By Trent Modglin When I was in my 20s living in Chicago, my roommate was from Milwaukee and we would go up every few months to bar hop with her friends and hang with her family. It was a friendly city and all, but nothing about Milwaukee ever wowed me except maybe the annual Summerfest ...

What you do for a living: It’s a corporate America gig. Specifically, I work in reinsurance for CNA (a commercial property and casualty carrier in Chicago). I have been there awhile now. My wife likes to joke that I started my career at CNA in the previous millennium. How long you’ve lived here: I moved ...