There are so many things in life we know intellectually but forget in reality before getting an unhappy reminder. The ever-later sunrises in October, for example, just suck, but we forget.
Since the end of daylight saving time moved from early October to early November in 1986 and 2007, October mornings are just grim, especially when it's overcast and gloomy, like today. The sun rises in Chicago before 7am until October 12th, but even at 6:45 (like today) many people still wake up before dawn.
My second-favorite city in the world has it worse, though. London sees the sun come up around the same time as Chicago in the middle of September, but today the sun came up there well after 7a. The day before the UK goes back to GMT at the end of October, London's sunrise is a depressing 7:43a on the 25th, but it gets worse for them. Boxing Day (December 26th) doesn't see the sun until 8:07a.
Chicago's latest sunrise this year is 7:24a on November 1st. Because Chicago isn't as far north as London, our midwinter sun comes up a few minutes earlier, at 7:19a on January 4th.
So much for quantifying misery. It's all cyclical. October mornings can just be depressing, though.