Struggles and Inspirations

[42:31] Understanding Family Dynamics

[45:29] Pilgrimage to Ireland

[46:28] The Power of Remembrance

[51:32] Speed Bumps in Life

[56:01] Discovering Lost Family

[01:09:26] Reflecting on Transitions

[01:11:39] Final Thoughts and Gratitude

Resources Mentioned

Reboot Podcast

Reboot.io

REBOOT: Leadership and the Art of Growing Up by Jerry Colonna

REUNION: Leadership and the Longing to Belong by Jerry Colonna

Chuck Exley

NCR Corporation

Barbara Walters

Control Data Corporation

Bill Norris

Seymour Cray

Parker Palmer

The Paranoid Style of American Politics by Richard Hofstadter

Rabbi Tarfon

The Price of the Ticket by James Baldwin

Virginia Bauman

Emma Colonna, Jerry's daughter

George Floyd

Let America Be America Again by Langston Hughes

Remember by Joy Harjo

Mary Heffernan, Jerry's biological grandmother

William Michael Heffernan/Jerome Vito Colonna, Jerry's father

Sam Colonna, Jerry's son

Jerry Colonna on Instagram

Beauty Pill

Producer Ben Ford

Questions Asked

When did you first understand the power of questions?

Do you recall any particular feeling or thinking about that freedom?

Why would you place a factory in this area?

Why would you do this?

Why are questions so important to you?

Why is this experience so important?

Why am I feeling the way I'm feeling?

What is it that I'm actually feeling?

How are you feeling in this moment?

How's my friend Ken feeling?

Why does the world behave the way we do?

Why are we attracted to powerful people in the way we are?

Why do we set aside what we say are our values, only to pursue what seems to be a destructive course?

Why do we treat each other the way we treat each other?

Why do we allow babies to carry guns and kill each other?

Why is the world the way it is?

What do I have to give up that I love or that makes me feel safe so that the world can be a little bit better and the climate doesn't feel threatened?

What does that look like in how we hold everything?

How have I been complicit in creating the conditions I say I don't want?

Have you ever considered therapy?

Why do we, as a populace, find ourselves attracted to someone who appears grandiose and narcissistic?

How can we move to the systemic belonging of a beloved community?

Who benefits from your fear?

Who gave you your boogeyman?

What is it that I have to give up that makes me feel safe so that the conditions of the world create belonging for everyone?

Why haven't you been the courageous ones?

What happened to the queer members?

What happened to the people who felt gender dysmorphia or misgendered?

What happened to those who were victimized by child sexual abuse?

What happened to the enslavers?

What happened to the people who profited?

What happened to the people who themselves were enslaved?

What does it mean to be a better human when adult men die under the knee of a cop?

What does it mean in the 21st century in America?

What does it mean to be a better human under these conditions?

How have I been complicit in and benefited from the conditions in the world I say I don't want to see?

How do I strip away the blinders that mythology creates?

Who were my ancestors?

Who am I?

How was I brought to this spot at this time, given this task of changing the pattern so that my descendants live a different life?

What is the work that I have to do to change the trajectory of our community?

What is the posture that one should have as they approach a question to be able to get everything that it has to offer?

Why would my father not call that out?

Why would my father not give me a sense of safety?

How did she give him up for adoption?

Why my biological grandmother gave up my father for adoption

What do we do?

Can you tell me their name?

What did you call your grandmother?

What did mama smell like?

What are your right now questions?

What is to become of me?

What will I be like a year from now?

Do you have any other thoughts or encouragements about questions that we haven't explored?

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