It occurs to me this morning that my problem (well, one of them) with AI training work is that I’m a perfectionist. As if you hadn’t noticed…. AI training companies want people who are “detail-oriented,” a trait that many people associate with perfectionism, but that’s a bit misleading. They want detail-oriented people who slot their insights into categories that have been vetted and aligned with pre-existing standards. They want to create universal rules and plow every bit of data into them. Some people thrive on that, but for me that’s pendanty and not perfectionism.
For several years I have been struggling with a particular type of virtual coworker. I have uncharitably dubbed them the Grammar Karens. They are the ones who insist that a comma goes here and only here. Who publicly screech about other people’s typos it would take them three keystrokes to fix. Who insist that the English language has perfectly regular, recognizable, codified, and agreed-upon rules, when, of course, no such things exist in English. They are walking style guides in their own minds, though no one has ever read them. They are very concerned with how we say things, but nearly heedless of why we are saying them or whether they need to be said at all. They revel in the means, but the ends, they feel, are not something they need to consider. They appear to be perfectionists. In fact, they are pedants.
You know them because they always asked the teacher if something was going to be on the test, and if it was, they hijacked the class’s time to make the teacher explain it all over again and explain it in a way they could put on flashcards. You know them because they are the ones who get on a transcontinental flight and, when they find themselves sitting between an English professor and a linguist, remark, “Oh, I better watch what I say.” They assume that the professor and the linguist are also pedants when the professor and linguist couldn’t care less about whether Karen splits her infinitives or not. Indeed, the professor and linguist are going to be much more interested in how Karen naturally speaks than they are in watching her try to recall every useless “rule” she’s ever learned. Unless, of course, the professor and linguist are bad at their jobs, which would make them pedants like Karen, and Kern is right to watch what she says.
When I tell my friend Landon about this, he shakes his head and says, “You and your standards.” He’s known me for over 40 years, so he knows what he’s talking about. I’ve been told (by much available literature, not by Landon) that perfectionists have “excessively high standards for themselves and others.” I know what those words mean, yet I don’t know what they mean in any sort of emotional or spiritual way. Excessively high standards? To me, this is like saying a fish is out of line were it to prefer “excessively clean water.” I might as well give up my expectations for excessively nutritious food while I’m at it. I’m also perfectionist enough to know that now I’m veering into another perfectionist trait: when we get frustrated with something, we navigate toward mockery and satire. It makes us insufferable to other people, especially to pedants, but hey, it’s how we perfectionists recognize each other. Many times in my life I have heard a friend say something like, “Oh, X is so difficult to work with.” Then I work with X and find that’s not true for me. What they really mean is that X is a perfectionist, and when he gets frustrated by a group focusing on less important details, he’s going to let go with some kind of zinger. It usually turns out that X and I get along well, that I find X a pleasure to work with. Friends are amazed at that, while I’m simply befuddled at their amazement. My people, my people.
Perfectionists and pedants focus on different levels of detail. For perfectionists, there are lots of useless details. There are details that are irrelevant to the larger goal; they can be ignored or omitted. For a pedant, that perspective is a scandal. In defense of us perfectionists, I will claim that we aren’t obsessed with excessively high standards. We are just obsessed with standards that are idealized. It’s not that we think we are going to reach those standards today, tomorrow, or next year. It’s that we don’t see much point in attempting to do things that we know are completely within our grasp. Those things are, frankly, boring. We will always fail, but our hope is to fail upwards. What frustrates us is being in an environment in which failure is not an option. We tend to believe that if we can’t learn from our mistakes, then we can’t learn anything at all. While such a belief is not entirely true, that’s what pedantry feels like to a perfectionist. It feels as if getting every little detail right obstructs real achievement. It feels like a lack of vision.
Perfectionists don’t actually care about the flawless execution of just any task, we care about the execution of tasks that we think matter. We care about choosing the correct tasks, about doing those tasks efficiently, about getting the perfect level (neither too much nor too little) of detail to move toward a larger goal. We want to know whether we need to modify the universal rules we use as assumptions, not whether we have perfectly boxed up all available information into those universal categories. Pedants adhere to rules; perfectionists break them when appropriate. It’s like the perfectionist George Orwell said when he provided a list of rules for good writing: Rule #6 “Break any of these rules sooner than say anything outright barbarous.”
However, in the lingo of tech, perfectionism doesn’t “scale.” It’s always mucking around in ambiguity. It’s always calling attention to presumptions. It’s always critical of a shiny self-image. (I’m told by psychology mavens that perfectionists often have low self-esteem, which would seem to put them at the opposite end of the spectrum, as it were, from pedantic Karens.) Perfectionists prefer something true to something correct. It’s damn near impossible to organize that mindset into something like ChatGPT which performs 100 trillion operations per second. It’s likely a Karen’s world, and I’m just living in it.

Great analysis and perspective! Hang in there!