Vladimir_M’s comment (and follow-up) is, in my view, the definitive response.
Vladimir says that if you only use “the discomfort to me versus the discomfort to the other person” as your only decision criteria, then you are incentivizing others to experience discomfort in order to manipulate you.
I agree with this point; and I also acknowledge that I have, in fact, fallen victim to such manipulation in the past. Just a naive comparison of discomforts should definitely not be your only decision criteria.
But I don’t think that falling victim to this behavior is an inevitable consequence of trying to make others feel comfortable. You can still set your own boundaries, and say: this is the length to which I’m prepared to go to make others feel comfortable, but I’m not willing to go beyond that. And you can say: these are the kinds of reactions which I consider reasonable and which I’m willing to accommodate, and these others I refuse to consider.
I think that there’s a thing here that’s kind of similar to type I and type II errors, in that it’s easy to reduce one type of mistake by drastically increasing the probability for another type of mistake, and vice versa. In this case it’s about two different kinds of discomfort:
The kind of discomfort which results from (conscious or subconscious) motives to have more influence. Caring about the discomfort of others may cause more of this to come into being, as it incentivizes people to experience more of this.
The kind of discomfort which results from something else and would exist even in the absence of any external incentive for it. Caring about the discomfort of others may actively help reduce it, either because this directly makes people feel less of it, or indirectly as people who feel safe have an easier time working through whatever issues that cause it.
One may show too much caring about others and spend all of their time trying to manage other people’s feelings, and in so doing just end up totally useless. But like Bucky suggests in the other comment, I don’t think that Vladimir_M’s comment establishes that one shouldn’t care about the feelings of others at all. Rather, it would be better to care about those feelings which are made better by having others care about them, and disregard the feelings which are made worse by having others care about them.
I could say that once we have begun to speak of being an “ally”, we have left behind the domain of human relationships which I am interested in having.
I think we mean very different things by “ally”, so let’s taboo that word. I meant “someone who (to at least some extent) values my well-being and the satisfaction of my desires for their own sake”. This definitely includes friendship: I wouldn’t call a relationship a friendship if both people involved didn’t care for their friend’s well-being at all.
I could say that people who conflate disagreement with hostility, and who tell you that your criticism, your opposition, your speaking up, makes them feel unsafe, are toxic; and that making it impossible to disagree, without thereby causing offense—making a difference of opinion into a transgression—is another all-too-common pattern of manipulation and abuse.
I mostly agree with this, with the caveat that feeling unsafe due to disagreement doesn’t necessarily make a person toxic: some people will say that but also acknowledge it as an emotional reaction which isn’t necessarily justified. But if it was impossible to disagree with some person without causing offense, then I would generally put that in the previously-mentioned category of behaviors which I refuse to accommodate.
Edited to add:
Take my word, then, for this: my friendships, and my experience with people in general, became tremendously more fulfilling once I stopped worrying so much about making other people feel comfortable and un-offended.
I have, historically, definitely been putting too much weight on making other people feel comfortable and un-offended. And I do think that I should correct in the other direction. But that’s a different thing from stopping to care about it at all; if I did, I would end up doing the things which you yourself said are wrong:
It is wrong to deliberately hurt innocent others, for one’s own benefit.
It is wrong to accidentally hurt innocent others, due to negligence where one has an obligation of knowledge.