Very good essay, katydee!
I think giving people tools to lower the likelihood of being offended is a worthwhile project. We live in an era in which there seem to be more ways of becoming offended than there were a few decades ago. People have always tended to be offended by personal attacks, but another layer has been added in recent times. That layer is based on identity. Identities can be based on race, religion (or lack thereof), ethnicity, political leaning, sex, sexual orientation, disability, etc. etc.
To an extent, we all perceive ourselves as having several identities, and we are more aware of that these days than previously. It's not that we didn't always belong to multiple overlapping groups, from which identities could be derived, it's that there was a time when we were much less likely to derive them.
With the rise of identity politics, people are encouraged to think of their identities not on a personal basis, but on the basis of membership in one or more "identity groups." Once people buy into this, and begin investing more and more in a group-based identity rather than a personal identity, the way is open for more avenues of perceived offence. Not only is a person prone to the personal level of perceived offence, but is now, not just allowed, but encouraged to take offence on behalf of any group to which she or he is affiliated. And even people not affiliated with the group in question are encouraged to become offended on behalf of the group, and without waiting to see whether members of the group see it that way.
I'm not denying the social utility of all manifestations of the processes suggested above, but am suggesting that the net effect has been to produce a society of people, many of whom have become hypersensitive in this domain, and this hypersensitivity at some level can have a number of deleterious effects on all concerned.
TheOtherDave, Thanks for your questions.
Just a quick comment. It's tricky to comment on some of these matters without allowing the comment to evolve into a full-blown essay.
I suspect the latter. I didn't detail what I think are the deleterious effects, leaving that for possible later discussion. However, among potentially negative effects are the following:
Those psychological effects which presumably motivated the essay of the OP, i.e., it's presumably not beneficial most of the time for people to be in a state of being offended.
A crying-wolf effect resulting from too many false positives. When there are too many false positives, then there's a tendency for people to pay less attention to what should count as serious instances of the offence in question.
This is a controversial point, and I don't expect all careful thinkers to agree with me. I'm not convinced that it's better for people to think of themselves in terms of group identity as opposed to thinking of themselves on a personal basis. One of the reasons this is controversial is that it quickly leads into a discussion of group versus individual rights , a point on which there's quite a bit of disagreement. I tend to be suspicious of claims of group rights, especially when they conflict with individual rights.
Perceived victimhood. Another controversial point. I don't think it's always good to encourage people to think of themselves primarily as victims, and I think this is the case even for obviously real victims, and some real victims are of this opinion.
Hypersensitivity can have a chilling effect on discussion of important social and political issues which could benefit, IMO, from more rather than less discussion.
These points are more to try to illustrate what motivates my position than to offer a complete justification thereof.
More general comment: It can be notoriously difficult to try to decide what the net social utility of any policy is, not just because reasonable people with disagree about the effects themselves, but also, and very importantly, they will disagree about how those outcomes should be weighted, even when they agree about the outcomes themselves.
When I wrote the first version of this post, I hadn't read "Keep Your Identity Small," linked in the OP. The notions expressed there overlap quite a bit with my own, though I didn't specifically mention how investment in an identity may cloud reasoning by bringing in overly emotional considerations, making discussion difficult.