Summary: Shelly Kagan, Yale philosophy professor, discusses the argument that death isn't bad for you, because when we are dead we won't care. He hunts around for justification, doesn't find anything satisfactory, or even paint a clear picture of what "satisfactory" would look like, and ends up conveying mostly mysteriousness to the audience.
There are a variety of right ways to approach this argument. One good goal is to understand what's going on in someone's head when they say that death is bad for you.
Reading the article, a bell rang for me about all this discussion of "possible worlds" - for example, the idea of feeling pity for people who don't exist. We usually don't interact with people who don't exist, so what process has led us to compare these different worlds against each other?
The answer is a decision-making process. "Possible worlds" doesn't mean spawning any physical universes - it's a convenient shorthand for imagined possible worlds, which we (in our capacity as intelligent apes) compare against each other, usually as part of a consequentialist decision process.
Once you start looking, you see the fingerprints of decision-making all over the article. It's the machinery that generates these possible worlds to think about, and the context that colors them. So I think noticing that "possible worlds <- us imagining possible worlds as part of our decision-making" is a good relationship for understanding topics like this.
Edit for clarity: The basic idea is that death being bad is, at its root, a function of the decision-making bits of our brains. This can be seen not just from a priori claims about "low utility = bad," but from the structure of what Shelly Kagan hunts around for, which mainly involves choices between possible worlds.