Substack fascinates me as a platform particularly because it bothers me. There is a type of writer who writes on Substack, and a type of essay that people publish there (yes, I know it’s not a monolith, but hear me out for a second) and it is its own ecosystem for having conversations, and it just seems to encourage a very reactive and online form of essay writing, like if you took Twitter and made it longform and more polished but you could also choose to paywall your more controversial tweets.

There is a specific type of article, almost always posted on Medium, that is clearly intended to be included in a LinkedIn post for personal branding purposes. I hate those articles. They drive me insane.

You shouldn’t just write because you want to brand yourself, because if you do that you won’t have anything real to say. Figure out something to say first! It is not that hard.

And these articles all have the same stupid upbeat marketing energetic tone. It drives me crazy. Does anyone actually read and enjoy these things? Who are they for?

The cool thing about asking questions no one else is willing to ask is that you get answers no one else gets, especially if you ask the right people.

The problem with doing this is that you’re probably also perceived as an annoying person who asks too many questions. I think one of the most useful skills when you’re like this is learning to vibecheck people to guess whether or not you can ask them certain things and get real answers.

One of my new favourite ways to write blog posts, especially the ones that contain advice, is to write them as an imagined conversation with someone who won’t stop asking questions.

I think writing the questions is fun, I think answering them is fun, and I get to take myself way less seriously than when I answer questions in real life. Plus, then I get to answer the questions that people should ask but don’t.

I’ve been attempting to use generative AI to help me write documentation because there’s so much pressure to be able to say you’re using it right now, and I honestly think the outputs are unusable without essentially rewriting the whole thing.

I find the outputs are:

• Excessively verbose (please get to the point)
• Subtly incorrect, and I’d rather just research and write correct information than spend time fact checking AI
• Not quite what I want, because the machine can’t read my mind, and I feel like prompting it correctly and then fact checking and editing the output would be more time consuming than just writing the damn thing
• Just like, tonally weird

I don’t know, it’s a weird experience. I will give it this: