9 The Essential Work of Becoming Unessential
This chapter is currently in draft form.
When I arrived at one organization, we deployed about twenty times a month. That sounds fine. It wasn’t. It meant multi-month projects, work stacked behind bottlenecks, nothing flowing.
One project had been “in progress” for two months. The team explained—proudly— that they couldn’t plan next sprint until they finished planning this sprint. They called it agility. I internally wept.
That’s first-order reality: inherited dysfunction that feels normal from the inside. When you’re there, you don’t get to design elegant systems. You fix what’s on fire.
It took years. The work described in the earlier chapters—political capital, leverage, momentum, structure, people. All of it. We went from twenty deployments a month to three or four hundred.
But at some point, if you’ve done that work, something shifts. You’re no longer just using the tools. You’re tuning the system that uses them. You’re working at the second order.
9.1 The Luthier’s Discipline
A luthier doesn’t play the instrument. They build it. Their craft is creating something that stays in tune across many hands, many tempos, many styles of play.
A poor luthier builds for careful musicians in controlled settings. When real musicians play hard, the instrument falls apart. The luthier blames the musicians. But the fault was in the building.
A master luthier builds for aggressive play. They anticipate stress, account for variation, create resilience. The instrument holds together precisely because it was built to withstand what real performance demands.
The question for leaders isn’t how to make better decisions faster. It’s how to build an organization where good decisions happen without you.
There’s no workshop phase. You tune the instrument while it’s being played. You handle today’s decisions and, in the same motion, build so this category of decision doesn’t need you next time.
Most leaders never make this shift. They stay first-order forever—heroically available, always in the room, always making the call. Indispensability isn’t impact. It’s a design flaw. If you’re always the answer, you’re also the ceiling. 55% of organizations have experienced leadership gaps due to unplanned departures, yet only 33% feel prepared. The goal is not to have key people at all.
9.2 How You Tune
You tune through levers and strategies. Not through lectures.
9.2.1 Structural Levers
For years, my team struggled with shared automation. One-off scripts scattered across repos, each solving one problem, nothing reusable. I explained why sharing was valuable. I showed examples. I pointed toward patterns. Nothing fundamentally changed.
I couldn’t talk the team into reuse. So I changed the environment: a monorepo with strong mechanisms for sharing libraries and high standards for what went into the shared space. Once the team was inside the structure, they understood. The behavior I’d been trying to explain for years became obvious—not because I explained it better, but because the structure made it the path of least resistance.
You don’t change behavior by talking about it. You change conditions, and behavior follows. Thaler and Sunstein call this “choice architecture”—the deliberate design of decision environments. The effects compound over time. The lever that works for your team might be completely different from mine. The point is to look for it—the structural change that makes the right thing the easy thing.
9.2.2 Strategy That Cuts
The other lever is strategy—but strategy that actually cuts. This connects to The Hierarchy of Leverage: strategy at its best is a decision you don’t have to make again.
Consider two statements:
“We want to be the most customer-centric company in our space.”
“We prioritize response speed over feature completeness for customer-facing work. Even when it annoys the perfectionists.”
The first eliminates nothing. The second is a razor. When someone asks “should we ship this now or wait?” the strategy answers. No meeting required.
9.2.3 When Intervention Is the Lever
I had a Tier 1 codebase that everyone hated. To be fair, it was garbage—years of accumulated neglect, brittle in ways that made engineers afraid to touch it. They’d route around it, putting code that belonged there into other repos because they didn’t want to deal with it. The codebase mostly worked, which made it worse. No fire forcing action, just slow avoidance calcifying into culture.
For a year I’d been preaching that we were firefighters—we run toward problems, not away from them. It wasn’t landing. The fear was stronger than the sermon.
Then one day we were discussing a new feature. Good feature, clear value. We decided not to build it because it would require touching that codebase. The team was terrified of the work.
I said enough.
I jumped in and fixed the codebase myself. Weeks of work. Refactoring, cleaning, documenting, getting it to a state where it was no longer scary. This was dangerous—CTOs writing production code is usually a mistake. But I was the only engineer senior enough to take on the problem, and the organization was otherwise running well enough that I could afford the focus.
I didn’t frame it as failure. I didn’t blame anyone. But I did ask my senior engineers a question: Why was it me in there?
That question was uncomfortable. It was supposed to be. For a year I’d been talking about running toward problems. Now I’d demonstrated it—and in doing so, made visible that they hadn’t been.
Once the codebase was in a good place, I backed out. I didn’t touch code again for a long time. The intervention was temporary. The question lingered.
This was a different kind of lever than the monorepo. That was structural—change the environment and behavior follows. This was embodiment—sometimes you have to demonstrate what you’ve been asking for. But even the intervention was aimed at the second order. I didn’t just fix the code. I used the fix to change how the team thought about fear and avoidance. The codebase was the artifact. The real work was the question.
I’d be lying if I said the intervention was purely strategic. Part of me wanted to be back in the code. Weeks of refactoring, solving concrete problems, seeing direct results—it felt like real work in a way that my normal job doesn’t. I knew it at the time. The justification was legitimate, but I really wanted to do it, and that made me suspicious of my own reasoning. It had the effect I wanted—but it was risky, and I’m still not completely sure it was the right call.
9.2.4 Compounding
Structural levers and sharp strategy both compound. Each structural change creates conditions for the next. Each strategic clarity enables faster decisions. The work builds on itself.
First-order work accumulates. Second-order work compounds.
9.3 What This Work Demands
Structure. When you’re fighting fires, the fires tell you what to do. The urgency is its own forcing function. When the system runs well, nothing is burning. Nothing demands your attention. If you wait for the work to announce itself, you’ll wait forever—or fill the time whittling away at things that don’t matter.
You have to use your calendar intentionally. Block time to think about the strategic gap no one is addressing. Block time to consider what capabilities you’ll need in eighteen months. Block time to reflect on what’s working and what isn’t. Treat those blocks like meetings you can’t cancel—because if you don’t, the urgent will crowd out the important, even when there’s nothing urgent. Strategic thinking requires protected time that you create, not time that appears on its own.
This requires running your personal projects well. I change my organization system every three to six months. Not because I haven’t found the right one— because the work keeps shifting, so the system has to shift too. The problems you’re tracking, the timelines you’re watching, the people you’re developing— these evolve. Your system for managing them has to evolve with them.
This sounds like productivity advice. It’s not. It’s a shift in how you relate to your work. First-order work is reactive: the problem arrives, you solve it. Second-order work is proactive: you create the conditions for your own focus. No one hands you a ticket that says “think about organizational resilience for two hours.” You write that ticket yourself.
Real choices. Most organizations default to ambiguity—keep things vague enough to preserve optionality, avoid the conflict that comes from committing to specific tradeoffs. But vagueness doesn’t preserve optionality. It creates recurring conflict. Every real strategy disappoints someone. If yours doesn’t, it’s not a strategy.
I’ve watched leaders spend months circling decisions because they couldn’t bear to cut off possibilities. They called it being thoughtful. It was avoidance. Meanwhile, their teams waited, their momentum bled out, and the decision eventually got made by circumstance rather than choice. That’s not leadership. That’s drift with extra steps.
Patience. You changed a structure six months ago; now the team operates differently. You set a strategic direction a year ago; now decisions happen without you. The causation is real but diffuse. First-order work earns applause. Second-order work earns silence—until it suddenly looks like “culture.”
Stakeholders want to see activity. They want to know what you’re doing. “I changed the conditions for decision-making and now I’m waiting for it to compound” doesn’t satisfy in a quarterly review. You have to bank enough political capital to survive the silence.
Ego sacrifice. If you need to be consulted to feel valuable, you’ll rebuild the dependency you just escaped. Most leaders would rather be on stage, making the call, demonstrating their judgment. But the heroic decision-maker creates dependency. The leader who accepts invisibility creates autonomy. One scales. The practices that actually account for leaders’ success are often invisible even in their own narratives—leaders attribute their effectiveness to heroic individual action while ignoring the distributed, system-building work that made it possible.
The hardest moment isn’t building the system. It’s watching it run without you and resisting the urge to insert yourself just to feel useful. Your value is no longer in the decisions you make. It’s in the decisions that happen correctly without you.
9.4 The Payoff
When I started, I couldn’t trust anyone to make a significant decision. The judgment wasn’t there. The context wasn’t there. Every call of consequence came through me.
Years of the work in this book changed that—building political capital, finding the right leverage, protecting momentum, developing people. Finding levers. Setting strategies that cut.
Recently, I realized the number of decisions I was making had dropped to nearly zero. I was providing clarity, strategy, direction—but not making calls. The calls were happening without me.
Then something significant came up—the kind of thing that used to land on my desk. I learned about it after it was resolved. One of my senior managers said, “It’s solved. We handled it.” He told me what they did.
It was exactly right.
That’s the payoff. Not that you make all the right calls, but that the right calls happen without you.
9.5 The Danger of Arrival
When this works, you run out of obvious things to do.
There’s no single day when it hits you. It accumulates. You realize you haven’t been pulled into a decision in two weeks. You notice the staff meeting ran itself—you spoke maybe twice, and neither time was necessary. You look at your calendar and see open blocks that nobody filled. You were heads-down on something for a week and nobody interrupted you, which means nothing broke, which means they didn’t need you.
The first time this happens, it feels like a vacation. The second time, it feels like a warning. By the third time, if you’re honest with yourself, it feels like loss.
The danger isn’t laziness. It’s that the work becomes invisible. When you were fighting fires, the fires told you where to look. Now the fires get handled without you. You’re no longer in the information flow. The work still exists— systems need tuning, strategy needs refreshing, people need developing—but nothing calls your attention to it. You have to seek it out.
The Blub Paradox bites hardest here. Systems hide the problems they can solve and only surface the ones they can’t. You might be missing entire categories of improvement because no one thinks to bring them up.
9.6 The Loss
Nobody tells you about the loss.
When you were fighting fires, the work was hard but clear. Problems announced themselves. Solutions were visible. You could point at what you did. The adrenaline of the crisis, the relief of resolution, the tangible evidence that you’d made something better—that was satisfying in a way that’s hard to explain until it’s gone.
I love writing code. Going into that garbage codebase and fixing it—even though it was a horrible mess—was fun in a direct, non-abstract way that nothing else I do is. Problem, solution, result. The satisfaction of making something better with your own hands. That’s the work I fell in love with. That’s why I got into this field in the first place.
The reward for being good at that work is you don’t get to do it anymore.
This isn’t just uncomfortable. It’s an identity death. If you built your sense of self on being the person who solves hard problems, the person others come to when things break, the person who saves the day—you’ve just killed that person. The status signals disappear. The adrenaline stops. The feeling of being needed, which for many of us is a load-bearing wall of self-worth, gets replaced by… what, exactly? The quiet satisfaction of watching other people do the work you used to do? It’s not nothing. But it’s not the same drug.
Hackman and Oldham’s research on job characteristics explains why: skill variety and task identity—seeing a whole piece of work through from start to finish—are core drivers of experienced meaningfulness. Senior leadership strips both away. You gain influence but lose the direct feedback loop that made the work feel real.
When everything runs well, the clarity disappears. The problems you work on are abstract—strategic gaps, organizational misalignments, capabilities that don’t exist yet. The feedback loops stretch to months or years. You can go weeks without a concrete win.
What’s left is mostly influence without authority. Engineering is in good shape. The rest of the organization isn’t. So I spend my time figuring out how to move pieces I don’t control. How do you surface a problem in a peer’s area without making an enemy? How do you get someone to own a gap that no one wants to own? How do you shape organizations that don’t report to you?
This is exhausting in a different way than firefighting. Slower, more political, less satisfying. You’re not building things. You’re creating conditions for other people to build things. The craft satisfaction is gone. What replaces it is quieter—the knowledge that the system works, that good decisions happen without you, that you’ve built something that outlasts your attention. It’s real. It’s just not the same.
The temptation isn’t just to reinsert yourself for relevance. It’s to reinsert yourself for satisfaction. The old work was hard, but it was rewarding in ways this work isn’t. You have to find a different kind of reward—or accept that the work is sometimes just… work. Important, necessary, and deeply unsatisfying.
That’s the honest trade. You give up the thing you loved to build something larger than you could build alone. Some days that feels worth it. Some days you just miss writing code.
The honest answer is that it ebbs and flows. Sometimes you’re fully in it—whether things are going well or not. Sometimes you’re grinding through and the improvements aren’t visible, but you’re finding ways forward and that’s enough. Other times you’re just going through the motions. As long as you’re moving forward on average, the dips don’t matter.
Engagement follows action more than feeling. It’s my job to be engaged, so I show up and do the work, and the feeling catches up eventually—or it doesn’t, and I do the work anyway.
What helps is keeping a small number of org-level goals in view. Not the team’s delivery goals—those matter, but they’re not what I mean. Your goals. Second-order goals. How are you trying to level up the organization? What capability are you trying to build that doesn’t exist yet? What systemic problem are you trying to solve? When daily work feels disconnected, these give you something to push on.
And occasionally stopping to look back—where were you six months ago, a year ago—makes the invisible distance visible.
9.6.1 What Remains
Recently, one of my senior engineers asked why I was focused on an organizational gap instead of a major feature in flight. From his vantage point, the feature was the important work. He could see it. He couldn’t see the wave coming, or why readiness mattered more than any single delivery. The Blub Paradox again—you can’t perceive threats at altitudes you haven’t operated at.
My answer: “That’s solved. The team’s going to deliver it. I’m worried about the thing that’s going to kill us if we’re not careful.”
This is the work when the system runs well. Spotting the fires no one else sees coming. And developing the people who will eventually spot them without you.
9.6.2 The Temptation
Sometimes reinsertion is legitimate—organizations backslide, gaps appear, the system isn’t resilient where it needs to be. That’s human and normal. You step in, handle what needs handling, then step back. The discipline is the stepping back: asking what you need to build so this doesn’t require you next time.
The failure mode is different. It’s reinserting yourself and staying. Reopening decisions that don’t need reopening. Manufacturing urgency so you feel relevant again. I’ve felt this pull. What you call engagement becomes withdrawal from the discipline that got you here.
The temptation never announces itself honestly. You don’t think “I’m going to sabotage what I built.” You think “I’ll just step in this once.” You think “they need me for this one.” You think “I should weigh in here—it’s important.” Each step feels reasonable. Each step undoes the work.
The leaders who break their own systems rarely do it through neglect. They do it by needing to matter.
Heroism is legible. Architecture is not.
Look for leaders whose areas run smoothly without constant escalation: decisions made at the point of action, problems solved without drama, pace sustained without their presence.
The tell is absence. If they disappear for a month, does the system keep running—or does it seize?
Full calendars packed with decisions “only I can make” aren’t leadership. They’re organizational debt. Organizations that delegate authority report dramatically higher productivity, and trust-based leadership accounts for the majority of variance in employees’ psychological safety.
Apply the same question to yourself. The pattern repeats at every level.
9.7 The Discipline
Becoming unessential isn’t retirement or abdication. It’s a phase transition. Builder to steward. Actor to environment. Hero to constraint-designer.
These aren’t happy truths. They’re irreversible ones. You don’t go back. The skills that got you here—the problem-solving, the firefighting, the being essential—those atrophy. What replaces them is different in kind, not degree. You’re not a better version of what you were. You’re something else.
The work that remains doesn’t feel like work. Horizon scanning—watching for threats no one else sees. Capability building—creating capacity for work that doesn’t exist yet. Succession—actively working yourself out of every remaining dependency. Influence across boundaries—shaping organizations that don’t report to you. Culture maintenance—reinforcing norms before they drift into dysfunction.
If this list sounds like a promotion, you’re misunderstanding it.
None of this has a ticket, a deploy, a visible output. But this is what leverage looks like at the top. You’re not doing the work anymore. You’re shaping the conditions under which work happens. That’s not a consolation prize. That’s the job.
I haven’t fully made this transition. I still fight it every day. The pull toward concrete work, toward the satisfaction of building something with my hands, toward problems I can solve directly—it doesn’t go away. I expect it never does. Everyone I know who operates at this level fights the same fight.
The goal isn’t to stop wanting the old work. It’s to choose the new work anyway. To block the calendar time even when nothing is burning. To reflect on the invisible wins even when they don’t feel like wins. To resist the urge to reinsert yourself even when reinsertion would feel so good.
The discipline this chapter describes isn’t delegation or scale. It’s withdrawing your ego from the control loop.
That’s the part almost no leadership book touches, because it’s not teachable in a seminar and it doesn’t sell frameworks. But it’s the actual work.