The headmaster’s study had a particular smell: varnish and something menthol, and underneath that the faint sourness of coffee that had been left to go cold on a radiator. I remember this in detail because I spent a lot of time there at the age of fourteen, and because I was trying hard to understand what had changed, and sometimes context clues are all you have.

Mr Grimwood — that’s what I’ll call him, though that’s not his real name — had a way of speaking that took me years to fully decode. He would call me ‘sunshine’ in the way other people use a person’s name, except it was never friendly. It came with a particular curl to the mouth, a downward inflection that made it clear that ‘sunshine’ was not meant as a compliment, that the brightness implied was sarcasm, that what he was actually saying was: I see what you are and it is not acceptable.

This is a pattern-matching problem, and it took me longer than it should have to solve it.

The naive approach — and I took it — is to process the words at face value. ‘Sunshine’ is a friendly term. Headmasters are authority figures. Therefore the headmaster is being friendly. Except the system was giving me contradictory signals: the friendliness of the word, the coldness of the delivery, the setting (his office, not a coincidence), the timing (always when something had happened, something small usually, some minor infraction). The signals were saying: you have made an error, and I am displeased, and I am going to frame it as warmth to make it worse.

That’s sophisticated. That’s mean-spirited in a way that takes a bit of thought to achieve.

I spent a lot of mental energy at fourteen trying to figure out whether I was misinterpreting it. Maybe he really was being friendly. Maybe the pattern I was detecting was something I was projecting onto it. Maybe I was being paranoid. This is the particular torture of communicating with someone in a position of power who uses ambiguity as a tool — you can’t call it out without looking ungrateful or defensive, and you can’t be sure you’re reading it right.

Here’s what I eventually understood: when you receive a signal, you have to look at the full context. Not just the words, but the timing, the setting, the tone, the previous pattern. You also have to accept that the sender might be using ambiguity deliberately, which means you can never be 100 percent certain, and you have to make a decision anyway.

This is a problem that appears everywhere once you start looking for it. In code review, when someone says ‘this is interesting’ — do they mean the implementation is elegant, or are they saying it’s a red flag? In security warnings, when a system logs something as ‘informational’ — does that mean it’s actually fine, or is it important and just being undersold? When someone in a meeting says ‘I don’t see a problem with that’ — are they genuinely OK with it, or are they registered disagreement in a way that’s carefully deniable?

The solution isn’t to become paranoid. You can’t read every interaction as hostile. But the solution also isn’t to assume good faith when the signal is genuinely mixed.

What I learned to do is to look at the pattern. One ‘sunshine’ could be coincidence. Twelve of them, each in the same context, each with the same delivery, each aimed at the same target — that’s a signal. That’s data. That tells you something about the intent even when the surface meaning is ambiguous.

The other thing I learned is that you don’t have to be certain to act. You can say ‘I notice that every time you use this word, it seems to come with a particular tone’, and then you wait for the response. If the person is genuinely friendly, they’ll be mortified and correct the pattern. If they’re not, they’ll get defensive. The response tells you which one it was.

I didn’t do that at fourteen. I just accepted the mixed signal and tried to figure out what I had done wrong. But now, when I’m reading something with ambiguous intent — a piece of feedback, a warning flag, a decision I don’t fully understand — I look for the pattern. I look for the context. I don’t assume I’m paranoid, but I also don’t assume I’m being attacked. I try to read what’s actually being said underneath the words.

Sunshine, in the end, was just a word. What made it a warning was the repetition and the context. The lesson was about learning to read beneath the surface of what people say, particularly when they have power over you and they might not be saying things entirely in good faith.