David Rakoff reflects on the feeling of regret in his quote, emphasizing a common sentiment of wishing one had made different choices, particularly the choice of staying home. He humorously suggests that a supercomputer is tasked with quantifying all the times he has expressed this regret, highlighting the notion that such reflections might be beyond human comprehension.

This statement captures the complexity of human experience, where decisions can lead to unforeseen outcomes that leave us wishing for a simpler time spent at home. Rakoff's use of humor adds depth to a shared feeling, making it relatable and poignant as it speaks to the universal nature of regret and the desire for comfort and safety in one's familiar space.