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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Hey JD
What do you plan to do for 46 hours(!) on the train?
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pssst…. the chicago’s nickname as the windy city derives from the fact that its politicians/prominent citizens are (or were) gasbags, not because of the weather…. at least that’s the legend.
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JD,
You put “or” instead of “for” in “Margaret had also been acting as a docent or the Chicago Architecture Foundation”
And I also wonder what you will do on a train for 46 hours.
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Haha, sweet business idea! I feel the same way sometimes — I want to do something, but I feel as if I need some sort of whacky credentials to do it… When I don’t.
I need to just get down to doing it!
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Thanks for the clarification, JM. I didn’t realize that.
What will I do on the train? What I always do. Write!
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Very motivating story for couples that are going through financial distress.
Point is to always have some backup money to be able to afford one spouse being laid off. It will save your marriage/relationship.
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J.D., enjoy the trip! What fun! That’s the route I traveled in 1996 when I moved from Boston to Portland via Amtrak. (Back in MY day, though, they allowed smoking in the observation car, which was a huge drag.)
I assume you got a sleeper car – I was poor (but young) so I did the whole trip in the general seating area. It was still really great, and the last leg down the Northern side of the Columbia is pretty sweet. I still feel super nostalgic when I see Portland’s GO BY TRAIN sign at Union Station.
Oh, and thanks for the Chicago tourism tip – I’ll be there in a couple of weeks!
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Great post
have fun in Chicago
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As a proud Chicagoan, I will further plug Margaret and say that the Architecture Foundation boat tours are one of the best things to do in the city – go on their website the day prior and book your tour – http://www.architecture.org. I myself take one or two every year. After the tour, walk over to the Hotel Burnham and have a drink in the very building where much of our city began, or go across the bridge to Trump Tower and enjoy a little history in the making…
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My husband and I are going to Chicago in Sept. primarily to take the train back to Seattle. I look forward to reading your thoughts on the train trip. Pro’s and con’s. We love trains and don’t need to ask what will you do for all those hours, the longer the better! Thanks for the tip on tours.
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Stories like Margaret’s are great! It’s good to hear a person take a negative and make it a positive!
Enjoy Chicago, I haven’t been there in at least 10 years… Great city though!
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Great city! Back in the Pleistocene, my mother & i rode the train from NYC to SF, with a 10-hour layover in Chicago. Trains were glorious then — can’t say the same for Amtrak experiences I’ve had, but at its best, Amtrak is more than just tolerable. Scenery is gorgeous, if you’re lucky enough to hit the Rockies in daylight. Bring plenty of food; one also may be happy to have brought some water, too.
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I wish you had come further East on this glorious book tour. We want you here,too.
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If you’re still there, there are some pretty cool spots I’d recommend. If you like blues, Buddy Guy’s Legends is a must. Also, more on the North side – The Green Mill. Legend is this is where Capone made some funny money – hence the name…
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If I would have read the article earlier I would have loved to meet you and get a copy of that book…Get rich slowly rocks!!!!
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I wish I knew you were in Chicago! I would have come out to have met you!
Interestingly enough, I’ll be in Portland next week…
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Nice. Although Suzanne, you actually plugged her competition instead of her…
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Cool story. Successful entrepreneurial stories are always inspiring for one who wishes to dream of his own.
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While I wish Margaret well, if you have the time to plan in advance and are flexible, the City of Chicago will set you up with a volunteer tour guide – and it’s free, free, free. Our guide was great at showing us what we were interested in (sites from a book) and things our kids were interested in.
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Man! I wish that I had been able to come out and meet you last night. It would have been nice.
And, I’m trying to convince my husband to read your blog. He once mentioned that a book might be a better idea—-and now you have a book. I’ll pick it up soon, I hope.
Good luck on your trip home!
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I know Margaret and her husband (have known her for many years, in fact). They are both amazing people. If you DO ever have a chance to get a tour she is a fountain of personality and is quite knowledgeable.
I’m glad you had a chance to know the Margaret we know and love.
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