Category: Manage yourself

Whose Accounting?

What we carry without knowing we’re carrying it

Everyone in business knows the phrase: “you’ve been too close to it, you need a fresh set of eyes.” Bring someone in who hasn’t seen it before. The assumption is that familiarity is the problem and distance is the cure.

It’s not wrong. Familiarity does blind. But the phrase quietly assumes that the eyes are neutral, that seeing freshly means seeing without the residue of how things are usually measured, what success is supposed to look like.

I’ve spent a lot of time in rooms where fresh eyes were brought in. What I’ve noticed is that they almost always see through the same lens as the people who were already looking. They see the content clearly, sometimes more clearly than those who’d stopped noticing it. But the frame they use to see it is the same frame. The same definition of performance. The same theory of what organizations are for. The same accounting.

Fresh eyes. Inherited lens.

This is what makes zero-based budgeting more interesting to me than it first appears. And also more troubling.

The appeal is obvious. Rather than assuming that what was spent last year deserves to be spent again this year, you start from zero. Every line item has to justify its existence. The burden of proof shifts from the new to the existing. Rational on its face. Rigorous, even.

But zero-based budgeting isn’t actually rigorous. It feels rigorous because it’s effortful. What it actually does is substitute the assumptions of the present for the assumptions of the past. You are not eliminating the bet. You are placing a new one: using today’s criteria and today’s sense of what matters against a future you cannot see. The examination is real. The certainty it produces is not.

Organizations almost never say this out loud. They call it rigor because rigor implies arrival. But what they are really doing is hypothesis testing, and they would rather not know that.

I was mulling this over on a walk in my new surroundings when the question turned inward.

If I zero-based my life (examined every commitment and chose consciously rather than merely inherited), what would I actually have done? The same thing. I would be using the criteria I hold today and the sense of what matters that I have assembled over time. Against a future I cannot see, for a self I don’t yet know.

The examined life is not the life of better choices. It is the life of more conscious bets.

That’s already a less comfortable claim than the one usually made for examination: that the unexamined life is the problem and looking closely is the answer. But scrutiny only relocates the uncertainty. The person who drifts inherits assumptions they never inspected. The person who examines owns assumptions they chose. Neither knows what the future needed them to carry.

And there is a harder problem underneath this one.

When you zero-base your commitment to success, the shape of a career, or what contribution looks like: what criteria are you applying? If they are the institution’s criteria, absorbed across years of moving through structures that assumed them without ever stating them, then the examination isn’t liberation. It’s ratification. The instrument is made of the same material as what it’s trying to measure.

Which means the person who examines their life using the institution’s definition of success, concludes that yes, this matters, and now owns it consciously. They may be more captured than the person who never looked. They now defend the framework as chosen rather than inherited. The examination reproduced the lens. They just signed for the delivery.

You cannot zero-base the categories using the categories.

I don’t have an exit from this. I’m not sure there is one. What I have is the distinction between two kinds of examined life: the one that achieves conscious ownership of its commitments, and the one that keeps asking whose commitments these are and by whose accounting. The first is more rigorous than drifting. The second is more uncomfortable than the first.

It is also, I think, the only version that earns the name.

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photo by Graham Covington

The question behind the question

The program had barely begun (just past introductions) when one of the participants interrupted the facilitator. Not with a question, exactly. More of a challenge.

“What could you possibly bring to this room, never having been a C-level executive yourself? Why are you worthy of my time?”

The room went quiet.

The facilitator took a moment. Then she said:

Off the bat, I can tell you two things I bring to this room.

First, I am a professional who deals with other professionals with respect. You can expect that from me at all times. And what that means, among other things, is that I will never interrupt others.

Second, before this program is over, you will have insights into what it is about yourself that led you to ask this question, at this moment, in this manner, and what impact that might have on your management practice.

Then the program continued.

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photo by Tim Mossholder

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.

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photo by CHUTTERSNAP

The False Promise of Compartmentalization: When the body lives what the mind denies

In coaching conversations, a recurring theme emerges: what the workplace requires often conflicts with who a person understands themselves to be. Again and again, I see professionals trying to resolve this tension through compartmentalization, by dividing who they are from what their role demands.

The false promise of compartmentalization

In professional settings, especially among managers, a common belief takes hold: that one can separate the professional and personal self. Kindness, respect, and integrity belong to private life; professional life demands something tougher, more strategic, less human. This is the logic of compartmentalization: the comforting idea that one can adopt a role without it altering who one is. But this assumption is mistaken: compartmentalization changes who we are.

The underlying belief suggests that the persona you adopt in another compartment (be it the tough manager, the efficient executive, or the strategic decision-maker) is just a role, separate from your ‘true self.’ But this assumption fails to recognize a crucial truth: playing a role repeatedly shapes who you become.

In other words, the more you choose to compartmentalize, the more you become compartmentalized. The unity and integrity of selfhood gradually erode. By choosing to divide yourself, to separate yourself from yourself, you initiate a process that one might call alienation.

The cost of divided selfhood

Alienation here means estrangement from oneself, an inevitable cost of compartmentalization. We never return to an unchangeable core self; each choice and action shapes who we are becoming. The illusion that we can behave one way at work and another in private life misunderstands human development. What we repeatedly do becomes who we are. The choices made in one compartment inevitably bleed into the rest of the self.

From an ethical standpoint, the notion that one can be “who one is not” makes little sense. Whatever we choose to do is precisely who we become. The manager who justifies callousness or disrespect in the name of professionalism is not playing a role; they are becoming callous and disrespectful. The division they imagine protects their “true” compassionate nature is actually eroding it.

This process creates potential for rupture, especially when individuals maintain the belief that they remain unchanged despite evidence to the contrary. The gap between how we behave and how we perceive ourselves widens, creating an internal dissonance that may manifest in various dimensions of human experience, not limited to the psychological realm alone. Karl Marx’s concept of alienation, where individuals become estranged from their labor and themselves, remains surprisingly relevant here [1]. His insight that systemic pressures can fracture our sense of self aligns with the dangers of compartmentalization discussed in this piece.

If alienation is the cost of compartmentalization, what does that cost look like in real terms? Beyond philosophy, does it have tangible effects on a person’s mind and body? Psychological research suggests that it does, often in ways we underestimate.

Potential psychosomatic implications

If alienation is the cost of compartmentalization, its payment often comes due in the body.

When the mind insists it remains unchanged, even as actions reshape identity, the body bears the contradiction.

While this extends beyond my area of expertise, the question remains: what are the psychosomatic consequences of such inner division?

What happens physiologically when someone insists they remain unchanged, even as their actions shape who they become?

There seems to be potential here for a profound rupture, in self-concept and potentially in bodily experience as well. The literature on mental health and physical wellbeing might offer insights into how such internal contradictions manifest somatically.

When the body lives what the mind denies, what toll does this exact on both mental and physical health?

While I am neither a scientist nor a psychologist and offer this perspective as a layperson’s observation, it appears that mainstream psychological science has documented this phenomenon through various frameworks. Research on cognitive dissonance, first established by Leon Festinger, demonstrates how psychological tension arises when beliefs and behaviors conflict, often manifesting as measurable physiological stress responses [2]. Similarly, studies in psychoneuroimmunology have established clear connections between psychological states and physical health outcomes [3].

The work of researchers like Robert Sapolsky on stress demonstrates how sustained internal conflicts can trigger cascading effects through the hypothalamic-pituitary-adrenal axis, resulting in compromised immune function, cardiovascular problems, and accelerated cellular aging [4]. Perhaps most relevant is the literature on “emotional labor” and “surface acting” in organizational psychology, which shows that consistently presenting emotions that differ from one’s authentic feelings leads to emotional exhaustion, burnout, and increased risk of physical ailments [5].

Taken together, these findings suggest that the rupture created by compartmentalization has concrete, measurable impacts on human physiology.

The disconnect between one’s actions and self-perception cannot be maintained indefinitely without consequences. The energy required to maintain these separate “selves” must find release somewhere, whether through psychological symptoms, physical ailments, or other manifestations of this fundamental disunity.

This line of inquiry invites further exploration into how the embodied self responds to compartmentalization, and what warning signs might emerge when the fiction of separate “compartments” begins to collapse under the weight of lived experience. When the compartments begin to fail, the body often speaks first.

Perhaps integrity is not a virtue of character alone, but of being.

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  1. Marx, K. (1844/1932). Economic and Philosophic Manuscripts of 1844. In Marx-Engels Collected Works, Volume 3.
  2. Festinger, L. (1957). A Theory of Cognitive Dissonance. Stanford University Press.
  3. Ader, R., Felten, D.L., & Cohen, N. (Eds.). (2001). Psychoneuroimmunology (3rd ed.). Academic Press.
  4. Sapolsky, R.M. (2004). Why Zebras Don’t Get Ulcers: The Acclaimed Guide to Stress, Stress-Related Diseases, and Coping (3rd ed.). Henry Holt and Company.
  5. Hochschild, A.R. (1983). The Managed Heart: Commercialization of Human Feeling. University of California Press; Grandey, A.A. (2000). Emotion regulation in the workplace: A new way to conceptualize emotional labor. Journal of Occupational Health Psychology, 5(1), 95-110.

photo by Anastasia

Learning from Leaders in the Spotlight

Most of what we think we know about leadership comes from a small, unusual subset of leaders: the ones who choose to be public.

They are the visible few: CEOs on stages, entrepreneurs in podcasts, billionaires with books. They explain how they became successful, often turning their particular path into a universal formula. This worked for me, so it will work for you. The memoir becomes a methodology.

Here’s the problem: leaders who teach are a self-selecting sample of leaders. They’re people for whom visibility is either a necessity or a desire for the business, for the brand, or for the self. Because they’re the ones we see, they become the ones we study. We mistake the most visible for the most representative.

Think about what it takes to write a book about your career, to build a personal brand, to position yourself as a thought leader. It requires comfort with self-promotion and belief in the value of your own story. It often draws on deeper motivations: a need for validation, an identity intertwined with being seen as successful, the ego-satisfaction of being a source of wisdom.

Once you step into that role, a feedback loop begins. The more you are recognized as a thought leader, the more your professional identity depends on maintaining that visibility. For some, this is a business necessity: visibility drives sales, attracts investors, or opens doors. For others, it’s about the self: a personal brand that must be fed.

That’s one kind of leader.

There’s another kind entirely: the invisible leader, the majority we never notice.

The CEO who slips out the side door after an all-hands. The founder whose name you’ve never heard because it’s on the product. The executive who transformed an organization and sees no reason to turn that transformation into a framework. The entrepreneur who created lasting value and prefers to spend it rather than explain it.

They’re quiet because their success doesn’t require an audience. They’re focused on results over recognition. Their effectiveness doesn’t hinge on being seen as effective.

And here is what gets lost: the lessons from these leaders don’t become books or podcasts, so they don’t circulate. Their ways of leading (often grounded in patience, craft, timing, and long arcs of trust) remain embodied in organizations rather than codified as “principles.” The subtle forms of leadership that shape cultures from the inside out are almost invisible to our theories. Our playbooks end up skewed toward charisma, communication, and visibility, while the quieter disciplines of listening deeply, building resilience without fanfare, and creating conditions for others to thrive remain undocumented.

Because we don’t see them, we don’t study them. Their approaches don’t enter our models of leadership at all.

This is a systematic skew. Our leadership canon is built not from the full spectrum of practice but from the sliver that comes with its own microphone. MBA programs lean on autobiographies and case studies of the visible few. Business media amplifies the same characters because they generate clicks and stories. Even organizational research is distorted by who agrees to be interviewed or written about. The structures that shape what we know about leadership are designed to reproduce the voices already amplified.

We mistake the loudest voices for the most representative ones.

How do we know what we know about success? How much of our understanding comes from leaders whose public presence is part of their strategy or their identity? How much comes from leaders whose success has nothing to do with being seen?

Visible leaders are not fraudulent. Many have built remarkable organizations. But visibility itself becomes part of the lesson, shaping both the path they took and the story they can tell.

The uncomfortable truth is that we may have built our entire understanding of leadership on this narrow, self-selecting group. We’ve been learning from leaders whose success depends on being visible, and ignoring the ones whose success never needed an audience.

What would change if we stopped learning from the leaders in the spotlight? What might we discover if we began to look for leadership in places where no one is trying to teach us a lesson? What might we find in the organizations that quietly endure, the teams that thrive without headlines, and the leaders who will never write a book because they are too busy leading?

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Photo by Joshua Hoehne on Unsplash

Base-10 Thinking

for Elizabeth and Santiago

What feels inevitable is often just familiar.

Once you see that our number system is arbitrary, it becomes a lens for questioning all sorts of assumptions we carry around.

Language is full of these. We think of “tree” as somehow naturally connected to that woody thing with leaves, but it’s just an agreed-upon sound. Other cultures carve up color differently. Some have one word for what we call blue and green; others have dozens of words for different kinds of snow or rain.

Even time, which feels so natural, is an invention. Our 24-hour days, 7-day weeks, and January-starting years aren’t written into the universe. The Mayans had entirely different calendars. We could have 10-day weeks or 8-hour days if we’d chosen differently.

Social structures do this too. The way we organize work, basic ideas like property ownership, these vary wildly across cultures and centuries. What feels inevitable to us might look bizarre from another time or place.

And here’s the tricky part: these conventions aren’t useless. They coordinate reality. They solve problems. But the moment we remember they’re conventions we can ask: Is this serving us well? Could we do better?

It’s liberating. And a little unsettling. Which is exactly where this begins.

I remember the moment it cracked open for me.

It was high school. Our math teacher, in one of those rare off-script digressions that end up mattering more than the syllabus, said the best way to understand numbers was to realize that base-10 isn’t sacred. It’s just one way of putting things together.

“We count in tens,” he said, “because most of us have ten fingers. That’s it.”

Then he mentioned that in some cultures, people count using their thumb to tap the twelve segments of their fingers. Twelve. Not ten. Which means you can build a whole number system from that, one with cleaner divisors. With twelve, you get halves, thirds, and quarters with no remainder. In base-10, you only get two and five.

That was the moment the universe opened up. Not just mathematically, but metaphysically.

If base-10 is just habit, shaped by anatomy and repeated long enough to become invisible, then what else isn’t fixed? What else have we mistaken for truth, when it’s only convention?

It wasn’t just about numbers anymore. It was about everything.

That moment never left me. It made me realize frameworks shape perception. What we think of as “real” is often a reflection of the tools we use to read the world.

Most of the time, we don’t question the lens. We just look through it. It’s the water the fish doesn’t see. But once you realize base-10 is just one way of seeing quantity, you start to suspect other “givens.” You wonder how many things feel inevitable simply because they’ve been framed that way. And how often we confuse familiarity with truth.

Once you’ve had that kind of moment, you develop a cognitive side-eye. A healthy suspicion that what looks natural may, in fact, be constructed. That’s the beginning of discernment.

Once you start noticing the frame, you start seeing defaults everywhere.

The 40-hour workweek. The fiscal quarter. The five-day school schedule. The résumé. The slide deck. The assumption that growth is always good. That busy is better than still. That what can be measured must matter most.

These aren’t laws of nature. They’re choices someone made. Some sensible at the time, others arbitrary from the start. But repeated long enough, they begin to feel inevitable. Just how things are.

These defaults are the epistemological base-10 of modern life: familiar and efficient in some ways. But limited. And limiting.

Because the moment we forget they’re choices, we stop imagining alternatives. We stop asking whether they still serve the problems we face. We optimize the existing base instead of asking whether it’s the right base at all.

That’s the danger of a default. Not that it’s wrong, but that it’s unexamined. Somewhere along the way, we confused standardization with wisdom. And we lost sight of the fact that other ways of counting might be more truthful for the world we actually inhabit.

This has everything to do with management.

Management is full of inherited frames: roles, reporting lines, performance cycles, job descriptions, incentive schemes, even the idea of “managing” itself. We step into these systems assuming they’re natural and efficient. But many were designed for problems we no longer have, or for conditions that no longer exist.

And yet we keep trying to solve new problems using old frames. We tweak. We optimize. We invest in tools and trainings to help people succeed inside a base-10 logic that may no longer fit the work.

What if we’re optimizing the wrong thing entirely? What if the frame itself needs examining?

When I watch managers wrestling with performance reviews or struggling to make team structures work, I sometimes see people trying to count in base-10 when the situation might call for something else entirely. The tools feel clunky not because they’re being used wrong, but because they were built for different mathematics.

What would it look like to ask not “How do I manage performance better?” but “What counts as performance here, and how did we agree on that?” Not “How do I make the team more efficient?” but “Efficient at what, and why does that matter most?”

I’m not suggesting we throw out structure. I’m curious about what becomes visible when we remember structure is designed, not discovered. That the way we organize human effort is a choice we can make, not something we inherit.

Once you realize ten isn’t the only way to count, management becomes design. A way of framing human effort. A way of shaping what is made possible.

And when the world around you is changing faster than your frameworks can keep up, continuing to count by tens out of habit starts to feel less like stability and more like stubbornness.

What frame are you looking through? What assumptions about work, performance, and human organization feel so natural you’ve stopped noticing them? And what might become possible if you adjusted the lens, even slightly?

The most dangerous defaults aren’t the obviously broken ones. They’re the ones that work just well enough to keep us from questioning whether there might be better ways to count.

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Photo by GVZ 42 on Unsplash.

Behind the Scenes: Where “What you lose when you lead” fits my thinking

Over the past few years, I’ve been circling a set of questions about what it really means to manage and lead people, not from a business school perspective, not through the usual lists of best practices, but from the ground level. From the quiet, often messy, always human experience of the people doing the work.

My recent piece, What you lose when you lead, came out of that ongoing reflection. It looks at the identity crisis that so often accompanies the move from individual contributor to manager. Not just a change in duties, but something deeper: a disruption in how we understand ourselves. What it means to contribute.

As I was writing it, I kept hearing echoes from other things I’ve been working on. This wasn’t a new insight so much as a convergence. Threads I’ve been pulling at for a while now were coming together. So I wanted to step back and show how this piece fits into the larger pattern of my thinking.

A foundation: Management as craft

When I first started thinking of management as a craft, not just a role, something clicked. I wrote then about how every craft has its own materials—wood, metal, clay—and how in management, the material is human nature.

That shift in framing helped me understand why technical excellence alone doesn’t prepare someone to manage. But this new piece took me somewhere more personal: what happens when someone who’s mastered one craft (engineering, finance, design) is suddenly asked to switch materials and identities. That disorientation isn’t just about skill. It’s about self.

I’ve seen it again and again. Someone who used to feel confident and clear becomes unsure of their value almost overnight. The rules are different, and so is the work. But the harder part is that their old sense of worth no longer fits.

From prose to poetry

This connects to an idea I keep returning to: that managing is prose, but leading is poetry.

New managers often try to lead like they used to work: with structure, logic, and precision. But what this new role asks for is something less linear. It’s relational, interpretive, often ambiguous. They’re speaking prose when the situation requires poetry.

In writing What you lose when you lead, I found myself thinking about that awkward middle place—where you’ve lost the fluency of your old language but haven’t yet learned the rhythm of the new one. It really does feel like phantom limb syndrome. You keep reaching for a way of contributing that no longer exists.

When good intentions backfire

One of the patterns I’ve seen—managers reverting to individual contributor work—isn’t just tactical. It’s existential. They’re trying to feel useful again. So they jump in. They fix things. They work late.

And I get it. I’ve done it. It’s satisfying, familiar, and immediately rewarding. But as I’ve written elsewhere, that instinct often leads to the exemplarity trap: trying to model the behavior you want to see, hoping others will copy it.

The problem is that management isn’t about creating copies. It’s about helping people become originals.

Reconstructing satisfaction

This part feels especially close to the bone. A lot of what I do in my coaching work is helping managers rediscover what satisfaction looks like now.

I’ve spent time thinking and writing about motivation (how it works, what drives us) and what I’ve learned is that new managers often lose their most familiar source of satisfaction (technical mastery) before they’ve found a new one. There’s a void.

Some mourn that loss quietly for years.

But there’s another kind of satisfaction that can emerge. Less immediate, but deeper. The quiet power of enabling others to rise. The long arc of shaping not just outputs, but people. You don’t get applause for it. But if you can shift your motives, it starts to feel meaningful in a very different way.

A practice of honesty

That shift doesn’t happen automatically. It takes reflection and often, community. That’s where the idea of the Manager’s README came from.

The README is a tool, yes. But more than that, it’s a way of practicing radical honesty with yourself and your team. Writing one forces you to confront the distance between what you intend and how you act. And I’ve found that kind of honesty to be a turning point for a lot of people going through this transition.

The change is real. Pretending it isn’t doesn’t help anyone.

Working with rather than against

If there’s a deeper thread running through all of this, it’s probably this: learning to work with rather than against.

That shows up in lots of places in my writing:

And it’s right there in the identity crisis that new managers face. Individual contributors succeed by controlling variables. Managers succeed by surrendering control and learning to work with what’s alive in other people.

That’s not a minor change. It’s a whole new way of relating to the world.

What it might mean for how we develop leaders

This brings me to the question that’s been tugging at me most:

So where does all this lead?

To me, What you lose when you lead marks something of a pivot. It brings together many threads I’ve been following—craft, poetry, exemplarity, motivation, honest self-reflection—but applies them to one of the most common, misunderstood, and under-supported transitions in working life.

But it also leaves me with questions I don’t yet have answers to.

How do we support people in this shift, beyond giving them tools and tips? What kind of development experiences could help them not just cope with the loss, but grow into the possibilities? How can we allow people to grieve what they’re leaving behind and still see what they’re stepping into?

I’m still working on those questions. And I’m open to being surprised.

This is the first of a series I’m calling “Behind the scenes.” A place for me to connect the dots between pieces, share what’s unfolding in my thinking, and invite you into the process. If you’re going through this transition yourself, or helping others through it, I’d love to hear what’s helped, what’s been hard, or what you’re still figuring out.

This isn’t a finished framework. It’s a conversation I hope we can keep having.

The question that cuts through every explanation

Everyone has a reason. Not everyone gets the prize.

Think about the last time you were puzzled by someone’s behavior: a colleague’s decision, a corporate announcement, a political move, even a personal interaction. You probably asked yourself why they did it.

But there’s an older, sharper question that might have served you better.

Cui bono. To whose benefit?

Most conversations rely on familiar questions. “Why did you do that?” reveals explanations and justifications. “What for?” —a question I’ve explored before— uncovers stated goals and purpose.

But there’s a third question that completes the set: Who benefits from this?

The Three-Question Hierarchy

“Why” questions get you reasons. “Because I’m tired.” “Because it seemed like a good idea.” “Because that’s how we’ve always done it.” These tell you about someone’s internal state but they’re often incomplete or misleading.

“What for” questions get you stated purposes. “To improve efficiency.” “To help the team.” “To serve the public good.” These sound more substantial, but they’re still what someone wants you to believe.

“Who benefits” questions get you evidence. They cut through the noise of motivation and stated purpose to reveal the actual stakes. Follow the advantage, and you’ll understand the real game being played.

It Works Everywhere

A dinner invitation? Sure, hospitality is real. But who benefits from having you there? Maybe they need a buffer with difficult relatives. Maybe they’re hoping you’ll introduce them to your boss.

A corporate restructuring? The stated goal is always “efficiency” or “customer focus.” But who actually gains power, budget, or influence?

A political proposal? Rhetoric talks about the public good. But ask: if this passes, who wins? The answer will tell you more than a thousand position papers.

Why This Works

The brilliance of cui bono is that it sidesteps the entire theater of stated intentions. While everyone else is debating whether someone “really meant” what they said, you’re already looking at the scoreboard.

Benefits don’t lie. They leave tracks clearer than words, harder to erase.

People misstate their motivations; sometimes deliberately, often without knowing it. They spin their purposes to sound noble, logical, or fair.

But benefits? Benefits are observable. They leave tracks.

When you ask cui bono, you’re not guessing at motives. You’re looking at results. You’re following the money, the power, the access. You’re noticing who actually comes out ahead when the dust settles.

This works across every scale. The colleague who volunteers for a high-visibility project “to help the team” might genuinely believe that’s their motivation. But who gets the career boost? The politician championing education reform might truly care about children. But whose districts get the new funding, and whose allies get the contracts?

The Real Power

Understanding who benefits doesn’t mean every action is selfish or every motive corrupt. Rather it strips away the fog of explanation and reveal what’s really at stake.

There’s something liberating about this approach. It frees you from having to be a mind reader or parse elaborate justifications. You don’t need to figure out if someone is lying, self-deluded, or completely sincere. The benefits speak for themselves.

Next time you find yourself puzzled, try skipping the guesswork. Skip the story-spinning.

Ask the question: Cui bono? To whose benefit?

And when it’s your own action under the spotlight, do you know who stands to gain? The hardest part might be applying this lens to your own choices, especially when you’ve built a narrative around serving others or pursuing principles. But that discomfort is usually a sign you’re onto something important.

Cui bono doesn’t make you cynical. It makes you honest about how the world actually works.

You’re not guessing anymore. You’re just watching who wins.

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The Five Dimensions of Strategic Career Choices

Every career is ultimately shaped by a series of decisions that make up a chronology of roles informed by the architecture of choices beneath them.

Having worked closely with professionals across industries and career stages, I’ve seen that the most resilient and meaningful trajectories aren’t built by accumulating positions. They’re sculpted by clarity: clarity about what matters, what aligns, and what can no longer be compromised.

Yet many career decisions still rely on surface metrics. Titles, compensation, organizational prestige. These markers are easy to track, but they rarely tell the full story. And they certainly don’t protect against regret.

What separates a strategic move from a reactive one is not the offer itself, but the lens through which it is assessed. In my experience, five dimensions matter far more than most professionals are encouraged to consider. They don’t show up on the offer letter but they determine everything that follows.

1. The Nature of Daily Work

Most job transitions begin with a sense of excitement. New possibilities. Fresh challenges. But this early lift fades quickly. What remains is the texture of your days: the meetings, the pace, the quality of thought required, the energy demanded and returned.

When I trace back the most regretted career moves I’ve seen, they often stemmed from a mismatch at this level. The work sounded right, looked right but it didn’t feel right once lived.

Satisfying work doesn’t just align with skills; it engages values, stretches capacity, and sustains interest over time. Strategic professionals learn to look past the role’s surface appeal and toward the rhythm it will establish in their lives.

2. The Human Ecosystem

Organizations are not structures; they’re systems, deeply human systems.

No matter how compelling the mission or the role, your experience will be shaped, day to day, by the people you work with and the culture they create. Growth, momentum, and resilience depend less on company vision than on interpersonal dynamics: trust, challenge, shared language, and psychological safety.

Some environments nourish ambition. Others quietly erode it. What distinguishes the two often isn’t visible from outside.

3. The Unwritten Rules

Beyond the formal job description lie the implicit codes that govern organizational life: who gets listened to, how decisions are made, what success actually looks like.

This informal layer — the rules beneath the rules — shapes influence, opportunity, and belonging. It’s not about gaming the system. It’s about understanding whether your way of working, leading, and contributing can thrive in the real dynamics of the organization.

Many talented professionals stall or burn out not for lack of skill. What happens is their instincts run counter to the local logic.

4. The Complete Value Exchange

Compensation matters. But it’s not the only thing that accrues value.

The most discerning professionals understand that each role offers a bundle of currencies: exposure, learning, flexibility, visibility, network, pace. Some of these are tangible. Others quietly compound over time.

Too narrow a focus on salary can obscure opportunities that offer greater long-term leverage or cost more than they first appear. Strategic choices require a broader view of what’s being gained, and what might be silently given up.

5. The Life Impact

Careers don’t happen in isolation. Every professional move reverberates through a life of relationships, routines, energy levels, and unspoken dreams.

I’ve seen too many promising roles unravel because they were out of sync with the broader life they entered. Transitions that succeed tend to occur within a supportive ecosystem where alignment exists. With work, of course, but also with what and whom the work is meant to support.

This isn’t a call for perfect balance. But it is a reminder that a career is a life structure. It has weight. It moves things.

Strategic Means Knowing Where You Stand

Few decisions offer perfect alignment across all five dimensions. But clarity around what matters and what cannot be compromised makes all the difference.

Strategy, in this context, isn’t about optimizing every angle. It’s about knowing which trade-offs serve your trajectory, and which ones quietly distort it.

The most intentional careers I’ve encountered weren’t assembled by accident or by algorithm. They were built through discernment, through decisions that reflected not just opportunity, but orientation.

That kind of clarity is difficult to find alone. But it’s what makes every move that follows more coherent.

 

From Framework to Focus: Personalized Career Strategy

The framework shared here is a starting point — not a prescription. Every career decision unfolds within a distinct context, shaped by your values, timing, and the particular constraints of your life.

If you’re navigating a significant transition or seeking to shape a more intentional trajectory, I offer personalized coaching to help apply these dimensions to your unique situation.

Together, we’ll clarify which trade-offs genuinely serve your broader vision — and which compromises might quietly erode it.

If that kind of clarity would support your next move, let’s talk.

You’re in the Room: Owning Your Place in Leadership

Here’s something that often happens in my leadership development programs. During breaks or over meals, someone will pull me aside. By then, they’ve usually heard that I come from a working-class family, and that I was the first in my family to graduate from college.

They lower their voice, like sharing a secret: “I’m from a humble background too. First in my family to go to college.”
Then they pause and quietly admit: “Sometimes I walk into meetings or boardrooms, and it hits me: everyone else seems to belong. They came from elite schools, well-off families. I wonder… how did I get here?”

They feel the need to justify their place in the room.

I’ve heard this many times, and every time, it carries the same undercurrent: self-doubt.
So I offer something that isn’t quite advice. More like a reframe:
You’re in the room.

Someone decided you should be there. And here you are.

Starting with “Should I be here?” is like showing up already a step behind.
That question is a drain on your energy, your attention, and your presence.
You don’t need to justify your existence. You’re already here.
So shape the room. Engage with it. Fill it with your full self.

This isn’t mysticism. It’s reality.
Or, as Sartre might put it: “We exist first, and it’s up to us to shape that existence.”
So, what will you do with it?

Acknowledging the Complexities

That’s the core message. But of course, the story doesn’t end there.
There are real tensions that complicate this picture. And I hear them often.

1. Being in the Room Isn’t Always Enough

Yes, being invited in matters. But what happens next is where the real work begins.
I’ve heard leaders say they still feel invisible once they’re in the room, as though the invitation was symbolic, not substantial.

That’s real. Power dynamics don’t vanish. But presence is power, if you claim it.
You may not control the room, but you can claim your place in it.
No one can erase your presence without your permission.

2. Bias and Inequality Are Real

Structural barriers don’t disappear just because you’ve made it through the door.
They persist. And pretending otherwise is naïve.

But here’s what I’ve seen over and over:
Internal barriers—like self-doubt—can be just as paralyzing as external ones.
If you can’t clear your own way, how will you face what’s outside?

3. Imposter Syndrome Isn’t Just in Your Head

Many capable, seasoned leaders have told me, “I feel like a fraud.”

The feeling may not go away. But here’s a reframe:
Imposter syndrome often means you’re pushing into new territory.
It’s a sign of stretch, not failure. Growth rarely feels like comfort.

4. Yes, Privilege Opens Doors

Privilege shapes access. Let’s not pretend otherwise.
Merit alone rarely gets you in.

But once the door opens, it’s what you do inside that defines your impact.
In my experience, those who had to fight to get in often make the strongest use of the opportunity.
They know what it took.

5. Preparation Still Matters

Being in the room doesn’t mean winging it.
You still have to show up prepared.

But I’ve seen people who’ve done the work still falter because they doubt their right to speak.
Preparation without presence won’t carry you.
If you’ve earned the seat, claim it.

6. Beyond the Boardroom

The room is a metaphor, of course.
It can be your role, your workplace, your family, your society.

Philosophers have long asked what it means to be in the world.
Sartre’s idea that existence precedes essence reminds us: we don’t earn our way into being. We begin with it.
From there, it’s on us to shape a life and to create meaning.

7. Isn’t This Too Simple?

Yes, the starting point is simple: You’re in the room.
But that simplicity is part of its power.

From that place, you can begin.
From that place, you can wrestle with bias, you can question the rules, and —why not?— challenge the system.
But not from outside it, wondering whether you belong.

You’re already here. So—what now?

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Photo by Antenna on Unsplash