John Hodgman is 44 years old, or in his own words an “elderly man.” Best known as a Daily Show correspondent and for his three books of invented history, the father of two recently spoke over the phone about how middle age and self-awareness are affecting his comedic approach as his new stand-up tour, “Vacationland,” comes to Thalia Hall on Thursday.

What do you think about Chicago?

As a former cigarette smoker, smoking cigarettes looks and feels cool. But whatever you might be vaping, if you look in the mirror while doing it, you will feel shame; it looks like you’re smoking an iPhone. Part of what is great about being in my 40s is not having to worry about looking cool anymore. I would advise young people to cease worrying about it immediately. Don’t waste your life like I did, trying to be interesting and cool. You’ll probably just end up failing, and end up being interesting and cool in ways you never anticipated.