I have only been out of school for two years, so I am still at the very beginning of my career. I would say insecurity and anxiety are two big ones. But I suspect most humans deal with these very same issues to some degree. I found running, seeing my friends more often and paying much more attention to sunrises and sunsets to be very helpful.

I would say you could start by being unkind, unthankful, pretentious...

I don’t really think I wish things had been any different for me. I was lucky to know just enough to get by and to enter situations that I could figure out slowly and force myself to learn more.

I prefer to work 7 days a week an equal amount (weekends a bit less) rather than 5 crazy long days. I also know that more than 8 hours of in front of a screen per day will make me depressed. I often work a full day at the studio (8 hours) and then go home and work a few more hours but not in front of a computer. I will make an object, work on my sketchbook, do some writing...

I recently read A Supposedly Fun Thing I’ll Never Do Again  by David Foster Wallace and really loved it. As for visual books, I would say find your own slowly. Ask your friends about which books are they into at the moment. I find that learning about these things through the people close to you is always most meaningful and likely to excite you most. I would also suggest looking at art books just as much as design books.