On Operational Drift

There is a specific stretch of road, somewhere east of Apache Junction, where the saguaros begin to lean toward you in the late light. The Superstition Mountains hold the sun for an extra twenty minutes after it has fallen for everyone else, and the air, which earlier in the day was the kind of dry that erases you, turns gentle. I drove that road home from a client site, on a Tuesday in late August, a few years into the build, and I remember thinking, with the strange clarity of a person watching themselves from a small distance, that I had been here many times and could recall almost nothing about any of them.

I could recall every Jira ticket from that week. I could recall the precise architecture of the auth flow we had argued about for two days. I could recall, with the unwanted fidelity of an audit log, what each person on the team had said on the call that morning, and which of them had said it because they believed it versus because they wanted the meeting to end. What I could not recall was whether the saguaros had been blooming the last time I drove this road, or the time before, or the time before that. I could not recall the road itself, only its function, which was to deliver me from one obligation to another at speeds that the obligations had set.

This is what I want to write about. Not the work, exactly. Not the satisfaction of having built something that real people use every day across a thousand industrial sites in three countries. Those things are true. They matter. The work mattered. I am not writing to apologize for it. I am writing because I have been trying, for the last year, to put a name to what the work also took, quietly and without ceremony, while it was busy giving me the things I had asked it to give.

The closest word I have found is drift.

The shape of the system

I spent the better part of five years helping architect a software platform called DocuPaint. The short version is that it is an industrial coatings inspection system used by a few hundred enterprise organizations across North America, endorsed by the relevant industry standards body, running in production on tablets carried by inspectors in Tyvek suits inside refinery tanks and on bridge underdecks and at marine drydocks. The longer version takes several pages and was, for those five years, the inside of my head.

What I want to convey is not the platform's complexity, which is its own subject, but the shape of the cognitive responsibility involved in holding such a system in attention for that long. Other systems-builders will recognize the shape. It is not a sequence of large decisions. It is a kind of permanent low-pressure weather inside the skull. You are at all times tracking the state of roughly forty conversations. Some are about a specific feature in the inspector mobile app. Some are about a customer in Texas who has interpreted a regulatory standard differently than every other customer in Texas. Some are about a junior engineer who is six weeks into a refactor that you suspect will not work and that you have not yet told them will not work because they need to come to it themselves. Some are about your own runway, your own pricing, your own next twelve months. Some, the worst ones, are about the question of whether the architectural choice you made eighteen months ago to solve the problem you had then is now the reason a different problem cannot be solved at all.

The conversations do not stop. You learn to put them in adjacent rooms in your mind and walk between the rooms. You learn that the rooms grow when you sleep. You learn that the rooms grow when you stop paying attention to them, and so you do not stop paying attention to them, and after some time you no longer know what attention to anything else feels like, because every faculty you had for it has been quietly converted into a sense organ for the rooms.

I want to be careful here, because the cliché version of this story is the burnout story, and the burnout story is, in its essence, a story of failure. It is the story of the person who broke under the weight. That is not the story I am telling. The work did not break me. It did something stranger. It did not break me because I did not let it break me, and the not-letting-it-break-me was its own discipline, a discipline I am now trying to understand the cost of. The version of me that finished those five years was competent, regulated, and reliable. He was respected by his team and by his clients. He had, by most reasonable measures, succeeded. He had also gone quiet in a particular way, and that quiet is the subject of this essay.

Always on

If you are the person on whom a system depends, you are never not the person on whom the system depends. The phrase "off the clock" turns out to be a relic of a different kind of work, the kind where there was a clock at all. There was no clock. There was, instead, the steady low frequency of attention, the question that lived behind every other thought, which was the question of whether something needed me right now.

The phone is not the cause of this. The phone is the symptom. The cause is internal. I was the cause. I had built a thing whose continued working required, at any moment, that one person be available to make a particular kind of call, and over time the part of me that could not make that call had quietly stopped showing up to the parts of life where it would otherwise have been useful. I did not stop having dinner with friends. I stopped fully being at the dinner. I did not stop going on weekend rides. I stopped being inside the rides while I was on them. I was, instead, half-present, a person performing the dinner and performing the ride while the other half of him tracked the rooms in his head.

This is hard to describe to people who have not lived it because it does not look like absence. It looks like attendance. You are there. You are laughing at the right moments. You are saying the right things to the friend going through the hard thing. You are, by any external measure, the same person you were five years earlier. The difference is interior. Some unmeasured percentage of your bandwidth has been permanently assigned to a separate process, and the process is not paying rent in the form of joy or insight or even legible thought. It is just running. It is monitoring. It is keeping the rooms in shape for the next time you need to walk between them.

I learned, after a long while, that I could tell where I was on the spectrum by paying attention to small things. Whether I noticed the music in a restaurant or noticed only that there was music. Whether the light through a window made me look at the window or just registered as ambient input. Whether the friend at the other side of the table had told me a story or had told me information. The difference between noticing the window and registering the window was, by the third year, the difference between two qualities of being alive. I do not think I had been told, at any point in my life, that there were qualities of being alive and that one of them could be lost without losing the appearance of being alive.

There is a sentence I caught myself thinking, more than once, while driving home from the office in those years: I will get back to my life later. The sentence is interesting because it concedes, in passing, that my life was a thing I was not currently in. It was somewhere else. It was on a shelf. I would return to it. The work was an interim arrangement, a temporary detour, after which the life would resume. The trouble with that sentence is that the years it covered are not coming back. There is no later in which I will retroactively be in those years. They were the life. I was just not in them.

The performance

What I did not understand at the time, and what I think very few of us are taught, is that competence at a sufficiently high stakes role does not stay external to the self. It moves inside. It becomes a posture you hold even when no one is in the room. You start narrating your own decisions in the language of leadership. You catch yourself, alone in the car, in a hard moment, saying the calming sentence you would have said to a senior engineer in distress, and you say it to yourself, and it works, and you note that it works, and you file the technique away for next time. The mind does not distinguish well between the mask you wear and the face underneath it. Wear the mask for long enough and the face begins to learn the mask's expressions.

I started to feel, somewhere around year three, that I no longer had a private register. Every register I had was, in some sense, a leadership register. When a friend asked me a difficult personal question, I answered with the framing I would have used in a one-on-one with a direct report: clear, paced, careful with the difficult parts, structured to land somewhere actionable. When I was alone with my own thoughts, the thoughts arrived already partly edited, already in a form that could be delivered to someone else. There was no draft. There was only the published version of me, going through the day. The unpublished version had quietly atrophied from disuse.

This is the thing nobody tells you about scaling a small company. The company scales by your output. Your output scales by your reliability. Your reliability scales by the stability of your internal posture. The stability of your internal posture scales by your willingness to perform that posture continuously, including when you do not feel it. So you perform it continuously. And after some time you no longer know which posture is performance and which one is you, because you have been performing the performance for long enough that it has, in the most literal way, become you.

The aesthetic of the modern founder, the way the role is depicted in profiles and on podcasts, is unusually well suited to making this trade and not noticing the trade was made. The founder is supposed to be relentlessly oriented. Relentlessly oriented toward what is being built. The interior life is, in this framing, an indulgence, or at best a tool, a thing to be managed so that the orientation can continue. There is a tone of voice that goes with this role, and the tone is calm, decisive, faintly amused, slightly remote. I performed the tone for years before I noticed I was performing it, and then I performed it for a few more years after I noticed, because by then I had built a company around a person who could produce that tone reliably, and to stop producing the tone would have been to break a contract with everyone who had agreed to work with that person.

I want to be honest about something. The tone is useful. It is genuinely the right tone for many of the situations a founder is in. The mistake is not in having developed it. The mistake is in not noticing how comprehensively it had replaced every other tone I had available.

The lonely substrate

There is a particular kind of loneliness that comes from being the person on whom others rely. It is not the loneliness of having no one. It is the loneliness of having many people, all of whom relate to you through your function. The team is around you all the time. The clients are around you all the time. The friends are around you, when you can clear the calendar. But the part of you that all of them are around is the part that holds the system. The part that exists outside the system is, for most of the people in your life, an inference. They have to take it on faith that there is anyone behind the function. Most of the time they will not ask. Some of them will assume it does not matter.

I noticed this most clearly when someone close to me would ask, as people do, how work was going. The honest answer to the question was about forty minutes long. The polite answer was three words. I gave the polite answer almost every time, because no one was asking for the forty minute answer, and over time the forty minute answer began to feel less and less true to me, because the only version of work I was ever asked to articulate was the version that fit in three words. There is a kind of cognitive entropy in this. The unsaid parts erode. The parts that are not externalized do not, in the long run, stay sharp internally either. You become legible to others mostly through the parts of you they have learned how to ask about.

The 11 p.m. Slack message is a specific texture of this. The person sending it does not mean any harm. They are doing their job. They are flagging an outage. They are asking a question they need answered tonight to ship something tomorrow. The trouble is not the message. The trouble is that the message arrives in your kitchen, while you are pouring a second glass of wine, talking to someone you have been trying to be more present for, and the message does not announce itself as work. It announces itself as the world. It is the world calling you back to the rooms in your head. The conversation in the kitchen does not formally end. It just loses the part of you that was holding it up. The person across from you does not know exactly what has changed, only that something has, that the room has lost a degree of warmth.

After enough of these moments, the people in your life learn. They learn not to ask the long question. They learn to make plans on the assumption that you will be partially absent. They learn to share things with you in the small windows of full presence they can detect, and to wait, on the other things, for the version of you that might one day return. This is itself an act of love, and I am grateful to the people who did it. But I want to be careful not to mistake the accommodation for a kind of normalcy. It is not normal. It is what people who care about you do when the version of you they get is not the version they used to get.

What the body remembers

Here is what I remember, with the kind of clarity that does not require trying.

I remember the road through the Catalina Mountains north of Tucson on a Saturday in October, the year was 2021 or 2022, I no longer remember which, riding my bike through a stretch of singletrack where the granite cools in the shade and the air smells of dust and creosote. I remember the precise dryness of the dirt under the tires, and the moment my friend ahead of me dropped into a switchback and disappeared behind a stand of ocotillo, and the strange small joy of knowing he would reappear a second later on the other side of the wash. I remember, after, the In-N-Out drive-thru in Marana, the Double-Double animal style at quarter to midnight, the four of us in someone's truck, parking lot fluorescents, laughing about something that was not funny in any reproducible way, only funny because of the company and the hour and the soreness in our legs from the day.

I remember a coffee shop on Roosevelt in central Phoenix, a Thursday afternoon, the south-facing windows holding the light that I have never seen anywhere else, the particular sodium-pale yellow of Phoenix in late autumn. I was, by accident, not on my phone. A couple at the next table was reading. Just reading. They had two books, two coffees, and an unhurried agreement between them that the afternoon would unfold without a deliverable. I watched them for what must have been twenty minutes. I do not remember thinking anything in particular. I remember being suddenly aware that I had not, in any recent memory, spent twenty minutes with another human being in which the medium of the time was not productivity. I felt, all at once, like a person watching a country he had been exiled from.

I remember the rooftop terrace of a building near Roosevelt Row, the night of an opening for a friend's show, the kind of Phoenix sky that gets the credit for the city in the photographs the rest of the country sees, low blue dissolving into salmon along the South Mountain ridge, the lights of the freeway coming on in the middle distance, and the texture of a conversation with a stranger who turned out to be a sculptor, which lasted an hour and contained nothing useful to anything I was building, and which I now think of as one of the most important hours of that year.

I remember Taliesin West, off the 101 in Scottsdale, walking through the rooms Wright designed for desert light to enter at specific angles, and the moment I stood in the drafting studio and understood, in a way I had been unable to understand from books, that the building was the argument and that everything else, the office, the lectures, the institutional life of the apprentices, were footnotes to the building. I remember thinking, with a small private surprise, that I had not, in the recent years of my life, been making arguments in this register. I had been making arguments about timelines, and resourcing, and risk surfaces, and acceptable trade-offs. These were necessary arguments. They were not, however, the kind of arguments that left a building behind.

I remember, also, the small things. A friend's apartment on a Sunday afternoon, sunlight on a worn rug, a record I cannot now name on the turntable, the conversation that goes nowhere because it does not need to go anywhere. The dive bar near my office in Tempe where the bartender knew my drink and never asked anything more, and the way that not asking was its own kind of company. The long walk from Tovrea Castle back toward Sky Harbor as the sun finished, the smell of the orange groves, the very particular Phoenix dusk smell of dust held in warm air just beginning to cool. The first cold day of the year, when the desert remembers that it can be sharp.

These are the moments I remember. They are not, by any external measure, the ones that should have weighted most. They are not the contract signings. They are not the launches. They are not the conference talks. The internal ledger that records what was real does not consult the external one. It records what reached me. What reached me, almost always, was the moments in which I was not being useful, and the moments in which I was not performing competence, and the moments in which the person sitting next to me was, for some reason, more important than the next thing on the list.

I do not know exactly what to do with this knowledge. I notice it. I write it down. I am suspicious of any framing of it that would put it in service of the work, that would reframe the desert evenings as a productivity input, that would treat presence as a recovery strategy for performance. The internal ledger does not work that way. The moments that count are not the moments that are spent in order to count. They are the moments that arrived because the part of me capable of receiving them was, briefly, awake.

What success buys

In the last year I have started to notice something about the most successful people I know. They are, in their forties and fifties and sixties, with companies sold or running, with the things they wanted, doing a strange thing with their money. They are using it to buy back what they had at twenty-three.

They book restaurants for the atmosphere. They hire someone to teach them to surf or to play the piano or to read poetry slowly. They renovate the kitchen they do not cook in. They take trips to look at architecture in cities they will never live in. They pay a guide to lead them through a country they could have backpacked through for free in 1998. They are not buying status, not most of them. Status, by this point in their lives, is a tax they have already paid. They are buying texture. They are buying slowness. They are buying the kind of afternoon that, in their twenties, was free.

This pattern, when I started seeing it, made a kind of sense I had not been ready to admit. The texture they are buying is the texture I am quietly losing, year by year, in the rooms in my head. The slowness they are paying premium prices for is the slowness I have been postponing on the assumption that I would return to it later. The afternoons they are buying are the afternoons in which one is undivided. You cannot buy an undivided afternoon, exactly. What you can buy is the conditions for it, and the absence of competing demands, and the right room with the right light. But the actual undivided attention, the part of you that shows up to receive the afternoon, is a faculty. It has to be exercised. It atrophies when not used. The successful people I am describing are not, mostly, paying to access the world. They are paying to access the version of themselves that could once access the world.

I think about this often. The work is the work. The work matters. We are building things, my colleagues and I, that move real value, that produce real outcomes for real operators in real industries. None of this is incidental, and none of this is being repented. What I want to flag, only because I have rarely seen it flagged elsewhere, is that the part of the trade that is rarely priced is the part that compounds invisibly. The afternoons accumulate, on the unmeasured side of the ledger, for many years before the ledger is consulted, and by the time it is consulted, the faculty for receiving afternoons has weakened, and you are left holding a number of resources you can in some sense exchange for what you had, before the trade began, for free.

The freedom that money buys, in this register, is not freedom. It is access to the conditions under which freedom is possible, if you have preserved the inner machinery for it. The inner machinery is not for sale. There is no version of the trade in which the inner machinery is included in the package. You can only develop it or fail to develop it, on your own time, in your own life, on Tuesdays and Thursdays when no one is watching. The successful people I know are, in middle age, trying to develop the inner machinery on schedule. Some of them are succeeding. Many of them, by their own quiet admission, are not. There is a kind of grief that accompanies that recognition, which I have begun to recognize in their faces, and which I want, for whatever it is worth, to avoid wearing on my own.

Toward a more human way

I am not concluding that the work was a mistake. I want to be careful about that. The work was, in many ways, the best thing I have done. The system we built does specific good in the world for specific people in specific industries, and I am proud of it. I will keep building. I will keep, in some form, being the person on whom other people rely. The temperament I have for the work is, for better or worse, the temperament I have, and the alternative versions of my life I sometimes imagine, in which I am a cabinetmaker in northern New Mexico or a writer in a coastal town, are sentimental imaginaries that do not match the actual person I am.

What I am revising, slowly, is the assumption that the work has to displace everything else in order to be done well. I think that assumption is, in fact, untrue. I have begun to suspect that the version of me that was completely consumed by the work was not, in the end, a better version of me at the work. He was a more reliable one. He was a more available one. He was easier to schedule. But the actual quality of the work he produced, when I look at the years now from a small distance, was not higher than the work I have been able to produce since I started, in small ways, to take parts of myself back from the rooms. The good ideas were not in the rooms. The good ideas were in the desert evenings. They were in the conversations with the sculptor. They were in the architectural rooms designed by people who had paid attention to a different kind of return. The rooms in my head were necessary for execution, but the inputs that fed those rooms came from elsewhere, and I had cut off the elsewhere in the name of execution.

This is a quieter realization than the burnout version of the story would suggest. It is not that the work was destroying me and I had to escape. It is that the work was producing a particular shape of person, and that shape was not, on closer inspection, the shape I wanted to be in five years, and the only way to be in a different shape in five years was to make small choices now, against the gravitational pull of the role, in favor of the parts of being alive that the role was quietly displacing.

So I have started, in unspectacular ways, to make those choices. I drive the long road home sometimes when the short one would have been more efficient, and I pay attention to the saguaros. I have started picking up books again, the kind that have nothing to do with software, and reading them slowly. I have started to leave certain hours of the day genuinely unscheduled, in a way that the version of me from three years ago would have considered irresponsible, and I have noticed, with the unwanted clarity of an experiment, that the unscheduled hours produce a different quality of thought than the scheduled ones, and that some of my best work in the last six months has come out of them. I am riding more. I am, in small ways, present at dinners. I am letting the long answer to "how is work" sit unsaid, when no one has asked for it, without feeling that the unsaid version is therefore disappearing. I have started, with a self-consciousness I cannot quite shake, to take walks. I have started to listen to records all the way through. I have started to go to architectural rooms and let them argue at me without trying to take notes.

None of this is a system. None of this can be a system, exactly, because the entire problem is that I had made everything into a system, and the systems were eating the substrate they depended on. The corrective is not another system. The corrective is a practice of refusal, a practice of leaving certain things unoptimized, of allowing certain hours to be exactly what they are, of resisting the small voice that whispers, throughout the day, that everything would go better if it were tracked.

I do not know exactly where this lands. I do not have a tidy ending. I am still building. I am still, in many of the senses I described earlier in this essay, the person on whom a system depends. The rooms in my head are still there. They will be there for the foreseeable life of the work. What has changed is that I have started to spend, on purpose, time in rooms that are not in my head. I have started to admit that the version of me that produced the company is, on balance, a less interesting version of me than the version that was once capable of an undivided afternoon. I have started to try to be both. I do not know if it is possible. I know that it is the only project, in the next phase of my life, that seems to me to matter as much as the work.

If you are inside the rooms now, reading this on a phone in a coffee shop you cannot see because you are reading on a phone, I do not want to give you advice. The literature of advice is, in my experience, the literature of people pretending to have figured out what they have not figured out. What I want to do is name, in some form, the thing that is happening to you, in case naming it helps. The thing that is happening is not burnout. It is not even unhealthy, by any normal measure. It is a slow assimilation of the inner self into the operational layer, a kind of architectural change in the person, undertaken in service of a system that for a while will need you to be exactly that shape. You may decide the trade is worth it. Many people do. The work is real and the work matters and the trade is not, by any obvious accounting, unreasonable.

What I want to flag is the unmeasured side. The afternoons. The desert evenings. The friend's joke at midnight in the In-N-Out parking lot. The hour with the sculptor. The light through the south-facing window in Phoenix in late autumn. These are not, on the standard accounting, important. They are, in the actual living of a life, almost everything. You cannot, in the end, buy them back. You can only protect them now, while they are happening, while the road through the Superstitions is still in front of you and the saguaros are still leaning toward you in the late light.

I am going to keep building. I am going to try to build differently this time. I am going to try to remain alive enough, while I build, to receive the years they are made of. I do not know if I will succeed. I think the only way to find out is to drive home the long way more often, and to notice, when I do, whether I notice.