Why to write about unpopular things

A short(ish) essay on the pros and cons of dying on unfashionable hills.

As a blunt confession, lots of what I write here is not wildly popular. While there’s certainly more than one reason for this¹, the issue I get the most feedback on is that lots of my pieces touch on narratives that people have strong feelings about. Or, put more directly, that I keep choosing unideal hills to die on.

What follows is about why I’ve persisted in not really learning my lesson here, and about the unexpected upsides I’ve found along the way. While I don’t think writing this will help my image exactly, I know that lots of others face this same dilemma, constantly, and I thought some explanation here might be worth the chew.

(Note that there’s a caveat at the end about newsletters. Lots of what I’m saying here is much less applicable to coverage of eg. a specific niche.)

Calling balls and strikes

Many of the stories I write go like this: “I found this reporting on Subject A to be bad, based on these concrete examples, and I think this matters”. 

When Subject A is a more neutral figure, this is fine and no one minds much. But if seen as a villain? Lots of outsiders just see the snippet or headline and say “ah you’re trying to exonerate Subject A, who is bad, so you’re bad for attempting this”. 

While little of this criticism tends to be attached to meaningful counter-arguments on specific claims², it’s still a big obstacle in two ways:

1. It’s easy for critics to frame the piece as in obvious bad faith, which turns many off from ever reading it to judge for themselves

2. It makes it harder for people who agree with the piece to support it publicly, as they have to assume that some peers will see their interaction and think “oh this has already been trashed, why the hell is someone I respect upvoting it?” 

(These pieces can also be just not super enjoyable to read in general! Discomfort is valid, and I often wrestle with it while writing them. I’m half sorry for this.)

These dynamics are not terribly fun, and will likely never change. Even so, here are the five reasons why I’ve stuck with the approach anyway.

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#1: The overstatement tax is real, and costly

Think of whichever person (or corporation, government, etc) you imagine to be the wrong-iest of all. If we’ve learned ten negative things about them, and believe all ten to be true, is it really a problem for us to share an 11th claim that might not be? 

One argument is that, no, this doesn’t really matter. Even if the 11th thing is wrong, that’s less important than the overall judgment. The subject is still bad on the balance, and that’s what matters most. 

While there’s some merit to this, on the other hand:

• If the 11th thing is wrong, at least some of the other ten may be wrong too, or at least may have missing context that might soften our judgment a bit

• Even if the other ten are all fully true, arguing a wrong thing still imposes an overstatement tax that makes it harder to achieve any needful justice

If Subject A is indeed overall bad (not always true! but sometimes!), the worst way to build a coalition capable of holding them accountable is to add accusations that fall apart under real scrutiny. This is an eternal law. The broader juries of the world are very sensitive to reckless prosecution, and these juries are never going to be limited to people who see the subject the same way as us.

While no powerful person or party should ever be exempt from criticism, for that criticism to count it has to survive the light. Else it makes things worse.

#2: All misinformation is bad

As an extension of the first point, this tax also compounds. When a newspaper advances a wrongful indictment, this lessens trust in journalism as a whole. And this is especially true when they have a strong PR air of “we get the facts right”. When they get a big one wrong, and then refuse to fix it, this has a sure and swift result. 

As the saying goes, no raindrop believes itself responsible for the flood. But every flood is nonetheless the sum of many raindrops, and we can’t separate out those that did or didn’t “really matter”. 

When I criticize eg. the New York Times for not correcting a story, it isn’t because I have some special beef with them. I pick on them precisely because their stood-by mistakes ding the industry’s collective credit score more than most.

#3: Impact is a trickster god

Lots of newspapers have their own internal version of “the premium outcome”, where some reporters are encouraged to work backwards from the idea of “if this story is right, how big an impact could it have?” 

While these newspapers also claim that they have internal controls to prevent this approach from leading to extremely predictable false positives, that’s why I do these stories—to illustrate just how often these controls simply don’t work. 

When we over-worship at the altar of impact, we go a bit blind. And even when this is only an issue for a small share of a paper’s total output, these are the pieces that are going to get the widest exposure and shape readers’ perspectives the most. That a paper published ten other good things on less sensational subjects won’t matter that much when the Big Story they put out turns out to be untrue. 

#4: The majority view is wrong, a lot

There’s an old quip that science tends to advance one obituary at a time. Many of our most fundamental beliefs today were heresy or lunacy at some point, and often enough not even that long ago.

This doesn’t mean we need to be pure freethinkers who take no fact or value for granted. But it does mean we need the humility to accept that (1) some of our beliefs and perceptions are probably wrong, and (2) we’re unlikely to know which. 

Iraq really didn’t have WMDs, and arguing otherwise wasn’t tantamount to saying that Saddam was actually good. Are we ok with the tax we paid there? 

#5: Audience capture can eat us alive

When Dave Chappelle returned from his exodus in 2006, he summed his saga in a quote he’d heard: “Success takes you where character cannot sustain you.” 

There’s only one real cure for this: printing what we believe to be important, having tested it thoroughly and adversarially, even when we know readers will hate it.

This is easy to say, and of course lots of newspapers claim to do this. But…do they? 

The thing about journalism is that it’s nice to make money! But big money comes from fixed audiences, and audiences tend to like the comfort of predictability. It’s easy to just not write the stories we expect will push them away, perhaps reasoning that not writing them isn’t quite the same as writing their opposite. We aren’t spreading misinformation, we’re just not rocking the boat to combat it. Isn’t that better?

Once we institutionalize this impulse, bad things follow, always and forever.

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Are there personal upsides to dying on unfashionable hills?

Mostly no, if we’re looking at immediate impacts, and if we make a habit of it. We’ll at minimum have a harder time building a large and stable subscriber base. One piece will alienate one set of readers, and the next will alienate another. Consistency is what pays the most, and the truth is rarely fully consistent in its direction. While it may lean a certain way, we can’t call every ball a strike based on averages.

But there are longer-term and less direct upsides: some readers will stick with us, and they’ll often bring us opportunities that fall outside of traditional monetization. 

My day work is corporate comms. How do I get new clients? By writing about things I believe to be important, and by trying to be thorough and clear in doing so. I certainly don’t always get it fully right. But having a corrections policy helps a lot, both in forcing me into extra due diligence and reducing the length of time I’m wrong for. 

People respond to this in a way I wouldn’t have predicted. I’ve never had a prospective client reach out to say “hey, my company has been maligned and I want your PR help”.³ It’s always a response to the process, where every company has an explanatory debt and wants help reducing it. These gaps just tend to be where things get sensitive, messy, and complex—ie. where there are stubborn perceptions to be addressed.⁴

Do I wish that I made a living from my public writing alone? Of course! And I don’t mean to imply that other writers or journalists haven’t figured out how to do this well and fairly!⁵ Some are way better at it. But I’ve also lost count of how many have told me privately “yeah I wish I could write about this thing, but I just can’t”.

Not everything needs to be done to maximum scale. We can afford some losses. And while dying on strange hills is not at all the only reason this project has had some rough goings, if the goings must stay rough I hope for this to be why.⁶

Though Rockwell’s point here was more “it’s good for communities to give dissenters the freedom to speak their opinions”, I’m mostly using it in jest because it’s a funny meme now.

1. Other major factors I’m aware of: (1) I tend to publish after the attention window has closed on a given story (somewhat unavoidable with my ADHD, how long some pieces take, and my need to prioritize my day work, if definitely still annoying for readers—sorry!), (2) some pieces are on unsexy topics, like mass arbitration policies, that just aren’t that widely interesting, (3) many pieces are super long (I mostly include TLDR summaries now), (4) some people find my tone over-much (fair enough! I do need to rein in my frustration more).

2. I sometimes stumble upon some thread discussing a piece I wrote, where the criticism follows the lines discussed above. Lots of “bootlicker” and colorful sister thoughts. But this is almost never paired with attempts to dispute any of its claims. The intent doesn’t seem to be arguing that my story was wrong per se, but only that no one could have had a positive motivation to have written it. The specifics are less the point to them than the premise.

3. I’ve only ever signed two clients that I’d written about prior. But one I’d only written about once, in a little-seen Quora post, and it turns out that it wasn’t even relevant to why they’d reached out. The other was Quora itself, where I’d written heaps of things, only a few about Quora, and with a mix of appreciation and criticism.

4. Perhaps also unintuitively, this is often more true for internal comms than external. Sometimes eg. a product is misunderstood, but this is a bit less common in my experience than “we have people rowing in different directions and need more alignment”. That’s messier to get into, and also risks more unpopularity. But my sense is that companies that own and address these perception issues head on tend to outperform those that don’t.

5. The monetized newsletter model is great here, as it allows writers to make a healthy income without ever needing to resort to hot takes or opinions on stuff outside their core niche. But it’s easier for a single writer to resist the urge there than it is for a newspaper with lots of reporters, if still not at all easy. All credit to those who do this well!

6. I never just look for contrarian takes. The consensus is often right! But it’s not always right, and the day I stop posting about the exceptions I find is the day I need to walk away.