The quiet ache of aging is discovering how many of my limits were self-authored.
I could have…
Three deceptively simple words that sit at the center of every leader’s private post-mortem. Every founder, every executive, every high-achiever eventually arrives at this same realization: the great barrier was never time, talent, funding, or circumstance. It was the narrative architecture of the self—identity, fear, inherited scripts, unconscious beliefs.
The pattern is universal because the mechanism is universal. People don’t fail because they’re incapable. They fail because they cannot see the story they’re living inside.
Coaching names this directly: the human psyche is built on protective narratives that once kept us safe and now keep us small. They operate automatically. They feel factual. They define the possible without announcing themselves.
Executives don’t walk around saying, “I’m living out my unexamined childhood survival strategy.” They say things like:
“I’ll take care of it.” “It’s faster if I just do it myself.” “I need more data before I make the call.” “This decision has to be perfect.” “My board won’t support that direction.” “My team isn’t ready for more responsibility.” “I shouldn’t ask for help.” “I’ll deal with it when things slow down.”
These sentences sound rational. They sound mature. They sound like leadership.
Underneath them is something far more primal: a story about who you must be in order to be safe, respected, valued, or in control.
This is where your years disappear.
A founder spends three extra years avoiding a necessary executive hire—not because the candidate isn’t good enough, but because somewhere in his internal logic, delegating authority threatens his very identity as the one who holds everything together.
An executive waits too long to address a toxic VP—not because she doesn’t know what needs to be done, but because a lifetime of conflict-avoidant conditioning interprets direct confrontation as danger.
A leader endures chronic overwork—not because the business requires it, but because the belief “I am only worthy when producing” has been running in the background since adolescence.
These are not operational challenges. These are identity constraints disguised as business decisions.
No one notices when the shift happens. It’s quiet. Gradual. It looks like routine. Deadlines, meetings, investor updates, product cycles. Another quarter. Another year. And then, during a rare moment of stillness—vacation, illness, burnout, a failed raise, a board conflict, a resignation—reflection sharpens into a painful clarity:
I could have hired earlier. I could have spoken up sooner. I could have trusted my instincts. I could have listened instead of defended. I could have slowed down before the crash. I could have asked for support instead of white-knuckling everything. I could have become someone different far earlier than I did.
It’s not regret. It’s revelation. The human equivalent of discovering a door you never noticed in a room you’ve lived in for decades.
This is the work we do in coaching: widening the field of vision beyond the stories that once felt like truth.
This is deep work to shift from subject to object. What once owned you becomes something you can see, name, and work with.
The belief “I am responsible for everything” becomes “I am carrying responsibility to avoid feeling unnecessary.”
The belief “I must prove myself” becomes “I learned early that love was conditional on performance.”
The belief “I cannot be vulnerable” becomes “I am protecting the parts of me I’ve never allowed into the light.”
When leaders begin to examine these foundations, their range expands. Decisions that once felt paralyzing become simple. Conversations that once felt dangerous become clarifying. Directions that once felt impossible become obvious.
You could have turns into you can. And eventually, into you are.
You can not rationalize and nod your way into it, anymore than you can read a book on how to swim and become a swimmer – it must be a lived experience.
Executives and founders don’t hire coaches for tactics. They hire coaches to expose the internal architecture shaping their tactics. They hire coaches to interrupt the unconscious flow of “you could have” before it ossifies into years lived on the wrong narrative. Trust me, I lost a lot of years before I learned these lessons and how to live by them.
Coaching is not about fixing. It is about revealing—what you’re carrying, why you’re carrying it, and what becomes possible when you stop mistaking old beliefs for current reality.
That is the pivot point – where “I could have” becomes “I did.”
If you feel coaching would benefit where you are in your journey, I welcome a chat.
It was 2007. I was living in Newport Beach, pocketing several hundred thousand dollars a year, and leading a company that had found its stride. I had a white SL convertible shipped to me from the east coast that I paid for on my Amex. To my friends and colleagues, I was living the entrepreneurial dream. But my reality was a different story. I was living with a level of suffocating anxiety that made it difficult to catch my breath. I suffered from multi-day migraines that felt like a violent protest from my own body. I was only 30. I was angry at the world for the endless list of problems it delivered to my desk, clearly unaware that my own methodologies for handling life were the primary source of my friction.
I walked into therapy that year not because I wanted to grow as a person, but because I believed everyone else was the problem and I needed to know how to better control the outcomes I sought. It wasn’t even seeking help about my anxiety, just anger-led to go see the bearded therapist to fix the problems of my life. That first step began a seventeen-year commitment to my interior work—a journey that would eventually lead me from the practical tools of the present, to the deep archetypes of my past, and finally to the strategic design of my future.
The Early Years of Therapy
My initial years were spent in the world of Cognitive Behavioral Therapy (CBT). As a CEO, I treated therapy like any other optimization problem. My therapist got into my dense head that at the very least, I can’t think clearly when I’m angry and so I bought into some CBT resources. I wanted a quick fix for anger and stress to gain better focus and make sharper decisions. CBT provided a structured, actionable framework that felt familiar enough to a business mind.
The Benefits of CBT as a Founder:
Immediate Grounding: It provided “battlefield” tools to manage my anger in the middle of a high-stakes meeting.
Identifying Distortions: It helped me recognize when I was “catastrophizing” a missed quarterly goal or simply one lost prospect, allowing me to return to a more rational baseline.
Habit Restructuring: It offered a way to challenge the immediate, negative thought patterns that led to reactive decision-making.
However, as the company continued to scale and I acquired another company, I began to hit the boundaries of what this approach could offer. For a founder responsible for the culture and strategy of a large organization, the limitations became clear.
The Limitations of CBT from a Business Perspective:
Symptom-Focused, Not Future-Oriented: CBT is designed to get you back to a baseline so you don’t feel so anxious. But as a leader, I needed to move toward “times ten.” I needed a vision and a methodology for the future, not just a way to survive the afternoon.
Individual vs. Organizational: CBT gave me a breathing exercise for my stress, but it had nothing to say about how to handle a co-founder who, I felt, was undermining the company’s mission.
The “Why” vs. the “What”: It could help me change a thought, but it didn’t help me understand the deep-seated belief system that created that thought in the first place. It patched the leak but didn’t address the structural integrity of the dam.
The Descent: Jungian Analysis & the Shadow
My search for deeper answers eventually led me to a Jungian Analyst. If CBT was about managing the surface, Jungian therapy was an archaeological excavation. I spent more than a decade in this work, which is rooted in depth psychology and the process of “Individuation”, or becoming a whole, integrated human being.
Working with an analyst is a rigorous process. It involves looking into the “Shadow”—the parts of ourselves we have suppressed or denied because they didn’t fit our image of a “successful leader.” For much of my life I had relied on a rigid need for control and feared and rejected vulnerability, believing that combination was the engine of my success. In reality, they were the sources that fueled my exhaustion and my problems in the company.
As Carl Jung famously observed:
“Until you make the unconscious conscious, it will direct your life and you will call it fate.”
In the context of leadership, this is profound. The parts of a founder that remain unconscious will eventually run the company.
If you have an unconscious need for validation, you will build a culture of “yes-men.”
If you have an unconscious fear of conflict, you will allow toxic behaviors to persist. And so forth…
My years in Jungian analysis allowed me to stop calling my patterns “fate” and start leading from a place of conscious choice. This work took deep root in me; it changed the very nature of my presence in the office.
When Therapy Met Mentor
The transition toward coaching began during a lunch at Killer Shrimp in Marina Del Rey with my mentor Fred — a former C-level executive at IBM and Mattel. For the first time in our long history, I didn’t talk about revenue, scale, or product-market fit. I talked about the internal toll. I told him about the migraines, the anxiety, and the feeling that success was starting to feel like confinement.
Fred listened with the perspective of someone who had seen the same patterns in the boardrooms of global giants. He shared his own struggles with burnout during the high-pressure years at Mattel, back when toys were built to last with die-cast metal, he would tell me. That conversation opened a new branch in my life. It was the realization that while therapy was tending to my soul, I needed a different kind of partnership to redesign my entrepreneurial journey.
Questions Only a Coach Asks
While therapy often asks, “Where does this feeling come from?”, coaching might ask, “What is this feeling costing your vision?”
The inclusion of coaching wasn’t a replacement for therapy; it was an expansion. My coach asked me questions that a therapist, focused on my psychological well-being, never would have considered.
Here are a few examples of how that coaching lens changed my company:
1. The Question of Identity vs. Role
The Question:“You say you ‘have’ to make every final decision to ensure quality. If you were to die tomorrow, would the company fail because of a lack of talent, or because you’ve designed a system that requires your permission to exist?”
The Application: This hit my need for control directly. We looked at the “methodology of permission” I had built and how approvals all routed to me (with a nifty workflow that I thought was efficient but all it did was funnel more problems my way faster).
The Change: I dismantled my “NASA-style” dashboard of 50 metrics and narrowed it to 3. I empowered my team to make decisions without my input. We created a committee that could arrive at their own decisions and justification and act on it. The result? Decisions were made faster, employee morale improved because they felt trusted, and I finally stopped got room to breathe and spend time doing what was truly my role – getting more clarity on our vision and our long term direction.
2. The Question of Value Alignment
The Question:“You are optimizing for ‘Scale,’ but your stress suggests you value ‘Peace.’ What would happen if you optimized for ‘Peaceful Scale’ instead of ‘Growth at all Costs’?”
The Application: This forced me to look at our sales strategy. We were taking on “toxic” clients who paid well but drained our team’s spirit.
The Change: We fired our most difficult clients and we fired our bottom of the barrel clients and repeated it every single year. It felt like professional suicide at the time, but it cleared the air and made space for more lasting and sustainable growth. We replaced them with partners who aligned with our values. Our customer service improved, our referrals increased and customer loyalty went through the roof. Later when I came to sell the company, we saw that our client retention average was an astounding 12 years.
3. The Question of the “Founder’s Shadow” in Culture
The Question:“Your team is hesitant to give you bad news despite you insisting its ok. What is it about your reaction to ‘failure’ that has made silence feel safer than honesty for them?”
The Application: Through my Jungian work, I knew I hated failure. My coach helped me see how that internal hatred was manifesting as a “culture of fear.”
The Change: I started a regular lessons learned forum where I shared my own mistakes first. By making vulnerability a leadership methodology, I unlocked the creativity of the team. I didn’t expect it but issues that had been lingering for months were solved because people were finally brave enough to speak the truth.
The Synthesis of Therapy & Coaching
I stayed in deep therapeutic work years after my company was acquired, for what would be over 17 years. I’m a big advocate for everyone doing deep work. The only journey worth taking, in my humble opinion, is the one within.
Therapy is the work of the roots—it ensures the tree is healthy and grounded. Coaching is the work of the fruit. It is about the harvest—the strategy, the methodology, and the design of the future.
For the modern founder and CEO, the two are not mutually exclusive; they are interdependent. Here is it how I have experienced it:
Therapy
Coaching
Primary Focus
The Soul and the Past.
The Company and the Future.
Key Question
“Why am I this way?”
“How do I lead from here?”
Scope
Healing and Integration.
Strategy and Methodology.
Outcome
Internal Peace.
Sustainable Success.
If you are building something significant and feel the pressure stretching you thin, remember: the business can only grow as far as you do. Seeking support is not a sign of weakness; it an act of leadership. If you ever feel you need someone in your corner that’s been through it, I’d welcome getting to know you.
