12 The Discipline of Stillness
This chapter is currently in draft form.
The hardest leadership decisions—whether to move someone off a team, how to restructure an organization, which architectural direction will actually scale—rarely resolve through direct analysis. You can gather data, consult advisors, run the numbers, and still find yourself stuck. The breakthrough, when it comes, usually arrives somewhere else entirely. In the car. On a walk. In the shower. During some routine activity where your body is occupied but your mind has space to wander.
This chapter is about creating the conditions where that breakthrough becomes more likely. Everything else in this book—political capital, leverage hierarchies, momentum conservation, ethical navigation—requires judgment that direct analysis can’t always provide. The discipline of stillness is how you access the thinking that makes those chapters actionable.
Most leaders never notice this pattern because they’ve optimized it out of existence. Every gap gets filled. The commute has a podcast. The walk has a phone call. The morning routine has news playing in the background. Every moment is maximized for input or output.
This isn’t productivity. It’s self-sabotage with good intentions. You’ve designed your life to make your best thinking structurally impossible, then wondered why you’re stuck on the same problems for months. The calendar full of back-to-back meetings, the inability to sit in silence for twenty minutes—these are signs of someone who has confused motion with progress and is paying for it in judgment that doesn’t arrive when they need it.
12.1 The Two-Phase Reality
I’ve come to understand breakthrough thinking as a two-phase process. The phases are different in character, and most leaders are good at one while systematically undermining the other.
The first phase is loading. This is the conscious, deliberate work of gathering context. You investigate the problem. You talk to the people involved. You look at the data. You hold the constraints in your mind. You try different framings. This is work you can schedule—you can put “research the platform migration options” on your calendar and make progress.
The loading phase is essential. You can’t skip it. The insights that emerge later aren’t magic; they’re the product of your mind making connections across the information you’ve gathered. If you haven’t loaded the relevant context, there’s nothing to connect.
Most leaders do this phase reasonably well. It looks like work. It produces artifacts. You can point to it and feel productive.
The second phase is processing. This is where your unconscious mind does its work, finding patterns across the information you’ve loaded, making connections you couldn’t force through direct analysis. Processing is not rest. I think of it as unsupervised cognition, real work that your conscious mind can’t direct. Spontaneous thought operates through different neural dynamics than focused analysis (Christoff et al., 2016). This is where the actual breakthrough happens.
But processing requires different conditions than loading. It happens when your conscious mind steps back. When you’re not actively trying to solve the problem. When you’re doing something routine enough that your attention isn’t fully required.
For me, driving in silence, walking without headphones—these create the conditions. The morning routine, shower, getting dressed, brushing teeth, done without any media playing. These are times when my body is occupied with something automatic, leaving my mind free to wander across whatever I’ve been loading.
The insight doesn’t come because I’m trying to have it. It comes because I’ve made space for it.
12.2 What This Looks Like in Practice
In one organization, one of my more senior engineers was struggling in a way I couldn’t diagnose. They would take recommendations from external groups at face value while being extremely critical of recommendations from internal group. The pattern made it hard to have confidence in their technical evaluations. I found myself having to get a second opinion or do my own evaluation of their evaluation in nearly every case.
I’d been thinking about this for weeks. Conversations with them. Observations in meetings. Data from different situations where the pattern showed up. I’d loaded the problem thoroughly but couldn’t see through to the underlying cause.
One morning, getting ready for work, brushing my teeth, going through the routine in silence as I usually do, the answer surfaced. Not the full solution, but the framing that made the solution visible. The pattern wasn’t about the recommendations themselves. It was about the relationships. They trusted external groups unconditionally while scrutinizing internal ones, a sort of organizational self-confidence problem.
That reframing led to a concrete set of recommendations that significantly helped this person over time. The insight didn’t come from more analysis. It came from creating space for my mind to find a pattern I couldn’t see by staring at it directly.
This isn’t just interpersonal judgment. The same pattern applies to technical systems. At one company, we’d been struggling for years to reduce operational load on a particular product. The team had tried various approaches. We’d made incremental progress but nothing that fundamentally changed the situation.
I’d been immersed in this problem, reviewing the architecture, talking through constraints with the team, understanding why previous attempts hadn’t worked. The problem was thoroughly loaded.
On a silent drive to work one day, radio off, the architectural insight came. We could move all of the complex processing out of the hot loop entirely. Not optimize it, not cache it, but restructure so it happened elsewhere in the system.
The impact was dramatic. We implemented the change, and then something almost comical happened: load on the product went up ten times because it was getting popular, and we didn’t notice until we saw the revenue numbers. The operational burden had dropped so significantly that a tenfold increase in usage didn’t trigger our usual alarms.
That solution was always available. The information required to see it was information I already had. But I couldn’t think my way to it through direct analysis. It emerged in the quiet space where my mind could make connections my conscious attention would have blocked.
Once I started protecting processing time, the difference showed up everywhere, people problems and systems problems alike. But I didn’t always understand this. Earlier in my career, I prided myself on intensity. Podcasts in the car, Slack on the walk to lunch, email while waiting for coffee. I was stuck on the same strategic problems for months, grinding through analysis that never quite broke through. I thought I was working hard. I was filling every gap where insight might have emerged with noise that felt like value.
I can’t get those years back. There’s a personnel decision I ground on for months, whether to move someone off a team, that should have taken days. The pattern was obvious in retrospect, but I couldn’t see it while I was actively analyzing it. Meanwhile the team worked around an ambiguity I could have resolved. That’s the cost of optimizing for input over insight.
Some of your stuck problems are stuck because you never stop long enough to let your mind work. How much longer are your decision cycles than they need to be?
12.3 The Blub Paradox of Stillness
If you tell someone you commute in silence for strategic reasons, they’ll probably think you’re eccentric. When I first introduce this to new directs, they smile and nod, no doubt thinking that humoring the new boss is the safest move. As I gain capital and credibility, they start trying it out.
This is the Blub Paradox applied to thinking itself—the trap where you can’t perceive what you’ve never experienced. To someone who has never had a breakthrough emerge from quiet processing time, your practice looks like laziness or inefficiency.
They see the time that could be filled with useful input.
They can’t see the conditions that produce thinking they can’t access any other way.
This isn’t their fault. The value of protected processing time, what I’m calling stillness, is invisible until you’ve experienced it. And if you’ve filled every quiet moment with input your entire career, you’ve never had the chance. Organizations reward looking busy over being effective. The person who looks like they’re thinking hard gets credit. The person staring out the window does not.
This means you’ll face pressure, internal and external, to “optimize” your processing time. Scrolling between meetings. Checking email on the walk to lunch. Filling every transition with input. Each one seems like a reasonable efficiency. Together, they eliminate the conditions for breakthrough entirely.
12.4 The Resistance
The same traits that made you successful are now limiting you.
You got here by being relentless. By filling every gap with productive activity. By learning constantly, optimizing obsessively, never wasting a moment. That intensity worked. It got you promoted, got you recognized, got you to the level where you’re reading this book.
And now it’s your biggest liability.
The habits that propelled your early career are actively preventing your next level of contribution. Every gap filled with input, every transition stuffed with content, every moment of potential quiet converted to consumption. These are signs that you’ve trained yourself out of the conditions where your best thinking happens. You’ve optimized yourself into a ceiling you can’t see.
Stillness feels wrong because your entire career has conditioned you to experience silence as waste. The itch to fill every gap isn’t a character flaw, it’s the shape that personality and expectations force on us. The discomfort you’ll feel in silence is the discomfort of unlearning what made you successful so you can become capable of something more. Understanding this doesn’t make the cost any lower.
Most executives never make this shift. They keep optimizing inputs, grinding harder, filling more gaps, and plateau without ever understanding why. The intensity that got them here keeps them here.
12.5 What This Isn’t
Let me be clear about what I’m not claiming.
You can’t schedule breakthrough thinking, and you can’t force it to come. You can schedule the loading phase, the investigation, the conversations, the analysis. But processing doesn’t work on demand. By loading problems thoroughly and creating conditions for processing, you make breakthroughs more likely. But they arrive when they arrive. Sometimes they don’t arrive at all.
And you can’t wait for insights to do your job. Most decisions have to be made with whatever thinking capacity is available in the moment. You use frameworks, experience, consultation, the normal tools of leadership. The practice of stillness is an optimization, not a replacement for doing the work.
The discipline isn’t about guaranteeing insight. It’s about not preventing it. Most leaders, through their relentless optimization of every moment, have eliminated the conditions where their best thinking could emerge. They’re not incapable of breakthrough insight. They’ve just made it structurally improbable.
12.6 The Capture Imperative
Insights that arrive during processing are fragile. If you don’t capture them immediately, you will lose them.
The conditions that generate a breakthrough insight are different from the conditions where you evaluate and implement it. When you shift from relaxed processing back to active thinking, the insight starts to fade. The shift to analytical mode suppresses the same neural networks that produced the insight in the first place (Kounios and Beeman, 2014). The connections that were vivid become vague. The framing that seemed so clear gets fuzzy around the edges.
You can’t trust yourself to remember. You have to capture it immediately.
This means always having some way to record what surfaces. For years, I carried a small pad and pencil. Now it’s my phone, voice memos, quick notes, whatever gets the idea out of my head and into durable form before it evaporates. More recently, I’ve been using conversations with language models to flesh out rough insights while they’re still fresh.
The method doesn’t matter. What matters is capturing before the state change erases what you just found.
Don’t try to evaluate the insight in the moment. Don’t try to improve it or figure out if it’s actually good. Just get it down. You can assess it later, when you’re back in analytical mode. The goal during processing time is preservation, not judgment.
12.7 The Practice
I’m not prescribing a method. What works for me, silent commutes, walks without headphones, quiet morning routines, might not work for you. The specific activities aren’t the point.
What I’m suggesting is that you pay attention to when your best insights actually come. Not when you want them to come, or when you’re trying to have them, but when they actually arrive.
Then protect those conditions.
If your breakthroughs come in the shower, stop listening to podcasts in the shower. If they come on walks, stop taking calls during walks. If they come during the commute, turn off the radio.
If you don’t drive or walk much, find analogs. Stare out the train window instead of scrolling. Block twenty minutes after meetings for decompression instead of immediately checking email. Fold laundry without a podcast. The principle is the same: routine physical activity, no competing inputs.
You’re not adding new activities to an already packed schedule. You’re removing inputs from activities you’re already doing. That’s sustainable.
The discipline is learning to tolerate the silence. To resist the itch to fill it. To trust that the quiet is working even when it doesn’t feel like it.
12.8 Why Some Leaders Plateau
Some leaders plateau. Others keep growing. The difference isn’t intelligence or work ethic. Often the ones who plateau have more of both. They’re grinding harder, filling more gaps, optimizing more aggressively—and it’s exactly that intensity that’s keeping them stuck. They’ve eliminated the conditions where breakthrough thinking happens, then blamed the world for not providing breakthroughs.
The ones who keep growing learned to stop. Not permanently, not as retreat, but strategically. They make room for the thinking that effort blocks.
Most leaders won’t do this. They’ll read this chapter, nod along, and fill their next commute with a podcast about productivity. The discomfort of silence is greater than their dissatisfaction with their current ceiling. That’s fine. Adequate leadership is still leadership. It’s just not what this book is for.
If you want better than adequate, you have to create the space where better becomes possible. No one is going to create it for you. Every gap you fill with noise is a chance for breakthrough you’ve decided to forfeit.
If your CTO seems to have unusual clarity about difficult problems, watch how they structure their time.
The leaders who consistently produce breakthrough thinking rarely do it through heroic analysis. They’ve learned to create conditions where insight can emerge. They protect processing time that looks unproductive to people who don’t understand what’s happening.
Don’t mistake constant visible activity for effectiveness. The executive who’s always in meetings, always on calls, always consuming information may be optimizing for the wrong thing. They’re loading without ever processing.
The test is output quality, not input volume. Are their decisions better than the complexity of the situations would predict? Do they occasionally see things that everyone else missed? That’s the sign of someone who’s figured out how to access their full cognitive capacity.
If you find yourself wondering why your CTO takes so many walks or seems to have suspiciously open calendar blocks, consider the possibility that they know something about how insight works that you don’t.
One concrete move: protect your CTO’s processing windows the way you’d protect a board meeting. Don’t let urgent requests fill their calendar gaps. The clarity you get from them comes from the space you’re tempted to take.