At first, I didn’t want to say anything. I played it off with platitudes and a bunch of “meh, you’ll be fiiinne”. I am often asked for advice, yet I have a long-standing reluctance about giving advice. I’ll spend most of this post explaining why. But this was my friend. Someone I love and care for. And his fear was so raw, so present on his face that I saw him like I see my own son, and my reluctance gave way. I told him to lean in. To stop managing the situation from a safe distance and instead be fully present in it — authentic, vulnerable, speak this truth gently but remain boundaried. I gave him my observation, which I preceded with the fact that I am looking from the outside and I can’t truly diagnose the situation, but I told him to sit with the uncertainty and stay in for as long as he could. How long, he asked. Give it time, six months I proffered. I believed, and still believe, that this was the right orientation for a person struggling with what he was going through.

What happened next slapped me in the face like a bag of bricks.

Over the following days, something shifted in him. Not towards patching up this pillar of his life. Toward clarity. The man who had come to me terrified of losing this amazing thing he had built, decided to unravel it himself. He went from gripping the pillar with both hands to letting it go. Completely.

I still don’t know what to make of it. I’m not sure it was wrong. I’m not sure it was right. What I know is that I watched my own advice travel through another person’s life and arrive somewhere I never anticipated, carrying weight I didn’t intend, touching parts of him I couldn’t see.

That’s the thing about advice. It never stays the shape you gave it.

Why People Ask

Before we talk about what happens when advice lands, it’s worth sitting with why people seek it in the first place.

The simple answer we like to go to is that people want guidance. They’re facing something hard, they don’t know what to do, and they hope someone else does. But I’ve come to believe that’s rarely the full picture. It’s the lie believed to preserve the hidden truth.

When someone asks for advice, they are almost always also asking to be relieved of something — the weight of not knowing, the discomfort of sitting with an open question, the anxiety of genuine uncertainty.

Advice feels like solid ground. A path paved by someone else can be stood on, at least for a moment, without the whole body shaking.

The psychologist Erich Fromm called this the “escape from freedom.” His insight was that genuine freedom (the freedom to choose, to author your own life) is experienced by most people not as liberation but as burden. It produces isolation and anxiety. And one of the most reliable ways to escape that anxiety is to hand your path forward over to someone else. An authority, an expert, a wise friend with a beard.

This is not weakness. It’s deeply human. But it means that the moment someone asks you for advice, they are often not really asking you to solve their problem. They are asking you to take the weight of their uncertainty off them, even briefly. And if you take it, if you give the advice, you have done something to them that neither of you fully recognizes. You’ve made their path yours. And however that path goes, some part of you will carry that. Not because it’s your fault. But because you made it your business.

The Invisible Lens: Projection

Carl Jung gave us a word for something that happens constantly in human relationships, mostly without anyone noticing: projection.

In simple terms, projection is the unconscious act of placing something from inside yourself onto someone outside.

In projecting, you attribute to another person a quality, a feeling, or a capacity that is actually a reflection of your own inner world.

We all do it. It’s not pathology. It’s the method of how the psyche manages what it cannot yet hold consciously.

When someone projects wisdom onto you, the mechanics are roughly this: they encounter something in you (your history, your willingness to sit with hard questions, your stature) that resonates with a quality they sense but haven’t fully claimed in themselves. Something in them knows their path. But they haven’t yet trusted that knowing. So they place it outside themselves. They put it on you. And then they ask you for it back.

“Everything that irritates us about others can lead us to an understanding of ourselves.” — C.G. Jung

The reverse is equally true: everything we idealize in others, the wisdom, the clarity, the groundedness we seek, is often a quality we are not yet willing to own in ourselves.

This is why people in my circles tend to come to me for advice. I don’t think it’s because I’m wiser than they are. It’s because something in the way I engage (the questions I ask, the pace I keep, the willingness to name hard things directly) reflects back a quality they are reaching toward. They project onto me a certainty I do not possess. And then they ask me to hand it back to them.

The trouble is: when you accept the projection, when you play the wise, bearded elder, you don’t give them the thing they actually need. You deprive them of it.

Because the thing they actually need is to find their way to their own knowing. To stop borrowing clarity from someone else’s face and find it in their own.

Advice, received through the lens of projection, almost never does what it appears to do. It doesn’t transfer wisdom. It confirms the receiver’s belief that the wisdom lives somewhere outside them. And that belief is the very thing keeping them stuck. And that’s a wild, wild thing to say and to see. And yet, that’s exactly why people go to motivational seminars and listen to the amazing Tony Robbins tell them they can do it! So they can package that feeling from their projection, handed back neatly by Tony, for them to carry into their lives for a little bit and then go right back to where they were before, and then repeat the cycle the next time his circus is back in town.

The Shape of Uncertainty

There is an old story from the Taoist tradition that I find myself returning to often. It goes something like this:

An old farmer’s horse ran away. His neighbors came to console him. “Such bad luck,” they said. The farmer replied: “We will see.”

The next morning, the horse returned, and with it came a dozen wild horses. The neighbors rushed back: “What wonderful luck!” The farmer said: “We will see.”

That afternoon, the farmer’s son tried to tame one of the wild horses and was thrown. He broke his leg. “Such terrible luck,” said the neighbors. “We will see,” said the farmer.

The following week, soldiers came through the village to conscript young men for war. The farmer’s son, with his broken leg, was spared. “How fortunate,” the neighbors said. The farmer said: “We will see.”

What makes this story worth reading again and again is not the twist. It’s the farmer’s refusal to give-in to the uncertainty prematurely. He doesn’t know if things are good or bad. Not because he’s passive or detached, but because he understands that life unfolds across a longer horizon than any single moment can reveal. The neighbors, always certain, do not sway the farmer’s resolve to stay in uncertainty.

I’m living my own version of this right now. My son is five. We’ve applied to six private schools — the kind where if he gets in, he’ll likely be there from kindergarten through twelfth grade. All six give their answers on the same day. Our first choice feels like the right fit, the porridge is just right – it’s got a little bit of everything we value. And it’s the closest drive for daddy and daddy cares a lot about that. The others are all genuinely great — one has a campus built for athletics, one is academically intense, one is deeply rooted in community and diversity. We want what’s right for him. We just don’t know what right looks like yet. And here’s what I keep coming back to: even if we get our first pick, I still won’t know. His life will unfold the way it will unfold, shaped by teachers and friendships and moments I can’t anticipate, inside whatever walls he ends up in. The school we’re hoping for might be exactly right. It might be the thing that costs him something we can’t currently see. So, we will see.

My friend pulling apart his own pillar in life might be the worst thing that ever happened to him and everyone involved. It might be the moment that saves a life. It might bring people closer, it might pull people apart. I genuinely do not know. I have my own strong feelings and I’m contending with it. But I have stopped pretending to myself, that the advice I gave was right or wrong. It moved through him and became something altogether unrecognizable to either of us from that moment we shared. That’s all I know.

This is not a comfortable place to stand. But I think it’s an honest one.

Why Advice is Two Cents

I’ve arrived, through years of reflection on my experiences with adversity and loss, at a position that life advice has very little value. I work hard to give very little of it and I seldom ask anyone for it.

This isn’t false modesty. It’s not that I think I have nothing to offer. It’s that I’ve watched advice, my own and others’, move through people’s lives and consistently land somewhere other than intended. The problem isn’t the person giving it, but rather the very nature of advice.

First: advice is always drawn from someone else’s life. When I tell you what I would do, I am telling you what I, with my history, my wounds, my particular relationship to risk and loss and love, would do. That person is not you. The advice that saved me might undo you, not because it’s wrong in the abstract, but because it was built for a different soul.

Second: advice, by its nature, skips the most important part. The most important part is not the answer. It’s the process of arriving at the answer — the sitting with uncertainty that the rockstar Jungian analyst, Marion Woodman, described as “holding an inner or outer conflict quietly instead of attempting to resolve it quickly.” The slow and uncomfortable clarification of what you actually value takes time. When someone gives you their answer, they rob you of that priceless process. You get the destination without the journey, and the journey was the thing that would have transformed you into who you sought to be all along.

Third: as we’ve already seen, advice passes through the distorting lens of projection. The person receiving it is not hearing what you said. They’re hearing it through who they believe you to be, which is mostly a fiction their own psyche constructed. We don’t see things as they are. We see them as we are. So the advice gets filtered, magnified, twisted. It arrives in a different shape than you sent it.

“I would like to beg you, dear Sir, as well as I can, to have patience with everything unresolved in your heart and to try to love the questions themselves as if they were locked rooms or books written in a very foreign language.” — Rainer Maria Rilke

He was saying, with great care, that the answer is not the point. Learning to live with the question is.

The Advisor Question

I want to draw a distinction here, because I think it matters.

There is a real and legitimate role for advisors, and it’s worth being precise about what that role is and where its limits are.

A good advisor is someone with deep expertise in a specific domain: M&A Finance, contract litigation, SaaS product strategy, consumer electronics go-to-market, cloud security architecture. When you bring an advisor into your orbit, you’re not asking them to weigh in on who you are or what your life should look like. You’re asking them to apply a concentrated body of knowledge to a well-defined problem. That should be genuinely useful. The best advisors I’ve known are extraordinarily disciplined about the limits of their expertise. They know what they know and they know where it ends and to say so.

But I watch founders reach for advisors — and mentors, and investors, and friends like me — for questions that are not domain specific to their tenured skillset. They’re sitting with something that doesn’t have a right answer. Something about whether to push forward or let go, whether a relationship has run its course, whether the company they built still fits the person they’ve become. They ask for advice on these questions because the questions feel unbearable, and because having someone else weigh in makes the unbearable feel momentarily more manageable.

No advisor can help with these questions. Not because advisors aren’t smart. Many of them are extraordinarily smart. But because these questions are not information problems. They’re not solved by more data or a better framework. They live in territory that expertise cannot reach.

This is where the advisor role ends and something else begins.

The Mirror

I became a coach not despite my reluctance to give advice, but because of it.

I have spent years sitting with people in the hardest moments of their work and their lives. Founders who built something real and then felt it slowly hollowing them out, myself included. CEOs who couldn’t understand why they kept recreating the same conflicts with different people, myself included. Leaders who had every external marker of success and felt, underneath, like they were running from something they couldn’t name, myself included.

What I noticed, repeatedly, was that these people (myself included) didn’t need other peoples’ answers.

They needed to see themselves more clearly.

They needed someone to hold up a mirror, not a flattering one, not a cruel one, but an honest one, so they could see the patterns they were living inside, the beliefs they were defending without knowing it, the story they’d been telling about themselves that had stopped being true.

That’s what coaching, at its best, is. Not advice. Not answers. Not even guidance in the conventional sense. It’s a particular quality of attention, rigorous, unhurried, willing to sit with what’s difficult, that allows another person to see what they couldn’t see alone.

Jung understood this. His whole psychology was built around the idea that what we cannot see in ourselves does not disappear. It reappears in our life, in the form of the circumstances we keep recreating, the relationships we keep damaging, the patterns we swear we’ve broken that keep returning – and of course, of course, it greatly impacts our careers. The work of becoming more conscious, more aware of what’s actually driving you, is not intellectual work. You can’t think your way to it. You need a relationship, a genuine encounter with another person, to bring the full you into clear view in the form of a mirror.

The Tao Te Ching puts it differently, and perhaps more simply:

“To the mind that is still, the whole universe surrenders.”

The coach’s job is not to speak wisdom into the room. It is to create enough stillness, enough safety, enough honest presence, that what the client already knows can surface. Most people are so busy managing their own anxiety, keeping up appearances, seeking validation, running from uncertainty, that they never get quiet enough for their deeper knowing to be heard.

The coach doesn’t give you anything you don’t already have. The coach helps you hear yourself.

What Changes, and How

I want to be specific about this, because I think it’s misunderstood.

When people imagine coaching, they often imagine something like a sophisticated version of advice: a smart person helping you think through decisions, offering frameworks, asking good questions that lead somewhere the coach already sees. And perhaps some coaching is like that – it’s a free market. That’s not the intent of my coaching work.

The kind of coaching I’m drawn to, and the kind I practice, goes to a different layer. It starts from the premise that the struggles leaders bring to coaching are rarely what they appear to be on the surface. The co-founder conflict is rarely just a conflict about decisions. The burnout is rarely just exhaustion. The inability to delegate is rarely just a management problem. These are the outer expressions of something happening at the level of identity — who the person believes themselves to be, what they believe they deserve, what they’re afraid to want, what they’re using the company to prove.

Working at that layer is slower. It asks more of the person. There are sessions that feel like nothing happened, and then something shifts weeks later in a conversation with a board member, co-founder, or a spouse and the person can’t explain why. The changes are not always traceable. But they tend to last, because they’re rooted in something real and the person goes through a transformation.

I’ve watched founders stop recreating the same conflict with different people, myself included. I’ve watched CEOs release a grip on control that had been slowly strangling their companies for years, not because someone told them to delegate, but because they’d done enough inner work that the compulsion to hold everything simply loosened, myself included. I’ve watched people whose companies were performing well finally let themselves feel it, instead of moving immediately to the next threat – myself included.

These are not small things. They’re the things that change how a person leads, how they love, how they inhabit their own life.

One Last Note on Advice

I still don’t know if what I told my friend was right.

I’ve turned it over many times. I’ve looked at the advice itself, lean in, be authentic, speak truth, be gentle but boundaried, and I believe those things. I still believe them. But I also know that my belief in them, and my love for him, and my reading of his situation, were all limited by who I am and what I can see from where I stood. He took what I said and carried it into his own interior, where it mixed with everything I couldn’t see, and arrived somewhere I didn’t expect.

Like the farmer, I will see, over time, what happened in my friend’s life and whether the path he’s on is one he can build something good from. So will he. And we will see what happens with my dear son, as we soon accept some school as our second home for the next thirteen years. Nobody knows yet.

What I do know is that the most useful thing I can offer, to my friend, to the founders I work with, to anyone sitting with something genuinely hard, is not my answer. It’s my presence. My willingness to sit with them in the not-knowing. My refusal to hand them a certainty I don’t possess.

That willingness is a different kind of help. It’s slower, and less satisfying in the moment, and it doesn’t let either person off the hook. But it points toward the place where real change actually lives: inside the person asking the question.

Further Reading

Memories, Dreams, Reflections – C.G. Jung

Letters to a Young Poet – Rainer Maria Rilke

Holding the Tension of the Opposites – Marion Woodman

Escape from Freedom – Erich Fromm

Tao Te Chin – Lao Tzu

The post Notes on Advice appeared first on Allen Adjamian.

Most founders I work with don’t lack support. They lack the right kind of support for what they’re actually going through.

They have advisors giving them playbooks. Friends telling them they’re crushing it. Board members asking for updates. Maybe a mentor they grab lunch with once a quarter. And yet, something isn’t moving. The same patterns keep showing up. The same friction. The same quiet weight that no amount of tactical advice seems to touch.

The issue is rarely a lack of help. It’s a mismatch between the kind of help they’re receiving and the kind of problem they’re facing.

I learned this the hard way over three decades of entrepreneurship. I spent years leaning on the wrong type of support for what I was actually dealing with — and the cost was measured not just in dollars but in years I can’t get back.I’ve written about that reckoning before, and it’s something I come across often in the entrepreneurial community.

The terms mentor, advisor, and coach get used interchangeably. They shouldn’t. Each serves a fundamentally different purpose, and knowing the difference can save you years of spinning your wheels with the wrong person in your corner.

Mentors Tell You What They Did

A mentor is typically an accomplished professional some steps ahead of you on a similar path. They’ve been where you are. They can help you see around corners, warn you about potholes, and offer the reassurance that what you’re feeling is normal.

The value of a great mentor is their business pattern recognition. They draw from lived experience and can say, “Here’s what I saw when we faced something similar.” When you know you have a specific, identifiable challenge — stalling in your target market, navigating a specific board scenario, structuring a fundraise with a specific VC — a mentor who has already walked that road can be quite helpful.

But mentorship has structural limits. It tends to be informal and unstructured, which works well when you know what you’re dealing with. It breaks down when the problem is something you can’t yet name — or when the issue isn’t strategic at all, but deeply personal. And mentors, with the best of intentions, can fall into a trap of assuming that what worked for them will work for you. Different era, different market, different person. The principles may translate. The playbook often doesn’t.

Advisors Tell You What You Should Do

Advisors are subject-matter experts. They operate in a specific domain — sales, product, finance, legal, go-to-market — and they bring deep, narrow expertise to a clearly defined problem. When you know the domain of your problem, a good advisor will get you to a tactical solution faster than anyone else. Fast answers. Laser focus. Over the course of my career, I built a bench of advisors for exactly this reason and have served as an advisor when it comes to revenue.

Where advisory falls short is when the real problem isn’t in the domain at all or is far more encompassing. Sometimes what looks like a sales problem is actually a leadership problem. What looks like a hiring gap is actually a boundaries problem. What looks like a strategy issue is actually an identity issue. Advisors have a hammer, and they’re excellent at finding nails — but they can miss the structural cracks in the foundation.

I’ve lived this. I once spent considerable capital hiring expensive talent on advisor recommendations to solve what appeared to be a capacity problem. The numbers supported it. The logic was sound. But the real issue was something no advisor was equipped to see — it was a human problem hiding beneath the org chart. I wrote about this in detail because the lesson cost millions, and it’s one I never want another founder to learn the hard way.

Coaches Help You Grow So You Connect To Your Wisdom Within

A coach — a good one — doesn’t tell you what to do. They help you see what you cannot see on your own. They work at the level beneath behavior, surfacing the assumptions, identities, and emotional patterns that quietly, but powerfully, govern your decisions.

Where a mentor shares their experience and an advisor shares their expertise, a coach holds up a mirror.

They ask questions that no one in your orbit would think to ask — questions that bypass the business problem and go straight to the human pattern driving it.

Founders don’t walk around saying, “I’m living out my unexamined childhood survival strategy.” They say things like, “It’s faster if I just do it myself” or “My team isn’t ready for more responsibility.” or “We aren’t ready for a sales leader yet.” Those sentences sound rational. Underneath them is something far more primal: a story about who you must be in order to feel safe, valued, or in control. That invisible architecture is where your years disappear — and it’s precisely what coaching is designed to make visible.

The results of good coaching show up in the business, but they originate in the leader. Decisions that once felt paralyzing become doable. Conversations that once felt dangerous become clarifying. Patterns that repeated for years — sometimes decades — finally break. In my own journey, a coach asked me questions that fundamentally changed how I structured my company, my team, and my life. No mentor or advisor would have gone there, because no mentor or advisor was trained to see what was operating beneath the surface.

Where coaching shines: When the real issue isn’t what’s happening in the business, but what’s happening in the leader. When the same patterns keep repeating across different teams, different quarters, different companies. When you suspect the ceiling on the company is actually a ceiling inside you. That may look like you’ve got all the right people in the company but the company just isn’t firing on all cylinders. Coaching works at the root, not the symptom.

Where it demands caution: Anyone can call themselves a coach these days, which makes finding a great one challenging. Low-quality coaching might feel good in the moment, but it can delay you from meaningful growth. A great coach has a clear theory of change, does deep work, and is along for your transformation – one that you can feel in your life and in your business. If it doesn’t change how you lead under pressure, it isn’t working.

So Which Do You Need?

Probably more than one, at different times.

When I look back at my own three-decade journey, the honest answer is that I needed all three — and the cost of not knowing the difference cost me years.

Here’s a simple frame:

You need a mentor when you’re facing a challenge someone else has already navigated and you want to hear how they navigated their terrain. The value is in their experience. In sharing their past experience, you may find a way forward for yourself.

You need an advisor when you have a domain-specific problem that requires specialized expertise. The value is in their knowledge. A great advisor will provide a solution to your specific challenge in the moment so you don’t have to spend more time pondering options. Adopt it, move on.

You need a coach when the barrier to strategic progress is something within — a pattern, a belief, an identity — that you can’t see clearly from the inside. The value is in their ability to reveal what’s been invisible and work with you to become who you need to become to make your future vision a reality.

The deepest work — the kind that changes not just what you achieve but who you become — that’s coaching territory. Mentors and advisors tend to the branches. But if the roots are not well nourished, no amount of pruning will save the tree.

If any of this resonates with where you are in your journey, I’d welcome getting to know you.

The post Do You Need a Mentor, an Advisor, or a Coach? appeared first on Allen Adjamian.

My co-founder was the quintessential “Servant Leader”—genial, calm, tireless, and always the first to jump into the trenches. He believed he was building a high-trust, flat culture. I watched as he eroded his own sovereignty, allowing the normalized audacity of his team to treat him as a safety net rather than operationalizing our vision at scale.

And I let it happen because it was convenient for me.

This didn’t make me a passive bystander; it made me an accomplice. My clean hands were actually a form of negligence. I was so focused on protecting my own comfort that I kept quiet on the fact that my trusted partner – a man I genuinely liked – was setting the building on fire with his heroism.

At some point, I knew my options. As majority shareholder, I could:

Fire him.
Demote him.
Hire more under him.

I wanted to avoid the conflict of the first two, so we kept hiring.

In failing to make the decision I knew I should have made, I did a massive disservice to the company. I should have fired him and replaced him with someone who could rebuild the team. But in my role driving revenue, I was “crushing it”—having fun, making friends, being interviewed—and I didn’t want to pivot into such a crucial, painful conversation.

The Costs of Avoiding Confrontation

Because I chose personal comfort over conflict, the rot in the organization didn’t just stay static; it metastasized. My decision to hire more under him was the exact moment the business model broke. I threw capital at a structural problem, increasing the velocity of our dysfunction. The results were devastating.

A Culture of Learned Helplessness

By hiring expensive talent under a “Hero,” we added to his work. Because my co-founder couldn’t set a boundary, he couldn’t delegate. The new hires quickly realized that they didn’t actually have to deliver excellence—they just had to cry for help and have it escalated to him. We were paying top salaries for people to watch my co-founder burn himself out.

This sent a silent but lethal message: “I don’t actually trust you to handle this.” The result wasn’t a supported or empowered team; it was a culture of learned helplessness.

The Skill Gap: Engineers stopped learning how to solve complex problems because they knew the boss would swoop in and do it for them. They got stuck in their skillsets and delayed their own promotions and career advancements. That later brewed resentment that showed up with sudden departures, sabotaged work, or simply checked-out employees.

The Ownership Void: Work was no longer seen through to the end; it was merely “started” and then “escalated” for the boss to finish. The team wasn’t owning their work; they were merely funneling the hard labor off to the equity holder.

The Hostility Pivot: As the stakes grew, the “high-trust” culture soured. Because no one was truly responsible for their own results, “dropping the ball” became the norm. They had the normalized audacity to say “Well, he wasn’t around to help us, he is always too busy.”

Writing this I just remembered how we had a long list of items under a ridiculous status “Waiting for Executive”.

Revenue Subsidized Risk

This is where my culpability cuts the deepest. Because I was crushing it on revenue, I masked the operational bleeding and increasing risk.

Every big deal I closed bought us more time to ignore the broken machine. My success created a false sense of security. I looked at the P&L and saw growth; I downplayed the spiraling risk of catastrophe of having reduced competency down to one person.

My poor boundaries around conflict avoidance blinded me. I told myself this chaos “was just part of being a successful startup.” Even though by any metric, we should have been operating like a mature organization. Revenue growth served as justification for my silence.

The Cost of Lost Clients

Eventually, the bill came due. Client deliveries began to miss their marks—massive, high-six-figure misses. Then catastrophe struck. Major outage – 100% caused by the environment we had allowed to take shape.

Millions lost overnight.

The genial atmosphere evaporated, replaced by defensive finger-pointing. Since the co-founder had touched every project, he took the blame for every failure. It was the antithesis of what I had envisioned. We lost years of sales efforts in a week, all because our COO was unable to focus on his role, and because I had allowed it to continue.

All this was a painful lesson more than a decade ago, but one I’ll never forget:

Leaders with poor boundaries are bottlenecks who prevent their people from growing up.

The Invisible Perimeter: How Boundaries Define Leadership

I experienced this in my company, but I see it everywhere. Lacking boundaries manifests in many ways across the C-Suite:

The Vague Visionary: Has poor boundaries around their own curiosity. They change the company strategy often, creating “Strategic Whiplash” for the team.

The Filterless Communicator: Has poor emotional boundaries. The leader “over-shares” their anxieties or half-baked ideas with the entire staff, causing unnecessary panic because they haven’t learned to use their board or a coach as a perimeter.

The Approval Seeker: Has poor boundaries around time. Because they haven’t set a boundary around their deep-work time, they become a high-paid administrator reacting to every department’s priorities.

And so on, and so forth with countless examples.

The Impact of Poor Boundaries

A boundary is the psychological and operational perimeter that protects a founder’s most valuable asset: Clarity of Judgment.

You are not measured by tasks completed, but by the quality of your decisions regarding Vision, Capital, and People.

Impact on Vision: The Competence Trap

Vision requires a CEO to look at the horizon. When you lack strong boundaries, you succumb to the gravitational pull of “doing what you’re good at.” Rewriting copy or debugging code feels safe—it provides a dopamine hit of “value.”

But when you do this, you are a symphony conductor who has sat down in the string section. You might hit the right notes, but the orchestra has lost its cohesion. You have traded the podium for a chair, and the music suffers.

Impact on Capital: The Dilution of Velocity

Without clear boundaries, your capital becomes a humidifier—misting the air in ten directions instead of a laser cutting through your target market. A leader who says “yes” to marginal ideas wastes the velocity of capital. The result may be a product that is feature-rich but profit-poor, sold in markets you have no business being in.

Impact on People: The Culture of The Shadow

When you have poor boundaries around role—answering Slacks at 2 AM or jumping into channels you don’t belong in—you cast a destructive shadow. You create a “theatre of productivity” where people stay online just to be seen. High performers leave for autonomy; those who tolerate micromanagement stay for the paycheck.

The Identity Trap: You Can’t Just “Read” This Into Practice

If you are nodding your head right now, be careful. That’s probably just a dopamine hit, not transformation.

Boundaries are tied to identity beliefs held for decades. “My value is my utility,” or “I am a good person because I help.” The list goes on.

Deep work is required.

Without the deep work, the brain will revert to its old identity the moment pressure spikes. You will justify stepping back into the trenches as “necessary” when in reality, it is a retreat to a comfortable, destructive identity.

True change doesn’t happen by learning a new “hack”; it happens in transformative work where you rewrite your identity and safely get to strengthen and practice it.

The Boundary Audit: A Process of Inquiry

If you want to move from “nodding” to “being,” you must audit your life through the lens of open, curious, self-inquiry. Often! I did the work for many years myself, and still do, and didn’t know it would lead me to eventually helping other founders and executives.

A great coach ask questions to your blind spot and holds space for you to show up and do the work. Coaching questions show up uniquely to every person, but some examples to uncover old beliefs might look like:

“How am I complicit in creating the conditions I say I hate?”
“What is the ‘payoff’ I get from jumping in?”
“Does solving this fire make me feel more valuable than the long-term work of strategy?”
“If I died tomorrow, which of these processes would stop immediately?“
“Why have I built a system where I am so needed all the time?”
“Am I actually helping my team, or am I stealing their opportunity to become competent so I can stay relevant?”

Examples of Boundaried Responses

Once your identify changes, your language changes. Leaders who go through the deep work learn to attune to their intuition and consequently develop language that helps them show up healthy under pressure. Again, from my own experience, I can share some examples:

The Shift

There is no hack. True change doesn’t happen in the reading. It happens in the deep work of transformation. You become who you need to be, or you revert to who you were.

Boundaries make the difference between a founder who “hustles” and a CEO who “leads by vision.” By defining where you end and the company begins, you don’t just save your sanity—you give your people the space they need to grow. And if you build a culture where your people grow, by extension and consequence and good fortitude, your company will grow and thrive.

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“I’ll get to it later, I have time” was a very seductive lie I told myself throughout my tenure as a CEO. I would get in great shape when my net worth hit X and I would hire a personal trainer, I had time. I would enter a meaningful, heartfelt relationship when the executive team could run the day-to-day without me, I had time. I would learn guitar (for my third attempt) and record my music, I totally had time. I’d start a family, plenty of time for that. I would spend more time doing what I loved.

I believed that circumstances would one day align when my calendar and bank account finally cooperate – which makes me chuckle now writing that. Over 17 years as a Founder and CEO, I paid the price for putting my dreams off, despite a lot of financial and outward success. And life looked as such for other founders in my network. They were gaining unwanted weight, getting depressed, withdrawn, cynical, divorced and disconnected from the vibrant life force that got them into entrepreneurship in the first place. And the companies were struggling, stagnating and the exit strategy had become a mirage.

As is the case, most leaders survive on deferred maintenance. Founders have normalized it. Executives institutionalized it. The drift away from what matters most is subtle, but the cost is absolute and very palpable.

The things that matter most – health, relationships, creativity, meaning – generally do not collapse suddenly. They erode. They degrade not through crisis, but through postponement. Health withers, relationships drift while purpose dissolves into mere output. It happens via the quiet internal whisper that says “I’ll tend to this when things calm down. When the product ships. When the round closes. When my net worth hits X.“

But that is not valid reasoning, it is a protective narrative hard at work. It is a psychological veil that shields you from confronting old beliefs you were trained to obey – beliefs about worth, safety, and what you’re truly allowed to experience out of life. I wore that veil for many, many years.

Because “later” is a soothing anesthesia.

It lets you avoid the exploration with the part of you that is afraid of deep change, afraid of your heart’s calling, or afraid of taking yourself and your life’s purpose very seriously.

But anesthesia always has an invoice.

You think you are investing in a better future as a leader, but you are making payments to your past.

“Later” compounds over time. Like interest on a loan, the cost rises quietly until one day the beliefs that no longer serve you have foreclosed on your dreams.

It’s commonplace that we discover these insights too late. The old stories of waking up to symbols of success with no meaning, no vitality and often depressed. So many founders and executives feel it as an inescapable fatigue, a hollowing gap between external success and internal stagnation. They assumed life would expand when success did. It didn’t for me and many in my entrepreneurial circles. It never does. The outside scales. The inside does not — unless you proactively work on it.

If you want a life you enjoy later, the only material you will ever have to build it with is how you act today. Not when you feel ready, not when the company stabilizes, and not when you have more money or more confidence.

Working on managing the psyche is the only point of leverage we have. It is the only environment where change is real rather than conceptual. Because we do not see things as they are, rather we see things as we are. And if what you see is no longer serving you, well.. what are you going to do with that awareness?

Whatever can be done about it is probably going to require ongoing support and resources to make a lasting impact. For me, it was having someone trusted and experienced in my corner – and it still is.

The work we do is not about forcing discipline. It is about dissolving the beliefs that keep you postponing your own high quality life and the success of your entrepreneurship. It is about identifying and growing out of the narratives that once kept you safe but now keep you stagnant. The coaching work we do together is to interrupt the automatic payments you keep making to your past and start cultivating the life you do want and deserve.

Later is too late. Your future is shaped only by what you intentionally put into practice today.

If you are feeling called to explore deeper, I’d welcome getting to know you.

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“Increase revenue 30%.”
“Improve employee engagement by 15%.”
“Increase NPS to 50”
“Execute product launches 20% faster.”

The CEO presents them confidently. Leadership nods. They cascade into OKRs. Employees update dashboards. Slack fills with optimism.

By April, execution is uneven.
By July, priorities have drifted to the shores of status quo.
By October, the goals are quietly revised or rationalized. PIPs rumble through the organization.
By December, everyone agrees the goals were “directionally right” but unrealistic given the year.

This cycle repeats so often that failure itself becomes normalized.

The problem is not effort.
The problem is how goals are conceived.

How CEOs Typically Set Goals

Most CEOs set goals using one of three approaches.

1. Goals as Numeric Targets

Revenue. Headcount. Market share.

These goals are easy to measure and easy to defend to a board. They are also emotionally inert, therefore they narrow staff attention to outcomes. But numbers do not guide people on who they need to be become in order to achieve these outcomes. Managers translate lofty targets into pressure. Employees respond by negotiating, optimizing locally, gaming metrics, or blaming unclear instructions. Fear replaces true ownership. Respect is lost. Culture becomes competitive instead of cooperative. And in the spirit of Peter Drucker – culture snacks on strategic goals all year long. Execution fails from fear-driven behavior implicitly embedded in the system to hit a new goal.

2. Goals as Aspirational Statements

“We will be best-in-class in support.”
“We will retain 95% of clients”
“We will execute faster across all departments.”

These statements sound motivating, but they do not change how work is done. They express intent without specifying what decisions, behaviors, or tradeoffs must change as a result.

Because nothing concrete is defined, each function fills in the gaps for itself. Product interprets “execute faster” as shipping more. Sales interprets it as pushing deals sooner. Marketing interprets it as launching campaigns earlier. No one is wrong, but no one is aligned.

Since no behavior is modeled or enforced, there is nothing to reinforce. The statements appear in decks and all-hands meetings, then quietly disappear from daily work.

With no change to decisions or incentives, energy returns to the existing way of operating. The goal fades, not because people disagreed with it, but because it never affected what they actually did.

3. Goals as Cascaded Tasks

The CEO defines objectives. Leadership breaks them into OKRs. Managers translate those OKRs into narrow, local metrics. Employees work to satisfy the metrics tied to their role.

This creates the appearance of alignment, but the original goal is fragmented into disconnected targets, to be optimized in isolation.

Because performance is evaluated locally, people prioritize what they can control and measure. When tradeoffs arise, they choose the metric over the intent behind it.

Over time, the system stops responding to the goal itself and starts responding to the measurements created in its name. Coordination breaks down. Teams succeed locally while the organization stalls globally. That means many OKR targets are hit and the company still misses its goal.

Execution suffers not because people ignore the goal, but because cascading it converted intent into competing incentives.

Why Goals Do Not Stick in Company Culture

Goals fail for structural reasons because the system they are placed into is not designed to support them. Effort increases, intent is clear, but the underlying mechanics of decision-making, incentives, and authority remain unchanged.

Goals Bypass Identity

People do not change behavior just because a goal exists. People change behavior when a goal fits how they see themselves and how they believe success is achieved.

When a goal conflicts with identity, people comply outwardly and resist inwardly. They follow the letter of the goal while preserving the behaviors that have kept them successful and safe.

Example.
A company may declare a goal to “move faster,” but if promotions, praise, and credibility have historically gone to those who avoid mistakes and maintain polish, the real identity remains being “risk-averse”. Under pressure, people revert to caution, escalation, and over-analysis.

The stated goal fails because it never became part of who the organization believes it is.

Goals Ignore Internal Conflict

Inside every organization are competing priorities, fears, and incentives. Leaders want growth and stability. Managers want clarity and protection. Employees want autonomy and safety. These needs can coexist, but they pull in different directions when pressure rises.

Traditional goals assume these tensions will resolve themselves. They declare a shared outcome without addressing what each group risks by pursuing it.

Example.
CEO announces a goal to “move faster.” In the meeting, everyone agrees. No one objects. Afterward, managers keep extra reviews in place to avoid mistakes. Employees escalate decisions instead of owning them. Teams move cautiously to protect their metrics and roles.

Publicly, the goal was accepted. Privately, the system made speed impossible.

Goals Are Detached from Real Decision-Making

Most goals live in documents. Decisions live in meetings. When goals do not change how tradeoffs are made in those meetings, they have no effect on behavior.

Example.
A company goal states customer retention is a priority. In a planning meeting, the team must choose between fixing a reliability issue or shipping a feature tied to a big sales deal. They choose the feature to protect the revenue number.

Under pressure, people fall back on familiar decision patterns, and the organization returns to the status quo precisely when it matters most.

Goals Are Treated as Outcomes, Not Constraints

CEOs often define what they want without defining what they will no longer tolerate. When CEOs define goals without setting boundaries on time, attention or capacity, teams try to do everything at once. No work is stopped, tradeoffs are avoided, and capacity is silently exceeded. The system becomes overloaded, and effort increases without progress.

Example.
A CEO says growth, reliability, and innovation all matter this year. No projects are cut. Teams stretch to deliver everything. Deadlines slip, quality drops, and people burn out.

Nothing changed because no constraints were introduced. The reward is burnout and frustration.

The Frustration Loop

When goals fail structurally, a predictable emotional loop forms.

CEOs see missed targets and conclude the organization is not stepping up. Managers feel trapped between ambitious goals and unchanged constraints. Employees experience shifting priorities and growing cynicism.

Each group reacts rationally to its position, but in isolation. CEOs push harder. Managers buffer and reinterpret. Employees disengage.

Each group blames a different layer. No one questions the goal-setting model itself.

The Principle That Changes Everything

Goals do not drive behavior.
Conditions drive behavior.

People act consistently with how they make meaning under pressure.

That means they act consistently with how decisions are rewarded, how risk is treated, and what feels safe under pressure. Meaning is not abstract. It is shaped by incentives, authority, and past consequences.

When pressure rises, people don’t consider the company goals. They follow the rules the system has taught them through experience.

Effective company goals change how decisions are made, who has authority, and who owns the outcome.

An Effective Way to Set Company Goals

The CEOs who break the cycle do something fundamentally different. They stop asking, “What should we achieve?” and start asking, “Who must we become for this goal to be inevitable?”

Step 1: Start With the Truth, Not the Vision

Before setting goals, the CEO surfaces the unspoken realities of the organization.

Where do decisions stall?
Where is accountability diffused?
Where does fear masquerade as professionalism?
Where do incentives quietly contradict stated values?

This requires restraint from fixing too quickly, defending past decisions, or softening the truth to keep things comfortable. The tradeoff is discomfort now versus failure later.

Until these truths are named, goals are fantasy.

Step 2: Define the Few Conditions That Matter

When too many goals exist, teams decide for themselves which ones matter in the moment. That creates inconsistency, politics, and slow execution.

Instead of many objectives, effective CEOs define a small number of non-negotiable conditions that govern how work gets done.

Examples:
Decisions are made with full ownership, not consensus. For any decision within a defined threshold, one person owns the call. Input is welcome. Agreement is not required. Once the decision is made, it is final unless materially new information appears.

Information flows directly to decision-makers, not through hierarchy. Customer data, risks, and failures are surfaced directly to the people who can act. Information is not summarized, softened, or delayed to protect layers of management.

Leaders trade personal comfort for organizational clarity. Leaders address conflict early, make unpopular calls when needed, and remove ambiguity even when it creates discomfort.

These are not slogans. They are constraints on behavior.

Step 3: Translate Conditions Into Observable Behavior

Each condition is translated into specific, visible changes in how work happens.

What meetings change?
What decisions move faster?
What behavior is no longer acceptable, even if results are good?

Examples:
If decisions are made with full ownership:
Which decisions are final unless materially new information appears?
Who owns those decisions and is expected to explain them when outcomes are poor?

If information flows directly to decision-makers:
What information now bypasses layers of management?
How quickly is it expected to reach someone who can act?

If leaders trade personal comfort for clarity:
Which conversations happen sooner instead of being deferred?
What behavior is no longer acceptable, even if short-term results look good?

Step 4: Model the Cost Personally

New conditions may ask people to take risks they were previously punished for taking. If the CEO does not publicly take those risks first, the organization will not believe the conditions are real. That risk is rarely financial. It shows up as reduced control, greater exposure, or delayed personal wins.

Who will the CEO become so that their organization thrives as it progresses towards those goals?

Examples:
Reduced control The CEO stops acting as the final decision-maker on product calls and lets an executive own the outcome, even when the decision is uncomfortable.

Increased exposure The CEO openly names a failed decision they made and explains the reasoning, without blame, signaling that mistakes are discussable rather than punishable.

Delayed personal wins The CEO supports a long-term product fix over a short-term revenue boost, even though it weakens a quarter’s narrative.

When the CEO takes that cost first, fear drops. Ownership rises. Authority stops enforcing compliance and starts making it safe to decide.

Step 5: Let Outcomes Emerge

When conditions are stable, outcomes follow. You cannot force growth through pressure any more than you can PIP a tree into growing faster. Pressure may increase activity, but it does not change what the system can produce.

Growth becomes inevitable only when the conditions that produce it are in place.

When decisions are clear and owned, teams stop revisiting the same issues and move forward faster. For example, a product decision made once and held allows Sales, Marketing, and Customer Success to align instead of hedging or constantly revisiting.

When behavior is healthy and consistent, culture strengthens. People stop guessing what is safe and start acting with confidence because expectations do not change week to week.

When ownership is real, execution accelerates. Work does not stall in review cycles or escalation loops. Problems surface earlier and get resolved by the people closest to them.

At that point, the goal is no longer chased. It emerges as a byproduct of a system designed to produce it.

A Goal Barometer

A company goal is well-set if the answer to this question is clear:

“When pressure hits, what will we do differently without needing to be reminded?”

If the answer is vague, the goal will fail.
If the answer is embodied, the goal will stick.

That is how effective company goals are set in a way that actually works. Of course, every company is unique and their goal setting must be unique. The examples provided are universal enough to drive the point but it is important to treat each company as its own – the goal setting methodology is universal, the solutions that come as a result are highly specific.

And if you need someone to talk to, I’d welcome getting to know you.

The post How to Set Effective Company Goals appeared first on Allen Adjamian.

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.

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Coaching operates in a space between potential and willingness. I can walk beside someone, ask the right questions, create space for reflection, but if they’re not ready to look inward and do the work, the process doesn’t land. Coaching isn’t about performance tricks or productivity hacks. It is not advice, nor consulting – those are mutually exclusive of coaching. It’s about confronting long-held and unaddressed beliefs and patterns, which requires courage, vulnerability, and a resolute, internal readiness.

So how do you know when you’re ready for coaching? Usually, it’s not from a book or a podcast. It shows up in lived experience. External signs emerge first: the nights where sleep won’t come because your mind keeps replaying the same decision; the creeping dissatisfaction even in success; the team that feels off; the company culture that doesn’t resemble the one you thought you were building; the results that no longer feel worth the cost; a desire to bow out of a company that’s doing well.

Then there are the internal signs. The silent weight of stress that no amount of strategy fixes. The dull fatigue that lingers under every achievement. The strain in your relationships. The loss of meaning, of purpose. The repeating thought, I can’t keep doing this like this. These are not failures. They are signals. Blaring signals, the psyche’s way of inviting you to take action towards growth.

Every single word I write, I have lived deeply. In addition to many roles and ventures, I was CEO of the same company for 15+ years. I’ve been in the deep trenches of founder burnout and I’ve also come out the other side, healthy and grateful.

If any of this resonates, coaching can help. It’s not about fixing what’s wrong; it’s about uncovering what’s true, beautiful and meaningful within you. The readiness isn’t about having answers; it’s about finally being willing to explore your deeper questions on this amazing journey you are on.

The post I Only Coach Those That… appeared first on Allen Adjamian.

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:

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.

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Somewhere along the way, what was once a passionate and life-affirming entrepreneurship journey had started becoming soul-sucking experience that I desperately wanted out of. I had dreams of crashing a plane into a moutain. I wasn’t even 35 yet.

At the time, it did not look like burnout. On paper, things were working. Deals closed. Teams moved. Projects delivered. KPIs good. Everyone was heads down, working. My days were filled and accounted for to the minute. But burnout rarely announces itself in the KPIs. It hid behind my competence. I kept producing because I didn’t know anything else, even as my body and life were sending signals of burnout.

You tell yourself relief will come after the next milestone, the next quarter, the next round or that elusive exit. I know now that relief and clarity never arrives on its own. It has to be deliberately designed into the system. Left unattended, burnout simply becomes a founder’s operating environment.

The first thing burnout distorted was my decision making.

I became narrower. Less curious. More reactive. Far more curt. Decisions optimized for my short-term relief rather than long-term vision. I deflected complex conversations because they felt heavy. I delayed strategic choices because I did not trust my own energy to see them through. Risk tolerance became like gambling at a casino. Some days I played it too safe, protecting myself from more load. Other days I took unnecessary risks out of quiet desperation, hoping momentum would shake something loose and I would find relief.

Company culture soon followed. Later I would learn that when a leader is burnt out, the organization feels it and absorbs it, whether they intend to or not. I became less present – hiding behind monitors at my home-office. Less available. Meetings shortened not out of efficiency but out of depletion. Patience thinned. I still cared, but care without energy and clarity translates poorly. Teams sense when decisions are made from survival instead of vision. Over time, that shows up as hesitation, second-guessing, and quiet disengagement. Our once-thriving company culture slowly disintegrated into something I don’t even have great words for… good people quit, the wrong people stayed.. etc etc. ufff.

I tried taking weeks off. Many times. Trips to Japan did not help. Neither did saunas, meditation, nor self-help books. I didn’t realize it then, but the problem was not tiredness. It was disconnection from purpose. Time away, followed by a return to the same incentives, the same internal pressure, the same unresolved questions, only reinforced my loop. It took years to realize rest without redesign of my life and habits just reinforced the burnout loop. What I needed was not another getaway. I needed honesty – about what was fueling me, and what was quietly consuming me.

Burnout thrives on avoidance and aloneness.

Avoidance of discomfort. Avoidance of parts of ourselves neglected. Avoidance of the question underneath all the motion. Why am I doing this in this way? And no one appropriate to talk to. Friends just sympathized and patted me on the back that I was a CEO and doing well. Therapy was helping my soul but not helping how I ran the business.

The shift for me began slowly when I began to reveal how I’m feeling to my mentor – a former C-level at Mattel & IBM, turned coach and confidant. I had never shared so deeply with him before, it had mostly just been conversations on driving revenue and scale. We were having lunch at Killer Shrimp in Marina Del Rey. He shared that I should turn towards the signals of my burnout and start listening to it. He shared his own struggles with burnout at Mattel back when they were launching one successful toy after another in the 70s and 80s. Back when they built toys to last using die cast metal, he would say often. With his council and ongoing support, I stopped asking how I can push through and started asking what is this trying to tell me. That question opened something within me and opened a pathway. Over time and with work with my coach, exhaustion stopped being an enemy to fight and became a signal to tune-in to. Awareness replaced brute force. And that awareness, applied consistently, opened the door to purposeful actions. All of this possible because I truly opened up to my mentor and had regular dialogue with him and began to do the work needed.

Getting help was not passive nor vague. It was uncomfortable at first.

He asked me key questions I would never have considered on my own, recommending I sit down and write out my responses in detail.

Working with my mentor meant slowing down enough to examine the stories I had been running for years. Stories about responsibility. Long held beliefs I had adopted, like “If you want something done right, you gotta do it yourself.” About self-worth being tied to output. About rest being earned rather than deserved and required. I used to have a magnet on my fridge I was proud of that read “I’ll sleep when I’m dead.” I threw it in the trash. Being coached, for me, looked like rigorous reflection paired with accountability. It meant tracing patterns across decades of my life, often back to my childhood. It meant recalling how influential my father’s voice had been when he had said just once “I don’t care what you do with your life so long as you make money.” It meant redesigning the company to be aligned with my values instead of habits.

Practically, it changed how I worked. Clearer boundaries. Fewer priorities. Decisions made earlier instead of postponed. Delegation that was real, not deflection. Whereas I used to make nearly all the decisions, I worked with our team to empower them all to make their own decisions in their capacity.

I let go of a lot of control I never should have had in the first place.

Space built into the calendar not as recovery, but as part of the work itself. No more meetings for me before 11AM. There were plenty of talented people in the company to handle daily small fires and get to resolution. Internally, it meant tolerating unease instead of numbing it with KPI analysis on dashboards. My NASA resembling dashboard got redesigned as well, down to just 3 metrics. Letting go of identities that were no longer serving me – tough one but ultimately very rewarding. Redefining success as something sustainable, repeatable, and meaningful.

This did not happen quickly. It was built steadily over years. But the result was a life and career that felt stable, peaceful, and successful in a way that was lasting. Burnout faded away like a smoldering fire that quietly extinguished itself because I was no longer ignoring its signals and had learned to attune and tend to those signals as a means to serve my purpose in life.

I retained my position as CEO and later sold the company to private equity – something I highly doubt could have happened as well as it did, if I had been operating under burnout.

If you are experiencing similar signals, invite yourself to take a pause. Step away from the next task. Do not ask what you need to finish. Ask what you need to feel whole again right now. That is where it began for me and what I work to pay-forward to the lives of other founders and CEOs. Working with my mentor became a very meaningful journey that uplifted my career to where I had envisioned it back in my 20s.

If you could use more support, it is not weakness, and maybe it’s a sign to explore coaching with someone you feel comfortable with.

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