Difficult people
A confession
Some people are – for lack of a better word – difficult to deal with. They take things personally, they are hypersensitive to criticism (or anything that sounds like it might be criticism), and they are focused primarily on themselves and what they think they need or deserve.
For some people, the difficult behavior is contextual, and the person is fine on a different day or with less stress in their life; for other people, the difficult behavior seems to just be a part of their personality. One can speculate about its origins in some childhood experience; it may be associated with that person’s neurodivergence; or they may just have a bad day more frequently than other people. In general, knowing those details doesn’t make much difference to its management in the moment that it’s happening.
And now, a confession: I admit that I am (at times) a difficult person myself. My vague memories of childhood, plus my family’s stories, confirm that I was a difficult child, insisting on certain privileges like riding in the front passenger seat of the car while my brothers were always in the back seat.
Difficult employee
More recently (although still decades ago), I was fired from one job essentially because I was relentlessly insistent on the need to make better technical choices. When my engineering-VP boss was asked to reduce headcount, it was easy to get rid of someone who was a chronic pain – me.
Fortunately, the story has a happy ending with three elements: first, my firing didn’t last very long because I was quickly hired by my former boss’s counterpart in product management. For him, the fact that I had been a thorn in my former boss’s side was an advantage. Second, I did learn from the experience, and changed my style; I have never been fired subsequently for being difficult. Indeed, I have been praised in the years since then for my collaborative and low-key style, working to make things happen without drawing attention to myself. Third, my experience as a product manager and a person who could bridge between engineering and product management was crucial for taking on the more senior roles I’ve had subsequently.
In work contexts, I can mostly avoid the kinds of reactions that would otherwise out me as a difficult person. Part of that is that my work is mostly remote, and has been for decades: as it happens, that product management job I mentioned was also my last one in a conventional office setting. I’m usually working in my comfortable study at my comfortable house. My schedule usually allows for breaks between calls, and my colleagues are smart and good at their jobs, so most of my interactions don’t prompt me to be difficult. If something is stressful, it’s usually not too hard to get my head back to a place where I’m calm and sensible.
I also find that as I’ve grown older, I’m less concerned about any given day’s crisis and more interested in larger-picture issues of organizational design and my colleagues’ opportunities for growth as people. Age brings a kind of calmer perspective that reduces my likelihood of behaving in a difficult way.
Difficult socializing
In non-work contexts, I suspect I haven’t made nearly as much progress. Part of the problem, naturally, is that a “remote friendship” or “remote relationship” is unappealing, even though I’ve been quite happy and successful with remote work. The natural “time out” and recovery that comes along with remote work isn’t very applicable to spending social time with people. It’s certainly possible to do some socializing via Zoom… but, as we all learned during the pandemic, it’s not very satisfying.
I find that I enjoy 1:1 interactions or small dinner parties for a small number of hours, depending on the people involved, but then I’m overwhelmed and need space. I’m not entirely sure whether my underlying issue is introversion, neurodivergence, or both – I tend to assume both. Regardless, in most cases, I can tell that there’s some kind of limit happening on the social side. I vary between using the metaphor of “a timer running out” or “a supply being exhausted” – but, either way, there’s some point at which I just don’t feel like I can continue interacting with people.
An intriguing aspect is that when I reach my limit, I’m pretty sure I’m the one who’s transitioning to become a difficult person, but I experience it as other people becoming increasingly difficult. A likely explanation is that I’ve also somehow run out of my capacity to process other people’s behavior: as a result, I both can’t tolerate their actions, and I can’t moderate my own.
There are a very few people for whom this timeout interval is much longer: my wife, my children, some close friends. I recognize the phenomenon without really understanding it. My children are of course a special case, where I’ve been required in some ways to be around them for hours at a time for essentially their whole lives. That habituation seems to somehow carry over even now that they’re fully functioning adults. For my wife and those close friends, they’ve been in a different category from most other people ever since I first met them. I don’t know what accounts for the difference, but it seems like some people are (for whatever reason) on my wavelength in a way that most people are not.
Meanwhile, I have a brother-in-law who is my exact opposite. Whereas I am comfortable on my own and want to limit my time in crowds, he is only comfortable when surrounded by people and works to limit his time alone. I don’t know whether he has an analogous experience of exhausting his supply of solitude in the same way that I may exhaust my supply of socializing, but I suspect so. (Of course, he has a structural advantage over me: if I get difficult, it potentially annoys the people around me at the time. If he gets difficult due to his solitude, no-one else is affected!)

