Abandon All Hope of Mattering

I’ve been wrestling with an idea that sits at the heart of how we think about leadership: intentionally influencing others. Two pieces I wrote, three years apart, led me somewhere unexpected—what if we’ve got the whole thing backwards?

What follows is both the story of how I arrived there and where that insight took me. Part I traces my journey from what seemed like a straightforward observation—leading by example—to something much deeper. Part II pushes that insight to its logical conclusion, challenging almost everything we assume about influence and leadership.

Read together, these two pieces reveal something fascinating about management thinking: when you follow a practical observation rigorously enough, it can lead you to a breakthrough that changes how you see everything.

Part I. A Critical Self-Review

The Evolution of the Argument

Rereading my 2021 and 2024 pieces on leading by example side by side revealed an intellectual journey: from empirical clarity to philosophical uncertainty, and toward a breakthrough still waiting to be fully articulated.

The Initial Empirical Strength

The 2021 piece was ruthlessly efficient. Its argument was simple and undeniable: people see everything you do, not just what you intend them to see. This exposes the central fallacy of leading by example—you cannot control which examples you set. The strength of that argument lay in its brutal honesty and grounding in observable reality.

The Philosophical Wrestle

The 2024 piece, inspired by Javier Gomá Lanzón’s ideas, aspired to something more ambitious. It tried to shift focus from demonstrating to being, but fell short of its full potential. Caught between rejecting leading by example and salvaging some intentional influence through being an original, the piece lacked resolution. It reached toward something radical but didn’t quite grasp it.

The Core Problem

The flaw wasn’t in moving toward the philosophical—it was in stopping too soon. By trying to rehabilitate influence through originality, I overlooked the more profound implication: real influence arises only when you abandon all intention to influence.

The Missing Insight

The insight that eluded me is this: You matter most when you abandon all hope of mattering. True influence is unintentional. It emerges when you are fully absorbed in the work itself, not in the act of setting an example or managing perceptions.

This is not just a semantic distinction—it’s a fundamental truth that resolves the tension between the two pieces. The empirical clarity of 2021 shows why intentional influence fails. The philosophical wrestle of 2024 hints at why unintentional influence might be the only kind that exists.

Toward a Course Correction

The task, then, is not to choose between empirical honesty and philosophical depth but to integrate them. The next step demands:

Fully embracing the 2021 observation that people see everything.
Pushing Gomá’s distinction between being and demonstrating to its limits.
Exploring the paradox: true influence emerges through its complete abandonment.
Understanding why any intention to influence corrupts the possibility of genuine influence.

The goal is not to influence better—it’s to understand why influence only becomes possible when you stop trying to achieve it.

Part II. The Paradox of Influence: A Radical Insight

True influence exists only in its complete abandonment. The moment you intend to influence others, you fail. Why? Because people see everything. They see not only what you want them to see, but also every contradiction, every struggle, every unconscious motive. The attempt to curate your impact creates dissonance that others detect instinctively.

Consider the master woodworker. They don’t approach their bench thinking, “I must demonstrate proper technique for my apprentices.” Their mind is fully engaged with the work—reading the grain of the wood, adjusting to its resistance, letting the shape emerge. If you watch them, you’ll notice something profound: the moment their focus shifts from the craft to their performance, something essential is lost.

This is more than a lack of self-consciousness. It is what Heidegger might call authentic being: a way of existing that arises from full engagement with the task at hand. The woodworker’s mastery isn’t about showing anything. It’s about being fully present to the demands of the work itself.

The Nature of Authentic Being

Authentic being means engaging deeply with what is real—responding to the grain of the wood, the shape of the challenge, and the needs of the moment. It’s not about trying to be authentic or setting an example. That effort corrupts the very authenticity it seeks. The woodworker’s focus is not on influence but on the work—and that’s precisely what makes them influential.

The Freedom of Non-Intention

Here lies the paradox: abandoning intention is not a strategy. The moment you treat it as a technique—“If I stop trying to influence, I will influence more”—you’ve fallen back into the trap of intentionality. This abandonment is not tactical but liberating.

Like the woodworker, we are freed when we stop performing and simply engage with the real work before us. This freedom allows presence—authentic engagement with others and the task—because it releases us from the exhausting need to manage perceptions or outcomes.

Rethinking Exemplarity

This insight reframes Gomá Lanzón’s idea of exemplarity. While Gomá emphasizes being over demonstrating, his framework still implies a function: that being exemplary serves a social or moral purpose. But what if true exemplarity requires abandoning even that intention?

The woodworker teaches not by trying to teach but by fully inhabiting their craft. Influence emerges organically, not as a performance but as a consequence of their deep absorption. This is a more radical vision of exemplarity—one that dispenses with performance entirely.

The Management Paradox

This challenges the very structure of management thinking. Influence, as conventionally understood, fails because intention corrupts authenticity. Yet this doesn’t mean passivity. It means reorienting ourselves toward engagement with the craft of management—solving problems, making decisions, supporting others—not as a performance, but as real work.

Beyond Leadership

This insight unravels our conventional understanding of leadership. If leadership is the intentional exercise of influence, what happens when we abandon intention?

The answer lies in the woodworker’s workshop. True leadership may emerge not from trying to lead but from full absorption in the work of managing. When we abandon the desire to perform leadership, we step into something deeper—presence, authenticity, and real engagement.

The Final Paradox

Here we confront a stark truth, akin to Dante’s inscription: “Abandon all hope, ye who enter here.” To matter, we must abandon the hope of mattering. To influence, we must abandon the desire to influence.

This is not comfortable terrain for management thinking. It demands letting go of techniques, strategies, and even the very concept of leadership as intentional influence. But in that abandonment lies profound freedom—the freedom to engage fully in the craft of management itself.

When you stop trying to be influential, when you let go of curating your impact, you might finally begin to matter. But only if you pass through these gates, leaving behind the comfortable illusion of control.

Beyond them lies something simpler and truer: the craft itself. The paradox resolves when you realize that, in abandoning performance, you become who you are. And it is in that simple being that real influence—unintentional, unforced, undeniable—can finally emerge.

Don’t Be an Echo, Be a Voice

We say “Here’s what I think” with confidence that sounds authentic but often isn’t. When pressed to explain why we hold these views, our honest answer frequently boils down to: “Because Bob said it.”

This is the intellectual equivalent of a child saying they did something “because Tommy did it.” We recognize this pattern in children. But as adults, our intellectual lives often follow the same pattern. We’re just more sophisticated about how we phrase it.

Confidence isn’t the same as clarity. The volume of your voice doesn’t prove ownership.

The real question isn’t whether we agree with Bob. The real question is: how do we agree with Bob?

The architecture of agreement

Genuine agreement requires more work than most people realize. It’s not enough to like Bob’s conclusion or find his position convenient. Real agreement works on at least three levels:

Bob’s reasons – What evidence is he using? What concerns drive his position?

Bob’s reasoning – How does he connect his reasons to his conclusions? What logical steps does he take?

Bob’s assumptions – Where is Bob coming from? What foundational beliefs shape how he sees the world?

Think of it this way: Bob’s reasons are the ingredients he uses. His reasoning is the recipe, how he combines and cooks them. His assumptions are his taste preferences, shaped by experience, culture, or mood. You can’t really cook the same dish until you understand all three.

But here’s what strikes me as crucial: you can only meaningfully agree with Bob’s reasons when you hold reasons of your own. Without your own foundation of thinking, all you can do is understand Bob’s position. You can’t genuinely agree or disagree with it.

If you don’t have your own reasons, then you’re not thinking. That’s intellectual vending.

The precision of disagreement

Most disagreement is lazy. We call people “idiots” or “morons.” Words that translate across cultures as universal ways to voice disagreement without doing any intellectual work.

But what becomes possible when disagreement gets precise? You might disagree with someone’s reasons, their reasoning, or their assumptions. Knowing where you disagree allows you to articulate what you disagree with specifically.

I find I can’t meaningfully disagree with Bob until I understand his position well enough to present it as well as Bob himself presented it. Or even stronger.

When I can make Bob’s argument better than Bob made it, something shifts. I’ve demonstrated sufficient understanding to meaningfully disagree. Not because I’ve earned some rhetorical right, but because I’ve done the work to know what I’m actually disagreeing with.

In other words, I need to find all the reasons to agree with Bob before I can explain which reasons, reasoning, or assumptions I don’t share.

The dance

When both parties commit to this standard, understanding each other well enough to strengthen each other’s positions, something remarkable happens. Disagreement transforms from adversarial battle into a dance.

You take turns making each other’s arguments stronger, then explaining precisely where and why you part ways. This creates space for genuine intellectual engagement rather than the exchange of borrowed talking points.

What I find beautifully ironic is that this approach relieves anxiety rather than creating it. When you know that Bob is committed to understanding your position well enough to present it fairly before he disagrees with it, you can relax. You don’t have to be defensive or perfect. If there’s a flaw in your reasoning, Bob will find it. But only after he’s done the work to understand and strengthen your position first.

An echo is what happens when you’re alone, yelling into emptiness. Even in a room full of people, if you’re just repeating borrowed thoughts, you’re essentially alone. Nothing meaningful comes back to you because you’re not engaging with anyone’s actual thinking.

But having a voice (your own reasons, reasoning, and assumptions developed through genuine exploration) enables you to engage in the dance of authentic disagreement. Voice enables connection with other thinking people.

The paradox is this: even though developing your own voice feels like solitary work, you can never complete it alone. The dance requires a partner. You need other voices to help you challenge your reasoning and strengthen your arguments.

If you’ve done the work, you’ll know the difference between shouting into an empty canyon and moving in step with another thoughtful person.

Related writings: I’ve explored the distinction between genuine and borrowed thinking: what intellectual presence requires, the cost of translating thoughts for comfort, and how understanding emerges through dialogue.

[photo by Andrew Seaman]

Dear Line and Middle Managers: I’m a Big Fan

I’m a huge fan.
There is no limit to the admiration I have for the life you lead and the work you do.
You are the heart of an organization.

The things you do and say—
And the things you choose not to do,
And not to say—
Have significant, direct, and immediate impact.

On the lives of your team members.
On the lives of their families.
On the communities they belong to.

Teachers of the Workplace

In my simple mind, I equate your impact to that of teachers.
I’ve been a professor in the classroom.
A program manager outside it.
A dean sitting in an office.

And I know this:
The immediate—unmediated—impact of a teacher
On the life of their students is immeasurable.

The further you are from the classroom,
The more mediated the impact.

So it is with managers:
C-level executives,
VPs of every sort—
They get the attention.

But your type of impact?
Immediate. Real.
Life-changing.

The Challenge of Being in the Middle

You are a manager.
You also have a manager.

Sandwiched between them, you create an environment
Where your people can get their work done,
Even while living in the environment
That your manager builds for you.

And we all know:
These do not necessarily align.

The devastating impact of a micromanager—
Could anything make it clearer?

You rely on your team’s talents,
On their readiness—
That mix of ability and willingness
You know so well.

And yet,
There they are,
In all the splendor of their self-importance,
Barking orders from above,
Sweeping in over your head,
Into the lives of your team members.

The Transition Paradox

What makes us successful at one level
Does not guarantee success at the next.

Being an excellent individual contributor
Does not make you an excellent manager
Of individual contributors.

It’s not automatic.
It requires different skills.
Different types of experience.

And yet, how often do we believe
That others will succeed
Simply by doing what we say?

The same is true for you.
What made you successful as a manager of individual contributors
Isn’t necessarily what will make you successful
As a manager of managers.

Different skills.
Different experiences.
More politics.
More complexity.

What I See in You

I see you.
I hear you.

In our coaching conversations,
I admire you.

Resilience.
That’s the word that comes to mind.

And wisdom—
That ability to separate wheat from chaff,
Day in and day out.

In the mix, I see those
Who truly care for their team members
And those who are focused on their own promotion.

These need not be mutually exclusive.
But sometimes, they are.

A Glass Office

Your team members see you.
They see everything about you.

Even if you’re not on site,
You’re in a glass office.

They see what you do.
They hear what you say.

And they notice—
What you choose not to do.
What you choose not to say.

They see your efforts to connect.
And the times you don’t.

They see the priorities you make:
Your promotion—or theirs.

Your success—or their success.

These need not be mutually exclusive.
But sometimes, they are.

An Ode to You

It’s a complex, layered, multi-faceted existence you lead.
And I applaud you for it.

I see you.
I admire you.
And I’m a big fan.

photo by Mel Poole

You’re Indispensable: That Sucks for All of Us

Protecting Our People’s Right to a Full Life – a policy

Core Purpose

Every person has the right to a full, rich life outside of work. It is fundamental to who we are as an organization. No one should sacrifice their personal life, family time, or wellbeing because they’ve become “indispensable” to our operations.

Why This Matters

1. Life Comes First

People deserve to be fully present for their children’s birthdays
Vacations should be times of real relaxation, not constant check-ins
Family events, holidays, and personal milestones should be celebrated without work interruption
Weekends belong to our people, not to our company
Sick days are for getting better, not answering urgent calls

2. Protecting Personal Time

No one should miss their child’s school play because “only they know how to fix it”
No one should have their vacation interrupted because “we can’t do this without them”
No one should lose sleep because they’re the “only one who can handle this client”
No one should miss family dinner because they’re the “only one who knows the system”

Our Stand

If anyone becomes “indispensable,” we have failed as an organization. We have failed to:

Respect their right to a life outside work
Build proper systems and processes
Foster true teamwork and knowledge sharing
Live up to our values

Corrective Action

When someone becomes indispensable:

Recognize this as an organizational failure – specifically, a leadership failure
Immediately redistribute knowledge and responsibilities to protect the person
Fix the systemic issues that allowed this to happen
Hold the responsible manager accountable through performance management
If a manager persistently creates conditions where people become indispensable or overworks people despite intervention, termination may be necessary because they have demonstrated inability to lead in ways that honor human dignity

Prevention

We protect our people’s right to a life by:

Building redundancy into all critical functions
Ensuring knowledge is shared across teams
Creating clear documentation
Cross-training as a standard practice
Planning for absences and transitions
Celebrating time off and work-life boundaries

Leadership Commitment

Leaders are responsible for:

Protecting everyone’s right to disconnect from work
Building systems that don’t depend on individual heroes
Creating a culture where taking time off is celebrated
Ensuring no one becomes a single point of failure

Remember: If someone can demonstrate they’ve become indispensable, we have failed organizationally and we’ve failed them as human beings. We’ve allowed a situation where their personal life can be held hostage by work demands. That sucks for all of us.

photo by Rahul Saraf

Lies, Damned Lies, and Performance Evaluations

You do their performance evaluations. Their survival in the company depends on your decision and your criteria. So when you say “I get along fine with the people who report to me because I always get good evaluations from them,” do you really think that’s evidence?

This doesn’t mean they lack courage or are being strategic. They might be entirely sincere. The asymmetry simply means you cannot know. When you hold power over someone’s professional life, that structural inequality is present in every interaction whether anyone responds to it or not. Their positive evaluation might reflect their genuine experience of working with you. Or it might not. The asymmetry makes the meaning of their feedback fundamentally indeterminate.

And while the surveys are anonymous, there are just too many managers who’ve told me they can recognize who wrote the comments by the way it was written and the words they used. So even the structural protection of anonymity often dissolves in practice. And if comments are too risky and you take them off, then you’re left with numbers. And as Disraeli said, there are lies, damned lies, and statistics.

You might deserve the praise. But their positive evaluation, given the context, cannot tell you whether you do.

The same dynamic appears when executives cite employee engagement surveys as proof their culture is healthy. The survey measures what employees are willing to say about a culture that determines whether they remain employed. What you’re measuring isn’t engagement. It’s what people are willing to have measured.

photo by Jon Tyson

Trust Doesn’t Work Like That

I keep seeing versions of the same claim: that trust is the natural result of psychological safety. Or that it can be engineered through a formula.

That’s tidy. It’s appealing and it’s convenient.

It’s also not true.

Psychological safety may create the conditions where trust could grow. But that’s all they are: conditions. Trust is never automatic, and never unilateral. It’s not a reward for checking the right boxes.

Trust is a decision. It’s someone else’s decision.

And that changes everything.

Trust works like foreign currency. It’s never strong in general, only strong against something else. The dollar is not stronger overall; it is stronger than the euro, the yen, whatever you’re measuring it against. Trust operates the same way: relational, contextual, and maddeningly specific. You might be someone’s anchor while remaining someone else’s question mark.

Here’s the thing: you can create the perfect conditions (open communication, demonstrated competence, unwavering reliability) and still manufacture nothing. You can create the environment where trust might grow, but the seed belongs to someone else entirely.

The other person chooses to trust. It doesn’t happen automatically. Their history, their scars, their appetite for vulnerability are all variables you’ll never control, no matter how trustworthy you become.

Which leaves you with a paradox in human connection: you can perfect your trustworthiness but never guarantee their trust. You can tend the garden but not force the bloom.

So create the conditions and then wait.

You can knock. But the door has to be opened from the other side.

The idea that trust is relational, chosen, and not guaranteed lies at the heart of my approach to leadership practice. It invites us to hold both our responsibility for trustworthiness and our humility about what trust ultimately requires.

Every orchestra needs a conductor. Really?

The Orpheus Chamber Orchestra has operated without a conductor since 1972. Representatives from each section meet to discuss how they’ll approach a piece. Leadership rotates. Decisions emerge from dialogue among those who will execute them.

They’re a Grammy Award-winning ensemble.

Each musician must listen more intently and communicate more directly. Take greater ownership of the whole. Lead when their expertise matters most. Follow when others’ does. This distribution of authority changes what becomes possible.

Your organization employs people who create knowledge, apply expertise, and solve novel problems. The work can’t be fully specified in advance. Solutions emerge through collaboration. Value comes from synthesis and innovation.

Management is coordination. Things need to be done, sometimes in certain ways, at certain times, by certain deadlines. The question is where the capacity for coordination resides.

Orpheus demonstrates that coordination can live in a system rather than in a person. This requires structure: the section representatives, the meeting protocols, and the rotation of leadership within sections. It requires discipline, deep engagement, clear communication, and shared responsibility.

It doesn’t require a conductor.

The musicians need a framework for deciding together how to play. They need engagement with each other and the work. They need conditions in which shared vision can emerge.

Remove the conductor and different questions surface. What does leadership look like when genuinely distributed? What does a manager do when the team coordinates itself? What changes about authority when those doing the work hold it?

Orpheus is smaller than a full symphony. They select members carefully. They’ve built practices over decades. Their approach takes more time and generates more conflict. It demands more from each musician. It’s not universal.

But it exists. And it produces excellence.

The conductor stands separate from the orchestra, interpreting the score and imposing coherence. Orpheus embeds interpretation and coherence within the ensemble itself. One model centralizes the capacity for coordination. The other distributes it.

Which model matches how knowledge actually gets created in your organization? Not the theory. Not the org chart. The reality of how problems get solved when the work goes well.

The conductor metaphor has shaped management thinking for decades. It suggests that coordination requires a central authority who stands apart from the work, sees the whole, and directs the parts.

Orpheus suggests something different. Coordination is a capacity that can be built into how people work together. Authority can reside in those doing the work. The manager’s role might be something other than conducting.

What if it never was?

photo by Luisa Wachsmuth

Quiet Giving

In the early 2000s, a group approached me with a simple but unusual question. They were earning more than they needed and wanted to give back. But their question wasn’t the usual “how do I give?” or “where do I give?” Instead, they asked something different: “How can we give without it being about us?” These weren’t people seeking tax advantages or recognition. They wanted to give in ways that left no fingerprints.

The Search

We held a few workshops exploring their question. And then they started experimenting. What if you gave in ways that created no relationship at all? What if resources flowed so cleanly that they left no trace of the giver? They noticed immediately what got in the way. Foundations. Named donations. Tax breaks. The entire apparatus that had grown up around giving.

Through frank conversations, patterns emerged. They realized something fundamental: if they wanted to improve circumstances for specific persons – with first names and last names – they had to understand who those people were and what their situations were. Not categories. Not demographics. Actual people in actual situations. Two questions became essential: What does this specific person actually need? And what is the broader context of that need?

But they learned to be careful with language. They weren’t “solving problems” – they were improving circumstances or enabling initiatives. This precision mattered. A scholarship might provide access to college, but if the student isn’t eating a nutritious meal today, the scholarship doesn’t improve the circumstances in which they’re trying to learn. The group learned to ask: What is this person already trying to do? What would actually improve the circumstances in which they’re acting?

They agreed to name conditions precisely. Not the sanitized language of nonprofit reports, but actual circumstances. Not “food insecurity” – not eating a nutritious meal today. Not “housing instability” – no place to sleep tonight. Vague language lets you avoid seeing what’s actually happening. Precise language forces you to see the person. Quiet giving wasn’t just about anonymity. It was about accuracy – seeing someone clearly enough that resources could move without distortion.

Cash worked better than checks. Paying someone’s overdue bill without telling them who paid it. Adding time to an expiring parking meter. Funding what someone actually needed after understanding their specific circumstances. Over time they discovered ways to give more substantially while remaining discreet. The methods were surprisingly simple: give without announcement, act without signature, build without claiming. Know the person, not the category. Name the circumstances precisely. Enable their initiatives rather than solving their problems. They were amazed at how value moves most freely when nothing echoes back.

The Reveal

Little did they know, someone had already answered their question. Not through philosophy, but through practice.

In 1939, a young man named Nicholas Winton sat at a small desk filling out papers long into the night. No medals. No spotlight. Just a typewriter and the desperate hope of saving as many children as he could before the borders closed. One by one, he found trains. Found families. Found a way. 669 children escaped because one ordinary man chose extraordinary compassion. He never spoke about it. The papers went into a dusty box in his attic.

Fifty years later, his daughter found them while cleaning. Had she not been curious that day, Winton would have taken the story to his grave. 669 lives saved, zero credit received, zero credit sought.

Shortly after the discovery, Winton sat in a TV studio, unaware of what was coming. The host asked the audience: “If you were saved by Nicholas Winton, please stand up.” Row by row, people rose. Mothers. Fathers. Grandparents. Lives that existed only because he cared. Winton turned, eyes wide. A lifetime of quiet love suddenly visible.

This is what the group had been searching for. Not the drama of the discovery, but the fifty years of silence. The genuine indifference to credit. The dusty box that might never have been opened. Resources flowing freely, leaving no trace, requiring no acknowledgment. Winton hadn’t strategized anonymity. He simply hadn’t thought to mention it.

The Tension

Ken Barrett runs laundromats. For years, he kept his WiFi password posted publicly. Nothing special. Just access. One day, a mother approached him in tears: “If it wasn’t for your free WiFi, my daughter and her friends may not have graduated.” Her family couldn’t afford internet. After the library closed, the kids walked to Ken’s laundromat to finish homework. Ken added benches and tables. Made it comfortable. Created study spaces in four of his five locations.

He didn’t announce this. Someone else noticed and shared his story. Now thousands know his name. Ken gave without signature. Recognition came anyway, as a side effect of genuine impact.

The question: Can giving be “quiet” if it becomes visible?

The group wrestled with this. Was Ken’s story evidence that they’d failed, or evidence that they’d succeeded? They landed somewhere unexpected: Don’t avoid visibility. Avoid seeking it. The goal is perfect indifference to credit. The quieter your intention, the louder the impact can afford to be.

Other Examples

They started finding more examples. Not people following a philosophy, but people who’d simply practiced this way of being.

Paul Newman walked into a Manhattan shelter on Christmas Eve in 1983 carrying two wooden crates from his farm. “Where’s the kitchen?” he asked, already rolling up his sleeves. For hours, he cooked. Garlic sizzled, bread rose, soup bubbled. He moved between the stove and the tables, serving over two hundred people. When the last guest left, he stayed to sweep the floor and stack chairs. Before slipping out into the snow, he said softly to a volunteer: “Food matters. But being here with them matters more.” The next morning, no newspapers called. Newman had told no one. One of the most recognizable faces in America, uninterested in leveraging it.

Bob Marley wrote “No Woman, No Cry” but gave the songwriting credit to his friend Vincent Ford, who ran a soup kitchen in Trenchtown. The royalties from that song flowed directly to keep the kitchen running for years. No foundation. No administrative costs. No naming rights. Just a steady stream of resources flowing exactly where they were needed. Ford’s name appeared on the credits. The motivation stayed hidden for years.

Ken created access through infrastructure. Newman created connection through presence. Marley created sustainability through redirection. Same principle: remove yourself from the equation and let resources flow where they’re needed. None of them had strategized it. Like Winton, they simply hadn’t thought it remarkable enough to mention.

Who Benefits?

The group started asking a different kind of question. If giving could be this simple and effective, why had charity become so complicated? What were all the other systems actually for?

Follow the infrastructure that has grown up around modern philanthropic giving: Professional fundraisers charge steep fees. Nonprofit executives earn six-figure salaries. A whole industry profits from monitoring and evaluating philanthropy. Corporate donors receive tax deductions and marketing value that often exceed their actual giving. Wealthy philanthropists gain social influence, naming rights, and legacy control. Grant-making foundations accumulate power while their assets often grow faster than they’re distributed. The people who need resources often receive less than half of what was originally given.

The financial incentives run deeper. Nonprofit organizations don’t pay taxes on property, income, or investments. Massive public subsidy. Meanwhile, donors deduct their contributions. Both benefits come at public expense. Decisions about deployment remain entirely private. Taxpayers subsidize private charitable choices twice over.

The Transaction

Walk through any hospital, university, or cultural institution. Notice how many surfaces bear donors’ names. Buildings, wings, rooms, benches, bricks. All for sale in exchange for recognition that outlives the donor.

Much of modern philanthropy purchases immortality. The institution becomes a monument to the donor. The hospital wing heals people, yes. It also ensures the donor’s name outlives them. Naming rights expose the transaction perfectly: the “gift” is contingent on perpetual recognition. The recipient becomes billboard provider. You’re purchasing something in return.

The System

Professionalization makes social problems more profitable to manage than to solve. Nonprofit organizations depend on the continued existence of the problems they address. Complete success would eliminate their reason for existing.

This creates an ecosystem whose livelihood depends on the perpetuation of need. The incentive structure rewards growth, visibility, and fundraising capacity rather than actual problem-solving. Grant-making processes favor organizations that can write compelling proposals over those that might be most effective at direct service. The apparatus privileges presentation over impact.

Much of what we call charitable giving has become a sophisticated system for extracting value from the human desire to improve others’ circumstances. Professional fundraisers need donors who need tax advantages who need recognition who need causes that need management who need oversight that needs funding. Everyone in the chain benefits. Except the people the charity claims to serve.

Ancient Wisdom

The group had thought they were pioneering something. But near the end of our workshops, someone brought in a passage: “When you give to the needy, do not let your left hand know what your right hand is doing.”

The wisdom was explicit: invisibility, ego-removal, the danger of making charity about the giver. Modern philanthropy has built an entire industry around making sure everyone knows. Elaborate systems for the left hand to track, publicize, and celebrate what the right hand is doing.

Winton had lived this differently. For fifty years, he forgot to mention it. The papers sat in a box. The children grew into parents and grandparents while he went about his ordinary days, not thinking of himself as remarkable. The group hadn’t discovered something new. They’d rediscovered something old, something that the complexity of modern philanthropy had buried.

What This Reveals

A small group of people developed effective ways to improve others’ circumstances that required no infrastructure, generated no overhead, created no tax complications, and left no traces. What is all the complexity of modern philanthropy actually for?

Modern philanthropy channels genuine human compassion into a system that socializes the costs through tax subsidies while privatizing the benefits: recognition, influence, tax savings. It transforms the simple impulse to improve others’ circumstances into a complex industry that serves everyone except those who need resources. By making charity complicated, expensive, and institutional, the system convinces us that improving others’ circumstances requires expertise, infrastructure, and mediation. The group discovered the opposite. Removing all those barriers made resources flow more freely.

The best giving leaves no trace. Impact flows most freely when nothing echoes back. Removing yourself from the equation is a stance.

The End

The group held their final workshop session on a Tuesday afternoon. They had found what they were looking for. A practice so simple it required nothing but commitment to its principle.

They understood what Winton had embodied, what Barrett and Newman and Marley had practiced in their different ways: that the best giving leaves no trace, that impact flows most freely when nothing echoes back, that removing yourself from the equation is a stance.

We closed the session. People gathered their things. A few conversations in the parking lot, then silence. I’ve never organized a reunion. Never sent a follow-up survey. Never asked what became of their practice. Because if they’re true to what they discovered, they’re somewhere right now improving the circumstances of someone with a first name and a last name. And I will never hear from them again.

photo by Kayra Siddik

What You Lose Every Time You Get Promoted

Organizations rarely name what actually happens when you get promoted: each transition destroys your identity. The capabilities and ways of working that made you successful at one level become obsolete at the next. Every promotion is not an expansion of capability. It is the death of one professional identity and the birth of another. And that destruction follows a recursive pattern that compounds with every promotion.

The recursive pattern

When you move from individual contributor to manager, you lose the satisfaction of creating tangible output and must find meaning in developing others. When you move from manager to manager of managers, you lose direct contact with individual development and must find meaning in shaping systems. When you move to organizational leadership, you lose decisive ownership of your domain and must find meaning in collaborative deliberation with peers.

Each transition asks you to surrender the identity and capabilities that made you successful at the previous level. The engineering manager who writes code at night isn’t integrating her technical skills. She’s trying to keep a dead identity on life support.

And each time, the new identity is more abstract:

IC identity: “I wrote this code. I designed this system.” You can point to the thing you made today.
Manager identity: “My team shipped this feature.” You can still see the output, even if your hands didn’t create it.
Manager of Managers identity: “The organization delivered these results.” The causal chain is longer.
Organizational Leader identity: “We navigated this tension productively and made a better collective decision.” Your contribution is the quality of the deliberative process itself, almost entirely invisible.

Each level is harder to inhabit, harder to feel competent in, provides less immediate satisfaction. The grief compounds because just when you’ve finally learned to derive meaning from the abstraction, just when you’ve built a new professional identity and found your footing, you get promoted. You spend two years discovering that your value comes from developing your team rather than doing the work yourself. You finally feel the satisfaction when someone you coached has a breakthrough. And then we promote you. That direct development work you just learned to love? Not your job anymore.

The refuge of power

Leaders retreat to what they know, seeking refuge in an identity they know how to inhabit. Where they can still feel competent. Where their expertise still matters in ways they can directly experience. Where they have control over variables that produce tangible outcomes.

When you can no longer derive identity from what you produce, you grab for identity through what you can control. Power becomes the refuge from abstraction and loss. You reach for certainty because deciding means you don’t have to sit in ambiguity. You seek visibility because when people do what you say, you can see your impact. You tighten control because determining outcomes means you’re not dependent on others. You validate your expertise by ensuring people defer to you, proving you still matter.

The CEO who micromanages is seeking the feeling of competence through control because they never successfully grieved the loss of hands-on creation. The executive who dominates meetings is grasping for the certainty of “being right” because the ambiguity of collaborative deliberation provides no ground to stand on.

Organizations full of individually capable leaders become toxic political environments because they promoted people into identity-destroying transitions without support. But this isn’t only psychological failure. It’s structural design. Organizations reward executives who “take charge” and “drive results,” language that encodes a bias toward unilateral control over collaborative deliberation. The very behaviors that indicate unprocessed grief are the ones that get celebrated and compensated.

Power is what you reach for when you’re drowning in abstraction and loss. The organizational debt of eroded trust, broken relationships, alliance-building instead of collaboration isn’t a failure of process or skills. It’s unprocessed grief manifesting as destructive behavior.

What I observe in those who navigate this well

The people who make it through these transitions share something I find interesting: they work as if they’re managing one team, the people who report directly to them. Not the team below them. Not peer domains. Not work that now belongs to their reports. Just their team.

This pattern holds at every level. The manager focuses on their direct reports (the ICs). The manager of managers focuses on their direct reports (the managers). The functional leader focuses on their direct reports (the senior managers). The organizational leader focuses on their direct reports and their peers as their working team.

When leaders violate that boundary, managing past their directs or trying to control peer domains, they seem to be using positional power to avoid grief. Staying in an old identity by force. What they’re missing is operational clarity about where their actual leverage is. A manager trying to manage two levels down is working on variables they don’t actually control. Their direct report sits between them and that team. Any attempt to go around them either undermines authority or wastes energy on influence they don’t have.

The leaders who navigate transitions well appear clearer about the actual nature of their work. They identify where their leverage is and stay focused there. But holding that boundary seems to require staying with discomfort when every instinct tells you to reach for the familiar.

What I notice in those who make it through is something that might be called the discipline of non-interference. The capacity to not act when action would provide comfort but undermine others’ development. Leadership as restraint practiced at scale. The hardest transition isn’t learning new skills. It’s learning when not to use the skills that made you successful. Tolerating the space where you’re not the hero, not the expert, not the decider. They hold the boundary as a commitment that seems to force them to discover what contribution means at this level.

What enables someone to stay there long enough to discover new sources of meaning? Those who make it through begin to notice impact in forms they didn’t previously recognize as contribution. They start to see that the abstract work (the quality of a deliberation, the strength of a system, the capability of their team) actually does produce something real, even if their hands never touch it. The question becomes: can you stay in the not-knowing long enough to discover what satisfaction feels like at this level of abstraction?

The expanding scope

What changes at each level isn’t the principle of “manage your team.” What changes is the scope of what you must consider. But here’s the paradox: your scope expands while your leverage contracts.

Manager: your team’s work, how it fits into the broader function, coordination with adjacent teams
Manager of Managers: the entire functional domain, resource allocation, functional strategy
Functional Leader: your function’s role in organizational strategy, dependencies with other functions, how your decisions affect the whole company
Organizational Leader: the entire enterprise (market dynamics, competitive landscape, cross-functional tradeoffs, long-term viability)

Yet at every level, you still only directly manage one team. The challenge becomes: How do I make good decisions that account for this massive scope of consideration, when my direct control is limited to developing this small group of people who report to me?

The organization works because everyone is applying the same principle at their level. Each person managing their team, considering their scope, with that same discipline recursing down through every layer.

The reframe

At every level, the people who report to you are contributors. They’re just contributing different things:

ICs contribute technical output, functional execution, tangible deliverables
Managers contribute team capability, people development, coordinated execution
Managers of Managers contribute organizational systems, functional strategy, leadership capacity
Functional Leaders contribute cross-functional integration, organizational outcomes, strategic direction

You’re always managing contributors. The nature of their contribution changes, but your job remains the same: enable your contributors to contribute at their level.

And you yourself are a contributor to the level you report to. The manager contributes team capability to the manager of managers. The functional leader contributes cross-functional integration to the organizational leadership team. Everyone is simultaneously managing contributors below them and contributing to the level above them.

You don’t stop being a contributor when you become a manager. You become a different kind of contributor. You don’t stop managing contributors. You manage contributors whose contribution is enabling other contributors. The grief isn’t “I’m no longer a contributor.” It’s “my form of contribution has changed.”

What we’re really asking

Becoming an organizational leader means surrendering decisive control and unilateral authority (the very capabilities that defined functional leadership excellence) and finding meaning in something maximally abstract: the quality of collective deliberation itself. You must derive satisfaction from outcomes you don’t fully control. You must feel competent at work that produces no tangible artifacts. You must find meaning in the deliberative process rather than in decisive action. Your contribution is the quality of your engagement with peers, an identity that only exists in relationship and can’t be fully controlled by any individual.

That’s grief work. Until we name it as such, we’ll keep promoting people into identity-destroying transitions without support, creating the organizational debt of broken relationships and toxic politics, then wondering why smart, capable leaders keep struggling with cross-functional collaboration.

Navigating these transitions requires yet another surrender of what made you successful, yet another grief process for what you’ve lost, and yet another discovery of meaning in increasing abstraction. All while everyone pretends it’s just learning new collaboration skills.

photo by CHUTTERSNAP

The Columbo Advantage: How cultural narratives create negotiation blind spots

When a culture invests heavily in a particular image of power, the blind spots become predictable. Americans consume Superman mythology daily: Iron Man, Captain America, the archetype where speed, polish, and overt competence signal strength. This creates a perceptual framework. Power looks like this.

In negotiation, this framework becomes a vulnerability.

Superman

Cultural narratives shape how people allocate attention, what cues they privilege, and where they expect power to reside. The Superman narrative teaches what strength looks like. More importantly, it teaches what doesn’t count as strength. That negative space becomes structural vulnerability.

When someone scans for Superman, they’re matching against a template: crisp strategy, decisive posture, visible capability. If you don’t fit, you slide beneath conscious attention. You’re not the negotiator. You’re just there.

The evaluation occurs pre-consciously, in seconds. If you don’t fit the schema, you’re filed as non-threat. That classification is remarkably difficult to revise.

Columbo

Go slow. Talk slow. Speak circuitously. Look unthreatening, and they won’t see you coming. By the time they recognize you’re negotiating, you’re already behind them.

Lieutenant Columbo: rumpled raincoat, apologetic tone, meandering questions. Suspects underestimated him because he violated every cultural marker of competence. By the time they realized what was happening, he’d already mapped their story and found the contradictions.

When you violate the template, you create a classification problem. They can’t place you. While they’re trying to understand what you’re doing, you’re already structuring the game.

Speed, polish, and visible efficiency can be tactical liabilities. When you present as Superman, you confirm expectations. You’re legible, predictable, and easy to respond to.

Someone who understands the narrative their counterpart has internalized gains leverage before any tactic is deployed.

Negotiation begins with the cultural stories that shape what people can see. Walking into a negotiation with Superman narratives running in the background isn’t a personal failing. It’s predictable cultural training.

Predictable patterns create predictable openings.

Notice the perceptual system you’re operating inside. Notice the one your counterpart is operating inside. By the time they see you, you’re already standing exactly where you need to be.