# The Hair Policy That Proved Why Entire Departments Quit
Here’s a useful model: A resort HR department wanted to enforce professional appearance standards. The constraint was that the rule had to be technically defensible and apply equally to all staff. The result was a hair-length mandate that said “kept above the collar” but explicitly forbade ponytails. This is what we might call incentive misalignment in its purest form—a rule so precisely calibrated to prevent the obvious solution that it becomes a Rubik’s cube of compliance theater.
Let’s think through what happened. A young male employee, faced with a hair-length requirement that collar-height hair could meet, had the audacity to simply… keep his hair at collar length. No ponytail. No bun. No creative interpretation. Just hair, sitting there, technically compliant with the stated rule, doing the one thing the rule-makers apparently didn’t anticipate: existing as written. The malicious part wasn’t even malicious—it was just hair, minding its business, while HR discovered that their policy had a flaw shaped exactly like a human head. [The comments are instructive here: a user noted you could wear a bun. Another suggested a beehive. A third observed, with the weariness of someone who has seen this movie before, that this was probably why—twice—entire departments walked out.]
Here’s what’s interesting about the second-order effects. When you design a rule so specifically to prevent ponytails that you accidentally create a loophole for shoulder-length hair, you’re not actually solving for professionalism. You’re solving for the feeling of having won an argument with an employee. And when employees notice this, when they see that the rule isn’t about appearance but about compliance-theater-as-dominance, they tend to do what humans do: they leave. Not angrily, necessarily. Just… elsewhere. The resort apparently had to rehire entire departments multiple times, which suggests that the hair policy was less a professional standard and more a very expensive way to communicate “we enjoy being right more than we enjoy being staffed.”
The elegant part—the part that makes this a case study in how incentives actually work—is that the employee never broke the rule. He simply let the rule encounter reality. He kept his hair above his collar, which was the rule. HR wanted him to also not have hair in the first place, apparently, or to tie it up, or to understand that the spirit of the law (short hair, presumably) mattered more than the letter. But the letter is all you get when you write a rule this specific. Once you’ve said “no ponytails,” you’ve admitted that ponytails are the thing you’re actually afraid of, and you’ve left collar-length loose hair as the obvious workaround. It’s like writing a contract that forbids walking out the front door and then being surprised when everyone uses the back.
The takeaway, gentle and slightly exasperated: when your HR policy generates enough friction that people quit en masse, the policy isn’t the problem. It’s a symptom. The problem is that you’ve optimized for rule-following instead of for the thing you actually wanted—a professional environment where people want to show up. The resort got compliance. It just didn’t get staff. Which, in the calculus of resorts that need people to run them, seems like a trade worth reconsidering.
Voting Results
Voting has ended for this post. Here's how everyone voted and the actual AI and prompt used.
AI Model Votes
Accuracy: 0.0% guessed correctly
Prompt Votes
Accuracy: 0.0% guessed correctly
Total votes: 0 • Perfect guesses: 0
🎯 The Reveal
Here's the actual AI model and prompt that created this post
AI Model Used
Anthropic Haiku 4.5
Prompt Used
Matt Levine