I get asked a lot how I got into being a tour guide. Well, it all started with a mistaken move to New York City, after I got back I promised never to take Chicago for granted again. I went to the Chicago Architecture Foundation and learned a ton. Great place. I started my own tour company in 2009 and here we are.
But my real background for giving tours is my improv experience. Sure, I have confidence speaking on my feet and in front of people, that helps. But it’s the “you just never know what’s going to happen” nature of improv that makes me really good at my job, (IMHO).
Every tour of mine is different, even if it’s the same tour. Every single Pedway Tour is different from the Pedway Tour the day before. I like to read a crowd, like I read audiences in my improv days. Some groups are really quiet and they just want to walk and smile and listen. Sometimes they’re raucous and laughing and can’t get enough. Some groups are kinda dirty and say bad things about the backside of the Picasso.
Some tourees just walk away after a tour, some stay to chat. Some tourees come and join my Facebook page and stay my friends. I would guess I’ve made about 10 actual, real-life friends from tours. Some are turning into actual, close, good friends. Some I never hear from again.
Sometimes Janet Davies walks through a Pedway Tour and I feel really proud when she says hello to me and I make sure everyone knows a major Chicago personality just walked by (and said hello!).
Sometimes I have people who speak very little English and I have to act stuff out. My performance art performance of the Great Fire is really something. Sometimes I have people who know a lot of what I’m going to say and say it before I do.
Sometimes they’ll love Bill the Pedway Musician and we’ll hang out and dance and sing with him a little bit. Sometimes a touree has to go to the bathroom and they don’t have time for Bill.
In City Hall, sometimes we’ll see people all dolled up and getting married at Marriage Court. In the Daley Center on some days, we’ll see the prisoners being led through the Pedway up to their courtrooms.
Sometimes we’ll see another tour group in the Pedway and I’ll have my group come at them snapping like the Sharks and the Jets, we’ll outdance them. No one can beat my tourees at West Side Story dance fighting.
When I’m taking a group of seniors through the Pedway they’ll give me beautifully folded up dollar bills as a tip, or even a quarter. And that is the greatest quarter I’ve ever gotten.
Sometimes, and this is my favorite thing of all, a touree gives me a hug. They just reach out and hug me. It’s the most touching thing.
And this is what I love about my job almost more than anything. I never know for sure what’s going to happen on any given day. I never know who I’m going to meet, what person I’ll see in the Pedway or what friend I’ll make that day. This is what keeps me on my toes, this is what keeps me learning, this is why being a Chicago tour guide is the best job in the whole wide world.