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Easiest way to get a job in a location is to BE in that location. Throwing resumes at Monster or LinkedIn will take forever. Get where you want to be and start networking. I still regret not going to college in Hawaii
Agree.
Get on CL and find a room to rent for several months so you have an address at an affordable price.
Get business cards made up with your photo on the front and contact information. Bulleted, brief resume on the back. Pass it out at every opportunity.
Join Toastmasters and get involved in any other networking group you can find.
Apply for every job you see or hear about that is a decent fit. Don't be afraid to turn down a job if it isn't the one.
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Check out the temp agencies. See if you can get short gigs to tide you over.
Spend 40-50 hours finding your next job.
If you are still unemployed in 2 months, you are not trying hard enough.
If you've want to live in Chicago, this is the time.
I think short periods at software and other IT jobs are pretty common, mostly because the workforce is very young.
To reference a dead technology, I once took a job at a small newspaper in a desirable city. The job and company were awful, the pay lower than low, but when they hired, they wanted somebody who was THERE. As did most companies, as I found when I went out looking for another job.
So I agree - go to where you want to wind up. Even if you have a job you don't like so much, you will be THERE and building up connections and friendships, which may well lead to a much better job.
ESPECIALLY if you are young. While I always knew I wanted to come back to my hometown to grow old, a part of me now regrets moving away from the much cooler city.
I have quit without a job lined up due to stress, too. It's not that bad and I felt great afterwards, so I don't blame you.
Since you're a software engineer, I'd really say go ahead and move to Chicago because you're likely to get something there. I'm saying that without knowing what languages you know/what exactly you do, but I still feel pretty confident that you'd get something. If it were most other fields, I wouldn't advise this--I actually moved to Chicago myself once without a job and it didn't work at all (I got a job in about a month, but it didn't work out and the job salary didn't match the cost of living in Chicago enough for my expenses anyways), but I was not working in technology back then. Also, in Chicago, you're in a tri-state area and have suburbs/other smaller cities an hour away, so you would not be limited to just Chicago for jobs if push comes to shove--they're just probably going to pay less.
Option 2. Option 1 would be a complete waste of time given you already know you want to be in Chicago. Besides, you've spent more than enough time in cities that weren't a fit. Don't continue to spin your wheels in that direction.
If you want to be in Chicago, then be in Chicago. Start establishing a network. It's a whole lot easier to interview when you can say "sure, I can be there tomorrow afternoon!" You have skills that are in demand. I look forward to reading your update with your success story in a few months.
Go to Chicago. It's always easier to find a job where you live. And it's way easier (morally) to survive difficult time in a place where you feel comfortable.
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