tedkx
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.