VoyageChicago features “Chicago’s Most Inspiring Stories,” along with highlighting neighborhoods and trends. Check them out.
And they recently featured me:
Today we’d like to introduce you to Wendy Bright.
Wendy, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
I’ve been leading tours for 25 years now. And it began as a hobby. I had an opportunity to volunteer as the historian and tour guide at my historic Milwaukee church. Then I trained to be an architectural tour guide for Historic Milwaukee, giving three downtown walking tours. I also moved downtown and began leading tours of St. John’s Cathedral.
I was finishing up my BA at the time hoping to go into computer consulting. But a choir trip to Europe in 2001 changed my path. While in Austria and Italy, I experienced all of these tour guides with all different personalities, sharing stunning things with people from all over the world, OUTSIDE for much of their workday, and making a living. Well, that did it. My hobby was going to be my career.
I proceeded to graduate school to study Art History with a focus on American architecture. That focus soon became an obsession with Chicago. Before I knew it, I had my MA and an ever-growing collection of books about Chicago’s history and architecture. I decided to make Chicago my home.
I trained with the Chicago Architecture Foundation, which was excellent preparation. I later gave tours for other companies, but I was frustrated with the content of some of the tours I was being paid to give – they weren’t as solid as I would have designed myself. Good friends suggested I start my own tours and threw me a business-starting party. How cool is that?
I started WendyCity to be able to share my own kind of small-group, personal, fun but solid tours. I use historic images, video, and music on my iPad to help the information come alive for my guests. With that added media I can take them places – back in time, to the tops or insides of buildings.
I’ve developed a number of thematic walking tours, but I often customize tours according to people’s interests. WendyCity has been a casual, small-ish endeavor, but I am now transitioning to a more serious business and expanding what I offer.
We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
Trying to make a living by only doing WendyCity initially proved to be impossible: I couldn’t ramp it up quickly enough. I took on a full-time day job, which of course took valuable time away from WendyCity. I decided to just back-burner my tours for a while and not push it.
But over the past couple of years, while I was lying low, I discovered that people were still finding me – as small as I am and with no marketing to speak of. Word of mouth and reviews made that happen.
Last year, for the first time, I was finally able to cobble together a way to make a living by leading tours – all different tours. Besides my own, I’ve been giving river architecture tours and doing a nice amount of freelancing. All of that work has only enhanced WendyCity. And now I am excited to move ahead and grow.
We’d love to hear more about your business.
Many years ago, I read about a group of New York women who dressed up in vintage and got together every month to dine out at one of the city’s classic restaurants. This completely inspired me and I began thinking about how I could bring a similar experience to Chicago.
The first tour I created was my 1950s Nightlife in the Loop. It’s an evening tour that focuses on midcentury nights out: what did people do, wear, see, eat, drink? We drink and talk history. What could be better than that?
I developed two more evening tours that focus on decades: my Roaring ’20s: Art Deco and Decadence walk around the Loop, and my 1960s in the Gold Coast walk that includes Rush Street and Playboy history.
All of my evening tours are really more immersive experiences than “tours,” with historic images, music, and video, along with stops at memorable Chicago restaurants, bars, and hotels.
One of my most popular tours actually began as a toss-off: Mag Mile in the Morning. I was curious about that stretch of Michigan Avenue and happened to be down there in the morning and found it so peaceful, that I created a two-hour walk based on deep research. We start at 7:30 AM and it is so fun.
Another favorite is my Marshall Field store tour, based on copious research. I offer it at Christmas time and it’s a favorite, and also year-round with a thematic approach based on a historical novel about Marshall Field and his lover (!): What The Lady Wants.
What were you like growing up?
I was a curious, creative girl. I did well in school and always wanted to learn. I loved music, writing, and drawing. I danced and sang. I made audiotapes with stories and sound effects as well as carefully curated mix tapes. I was a reader and a dreamer.
WendyCity walking tours are $50 per person