I’ve recently been telling anyone who will listen that I am excited to be on the precipice of using Sorbet to write a type-checked edition of Mocktail that has the potential to unlock productivity workflows never before possible in Ruby.

I’m not there yet.

I don’t want to say it’s been a “quagmire,” but I’m over 150 commits in, and there’s a lot left to button up before release. It’s been a real challenge. Learning Sorbet at all takes a good chunk of time, to be sure. I’ve also hit a number of thorny edge cases and elusive bugs along the way (both in the type system itself and that the type system exposed in my code). And, like usual, I’m trying to do something that’s never quite been done before, so I’m constantly oscillating between feelings of nervous excitement and fear that I’m attempting the impossible. (Though it’s been made far more possible thanks to the generous assistance of Ufuk Kayserilioglu, Kevin Newton, and Jake Zimmerman!)

Beyond this, any specifics I might share about my current quest are so banal as to not be worth your time. (If you somehow find this interesting, please email me so I might feel less alone in this world.) That said, there is something generally interesting here that programmers don’t often talk about. And that’s the deeper question: why do I keep doing this to myself?

What makes me “special”

I am an enthusiast programmer.

I stumble on a problem like this one and I stay up late every night until I find the solution. I wake up early each morning with new ideas of things to try. I don’t take enough breaks, but when I do, they’re tactically-designed to exploit my brain’s asynchronous processor to generate solutions for whatever I’m currently stuck on. I irresponsibly defer responsibilities from other areas of my life. Eventually, I realize I’m only at the 20% mark and that a pattern is repeating where a month or more of my life is about to disappear from the calendar. Towards the end, I find myself rushing to find the maze’s exit because my desire to unlock the puzzle’s final secret starts to be overtaken by the shame of all the other balls I’m dropping. It’s excruciating as I approach that inflection point—as intense as an overbearing manager’s “do or die” deadlines ever were, except in this case the pressure I feel is entirely self-imposed.

And then, at some uneventful moment at 4 pm on a Sunday, it’s done.

Sometimes people care about what I made. Usually they don’t. Often, even I don’t.

I give myself enough time to clear my inbox, tidy the house, and shave. Then I move onto the next Sisyphean task I’ve laid before myself.

This describes how I’ve lived my life since I was 13 years old, with few exceptions. And let me tell you, it’s very difficult to juggle a healthy personal life and a sustainable work life when you’re simultaneously engulfed in an endless series of side quests to will every creative curiosity into existence.

When I was a consultant at Crowe, there was one year I billed clients for nearly 2100 hours, which averages out to more than 40 hours per week every week of the year with zero days off. And that’s not counting travel time. Or the half-dozen hours of weekly administrative work that wasn’t considered billable. Nevertheless, I found time in my nights and weekends that year to build an app with Apple’s buggy, mostly-undocumented initial iPhone SDK. The app was a native client to vBulletin web forums, allowing users to browse threads and compose replies. Despite knowing nothing about any of the underlying technologies, I obsessively polished the app to perfection. Did I make time to sleep? I don’t remember. The whole year’s a blur.

All so that Apple could reject my app because users might post swear words or dirty pictures. Oh, well. Onto the next thing.

I don’t know what word best describes my behavior above without inflecting significant value judgment. Perfectionist? Obsessive? Passionate? Whatever we call this compulsion, it’s hardly an unalloyed good and it comes with its share of downsides. Nevertheless, it’s one of a number of idiosyncrasies and character flaws I’ve decided to lean into and find productive outlets for rather than attempting to repress or rewire.

Other examples:

  • I ruminate endlessly under stress, so I wrest back some control by manufacturing stress responses over things I’m building to trick my brain into ruminating on work that’s useful to me. This both overrides the unhelpful, irrational worries that surround me every day and unlocks a “second shift” where I accomplish almost as much away from the keyboard as in front of it
  • I’m a terrible listener and struggle with auditory processing, especially in groups and loud environments. (One reason I talk so much is that it’s always felt safer to drive the conversation than risk mishearing and offending someone.) Parsing others’ sentences often feels like I’m filling in the blanks to make sense of them, like playing a game of Mad Libs. Over the years, I’ve redirected this into a source of creativity and humor. Most of my puns and wordplay are happy accidents as I fill in the gaps in my own listening comprehension. Some of my most creative ideas are things I swear I heard someone say when it turns out they were actually talking about something else
  • I’m a really bad learner—disinterested, distractible, and disagreeable. I’ve never enjoyed learning and generally avoid it, especially learning for its own sake. At the slightest discomfort when struggling to understand something, I’ll grasp for any distraction that might offer me a momentary escape. When I do manage to get traction, I inevitably find myself disagreeing with the premise or subversively trying to prove the authors wrong. The upshot is that once I actually do learn something, I know it cold. It means I will have scoured every nook and climbed out of every pitfall. Professionally, this apparent weakness has turned out to be a superpower. Learning everything the hard way has made me a natural consultant and mentor. Because I’ve already explored all the wrong paths, I often know someone is stuck before they do, understand what threw them off course, and show them how to get back on track

The reason I landed on this topic today is not that any of the above makes me special, it’s actually that contradictions like these—whatever their origin—are so typical among programmers born before 1990 that they’re entirely mundane.

An aberrant generation of programmers

Squint and everything I just said about myself could have described a character from The Big Bang Theory or Silicon Valley. I’m at peace with the fact that on my best days, I’m an overplayed, abrasive character trope come to life. For decades, we’ve associated a slew of mostly-negative traits like these with programmers as if the linkage is inherent and inevitable. I’ve always thought that stereotype was arbitrary—anybody can learn programming and be great at it—but now I’m starting to think it’s a product of our times as well.

That is to say, I’ve come to believe the era typified by the enthusiast programmer—autodidactic, obsessive, and antisocial—is drawing to a close.

Why do I think that? Because there was a specific, generational moment that attracted a bunch of people like me into the software industry. It occurred during the brief window between home computers becoming widely available and their becoming sealed airtight by platform holders. For a fleeting moment, computers were simultaneously accessible and scrutable during a necessary but temporary stage in the maturation of information technology. Before they were rendered irreducibly complex as consumer devices, merely using a computer required figuring out a lot about how it worked. And coming of age with an understanding how computers worked made programming them far more approachable. And thanks to cosmic coincidence and the marketing teams of companies like RadioShack, society unwittingly handed a generation of social mobility to the boys of upper-middle-class families in the US who felt more comfortable at home with their computer than outside engaging socially with their peers. I was definitely one of those awkward, anxious kids and a whole lot of the programmers I’ve met along the way were too.

But one reason to believe that programmers don’t have to be like this is that programmers weren’t always like this. I remember asking a computer science professor in 2003 about our school’s gender disparity (we only had a single woman in my class, and she later switched majors). He recounted that before 1990 and the advent of hacker and gamer subcultures, my college touted robust majorities of women in computer science. (Nationally, women’s enrollment in CS doubled in a decade, peaking at 37.1% nationally in 1984 before dropping precipitously.)

And one reason to believe programmers won’t always be this way is that there’s plenty of evidence that the next generation of professional programmers is no longer dominated by enthusiasts. People becoming software developers today look markedly different than those who came before. (Sadly, I wish I could say I’m referring to the success of movements to increase representation from traditionally marginalized groups—tech is still dramatically over-indexed on white dudes who enjoyed affluent upbringings.) I’m just pointing to all the money sloshing around here: it catapulted programming from a firmly middle class job that appealed to people who really loved computers into a comfortably upper-middle class profession that attracts anyone who wants to secure their financial future. Ask anyone who switched careers in the last decade how many times someone suggested they “learn to code.” Countless people are entering the industry simply because programming is a relatively secure, well-paying profession. (And there’s nothing wrong with that!)

Inter-generational conflict is brewing

I’m not sure if anyone has ever said “OK boomer” to my parents, but I can imagine it wouldn’t feel awesome to hear.

Nor do I know whether anyone will coin a term to dismiss my generation, but I have faith that there’s enough societal exasperation out there for someone on TikTok to come up with something snappy. A lot of people in my professional cohort still see themselves as social outcasts who grew up in front of a CRT in their parents’ basements, but I suspect the next generation sees a homogenous monolith of 40-somethings wearing hoodies and sandals (with socks!) that lucked their way into capturing control of the software industry just as it settled into a state of economic maturity.

Sit with this distinction for a while, and you might start to see these old-hat programmers as belonging to an Enthusiast Generation, one that—due to its unique initial circumstances—is unlikely to be replicated. Once I introduced the word “generation” to my thinking, it became easier to make sense of many contentious, unresolved issues in tech that flared up over the past decade by looking at them through the lens of intergenerational conflict. And just like any discussion of generations, it’s important to caveat that there are no firm boundary lines, that exceptions are plentiful, and that many observations will be isolated to a single locale and culture (the U.S. in this case, maybe Canada?). The only thing that bucketing people into generations can do for us is provide a new way to look at how a population may be changing, thanks to a big enough time-step to perceive the accumulation of decades of gradual change.

To illustrate, I’ll highlight three high-profile conflicts that make a different kind of sense when viewed as a generational shift.


I remember about 8 years ago, people got passionate about the word passion.

This rubbed me the wrong way at first. Then again, everything does.

I remember thinking, “banning the word ‘passion’ will just lead people to pick others like ‘self-driven’, ‘highly-motivated’, and ‘ambitious’.” I remember asking, “are we supposed to screen out candidates for whom programming is a hobby outside work?” What I don’t remember was pondering whether this was an indication that the times were changing.

When I entered the industry, my salary was lower than it would’ve been if I’d gone into accounting, or become an actuary, or majored in civil engineering—myself and most of the people around me did get into software because we were passionate about it. Reading tweets and thinkpieces that suggested “passion” was a four-letter word felt like a personal affront, so I responded defensively.

What I wasn’t thinking about was what it must have felt like for everyone who entered the industry expecting their job to be a job but who found themselves managed by people from my generation who didn’t leave them room to have a life outside work. Maybe everyone else on the team worked overtime without being asked. Maybe taking “too much” supposedly “unlimited” time off would foreclose any chance for a promotion. Maybe building rapport at lunch required holding evolved opinions on Emacs vs. Vim, or mechanical key switches, or whatever was on the front page of Hacker News. That sounds like a pretty miserable existence, especially if programming isn’t what gets you out of bed in the morning.

If you allow for the possibility we’re undergoing a generational change, maybe this debate over “passion” is evidence that the assumption that most programmers will always be passionate about programming was mistaken and counter-productive.


This brings another contentious word to mind: “craftsmanship.” Its origin, as I witnessed it, was a reaction to the watering down of the technical aspects of the agile software movement in the late 2000s in favor of more lucrative soft-skills training and consulting services. In case you missed it, most of the craftsmanship meme could be summed up as a Slow Code movement. There was a lot of talk about measuring twice and cutting once, establishing apprenticeship programs to train new programmers, and a million ways to leverage automated tests for purposes other than testing things.

I was an active participant in this community, speaking at the conference several times, putting my name on the manifesto, and generally exhorting anyone who would listen to please make their software less terrible.

But looking back, the craftsmanship movement wasn’t only about rekindling the tremendous engineering insights of agile methods like Extreme Programming, it was also a response to a rapid influx of a generation of programmers who didn’t care about code quality the same way we did. There was a sense that serious programmers were under threat and hopelessly outnumbered by unserious ones. That if your team didn’t get more disciplined about what you allow in your codebase, you’d find yourself mired in a maze of complexity, beholden to epochal build times, and left holding the bag with yet another legacy system.

Thinking about this point of tension as another manifestation of the generational shift we’re experiencing, it’s easy to spot the problem: “what you allow in your codebase” is a wee bit too easy to conflate with “who you allow in your codebase.”

Shibboleths like “test-driven design” were so numerous that, to outsiders, even perfunctory conversations were riddled with rhetorical land mines. The emphasis on apprenticeship also carried assumptions nobody seriously grappled with: that it implied “one true path” to programming, that somebody (us) had uniquely figured it out, and that the only way to learn it was to imitate the people who came before you. I watched more than one conference talk advocating for professionalizing software like any other trade by licensing programmers just like we do plumbers, electricians, and Canadian engineers. Everyone’s intention was to prevent people from writing bad software, but some of the movement’s prescriptions would have prevented many people from writing software at all.

10x Developers

Before you say anything, I know you probably already have an opinion on the idea of a “10x” developer. If you aren’t familiar, the term refers to debatably-mythical programmers whose output is worth that of ten other programmers. What aspects of that output? Which ten other programmers? Unclear.

The concept behind the “10x” term predates either of the generations of programmers being discussed here. It seems to have originated in this (flimsy) 1968 study that among experienced programmers, the best were ten times more productive than the worst (as opposed to the average). We remember it because it was referenced in the late Fred Brooks’ seminal Mythical Man-Month.

That some people are better at their jobs than others is (usually) uncontroversial. At least, it was, until it bubbled up in The Discourse during the 2010s as a flashpoint over who the industry chooses to valorize, often sparked by tweets from people affiliated with venture capital and advocating that founders should strive to “only hire 10x developers.”

In response, many people who reasonably identified this framing as unproductive chose to pick a weird fight by claiming that 10x developers don’t exist instead. This invited a lot of counter-criticism, as I think most of us can dream up examples of people whose work is 1/10th as valuable as their own. From there, the conversation shifted to counter-counter-critiques enumerating the adverse knock-on effects of adding a toxic actor to a team, no matter how much of a ninja/rockstar they are at coding.

And it was here that the conversation settled into a stalemate, with clear battle lines dividing the two camps. On one side were proponents who believed a lot of well-compensated programmers aren’t very good, but that a few programmers are so good that the value they generate far exceeds the range of a typical payscale (which was why Google used to brag that they “pay unfairly”). On the other side were critics who were more than happy to project every negative stereotype about programmers onto these supposedly hyper-productive ones, suggesting a 10x developer’s easy-to-measure output often came with hard-to-measure organizational and technical costs.

But now, looking back, this debate would have gone a lot differently if we’d considered it through the valence of inter-generational conflict.

I’ll come clean: do I believe some programmers are at least an order of magnitude better at programming than others? In my experience … yes. I’ve worked with programmers who routinely solve problems in minutes after I’ve wasted days or weeks on them. I’ve witnessed a programmer singlehandedly build something in a day that an entire team struggled to deliver in two weeks—without any of the catastrophic antisocial, unsustainable downsides one might imagine. I’ve honestly seen more socially corrosive behavior from the other end of the productivity spectrum, because programmers who spin their wheels and make zero forward progress for days, weeks, or months will inevitably scramble for a way to save face.

It may be uncomfortable to admit, but it’s not altogether unreasonable to speculate that enthusiast programmers may, in aggregate, outperform professional programmers who hang up their keyboard at the end of each shift. In my experience, these traits differentiate the former from the latter:

  • Tireless: spending more time practicing programming—not under coercion to work long hours, but being intrinsically motivated to do so—will generally make someone a better programmer
  • Tenacious: chasing down answers with limitless curiosity and relentless, no-holds-barred tenacity—whether or not it’s in their job description to spelunk open source stack traces or debug other teams’ code—will yield better information and faster progress
  • Thorough: priding oneself on the quality of one’s work and pursuing excellence in the (brace for it) craft—not falling victim to perfectionism, but cutting the right corners when necessary—will produce better-working software that’s easier to maintain

In the context of this generational rift, all three of the above are exemplified by (but by no means exclusively limited to) us last-gen models: the individual that programs in their spare time, obsessively refuses to let a hard problem go, and is personally invested in the quality of their work product.

I can’t imagine this dynamic feels awesome for members of the new generation who don’t want to spend more than 40 hours a week at their computer, or who have significant family commitments, or who aren’t inclined to asynchronously ponder refactoring techniques as they run errands. Will they be forever outpaced by more enthusiastic colleagues for whom “programmer” is an all-encompassing identity as well a career? I don’t know.

It’s an uncomfortable conversation because it’s an uncomfortable reality.

What do we do with this?

The power of an analogy lies in what it empowers people to do. Envisioning programmers as belonging to discrete generations who are ushering in a dramatic transition in the industry can equip us to identify the common threads between many of the challenges we’re currently facing. It may even enable us to predict and plan for inevitable difficulties in the future, as more members of the earlier generation age out.

Suppose you’ve read this far and you can buy both these arguments:

  1. The next generation of programmers are less likely to be motivated by a love of programming than the previous generation and may differ in profound ways as a result
  2. Software, as an industry, has structurally organized itself around the assumption programmers will continue to resemble members of the outgoing generation

If so, then you can probably imagine there will be a lot of problems to be solved here. The hot-button issues we revisited above are already known, even if we failed to put our collective finger on a common cause at the time. It’s likely that countless more challenges lie beneath the surface, waiting for the spark that causes them to boil over. It’s up to us whether we put in the work to uncover and address these problems proactively.

Here are a few examples of questions I find myself asking after sitting with this for a few days:

  • The new generation is more likely to expect structure and support from human resources and management, whereas the previous generation is more likely to find active management (e.g. career pathing, coaching, goal-setting) actually saps their autonomy and intrinsic motivation. Can organizations effectively cater to the needs of both groups?
  • It’s an open secret that the industry has no idea how to teach people to program. Computer Science degrees famously don’t prepare programmers for the job of programming, which has always been left as an exercise to the student to figure out on their own time. If the industry is going to outlive us enthusiast programmers, will it adopt a sustainable approach to educating the next generation that doesn’t require people to teach themselves everything?
  • Betting your business on a limitless supply of self-starting, self-sufficient, self-disciplined candidates seems a lot like investing in the long-term prospects of fossil fuel extraction. How will companies that built their cultures around enthusiast programmers adjust to a generation needing more direction, more support, and more accountability?

All we know for sure is that time keeps marching forward and change is a constant, so planning for a future that looks different than the past is usually time well spent.

What challenges do you see in this generational transition? Join the conversation on our N.E.A.T community

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Justin Searls

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Double Agent
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