"The article somewhat misses the point about the Sleep with Me podcast: it's not boring content; it is boring by design."
I have not yet tried the Sleep with Me podcast, but based on what I've read, it is its "by design" part that got me more interested in trying the author's methods.
I could instantly relate when I read that "I need to convince myself that I’m doing something meaningful in order to finally disengage". Many people go to bed with a feeling of not deserving their rest, of having a debt to themselves because they missed opportunities or procrastinated heavily during the day, a debt that can be repaid by using their last minutes of the day to do something meaningful to compensate for the wasted time. Presidential speeches, old radio shows, financial crisis analysis, all these create the illusion that you take full advantage of your time, keeping your brain active and broadening your knowledge. Them being boring is an added bonus.
On the other hand, actively trying to get myself bored would most probably get me anxious, wondering exactly how wisely I am spending my time, which is not really what you want when trying to fall asleep.
I think the point is it has to be interesting enough to keep you preoccupied, but not interesting enough to keep you awake.
I sleep to old Simpsons episodes. I know them inside out, and at least the older ones have a fairly calm rhythm. I don't need to pay attention because I know what is happening but it still distracts me from all the kinds of thoughts you mention. I love the episodes, so I don't feel like I'm wasting my time.
Said another way: just because you don't give Google permission, it does not mean that they don't have the data. This isn't a paranoid outlook, just stated facts: many organizations store information in an unauthorized manner. Just because they say "we have no history," it does not mean that they actually don't have it.
Similarly, Google has a notion of "Web History" which is distinct from what they know about users. The Web History can be displayed to (and deleted by) the user, but that's not the same as displaying or deleting all of Google's records about the user's activity:
