Why You’re Not Speaking Up (And How To Fix It)

Key Insights

On Personal Development and Identity:

Difference becomes a superpower only when you stop trying to conform. The realization that "I can only be me because everybody else is taken" represents a fundamental shift from seeking acceptance to embracing authenticity. This typically occurs in the mid-20s to early 30s when individuals recognize that conforming denies them the ability to shine.

Shadow work—understanding past trauma and experiences—transforms perceived weaknesses into strengths. What we've been conditioned to hide or suppress actually contains our greatest potential when properly understood and accepted. The goal is to turn "dark shadow" into "golden shadow."

Assumptions versus known facts determine behavior patterns. Most people operate on assumptions conditioned by parents, society, or external forces, believing these protect them when they actually prevent growth. Challenging these assumptions reveals they're often a "house of cards" with no real foundation.

On Leadership and Management:

Leadership differs fundamentally from management. Managers handle themselves and their teams, but leaders create space and time—for themselves, their teams, and their business. The greatest leaders remain calm when chaos surrounds them, able to pause, assess facts versus unknowns, and engage in "best level thinking."

How you do one thing is how you do everything. The small, subtle, often unspoken actions—how someone enters a room, conducts themselves in meetings—reveal true leadership capacity more than grand gestures or stated values.

The transition from employee to manager to leader requires distinct developmental stages. Many people get promoted into leadership roles when they're actually just managing, lacking the capacity to create strategic space and handle uncertainty with composure.

On Growth and Transformation:

Discomfort signals growth opportunity. Transformation occurs when you become comfortable being uncomfortable. The perception in your mind about what will happen rarely materializes—we suffer more in imagination than reality. Consciously placing yourself in challenging situations 99 times out of 100 reveals the catastrophe you imagined doesn't occur.

Radical accountability precedes all change. Taking full ownership means examining your role in every situation rather than blaming external forces. When you own it, you can change it. Without accountability, you remain stuck in victimhood.

Momentum and energy matter more than perfect conditions. Like a golfer assessing every variable before taking a shot, people often wait for perfection before acting. The most important thing is to hit the ball—to start moving—because momentum generates energy and opportunities that planning alone cannot.

On Vulnerability and Authenticity:

Authentic vulnerability differs from performed vulnerability. Leaders who say they're being vulnerable while maintaining carefully crafted personas lose trust with those who can read deeper. True vulnerability requires genuine discomfort and risk, not strategic self-disclosure.

Imposter syndrome stems from unexamined shadow work and conditioning. Understanding why you have it allows you to transform it into a superpower. The work involves self-awareness, acceptance, and ownership rather than suppression or denial.

On Cultural Conditioning:

Tall poppy syndrome—the cultural tendency to cut down those who stand out—operates differently across societies. In New Zealand, it manifests as an aspirational ceiling (the "3Bs": batch, boat, BMW) beyond which wanting more becomes socially unacceptable. This societal pressure prevents people from living their true value and worth.

Education systems condition conformity over creativity. Designed in the late 1800s for factory work, modern education emphasizes rote learning, acceptance, and behavioral compliance. This "dumbs down" natural curiosity and experimentation seen in toddlers who fail repeatedly while learning without stigma.

On Decision-Making and Focus:

The "hell yes or hell no" framework eliminates ambiguity. If something isn't a definite yes or definite no, you're stuck in "hell"—the unclear middle ground that wastes time and energy for everyone involved. Clarity requires decisive commitment or rejection.

Time protection requires intentional filtration. Asking potential coffee meetings for five questions they want answered, then asking what they think the answers are, filters 60-70% of requests while helping the remaining 30% find their own solutions.

Event plus response equals outcome. You cannot control events, but you can always control your response. This control over response directly impacts outcomes, making it the most leverageable factor in any situation.

On Coaching and Facilitation:

The less a coach says, the more effective the interaction. The role is sherpa, not guru—guiding others up their mountain rather than carrying them or showing off your own climbing ability. If you feel uncomfortable in the coaching space, you're likely asking the questions others won't.

Questions matter more than answers. The "question of questions" approach recognizes that coaches don't have solutions—they have inquiry tools that help individuals and teams discover their own insights and directions.

Mastermind groups reveal that isolation is an illusion. The issue one person faces now, someone else has already solved, another will face soon, and a third is currently navigating. Industry and sector differences matter less than leaders believe; human and organizational challenges follow predictable patterns.

On Journaling and Reflection:

Thoughts remain just thoughts until verbalized or written. For the majority who have internal dialogue, externalization through journaling or speaking aloud transforms abstract rumination into concrete material that can be examined and acted upon.

Journaling works for some, not everyone. The key is finding your externalization method—whether written reflection, audio notes, conversation, or experiential learning. The tool matters less than the consistent practice of converting internal processing into external clarity.

Single-question journaling provides maximum impact with minimal time. Rather than elaborate reflection sessions, asking one key question daily—"What's the most important thing I need to do today?" or "Who do I need to connect with?"—creates focus and accountability.

On Parenting and Role Modeling:

Children learn more from watching you fail than succeed. Seeing a parent consistently attempt improv, fail, and immediately move to the next challenge teaches resilience better than any conversation about resilience. The "do, try, fail" cycle normalized through observation becomes their operating system.

Permission matters more than it should but less than people think. Adults and children alike need explicit permission to be themselves, make mistakes, and pursue unconventional paths. Granting yourself permission unlocks transformation, though ideally this shouldn't be necessary.

The parent-child relationship transforms when distance allows mutual adult recognition. Physical separation through moving out creates appreciation and the ability to see parents as complete humans rather than just authority figures. This transition, while challenging, enriches the relationship.

Structural Patterns

Narrative Framework:

The conversation follows a hero's journey structure, beginning with a childhood memory of difference (the Jewish boy at Christmas), progressing through struggle (teenage years of trying to fit in), transformation (mid-20s realization), and current mastery (coaching others through similar journeys). This personal narrative validates the coaching philosophy—Adam teaches what he's lived.

Questioning Techniques:

The dialogue demonstrates masterful question progression: starting with identity ("Who was young Adam?"), moving to methodology ("How do you define purpose?"), exploring application ("How does one get past artificial blocks?"), and ending with vision ("Where are you going?"). Each question builds on previous answers while opening new exploration territories.

Metaphor and Analogy Usage:

Complex concepts become accessible through relatable metaphors: fleas in a jar for artificial limitations, golf for decision-making processes, space monkeys on a rock for perspective, bungee cords for parenting, improv for life itself. These analogies transform abstract leadership principles into visceral understanding.

Vulnerability Demonstration:

Rather than claiming vulnerability, the speaker demonstrates it by sharing specific moments of struggle, admitting that only three people can trigger him (wife and two daughters), and acknowledging times of discomfort. This modeling of authentic vulnerability reinforces the teaching about authenticity versus performance.

Framework Introduction:

Multiple actionable frameworks appear throughout: Event + Response = Outcome, Hell Yes or Hell No, Assumptions vs. Known Facts, the scale of 1-10 where 10 is death, being plus or minus 10% of your five closest people. These frameworks provide immediate tools readers can apply without requiring the full coaching engagement.

Hidden Implications

The Industrialization of Human Potential:

The observation about education systems designed for factory work in the 1800s reveals a deeper truth: most societal structures weren't built to maximize human potential but to create compliant, predictable workers. Modern coaching and personal development essentially "de-programs" this industrial conditioning, suggesting that corporate and educational reform may be less effective than individual transformation.

The Commodification of Authenticity:

The distinction between authentic and performed vulnerability highlights a paradox in modern leadership: as authenticity becomes valued, it also becomes strategic and therefore potentially inauthentic. This creates a second-order problem where leaders must now be authentically authentic, raising questions about whether true vulnerability can exist once it's recognized as a leadership tool.

Geographic Impact on Mindset:

The conversation reveals how physical location shapes possibility—British reserve, New Zealand's tall poppy syndrome, American exceptionalism, and Canadian middle-ground thinking demonstrate that geography doesn't just influence culture but fundamentally constrains or expands what people believe they can achieve. This suggests that location changes might be necessary for certain transformations, not just helpful.

The Professionalization of What Was Once Free:

The coaching industry's growth and the acknowledgment that it's unregulated with zero barrier to entry suggests a broader trend: intimate human relationships that once happened naturally (mentorship, honest feedback, challenging conversations) now require paid professionals. This commodification raises questions about social fabric deterioration and whether coaching is treating symptoms of atomized society rather than root causes.

The Permission Economy:

The repeated emphasis on needing permission—to be yourself, to fail, to want more—reveals an implicit understanding that modern society operates through invisible constraint systems. These aren't legal or explicit but psychological and social. Breaking through requires not just personal change but actively rejecting collective agreements about limitation, suggesting individual transformation is inherently counter-cultural.

COVID as Natural Experiment:

The observation about how leaders handled COVID reveals that crises don't create character but expose it. Organizations with leaders who had developed "pause and assess" muscles thrived while others flapped. This suggests that current relatively stable periods are actually preparation time for inevitable future disruptions, making personal development work not optional luxury but essential infrastructure.

The Externalization Requirement:

The insight that thoughts remain "just thoughts" until externalized points to a fundamental human limitation: we cannot fully process or act on purely internal cognition. This explains why therapy, coaching, journaling, and conversation work—they force externalization. The implication is that pure self-reliance is impossible; we need external mirrors (human or written) to see ourselves clearly.

Improv as Life Training:

The emphasis on improv—accepting offers with "yes, and" and moving immediately from failure to the next scene—suggests that traditional education's focus on preparation, planning, and getting it right the first time fundamentally misaligns with reality. Life operates more like improv than like prepared speeches, meaning improvisational skills may be more valuable than expertise or knowledge.

The Mastermind Revelation:

The observation that someone in a mastermind group has already solved, is currently facing, or will soon face your exact challenge suggests that innovation and unique problems are rarer than believed. Most leadership struggles are pattern repetition, not novel situations. This implies that connection and perspective-sharing may be more valuable than creative problem-solving skills.

The Frank and Fearless Filter:

Naming a business to repel wrong-fit clients reveals a sophisticated understanding: the right positioning attracts ideal clients while actively deterring poor fits. This suggests that in saturated markets, clarity about who you're NOT for matters as much as clarity about who you serve. The best marketing may be selective exclusion rather than broad appeal.