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#373: Jerry Colonna — The Coach With the Spider Tattoo

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Jun 12, 2019

Guest

Jerry Colonna

In this insightful conversation, Jerry Colonna, CEO of Reboot.io and a seasoned executive coach, shares his journey from private equity to personal growth. He discusses the symbolism of his spider tattoo as a reminder of introspection. The dialogue covers tackling inner critics, the importance of communication, and how journaling can facilitate emotional healing. Colonna emphasizes the necessity of setting boundaries, navigating success-related stress, and courageously making choices that align with personal fulfillment.

01:55:53

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ANECDOTE

Path to Coaching

Jerry's path to coaching began after an encounter with a young lawyer.
The lawyer's distress and Jerry's subsequent advice led him to a coach training program.

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ADVICE

Coaching High Achievers

Ask high-achievers, "How's it working for you?" to address their underlying anxieties.
High achievers often fear being exposed as frauds and worry about impending failure.

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ADVICE

Addressing Busyness

Address "busyness" by exploring how it serves the individual.
Busyness can be a distraction from deeper unhappiness or a way to feel important.

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Webs of Self-Discovery

04:59 • 8min

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Navigating Turmoil: A Journey to Healing

12:40 • 7min

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Unpacking Complicity in Life's Challenges

20:09 • 2min

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The Power of Communication and Connection

22:39 • 16min

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Navigating Success and Overwhelm

38:32 • 23min

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Navigating Boundaries and Personal Growth

01:01:15 • 17min

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Confronting the Inner Critic: The Crow Metaphor

01:18:16 • 3min

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The Healing Power of Journaling

01:21:22 • 13min

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Navigating Tough Choices

01:34:32 • 12min

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Opening the Heart Through Meditation

01:46:09 • 6min

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Embracing Worthiness Through Struggle

01:52:11 • 7min

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#480

• Mentioned in 63 episodes

When Things Fall Apart

Heart Advice for Difficult Times

Pema Chödrön

In this book, Pema Chödrön offers life-changing tools for transforming suffering and negative patterns into habitual ease and boundless joy. Drawing from traditional Buddhist wisdom, she advises moving toward painful situations with friendliness and curiosity, rather than trying to escape them. The book emphasizes the importance of embracing uncertainty, impermanence, and groundlessness, and provides practical advice for dealing with difficult emotions like fear, anger, and sadness. Chödrön encourages readers to stay present with their feelings and to cultivate nonaggression and compassion, leading to deeper healing and understanding.

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• Mentioned in 20 episodes

Let Your Life Speak

Listening for the Voice of Vocation

Parker J. Palmer

In 'Let Your Life Speak', Parker J. Palmer reflects on the journey of finding one's true vocation through a deeply personal and compassionate lens. The book encourages readers to listen to their inner selves rather than external expectations, and to embrace their true identities and integrity. Palmer shares his own experiences, including struggles with depression and unconventional career paths, to illustrate the importance of authenticity and self-awareness in discovering one's calling. The book emphasizes that vocation is not a goal to be achieved but a gift to be received, and that it involves aligning one's life with one's natural gifts and interests.

#761

• Mentioned in 45 episodes

Radical acceptance

Embracing Your Life With the Heart of a Buddha

Tara Brach

Radical Acceptance by Tara Brach offers a transformative practice to help readers overcome habitual feelings of deficiency and better relate to their experiences and emotions. The book emphasizes two key pillars: observing one's experience clearly and responding with compassion. Through personal stories, case histories from her clinical psychology practice, and guided meditations, Brach provides practical guidance on mindfulness, compassion, and acceptance. The book helps readers stop being at war with themselves and live fully in every moment, addressing issues such as self-judgments, conflicts, addictions, and perfectionism. It also clarifies that Radical Acceptance does not mean self-indulgence or passivity but rather empowers genuine change and healing.

#2158

• Mentioned in 21 episodes

Reboot

Leadership and the Art of Growing Up

Jerry Colonna

In 'Reboot,' Jerry Colonna shares his approach to leadership development through radical self-inquiry. The book helps leaders identify and address the emotional baggage and psychological habits that have both driven their success and hindered their relationships and well-being. Colonna draws on his experiences as a venture capitalist and executive coach, blending Buddhism, Jungian therapy, and entrepreneurial insights to guide leaders in finding meaning, building healthy interpersonal bonds, and becoming more compassionate and bold leaders. The book emphasizes the importance of self-awareness, mindfulness, honesty, and self-critique in transforming both personal and professional lives.

#9003

• Mentioned in 6 episodes

Faith

Trusting Your Own Deepest Experience

Sharon Salzberg

In this book, Sharon Salzberg explores the concept of faith in a way that is distinct from traditional religious interpretations. She draws on Buddhist teachings and her own life experiences, including a tumultuous childhood, to explain that faith is about trusting one's deepest experience and maintaining the strength to move forward even in difficult times. Salzberg emphasizes the interconnectedness of all beings and how faith can be a source of healing and peace, accessible to anyone regardless of their spiritual tradition.

"You are not alone. And just because you feel like shit doesn't mean you are shit." — Jerry Colonna

Jerry Colonna (@jerrycolonna) is the CEO and cofounder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders.

Prior to his career as a coach, he was a partner with J.P. Morgan Partners (JPMP), the private equity arm of J.P. Morgan Chase. Prior to that, he cofounded New York City-based Flatiron Partners with Fred Wilson, which became one of the nation's most successful early-stage investment programs. His first leadership position, at age 25, was Editor-In-Chief of InformationWeek magazine, and now he has returned to the written word with his first book, Reboot: Leadership and the Art of Growing Up.

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