What differentiates a good essay and a bad essay?

With a great essay, you can see the larger tree that connects all those branches, leaves, and twigs together into a single unit of a 'tree'. A bad essay is where you only see the random assortment of leaves and branches. You don't see the larger tree among the branches.

While listening to one of the podcast episodes from David Perell's Writes of Passage where he interviews writer-operators to deconstruct their writing process, I noticed the podcast episodes to be very free-flowing, without losing the central theme of the conversation.

And this made the format engaging. In fact, the most boring podcasts I've listened to are the ones which start with the premise, and then the supporting arguments, and then the conclusion. That's not what podcasts/conversations are supposed to be. A conversation has to be fluid. It should not be confined by a specific agenda/bullet points. It's a discourse, or a 'meeting' in the business-sense with specific agenda / bullet points.

Maggie talks about this tumor that has become malignant in technical documentations and academic papers:

Another bad way to start a piece of writing is with a statement of what you're going to write about, followed by a definition.

“This post will outline the most common misconceptions in astronomy. Astronomy is the scientific study of celestial objects such as the stars and planets, and misconceptions are falsely held beliefs by a large number of people.”

“Bad” is obviously subjective and contextual here. I find up-front outlines and definitions dull for narrative non-fiction writing. But they're standard practice for technical documentation and academic papers. Signposting what you're going to write about is good, but starting with an exhaustive list of definitions is extremely boring.

After listening to a couple of the episodes, I unearthed Perell's mental model on how he approaches his interviews with his podcast guests. The tree is the mental model here.

Perell starts with the central theme (the tree), and then goes into the various sub-topics (the branches), goes deeper into the sub-topics of the sub-topics (twigs, leaves), and before it gets more deeper than that, he takes a step back, and directs the user back to the central-theme (the tree). In this way, the viewer/listener is not trapped in some version of a prime-number maze, where they're not able to see where they are heading. They are still directed back to the tree, and can also capture the gist of what the author is saying. And this is a common pattern among other seasoned podcast hosts such as Joe Rogan, Lex Fridman and others.

To be clear, I'm a mediocre essayist, trying to be a better essayist. And an attempt to progress is by following this principle: Go deep into the sub-topics, suspend, and take a step back and come back to the main topic. You're the spider, and you are interweaving all the webs. Perell's approach on podcasting has inspired me to do the same with my writing process. Essays are also supposed to be more 'loose' than be 'rigid'. Even etymology wise, essays originate from the French word 'essais' which means an attempt.

To understand what a real essay is, we have to reach back into history again, though this time not so far. To Michel de Montaigne, who in 1580 published a book of what he called "essais." He was doing something quite different from what lawyers do, and the difference is embodied in the name. Essayer is the French verb meaning "to try" and an essai is an attempt. An essay is something you write to try to figure something out.

So, I can very well add side-notes, callouts, footnotes, and make side-steps throughout my essay, but the reader has to still see the forest among the trees.

The plot should not be lost in the mess. And this is a creative tension worth pursuing.