Why my titles are terrible, and what I intend to do about it

Thursday May 15th, 2025

Tags: blog, meta, writing

The age of online diaries

I started writing on the internet a few months before the term "blog" was invented. I started on websites like scribble.nu, diaryland and livejournal, which all were very much intended as "online diaries". Being public and writing for an audience was more of a side effect than the intended function. Scribble.nu was first, and I don't remember it having a directory or built-in way to find other people who used it. The only way anyone would know it exists is if I gave them the URL directly, or if they saw it linked on my geocities site.

When you write in a paper journal, you generally don't give your entries titles. At least, I never did. I would write the date at the top of each entry, and it was a chronological log of thoughts and events from that day. A title would feel out of place and maybe a little pretentious. Like what, do I fancy myself a newspaper columnist? My "articles" need "headlines" now? Give me a break, me 🙄

This was very much the mindset with these early online diaries—I don't think scribble.nu even had a way to set a title on a metadata level. Like, I could write one at the top of each entry, but why would I? It has the date.

Livejournal had a "subject" field, but it was optional. I usually left it blank. My journal had a title, and when you read it, it has the entries in reverse chronological order with the date. You rarely look at individual entries, so it was easy to keep thinking of it as a paper diary in a slightly different form. There was a calendar view, where you can view entries written in a given week, month, or year. This was the only time I viewed multiple entries in list form, and they were mostly "(no subject)" followed by the date. Pretty unhelpful when I went searching for something I've written! This also predates tags, which wouldn't be added until 2005, so I was still very much thinking of it as a paper journal in website form, with no organizational structure whatsoever.

I remember at one point lamenting on livejournal that I was "bad at thinking of titles", so pretty early on I thought of titles as something that should have some quality of attention-getting or entertainment value that I was simply unequipped to provide; I don't know why I thought this, or why I never thought to just use simple descriptive titles that would if nothing else allow me to catalog my old entries. It would take awhile for this to occur to me.

The commercial blog era

In the mid-2000s, blogs became big business. This brought about the rise of "click bait", a phenomenon where commercial blogs and news outlets would trick people into clicking links to their articles with headlines that are sensationalist or misleading, because the only metric that mattered was ad impressions. This practice exploded once social media came about, and we all know the tactics they used, even the parodies have become cliches: one weird trick. Top 10 tips they don't want you to know. Is absurd statement true?? (Betteridge's law: no). I won't belabor it.

The point is, in protest against click bait, I tried to make sure, once I did start using titles, that they were as boring or as offputting as possible. I wanted my headlines to be anti-clickbait. I wanted expectations to be zero. I wanted no one to ever think "that didn't really deliver on the promise in the headline."

Because in my mind, clickbait isn't just an intentional tactic to mislead: if a headline is interesting enough to make me click, but the article isn't interesting, that's clickbait. Much the same way I define spam as "any message I don't want".

The sad part

Am I saying I don't think what I write is interesting enough to read? On some level, yeah. Like many childhood abuse survivors, I grew up with an extreme negative opinion of myself, and no matter how much teachers and other positive adult figures in my life encouraged me, I never managed to shake this kind of negative self-thought. The proof, in my mind, was that nobody has ever seemed all that interested in reading the things I write independently. I got good grades on assignments, and scored well on tests, but for all the praise I got academically, no one ever volunteered to read the stuff that's actually important and meaningful to me when I told them about it. I think this is probably true for most writers, right up to the point that it isn't, but with my internalized sense of inferiority instilled in me by my father, I never thought my writing was worth anything. So writing for other people to read was never my priority: I'd write for my own satisfaction, put it out there, and if anyone happened to like it, I'd consider it a nice bonus. So there was some truth to my "anti-clickbait" justification, but it was and is rooted in my insecurity.

Why I'm thinking about this

I read How to title your blog post or whatever by Dynomight (h/t maya, the source of most of the interesting articles I read these days) and it got me thinking about my own relationship with titles. I like how this person writes, and most of what they say makes sense to me, so I thought it'd be a good idea to apply their thought process to my own writing and see if it still makes sense.

You should try to make a good thing, that many people would like. That presents certain challenges.

I think it'd be prudent of me not to gloss over this. Do I make good things that people like? I think, in genre of personal blogging, my stuff is above-average. I try to write the kind of blog I want to read. I value nuance and introspection. For people who value the same things I do, I think my blog would be, if not one of their favorites, at least a respectable example of the genre. I tend to compare myself to the best of the best, the nonfiction books and podcasts and video essays that make up the bulk of my media diet, and that's not fair to me. That's not my genre. I wish it could be, and maybe someday it will be, but that's not what I'm doing here.

A title has two goals. First, think of all the people in the world who, if they clicked on your thing, would finish it and love it. Ideally, those people would click. That is, you want there to be people in the like + click region.

Other people will hate your thing. It’s fine, some people hate everything. But if they click on your thing, they’ll be annoyed and tell everyone you are dumb and bad. You don’t want that. So you don’t want people in the hate + click region.

Since starting therapy and dealing with some of my trauma, "person who hates everything" is a type of person I've become quite familiar with. I've become pretty good at identifying haters, and telling when criticism isn't being made in good faith. I'm not perfect, but I'm a lot less sensitive than I used to be. My dad was a hater; I've learned I can disregard everything he ever said to me. There's no point trying to separate the useful criticism from the abuse, because the source is poisoned.

My bad title philosophy was mostly about avoiding haters, who proliferated on the internet communities I found myself in and mainstream social media. Now I'm on the fediverse, here, and nowhere else. I don't have to worry about an onslaught of haters. If one pops up, I can simply block them and move on.

One must be careful not to fall into a mindset where you think everyone who disagrees or criticizes you is being a hater. I'm a fairly perceptive critter, so I don't think I'm at much risk of that, but I can't let myself get complacent.

Everyone is deluged with content. Few people will hate your thing, because very few will care enough to have any feelings about it at all.

The good news is that it’s a big world and none of us are that unique. If you make a thing that you would love, then I guarantee you at least 0.0001% of other people would love it too. That’s still 8000 people! The problem is finding them.

This basically sums up the reason I still write on the internet, and is a good reminder of why my "intentionally bad title" strategy is self-defeating: there's a vanishingly small chance of the 0.0001% of people who would like my work finding me, and if I make the titles intentionally bad, you can tack on a few more zeroes.

That’s hard. Because—you don’t like most things, right? So you start with a strong prior that most things are bad (for you). Life is short, so you only click on things when there’s a very strong signal they’ll be good (for you).

This is a great point, and it seems so obvious to me now: I should pay attention to the titles that (1) make me click on them, and (2) aren't, in retrospect, annoying or misleading, and try to emulate them. "Trying to emulate people" is something I struggle with, because I don't want to be seen as hack or derivative, but a title isn't really a creative pursuit in itself, and I should try to start treating it as functional. Cuz that's what it is.

Say you write a post about concrete. Should you call it, “My favorite concrete pozzolanic admixtures”, even though 99.9% of people have no idea what pozzolanic means? Well, think of the people who’d actually like your thing. Do they know? If so, use “pozzolanic”. That gives a strong signal to Concrete People: “Hey! This is for you! And you know I’m not lying about that, because I’ve driven away all the noobs.”

Another great piece of advice that should be obvious---the title should match the content. I do occasionally write about very niche interests, and I should make sure the title reflects that to draw in the people who would be interested and let the people who aren't interested know they can skip it.

Be careful imitating famous people. If Barack Obama made a thing called “Thoughts on blockchain”, everyone would read it, because the implicit title is “Thoughts on blockchain, by Barack Goddamn Obama”. Most of the titles you see probably come from people who have some kind of established “brand”. If you don’t have that, you probably don’t want to choose the same kind of titles.

I'm definitely not trying to write like I'm a celebrity, but I do tend to pick titles that will only draw in people who already know who I am, and that they like my work, for all the aforementioned reasons.

Traditional advice says that you should put your main “message” in the title. I have mixed feelings about that. On the one hand, it provides a lot of signal. On the other hand, it seems to get people’s hackles up. The world is full of bad things that basically pick a conclusion and ignore or distort all conflicting evidence. If you’re attempting to be fair or nuanced, putting your conclusion in the title might signal that you’re going to be a typical biased/bad thing. It will definitely lead to lots of comments “refuting” you from people who didn’t read your thing.

This touches a bit on my anti-clickbait ethos: a title with a really strong take can get people to click, but it can also be a source of backlash. I think I'm somewhat insulated by not having a "comments section": when people won't see their comments appear immediately, they won't get the same dopamine rush of having "owned" me. People who would take the time to write their own response on their blog or send an email are usually going to be the same type of person who would actually read what you wrote.

I'm also protected from backlash because, well, my takes usually aren't all that spicy. Take one of my recent posts with one of the worst titles: Ren and Stimpy. I have no idea what an interesting title for that post would look like. I don't have any grand conclusions. It's sort of a book review, sort of a show review, and sort of a jumble of personal thoughts. I could've called it "Reviewing the unauthorized Ren and Stimpy book", but that's only partially true, and it's not exactly a barn-burner either. I could've called it "The Ren And Stimpy Book Is Okay But I Have Problems With It". Is that attention-getting? I don't feel like it is. People don't want wishy-washy, they want confidence! But like, these are my actual opinions. Sometimes I don't have a strong take. Sometimes an experiment is inconclusive. Sometimes I'm not sure how I feel.

Conventional (i.e., commercial) wisdom would suggest that I either lie in the headline or don't write the thing at all, but this isn't a commercial endeavor. It's blogging. The honest personal experience is the point. So I should probably accept that some things I write will be more interesting than others, and pick my titles appropriately. I settled on "Ren and Stimpy" because, well, it's probably the only thing I'm going to write about Ren and Stimpy. The title serves the function of making people be able to find that post. That was all the thought I put into it. But honestly, I could do better. Even "I'm conflicted about the Ren and Stimpy" book contains a kernel of an idea, and it still contains the keywords. It's boring, but as Dynomight goes on to point out:

Boring titles are OK. I know that no one will click on “Links for April” who doesn’t already follow me. But I think that’s fine, because I don’t think anyone else would like it.

But then suggests a tactic I'm not on board with:

Consider title-driven thing creation. That is, consider first choosing a title and then creating a thing that delivers on the title. It’s sad to admit, but I think there are many good things that simply don’t have good titles. Consider not making those things. The cynical view of this is that without a good title, no one will read your thing, so why bother? The optimistic view is that we’re all drowning in content, so what the world actually needs is good things that can find their way to the people who will benefit from them. In practice, it’s often something in the middle: You start to create your thing, then you choose a title, then you structure your thing to deliver on the title.

Even if I wanted to, my brain doesn't work like this. The writing will always come first. If I tried to think of a good title for my post about the Ren and Stimpy book first, I wouldn't have written it. If I approached writing from the perspective of "will anyone be interested in this?" I wouldn't have a blog at all. I'd second-guess myself and talk myself out of writing anything. This is probably good advice if attracting readers is your main motivation.¹

My favorite thing category is “Lucid examination of all sides of an issue which finds some evidence pointing in various directions and doesn’t reach a definitive conclusion because the world is complicated”. Some people make fun of me for spending so much time researching seed oils and then lamely calling my thing “Thoughts on seed oil”. But what should I have called that instead? Lots of bloggers create things in this category, and no one seems to have solved the problem.

I like that category of thing too. I think attracting this type of reader is hard because curiosity goes hand-in-hand with skepticism. One strategy could be a title like "Seed oils are more complicated than you ever imagined" or "Forget everything you thought you knew about seed oils". But the sort of person who'd be interested in the topic is also more likely to judge it as clickbait, even if, had they read the article, they would find it to be true.

I think a good approach could be a personal connection to your own curiosity, like "I fell down a rabbit hole about seed oil" or "I never thought I'd care this much about seed oil." Curious people like reading about other curious people's rabbit hole journeys. But if you do it too much it might come to be seen as formulaic. Finding the right balance is key.

Conclusion

I'm going to be thinking about all these ideas when I blog in the future, and I'm going to spend more than 0.5 seconds thinking about the title. I'm going to try to figure out a title that I would want to click, that matches the content of the post and wouldn't leave me feeling disappointed. It might attract more haters, but I think I'm at a point in my life that I can deal with them. Not every post will have a natural good title, so if one doesn't come I'm not going to force it. I will do this for one year, and see if it increases the satisfaction I get out of this blog. Even if it doesn't, it probably won't hurt anything, and it'll be a habit by then, so I reckon I'll keep doing it.

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