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Jerry Colonna, 'CEO Whisperer' and Reboot.io Founder

Mar 29, 2017 59m 55s 16 insights
Jerry Colonna was working as a venture capitalist in New York City during the 9/11 terrorist attacks, and as he walked by wreckage of the World Trade Center towers, he said he felt like his "world was falling apart." Colonna went on to become a practicing Buddhist and in 2014 he founded Reboot.io, a CEO-coaching company where he serves as a certified professional coach for the heads of some of the most dynamic start-ups in the United States.
Actionable Insights

1. Radical Self-Inquiry & Acceptance

Engage in radical self-inquiry to clearly see and acknowledge personal problems and delusions, combining it with radical self-acceptance to welcome and integrate all aspects of oneself, especially fears and ‘messiness’.

2. Cultivate Inner-Outer Alignment

Strive to align your inner self with your outer presentation, and when caught in moments of misalignment or shame, practice self-regulation to regain balance.

3. Practice Radical Openness

Continuously strive to ‘just keep opening’ to experiences as they are, rather than resisting or trying to control them, as this fosters deeper understanding.

4. Meditate for Resilience, Not Perfection

Engage in meditation to cultivate resilience for the inevitable challenges of daily life, rather than seeking perfect meditation experiences or using it for self-recrimination or self-aggrandizement.

5. Observe Judgment in Meditation

When distracted during meditation, gently return to the breath and intention without immediate self-judgment; if judgment arises, observe it mindfully before redirecting attention back to the breath.

6. Apply Mindfulness to Daily Frustrations

Extend mindfulness to everyday situations, such as waiting in line, by observing feelings like anger with curiosity, compassion, and humor, recognizing your own contribution to suffering.

7. Identify & Challenge “If Only” Thoughts

Become aware of ‘if only’ thoughts that externalize happiness and lead to suffering, and actively challenge this pattern of outsourcing your sense of well-being.

8. Confront Deepest Fears (Charnel Ground)

Engage in ‘charnel ground practice’ by intentionally going to and exploring the places that most scare you, embracing raw and visceral life experiences to foster growth.

9. Engage in Long-Term Therapy

Consider engaging in long-term therapy or psychoanalysis for deep self-understanding and healing, as demonstrated by the speaker’s 24-year relationship with his therapist.

10. Establish Daily Meditation Habit

Aim for a daily meditation practice, establishing a consistent time (e.g., morning) and a dedicated, sacred spot to reinforce intention and build habit.

11. Practice Shamatha (Breath Awareness)

Use Shamatha (breath awareness) as your primary meditation technique, focusing on the breath as the object of your meditation to anchor your attention.

12. Meditate with Flexible Duration

Sit for meditation anywhere from five minutes to an hour, adjusting the duration based on how you are feeling and your current capacity to maintain consistency.

13. Use Rituals Mindfully (Optional)

If it aids your practice, use a timer, incense, and a candle to create a sense of sacredness in your meditation space, but ensure these rituals do not become a form of spiritual bypassing from actual inner work.

14. Practice Compassion & Empathy

Break out of self-focus to practice compassion and empathy by actively listening to and understanding the struggles of others, offering support without needing to ‘fix’ anything.

15. Read Foundational Books

Read books like ‘When Things Fall Apart’ by Pema Chodron, ‘Let Your Life Speak’ by Parker Palmer, and ‘Faith’ by Sharon Salzberg for insights into self-reflection, depression, and spiritual practice.

16. Explore Reboot.io Resources

Visit reboot.io to access free five-day reboots, guided practices, and peer support groups designed to explore the existential relationship with work and self.