The art of decision-making


Once, when contemplating the apparently endless growth of administrative responsibilities in British academic departments, I came up with one possible vision of hell. Hell is a collection of individuals who are spending the bulk of their time working on a task they don’t like and are not especially good at.

I might live in hell.

As a software engineer (not my exact title, but close enough), starting a new job is usually exciting. Suppose you are one of the company’s first “tech” employees. You were hired because the company’s processes were beginning to strain under growth. The website that was originally built for thousands of clicks per day is now seeing millions. The garage that was used to store goods is overflowing, and a new warehouse is being rented out and staffed by dozens of workers. People have dozens of ideas on how to ease the user’s flow through the website, but no scientific way to test those ideas. As a new developer, you will build the requisite infrastructure: the slicker, more performant website, the inventory management and labor tracking systems, the A/B testing framework. There is a thrill inherent in creation, in deciding which language to code in, in drawing up the virtual blueprints for the program, in figuring out how all the pieces fit together. It combines the practical and the artistic in a beautiful way; solutions that work but are inelegant are viewed, derisively, as “kludges”, but solutions that are elegant but don’t work are viewed as useless.

The thrill of creating something is partly intrinsic and partly extrinsic. The extrinsic part involves the approval of the end user: the customer, the chief operations officer, the product manager. But the problem of creating something that people like and use is that it can’t simply be discarded when it, too, begins to strain under growth. The irony of technology is that it is designed to overcome human limitations but ends up reproducing them. The pre-technology problems stemmed from the lack of scalability and reliability of humans; the post-technology problems from the lack of scalability and reliability of what humans have written.

(I’m reminded of this passage from The Mythical Man-Month: “Computer programming, however, creates with an exceedingly tractable medium. The programmer builds from pure thought-stuff: concepts and very flexible representations thereof. Because the medium is tractable, we expect few difficulties in implementation; hence our pervasive optimism. Because our ideas are faulty, we have bugs; hence our optimism is unjustified.”)

Anyone who has built something useful spends ever larger fractions of time maintaining it. That shift — from creation to preservation, or, more poetically, from Brahma to Vishnu — is one that I did not fully recognize as it was happening at my current job. I think that’s because “maintenance” encompasses a range of tasks that superficially don’t have much in common. Writing documentation and giving presentations about how the product and its technology works; talking with the end users or stakeholders about its strengths and weaknesses; building incremental improvements for it; preserving its existing functionality even as the business changes: each of these is an act of maintenance, broadly construed. The process of creation is self-regulating: build too many new things, and the sheer effort of maintaining them will prevent you from building more.

There is a beautiful essay in the New Yorker, called “The Art of Decision Making”, by Joshua Rothman. I’d encourage you to read the whole thing, but first consider this passage:

I’ve made my share of big decisions. This past summer, my wife and I had a baby boy. His existence suggests that, at some point, I decided to become a father. Did I, though? I never practiced any prudential algebra; rather than drawing up lists of pros and cons and concluding, on balance, that having kids was a good idea, I gradually and unintentionally transitioned from not particularly wanting children to wanting them, and from wanting them to joining my wife in having them. If I made a decision, it wasn’t a very decisive one. In “War and Peace,” Tolstoy writes that, while an armchair general may imagine himself “analyzing some campaign on a map” and then issuing orders, a real general never finds himself at “the beginning of some event”; instead, he is perpetually situated in the middle of a series of events, each a link in an endless chain of causation. “Can it be that I allowed Napoleon to get as far as Moscow?” Tolstoy’s General Kutuzov wonders. “When was it decided? Was it yesterday, when I sent Platov the order to retreat, or was it the evening before, when I dozed off and told Bennigsen to give the orders? Or still earlier?” Unlike the capture of Moscow by Napoleon, the birth of my son was a joyous occasion. Still, like Kutuzov, I’m at a loss to explain it: it’s a momentous choice, but I can’t pinpoint the making of it in space or time.

I find myself wondering about my career transition in the same way. It is certainly not as momentous as having a child, but somehow, in the span of little more than 2 years, I went from being one of the first engineers at my company to the director of a team of 7. I made the choice, supposedly, of transitioning from spending most of my time building things to managing and advising people on how those things should be built upon. Engineers become managers, academics become administrators, lab-bench scientists become heads of those labs. Skill at one does not necessarily translate into skill at the other, and the same goes for joy: this is how brilliant people can “spend the bulk of their time working on a task they don’t like and are not especially good at”. It is because, to borrow Rothman’s phrase, although they made a decision, it wasn’t particularly decisive.

Deciding without being decisive breeds resentment, but often the kind that can’t be directed towards any productive end. I have indulged in the seemingly rational exercise of deconstructing the last few years to arrive at some hidden wisdom. I am less happy now at work than I was two years ago. True, but why?…Well, what do I value? I like creating things, mostly for the intrinsic aspects. (If I cared about the extrinsic aspects more, I certainly wouldn’t be writing blog posts for an audience of two.) I like solving the puzzle of translating the business requirements into a technical design, and, in turn, of translating that design into words on a computer. And if that process forces me to learn about and use novel technologies, frameworks, or programming languages, all the better. I like reading and learning for fun. I like having undivided time to do all of these activities. I like entering a state of flow, which, increasingly, I find I can visit only when I’m supposed to be on vacation and am working instead.

(As I read the “Bullshit Jobs” essay quoted at the top, I vacillated between thinking I had a bullshit job, and lamenting that I did not. There are certainly aspects of my job that are bullshit, but I wish I was more like the “more and more employees [that] find themselves, not unlike Soviet workers actually, working 40 or even 50 hour weeks on paper, but effectively working 15 hours just as Keynes predicted, since the rest of their time is spent organizing or attending motivational seminars, updating their facebook profiles or downloading TV box-sets.” At least then I could use that 25 hours of pseudo-work to do something I enjoy.)

I find myself drawn inexorably to the conclusion that my fate of (relative) unhappiness at my job was predestined. Rothman asks the question, “Are we in charge of the ways we change?”. Discouragingly, at least in this case, my answer is no. The systemic forces pulling me, ineluctably, into my current role seem more powerful than my individual ability to alter my own course. The shift from having few meetings to many, from supervising no one to several, from working by myself to operating in a team, from having spare time to explore my technical interests to having virtually none, from entering flow regularly to context-switching so much that my brain becomes fried — this shift was inevitable, wasn’t it? It was an outgrowth of my success. If I had failed, no one would have wanted to meet with me, or be supervised by me, or Slack me, or bombard me with emails. But because I didn’t, I was carried along, by the natural logic of business, into positions of ever more responsibility.

I worry that this essay is my most absurdly self-pitying yet. I am a very privileged individual who has spent 1500 words complaining about an equally privileged tech job. I don’t expect sympathy; if anything, I’m writing for myself, and hoping that laying the words out on the page forces the thoughts to make more sense.

I’ve always been an overly rational person, the kind who, like Charles Darwin, would write an excessively thorough meditation on the pros and cons of marriage (pictured above) before making that decision. What worries me, deeply, is that I’ve lost the thread on my own life, and that my rational approach is too lumbering or too poorly equipped to deal with how life actually works. The meditation on marriage should be written before getting married, not after. My rationality seems more like a rationalization than anything else: a way to be decisive after having already been decided for.


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