Here I am in Chicago, the Windy City. It hasn’t been very windy at all so far (though strong winds delayed my flight’s landing time); it was rainy last night, and it’s sunny today. I’m here with Chris Guillebeau to hang out, meet readers of our blogs, and to take a 46-hour train ride back to Portland.

If you’d like to join us, we’ll be gathering at 7pm at Rockit Bar & Grill, which is located across from Wrigley Field. I brought a dozen copies of Your Money: The Missing Manual with me from Oregon, and will sell them for $15 each (which is what they cost me on Amazon). I’ve also brought a bag of Lollyphile gourmet lollipops to share. (No charge!) Hope to see some Chitown readers tonight…

Margaret’s story
This morning, Chris and I spent time with Margaret, the brains behind Chicago Elevated, a one-woman company that gives Chicago tours to people like you and me. It was awesome to talk with her and to hear her story.

During the summer of 2008, Margaret’s fiance lost his job. A month later, in September, they got married. And one month after that, Margaret lost her job. She was working as a secretary for a real-estate development firm, and when the economy crashed in late 2008, her job was one of the first to go.

“That’s about when I started reading Get Rich Slowly,” Margaret told us. And she started reading The Art of Non-Conformity when she decided that she didn’t want to go back to work as a secretary.

Margaret had also been acting as a docent for the Chicago Architecture Foundation, and really enjoyed the work. It occurred to her that maybe instead of returning to a regular job, she could start her own business giving tours of the city.

“It’s kind of scary,” Margaret told us as she led us through Millennium Park. “I keep waiting for somebody to give me permission to do this, but there’s nobody to give me permission.” Chris nodded enthusiastically; this is one of his Big Ideas, that you have to take control of your own life and do what you want. Nobody’s going to give you permission — you have to give yourself permission.

Fortunately, Margaret’s husband is back at work, so they can rely on his income while she gets her business established. She says that although she’s just getting started, she’s already faced a few “tortured decisions” about how to grow her business. Based on what I saw today, I’m sure she’s going to do fine. She loves the town, knows its history, and is an enthusiastic guide.

So, if you’ve got plans to visit the Windy City and are looking for a tour of Chicago, drop Margaret a line.

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