What will I learn about: why true leadership requires radical self-exploration to help you analyze past patterns, build self-esteem, and accept your inherent vulnerabilities?

Understand why true leadership requires radical self-exploration to help you analyze past patterns, build self-esteem, and accept your inherent vulnerabilities.

What will I learn about: how unlearning childhood belief systems—like treating life as a relentless game of Monopoly—can free you from the exhausting pursuit of external validation?

Discover how unlearning childhood belief systems—like treating life as a relentless game of Monopoly—can free you from the exhausting pursuit of external validation.

What will I learn about: Learn to cultivate a 'strong back and an open heart' so you can navigate the painful process of self-leadership and transform inevitable failures into valuable lessons?

Learn to cultivate a 'strong back and an open heart' so you can navigate the painful process of self-leadership and transform inevitable failures into valuable lessons.

What will I learn about: the art of standing still to overcome the toxic addiction to constant busyness and find profound peace of mind independent of your job title?

Master the art of standing still to overcome the toxic addiction to constant busyness and find profound peace of mind independent of your job title.

What will I learn about: why sharing your personal struggles and shedding the myth of the solitary leader helps you build deeper trust and genuine connection with your team?

Find out why sharing your personal struggles and shedding the myth of the solitary leader helps you build deeper trust and genuine connection with your team.

Reboot

Leadership and the Art of Growing Up

Jerry Colonna

★ 4.4 / 5(84 ratings)

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Categories:

Management & Leadership

If You're Curious About These Questions...

You should listen to this audiobook

💡Have you ever wondered how the unexamined parts of your past might be silently sabotaging your effectiveness as a leader today?
💡What if the secret to overcoming your biggest professional hurdles wasn't a new business strategy, but a process of 'radical self-inquiry'?
💡Are you curious about how slowing down and facing your inner demons can actually make you a more resilient and humane CEO?

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Key Takeaways from Reboot

✓Understand why true leadership requires radical self-exploration to help you analyze past patterns, build self-esteem, and accept your inherent vulnerabilities.
✓Discover how unlearning childhood belief systems—like treating life as a relentless game of Monopoly—can free you from the exhausting pursuit of external validation.
✓Learn to cultivate a 'strong back and an open heart' so you can navigate the painful process of self-leadership and transform inevitable failures into valuable lessons.
✓Master the art of standing still to overcome the toxic addiction to constant busyness and find profound peace of mind independent of your job title.
✓Find out why sharing your personal struggles and shedding the myth of the solitary leader helps you build deeper trust and genuine connection with your team.

Learning Tools

Reinforce what you learned from Reboot

Mind Map

Reboot

Radical Self-Inquiry+

Facing Crises+

Stillness & Pacing+

Truth & Vulnerability+

Embracing Irrationality+

The Pathless Path+

Inner Voices+

Empathetic Leadership+

Self-Care+

Quiz — Test Your Understanding

Question 1 of 10

When executives ask Jerry Colonna for a 'quick fix' to their professional anxiety, what approach does he recommend instead?

A. Radical self-inquiry
B. Strategic restructuring
C. Broken-open-hearted warriorship
D. The pathless path

Question 2 of 10

According to the author, what is often the true underlying cause of a high-powered executive's feelings of anxiety and helplessness?

A. A lack of technical management skills and training
B. Rapid shifts in the global economic market
C. Unresolved childhood trauma and deep-seated fears
D. Insubordination and a lack of connection from middle management

Question 3 of 10

What leadership lesson is illustrated by the story of the Buddhist saint Milarepa and the demons in his cave?

A. Leaders should delegate their most toxic problems to others.
B. Leaders must forcefully banish negative influences from their organizations.
C. Leaders need to ignore their problems until they naturally resolve themselves.
D. Leaders should face their crises and toxic situations head-on by surrendering to them.

Question 4 of 10

Why does the author argue that leaders need to learn to 'stand still' rather than constantly rushing to the next task?

A. Rushing makes leaders appear too eager and inexperienced to their boards.
B. Endless movement creates a toxic work culture where everyone feels they must frantically catch up.
C. Standing still is the only proven way to increase a company's quarterly profits.
D. Rushing prevents leaders from reading management books that solve daily problems.

Question 5 of 10

What does the concept of 'broken-open-hearted warriorship' entail in the workplace?

A. Fostering a highly competitive environment where only the strongest survive.
B. Cultivating a culture where leaders are unafraid to be vulnerable, truthful, and strong.
C. Encouraging employees to share every personal detail of their lives during meetings.
D. Hiding corporate mistakes to protect the emotional well-being of employees.

Question 6 of 10

In the context of our professional lives, what do the 'ghosts in the machine' represent?

A. Hidden software bugs that disrupt company communications.
B. Leftover psychological habits and fears from childhood that interfere with current behavior.
C. Former CEOs who continue to influence company policy from behind the scenes.
D. Unconscious biases against new employees in a corporate setting.

Question 7 of 10

How does the author apply the childhood concept of a 'do-over' to professional life on the 'pathless path'?

A. By letting go of mistakes, forgiving, and moving forward refreshed.
B. By repeatedly firing and hiring staff until the perfect team is built.
C. By completely rebranding a company every time it faces a financial loss.
D. By demanding that colleagues apologize for their past professional errors.

Question 8 of 10

What do the metaphors of the 'Crow' and the 'Loyal Soldier' represent, respectively?

A. The Crow is ambition; the Loyal Soldier is corporate loyalty.
B. The Crow is external criticism from competitors; the Loyal Soldier is the HR department.
C. The Crow is a toxic business partner; the Loyal Soldier is an ideal employee.
D. The Crow is self-criticism; the Loyal Soldier is our instinct for self-preservation.

Question 9 of 10

Why does the author advise against 'shooting the damned Crow' (silencing our inner critic)?

A. Because the Crow provides the competitive edge needed to defeat rival companies.
B. Because the self-criticism signifies that we actually care about our actions and are invested in what we do.
C. Because silencing the Crow will cause the Loyal Soldier to abandon its post.
D. Because the Crow is the only source of true innovation in a stagnant workplace.

Question 10 of 10

What unique leadership insight does the author draw from observing how a herd of horses chooses its leader?

A. Horses choose the strongest and most aggressive member to protect them from predators.
B. Horses choose the most visually striking member to establish dominance over other herds.
C. Horses choose the member that feels the group's needs best and leads with intuition and compassion.
D. Horses choose the fastest member to ensure they can escape danger quickly.

Reboot — Full Chapter Overview

1Recommendation
2To confront our challenges as business leaders, we must first truly practice radical self-inquiry in earnest.
3How we handle a crisis truly defines us as leaders and as human beings today.
4Instead of constantly rushing to the next task, we must learn to stand still.
5As a leader, you will find that truth is always your ally.
6We must learn to live with irrationality within ourselves and in others.
7Instead of viewing our lives as a linear progression, we should embrace the pathless path.
8We must accept our personal Crow and Loyal Soldier.
9The finest leaders make room for others to become truly themselves.

Reboot Summary & Overview

Reboot (2019) shows us that to become better leaders, we must first become better human beings. Through the process of radical self-inquiry, Jerry Colonna asks us to reflect deeply on all of the things that have shaped us and continue to influence our professional behavior. Drawing from raw personal experience, he guides us toward a more rooted, humane form of leadership.

Who Should Listen to Reboot?

CEOs struggling with existential crises
Businesspeople who’d like to learn how to slow down
Anyone who wishes to be a humane leader

About the Author: Jerry Colonna

Jerry Colonna is the CEO and cofounder of Reboot.io, an executive coaching firm, whose main focus is developing leaders with humanity, resilience and flair. He also cofounded Flatiron Partners, one of the most successful early-stage investment programs in New York, and is a former partner at JPMorgan Partners. He lives in Boulder, Colorado.

Reboot

If You're Curious About These Questions...

Listen to Reboot — Free Audiobook

Key Takeaways from Reboot

Learning Tools

Mind Map

Quiz — Test Your Understanding

Reboot — Full Chapter Overview

Reboot Summary & Overview

Who Should Listen to Reboot?

About the Author: Jerry Colonna

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