Considerations for deciding when to write angry
For those of us too small-time to impact the national conversation.
Picking up where Part I left off…
10. People with large audiences should factor in the above more than people with small audiences.
Every political Substacker dreams of going viral, gaining a massive audience, and shaping the national conversation. Maybe one day, we’ll get there. But the truth is that most of us are complete nobodies, myself included. As grateful as I am for my 450 subscribers, we are far too few to budge the titanic forces shaping our country’s path. So it feels grandiose to imagine that my personal tone needs to account for points 1-9, which are more relevant to how influential people should write about politics.
Again, this argument can be used in both directions. Small audiences could liberate us to write however we want, or make it harder to justify the risk of offending people in our personal or professional circles. It does not answer the question, it just reduces the stakes of getting it right.
11. Factor in what sort of writing comes easiest, feels best, and is likeliest to get done.
I hate writing. I love having written.1 I’ve found that my liveliest writing is completed in as few sittings as possible. Expressive writing is often faster, and easier to start and finish. It is less of an ugh field, and I am more eager to return to it. That helps me churn out more and more regular posts, which in turn is rewarded with reach by the Substack algorithm.
Thus, overly moderating my tone would reduce the enjoyment, volume, regularity, and reach of my writing. This is a small update in favor of letting loose, especially if I vainly assume my writing is a net positive contribution to the discourse. Even if careful writing were slightly more valuable than angry writing, that would have to be weighed against a lower volume of content overall, which could mean fewer of my good ideas influencing the debate.
In my case, this point is mostly outweighed by point #10. But for people with bigger audiences, I think it’s more important to increase the volume of good arguments they produce than to perfect the tone or framing around them. Those unable to see through the noise are probably less persuadable anyway.
Depending on your personal preferences, this factor could also cut the other way. Some people are stressed out by confrontation and get anxious about writing too combatively. They shouldn’t write that way! I myself have gone back to amend overly hostile lines that weren’t sitting right with me the next day. What you’ll feel proudest of after it’s published is even more important than what feels best as you type it, because the after will last much longer.
12. Factor in personal and professional risks, again in proportion to your audience and the stakes of your job.
One concern about angry writing is that it could have bad personal or professional consequences one day, perhaps by alienating a prospective employer, colleague, client, partner, friend, or that one estranged auntie your Mom hoped would finally rejoin Thanksgiving dinner. Angry writing sounds less professional and incites more defensiveness, so it carries a higher risk of bad consequences if the wrong people find your post. Moderation is personally and professionally safer.
How much safer depends on how many people shouldn’t see it, how likely they are to find it, how bad it would be if they did, and how much less offended they’d be if the same ideas were phrased more gently.2
13. Criticize ideas more stridently than people, and powerful people more stridently than regular people.
Trump, his lackeys, his policies, and his supporters are four different things. Calibrate your rhetoric accordingly, even if we think his supporters share indirect responsibility for what’s happening. This requires us to know our audience and to clarify what or who we’re specifically criticizing. For example:
If you’re refuting a general class of argument—ex: “Contra common conservative talking points, immigrants commit less crime than native-born citizens.”—it’s best to steelman the strongest arguments you can find or think of on the other side. This requires a degree of cognitive empathy.
If you’re refuting a specific argument from a powerful person—ex: “Due process doesn’t mean what J.D. Vance said it means.”—you have more leeway to “punch up” and ridicule the lies and hypocrisy of those with power. Stronger arguments may exist, but they’re not the ones he made.
If you’re refuting a specific argument from a more accessible person—perhaps in a post, comment, or restack tagging a Substacker who might actually reply—you should start out civil and then follow point #15.
That said, the criticism should also be proportional to what the government is actually doing, which is the great focuser of political conversation. Not all Republicans in Congress are as unreasonable as Trump, but that matters little if Congress is reduced to a vestigial rubber stamp, with a majority too cowardly to do anything but follow the administration’s lead. In that case, it’s perfectly understandable that our rhetoric is going to be calibrated to what Trump’s doing, and to what Republicans are enabling or trivializing.
14. Don’t write for the crowd when the person you’re debating is reading and trying.
Part of why social media polarizes us is that we’re aware our conversations are visible to a larger audience. Angry writing is more persuasive to third-party onlookers (who fear social exclusion, and don’t want to be the object of that anger moving forward) than it is to its recipient (who feels defensive and needs to save face). This tempts us to write for the crowd—for those sweet sweet likes, which are seen as votes about who’s winning—instead of optimizing our language to persuade, inform, or understand the person with whom we’re in direct conversation.
I think this is bad, at least when the other person is honestly trying to persuade, inform, or understand us. It seems wrong, or at least rude, to use others as a means to validation from your ingroup—sort of like mocking the new kid to get high-fives from your buddies. And it makes it harder to truly listen or change our minds; then we would lose face to the crowd.
To overcome these dynamics, consider taking one-on-one conversations to a private forum, or publicly bragging about changing your mind when presented with new evidence.
15. My personal policy is to address people with the same level of vitriol with which they address me.
I could swap several words in for vitriol—respect, snark, condescension—and the policy would stand. I base it on the highest principles in moral philosophy, namely: “what goes around comes around;” “I am only human;” and “if you come at the king, you best not miss.” I extend an assumption of good faith until that assumption proves unfounded, at which point I give them their own medicine.3
You don’t need to follow this policy, and sometimes I ignore it too.4
16. Anger is like cursing: use it sparingly for maximum impact.
Trump’s America has ample cause for fresh daily outrage, but humans aren’t built for that. You don’t want to desensitize your readers, nor yourself, to the fights that matter most.
17. People engaging in good faith deserve more empathy and civility than people who aren’t.
I’ll close with the point I alluded to in my introduction. Calls for empathy and listening to MAGA supporters cannot be naïve to the reality that MAGA leadership habitually produces large volumes of content that intend to mislead the listener; content they know to be false, which does not reflect their true beliefs, and instead attempts to prevent, confuse, or shut down productive debate.
I am rarely angered by people who simply disagree with me on the policy merits. I long ago internalized that people can have different values on issues like crime, abortion, immigration, taxes, foreign policy, drugs, etc—even on high-stakes moral issues I’m passionate about. As long as people acknowledge nuance, are honest about why they believe what they do, and own the implications of those beliefs, we typically get along fine.
The times I get hot are when I realize that the person in question—from Jeff Bezos to JD Vance to Hans von Spakovsky—treats the whole project of exchanging ideas as a game of manipulation, in which honesty and consistency are for suckers.
The challenge of trying to engage in good faith in 2025 is that this latter group includes the most powerful people in the country, as well as the loudest voices in the conservative media diet. This makes it genuinely difficult to find original, good-faith versions of that side’s arguments to engage with. And even when you succeed at that, the ensuing conversation may bear little relation to what the President is doing or why, which naturally controls the media’s attention.
A decade of effort to engage in the productive conversations that so many on Substack claim to want has forced me to accept that some people are not worth the effort. You cannot reason people out of positions they did not reason themselves into. And you certainly cannot reason with people who aren’t even trying—or worse, are trying to mock you and waste your time.
To truly value, engage in, and amplify productive exchange requires that we first identify, call out, and exclude the people intentionally trying to confuse and frustrate it.5 It is necessary to call dishonest people dishonest; it is difficult to do it nicely; and yes, this includes most MAGA messengers, from Karoline Leavitt to Stephen Miller to Tucker Carlson to Laura Loomer. If my expressing that opinion prevents you from listening to me, you are the one closing your mind to genuine attempts at persuasion.
I thought this quote was from Dorothy Parker, but Google tells me I was wrong.
This could also be a case for going anonymous, which has its own pros and cons. I’m considering going that route myself, and will elaborate in a separate post if I do.
Mark Twain once said “Never argue with an idiot; they will drag you down to their level and beat you with experience.” That’s good advice for in-person shouting matches. But on the internet, I confess that I sometimes enjoy the challenge of beating idiots at their own level, too.
Sometimes it’s fun to flex on the jerks by pretending not to notice their tone, and being super nice to them in return. This works best when they’re clearly out of their depth in the conversation, because it heightens the contrast they’re compensating for.
The challenge is not confusing good-faith mistakes with bad-faith dishonesty, which can be harder for politics mega-nerds who see those discrepancies more quickly than ordinary people. Try to assume good faith until proven otherwise, even when you’re like 75% certain they’re full of crap.