Jerry Colonna: The CEO Whisperer
Jerry Colonna, Co-Founder of Reboot.io and executive coach, shares his journey from unfulfilled venture capitalist to finding purpose in coaching. He offers raw insights on resilience, discernment, self-esteem, anxiety, motivation, and the rituals that foster fulfillment.
Deep Dive Analysis
16 Topic Outline
Jerry Colonna's Journey from VC to Executive Coach
The Disconnect Between External Success and Internal Fulfillment
Recognizing and Breaking Ancestral Patterns of Pleasing Others
The Relationship Between Work, Identity, and Self-Worth
Understanding the 'Secondary Benefit' of Unconscious Behaviors
The Challenge of Accepting Positive Feedback and Self-Forgiveness
Overcoming Negative Motivation and Embracing the Concept of 'Enough'
Equanimity as the Goal Beyond Mere Resilience
Jerry's Personal Process for Managing Negative Thoughts and Feelings
The Societal Impact of 'Not Enough' and Collective Innovation
The Power of Journaling and Processing Emotions
Developing Resilience and Discernment in Children and Self
Navigating Stubbornness and Old Programming in Relationships
Building Psychological Safety and Vulnerability in Relationships
The OFNR Framework for Nonviolent Communication
Defining Personal Success as Equanimity and Fulfillment
7 Key Concepts
Shape-shifting Identity
This refers to the unconscious adaptation of one's self to fit the expectations of others, often driven by a desire for love, safety, and belonging. This can lead to a profound disconnect between one's inner and outer self, causing feelings of hollowness.
Secondary Benefit
This is the often-unconscious advantage or protection gained from a particular behavior or pattern, even if that behavior seems negative or unwanted. Recognizing this hidden benefit is crucial for understanding why we maintain certain patterns and for initiating change.
Equanimity
The ultimate goal beyond mere resilience, equanimity is the state of being able to acknowledge mistakes with remorse and learn from them without one's fundamental sense of self-worth being threatened. It allows for the joy of doing good work without being devastated by failure.
Hungry Ghost
A Buddhist concept describing a wraith-like figure who eats endlessly but never feels satisfied, used to illustrate individuals who accumulate vast amounts of wealth or success but still experience an insatiable emptiness and a feeling of 'not enough'.
Processing Emotions
This involves consciously taking the time to examine, acknowledge, and feel one's emotions rather than suppressing them. This practice allows feelings to dissipate naturally, preventing them from unconsciously spilling out and negatively impacting others or one's own well-being.
Radical Self-Inquiry
This is a deep, honest, and non-judgmental examination of one's own motivations, patterns, and behaviors, particularly by asking the core question: 'How am I complicit in creating the conditions I say I don't want?' It aims to uncover unconscious structures.
Discernment
The ability to understand what is truly motivating one's actions and to differentiate between beneficial and detrimental paths. It involves asking 'What's really motivating me?' and 'Why do I do this?' to make conscious choices.
8 Questions Answered
We are often unconsciously shape-shifting to fit others' expectations for love, safety, and belonging, a pattern that can be recognized by observing the disconnect between our inner and outer selves. It's important to remember that it's never too late to shift out of this pattern.
Very early in life, often within family or school dynamics, we learn to attach our sense of self to external roles or accomplishments (e.g., the peacemaker, the good student) as a protective mechanism to feel loved, safe, or to belong.
Self-forgiveness starts by understanding the 'secondary benefit' of our behaviors and extending the same compassion to ourselves that we would to a child. This involves shifting away from negative self-motivation towards a desire for equanimity and self-acceptance.
Learning to feel 'enough' involves acknowledging the 'hungry ghost' phenomenon and recognizing that the relentless drive for 'more' often stems from a fear of not being enough. The antidote is to be motivated by 'reaching for heaven' – pursuing magnificent things for the intrinsic joy of creation, rather than out of fear or lack.
Processing emotions means consciously examining, acknowledging, and feeling them, rather than suppressing them. This practice allows feelings to dissipate naturally, preventing them from unconsciously spilling out and negatively impacting others or causing internal and external harm.
The goal is not just resilience, but equanimity – the ability to handle setbacks without one's self-worth being at risk. This is developed by shifting focus, understanding true motivations through discernment, and realizing that one can be okay even when things don't go as planned.
Couples can navigate this by practicing 'radical self-inquiry' to understand their own triggers and programming, and by using tools like 'the story I'm telling myself' to communicate these internal states to a partner, thereby fostering psychological safety and mutual understanding.
The practice involves having the conversation, letting go of the hope of changing the other person, and taking responsibility for your own needs and boundaries. An example is stating, 'one of the values I get out of the relationship is that it feeds a part of me that I don't really want to feed anymore,' and then setting new boundaries.
31 Actionable Insights
1. Process Emotions, Don’t Suppress
To be fully present and prevent unprocessed emotions from negatively impacting others or yourself, take time to examine and feel your feelings rather than suppressing them, allowing them to naturally dissipate.
2. Achieve Self-Safety First
Prioritize achieving a sense of safety and acceptance within yourself, as you cannot truly create safety with another person or model healthy relationships for your children if you are not first safe and accepting of yourself.
3. Question Unconscious Patterns’ Benefit
To understand unconscious behaviors and motivations, ask yourself ‘what is the benefit?’ of a particular behavior or attachment, as these patterns often serve a protective purpose (love, safety, belonging).
4. Ask: ‘How Am I Complicit?’
Regularly ask yourself, ‘How am I complicit in creating the conditions I say I don’t want?’ to identify your role in maintaining undesirable situations and break ancestral patterns.
5. Risk Perceived Benefit for Freedom
To truly change, you must be willing to risk the very thing that an unconscious system was set up to protect, such as a sense of identity or safety, to achieve genuine freedom.
6. Embrace ‘Enough’ as Antidote
When faced with feelings of inadequacy or the desire for more, consciously remind yourself that ‘you have enough’ as a powerful antidote to the elusive concept of insatiable hunger.
7. Motivate by ‘Reaching for Heaven’
Shift your motivation from the fear of ’not being enough’ to the inspiration of ‘reaching for heaven’ – striving to do something magnificent and impactful for the joy of it, rather than out of insecurity.
8. Redefine Success as Equanimity
Shift your definition of success from material achievements to an internal sense of satisfaction and equanimity, focusing on experiences that bring joy, love, safety, and belonging, rather than external containers.
9. Define Your Desired Legacy
Reflect on what lineage you want to leave behind, whether for your family, society, or the planet, using this purpose to overcome self-doubt and external pressures.
10. Create Stimulus-Response Space
Consciously create space between a stimulus and your response, using tools like OFNR, to interrupt automatic storytelling and improve relational outcomes by allowing for reasoned rather than reactive behavior.
11. Engage Adult Brain with Pause
When triggered, consciously separate the stimulus from your emotional response, allowing your prefrontal cortex (adult brain) to take control from the amygdala, leading to more thoughtful and less reactive decisions.
12. Apply OFNR Communication Framework
Utilize the OFNR (Observation, Feeling, Need, Request) framework for communication: state a value-neutral observation, express your feeling, identify your underlying need, and make a clear request, to separate facts from interpretations and foster self-responsibility.
13. Use ‘The Story I’m Telling Myself’
When triggered in a relationship, articulate ‘The story I’m telling myself is…’ to your partner, allowing you to name your feelings and assumptions without blaming, and invite a clarifying response.
14. Morning Ritual for Self-Awareness
Engage in a morning ritual, such as journaling, to take stock of your feelings and experiences, process what happened, and raise your consciousness to avoid operating on autopilot throughout the day.
15. Embrace Early Morning Silence
Wake early and dedicate a few hours to silence and not engaging with the world, using this time for meditation and mindful attention to process and be present, rather than immediately focusing on productivity.
16. Teach Emotional Vocabulary
Actively teach children and ourselves how to use words to express feelings and needs, fostering the ability to articulate relational challenges without blame, rather than resorting to passive-aggressive or aggressive behaviors.
17. Initiate Direct Relationship Conversations
When a relationship isn’t serving you, initiate a direct conversation to express your changing needs and boundaries, taking responsibility for your own choices without expecting the other person to change, thereby building a crucial communication muscle.
18. Analyze Relationship Patterns’ Benefit
When observing recurring patterns in relationships that cause harm, ask yourself ‘what is the benefit?’ of maintaining the relationship, without shame or blame, to uncover underlying motivations.
19. Prioritize Personal Pride in Work
For creative endeavors, lean into the edge of external criticism by asking yourself, ‘Am I proud of what I’ve written?’ to find liberation and a sense of meaning beyond others’ reactions.
20. Apply Resilience with Discernment
Practice resilience with discernment and skill, ensuring that perseverance and stick-to-itiveness are applied in the right ways and towards appropriate goals, rather than blindly continuing on the wrong path.
21. Create Personal Safe Moments
When triggered, pause, acknowledge the old programming (e.g., ‘I just went right back to childhood’), and communicate that the other person did nothing wrong, thereby creating your own psychologically safe moments through discernment.
22. Love Must Be Safe
Understand that true love is inherently safe; if a relationship does not feel safe, it is not love, and this realization can guide your relational choices.
23. Discover Self, Live Kindly
Dedicate your life to discovering your true self, living authentically, and integrating kindness into your actions to achieve full actualization.
24. Believe It’s Never Too Late
Recognize that it’s never too late to discover who you really are and live into that, even at an advanced age, as transformation is always possible.
25. Stop Pleasing Others
Understand that continually pleasing others comes at the cost of giving up your true self, leading to a disconnect between your inner and outer identity.
26. Be Curious, Not Critical
When exploring unconscious patterns, resist the impulse to criticize yourself; instead, approach these structures with curiosity to understand their protective function and facilitate transformation.
27. Release Negative Self-Talk Loops
When negative self-talk loops begin, acknowledge them (e.g., ‘blow it a kiss’) to release their grip, understanding that not every effort will be perfectly received, but that doesn’t equate to failure.
28. Identify Praise Rejection Benefit
Explore the unconscious benefit of not accepting positive praise, as it often serves as a motivator to continually improve and avoid complacency, but at the cost of internal rewards.
29. Practice Self-Forgiveness First
To foster resilience and self-worth in your children, you must first cultivate these qualities in yourself, as your unconscious patterns and self-rejection are modeled and passed down.
30. Challenge Complacency Fear
Re-evaluate the belief that accepting positive feedback will lead to complacency or victimhood, as this fear often prevents individuals from taking in positive experiences.
31. Cultivate Self-Awareness for Safety
Recognize that creating psychological safety in a relationship is also your responsibility, requiring you to overcome childhood subroutines and develop awareness of your own feelings to approach interactions from an adult perspective.
7 Key Quotes
The cost of pleasing others is giving up yourself.
Jerry Colonna
How am I complicit in creating the conditions I say I don't want?
Jerry Colonna
Being able to be resilient is a wonderful adulting skill, but what we're really after is the equanimity that says, I may have made a mistake, and with remorse, I will learn from that mistake, but my sense of self-worth is not at risk.
Jerry Colonna
You have to do that for yourself first because the Teflon rejection of the negative that motivates you, they're learning every day.
Jerry Colonna
Love is safe. And if it's not safe, it's not love.
Jerry Colonna
The story I'm telling myself is the most powerful story in the world.
Jerry Colonna
Man's reach should exceed his grasp or else what's a heaven for.
Jerry Colonna (quoting Robert Browning)
2 Protocols
Morning Ritual for Self-Awareness and Processing
Jerry Colonna- Take stock of yourself, noting how you're feeling and what happened recently (e.g., physical state, recent interactions).
- Process your experiences and feelings by writing in a journal.
- Meditate.
- Exercise.
- Dedicate a few hours to not engaging with the world, waking early without immediate focus on productivity.
- Practice paying attention to your immediate surroundings and observations.
OFNR (Observation, Feeling, Need, Request) Communication Framework
Jerry Colonna- **Observation**: State a value-neutral, non-assumptive fact about what happened (e.g., 'Jerry walked past Ali carrying laundry').
- **Feeling**: Express your subjective feeling in response to the observation (e.g., 'When Ali looked Jerry up and down, it felt like she was judging his body').
- **Need**: Identify the underlying need that is not being met (e.g., 'Jerry has a need to feel safe in his body').
- **Request**: Make a clear, specific request for what you want in the future (e.g., 'When you're judging whether or not the jeans fit, can you tell me what you're doing?').