July 12, 2010
I Will Now Be Taking Questions
As long-winded as it was, the rundown of my plan to move to Chicago did leave a few questions unanswered. An oversight that I would like to take this opportunity to rectify.
Why Chicago?
Why not Chicago?
I didn’t have any specific city in mind; I just wanted one with a solid urban infrastructure. New York came to mind first, but it’s is just too big. I wanted a city that I could actually digest. Seattle, Boston, and Chicago came to mind next. For some reason Chicago just stuck out. It seems like a charming town, and I’d heard good things about it. Ok, sure! Let’s do Chicago!
Since then, I’ve heard phenomenal things about it, only solidifying my decision. But initially, it was a pretty arbitrary choice. I’ve never been to Chicago, but I’ve never been to any of the other candidates either.
So, you know some people there, right?
Outside of a few second-degree acquaintances, I don’t know a soul within 400 miles of Chicago. Half of the purpose of the move is to completely break out of my established comfort zones and see what I can make of myself without the influences that I have in my life now, be them good or bad.
Do you have a job lined up?
Yes and no. At this point, I don’t have a specific job lined up, no. Initially, I was hoping to find some contract web development work that would last from 4-9 months. But in talking with a few placement agencies, while I’m qualified for some high-demand positions in the Chicago area, most are very quick hire. They want to interview and hire within a week. That wouldn’t leave me much time to quit my job, pack, find a new place and move.
So, I asked anyone I know in the web development industry to pass along any freelance opportunities that they came across. As long as I could get enough work to get up to Chicago with a decent work/cash buffer, I figured I could land a job in a few weeks. From those contacts (read: friends), I have several projects that I’m working on now, that will last me for a few weeks yet, with several more that should be coming down the wire soon.
I’m not sure if I’ll stick with freelance, find contract work, or do a little of both. It completely depends on what immediate opportunities present themselves. So, no, I don’t have work lined up, but yes, I feel fairly confident that I’ll be able to find some.
But not so confident that it’s completely out of mind. This is by far the biggest unknown with the whole plan, and the piece that is most guilty of keeping me up at night.
Where are you going to you live?
I’m planning on getting a furnished apartment in the northern half of the downtown area. Right now, I’m leaning towards Lincoln Park or the surrounding areas, though pricing and availability of studio or one bedroom apartments will vastly influence that decision.
A lot of furnished apartments are fairly quick turnaround, and since I’m still not 100% sure when I’ll be moving, I’ve only been able to generally price out apartments without taking any steps towards actually leasing one. I’ll probably end up picking one a week or two before moving in. I hope it doesn’t smell funny.
It should be pretty evident that nearly every piece of this is still up in the air. For it all to come together, a dozen things will have to simultaneously fall into place. And I’m sure I’ll be taking some blind leaps along the way.
But, hey, that’s half the fun!

Caleb, this is exciting, and you know that I am honored to have worked with you and your humor as well. I look forward to reading about your journey and your cardboard box under the bridge at Lincoln Park. Chances are good you may find some good Irish pubs there to imbibe a few pints when need be. You will be missed, and vicariously enjoyed at the same time. May the wind be always at your back.
when do we start our weekly wine and cheese dinners ?
I’m happy for you. Enjoy it!
cheers!
I have a question:
Why do we all have British accents, when we’re all from outer space and there is no Britain?
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Caleb . . . you BEAST! SOOO happy for you. This clearly won’t be easy but it will no doubt be worth it. Don’t be surprised if you end up out of your comfort zone for a LONG time after this. Proud of you man.
Hey man. I’ve visited Chicago several times and I love it. The fall’s gorgeous and the lake is something else. Best part is probably the 4th of July. Last time I went for the 4th, (not sure if it’s still allowed) the whole downtown area is allowed to do their fireworks. So you can see them going off for miles. It’s really the best. Good luck on the move man!