Jerry Colonna, 'CEO Whisperer' and Reboot.io Founder
Jerry Colonna, founder of Reboot.io and CEO coach, discusses his journey from venture capitalist to Buddhist practitioner, overcoming depression, and how meditation and radical self-inquiry help align one's inner and outer self, impacting leadership.
Deep Dive Analysis
12 Topic Outline
Jerry Colonna's Introduction and Meditation Origin Story
Childhood Trauma and the Roots of Depression
External Validation vs. Internal Self-Worth
Discovery of Pema Chodron and the 'If Only' Mindset
Encounter with Pema Chodron and the Nature of Impermanence
Evolution of Jerry Colonna's Personal Meditation Practice
The Role of 'Form' (Incense, Candles) in Meditation
Cultivating Resilience Over Fleeting Happiness
Applying Mindfulness to Daily Life and Reducing Suffering
Jerry Colonna's Life Transformation and Current Work
Integrating Buddhist Practice into CEO Coaching
The 'Charnel Ground' Analogy for Startup Life
7 Key Concepts
Inner and Outer Conflict
This describes a prolonged state where one's internal reality (feelings, self-perception) is in conflict with their external persona or perceived success. This misalignment can lead to imposter syndrome, self-recrimination, and deep unhappiness, even when outwardly successful.
Outsourcing Self-Worth
This is the act of deriving one's sense of value and identity from external factors such as fame, affirmation, money, or status. When these external factors inevitably change or are removed, it reveals a hollowness and lack of an independent sense of self, contributing to suffering.
'If Only' Thoughts
This refers to a seductive pattern of thinking where one believes that happiness or a better state of being will be achieved only if a specific external condition or event occurs. This mindset externalizes happiness and prevents contentment with the present moment, perpetuating a cycle of striving.
Impermanence (Dukkha)
A core Buddhist teaching that all phenomena, including our sense of self, are constantly changing and falling apart. Suffering (dukkha, or unsatisfactoriness) arises from clinging to the illusion of permanence or striving to maintain structure in a world that is inherently transient.
Second Arrow
An analogy from Buddhist scripture illustrating that while initial pain (the first arrow) is an inevitable part of life, suffering (the second arrow) is optional. The second arrow represents the voluntary mental and emotional reactions, judgments, and narratives we add to the initial pain, thereby increasing our own distress.
Spiritual Bypassing
This term describes the use of spiritual practices, concepts, or beliefs to avoid confronting unresolved emotional wounds, psychological issues, or developmental tasks. It can manifest as using rituals or spiritual ideas to escape rather than engage with one's true experience.
Radical Self-Inquiry
This is a process of deep, honest self-examination, particularly focusing on the 'shadow qualities' or denied parts of oneself that are deemed unacceptable. When combined with radical self-acceptance, it helps individuals break through delusion and address the true sources of their suffering.
7 Questions Answered
Jerry Colonna started meditating after a period of intense depression in February 2002, following 9/11 and personal turmoil. He read books by Pema Chodron, Parker Palmer, and Sharon Salzberg, and had a transformative guided meditation experience at Canyon Ranch.
His depression stemmed from a traumatic childhood with a mother suffering from schizoid affective disorder and a violent, alcoholic father. This led to a prolonged conflict between his inner self and his successful external persona, and an unhealthy reliance on external validation for his self-worth.
Impermanence is the teaching that all things are constantly changing and falling apart. Suffering (dukkha) arises from our attempts to cling to the idea of permanence and maintain structure, including our sense of self, in a world where everything is inherently transient.
His practice is primarily shamatha (breath awareness), sitting in a traditional posture on a cushion for 5 minutes to an hour, usually in the morning in a dedicated sacred space. He sometimes uses incense and candles, viewing them as 'form' that supports intention, but not the essence of the practice itself.
The goal of meditation is not to achieve perfection in the practice or use it for self-recrimination, but to sharpen the experience of being human and cultivate resilience. He emphasizes that the benefit is not just a 'cool' experience on the cushion, but increased ability to navigate the inevitable challenges of daily life.
He combines pragmatic business experience, psychological insights (like Jungian shadow qualities), and spiritual concepts (like radical self-inquiry and self-acceptance). He helps CEOs become aware of how they might be complicit in creating their own unwanted conditions, without explicitly teaching Dharma or requiring meditation from his clients.
He believes it is his 'karma' to combine his deep experience in the tech/venture world with his psychological and spiritual background. By helping leaders, whose personal pathologies can spread throughout their organizations, he can have a profound, positive ripple effect on many people's lives and work environments.
16 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.
8 Key Quotes
See, today, I love the man I am, and I am a freaking mess.
Jerry Colonna
The goal is not to get meditation right. The goal is not to turn meditation into yet another form of self-recrimination and self-punishment. Or self-aggrandizement.
Jerry Colonna
The mess in me bows to the mess in you. Because there is no difference between the mess and the light.
Jerry Colonna
I sit on the cushion so that when I encounter the inevitable vagaries of day-to-day life, I'm that much more resilient.
Jerry Colonna
Between stimulus and response is a gap and in that gap lies our choice and our freedom.
Jerry Colonna
I don't give a f*** about enlightenment. I care about not suffering. I just don't want to hurt anymore.
Jerry Colonna
It's hard to fix your problems if you can't see them clearly, so that's the first step.
Dan Harris
Being the CEO of a startup is like a charnel ground practice.
Jerry Colonna
1 Protocols
Jerry Colonna's Daily Meditation Practice
Jerry Colonna- Sit in a traditional posture, with your butt raised on a cushion.
- Focus on breath awareness (shamatha) as the object of your meditation.
- Sit for anywhere from five minutes to an hour, depending on your current state.
- Sit in the same spot, ideally in the morning, in a dedicated sacred space (e.g., a meditation room) to establish intention.
- Use a timer, and optionally incense and a candle, to create a sense of sacredness, understanding these are 'form' and not the ultimate point of the practice.