Chicagoland 1099

Let’s suppose that I only wanted to drive for 6 months out of the year, is Chicagoland the best place to live/work if I wanted to jump from company to company? I am fortunate enough to be in a position where I do not require benefits. However I don’t have any documented W2 work and it’s been nearly 20 years since my last regular job… so a 1099 job is likely all I can get right? I also have an 18 year old DUI that worries me. But from what I’ve read on this forum, I should be ok for 1099 Chicagoland jobs under my LLC.

I’m currently in Austin, Texas and my wife who is Polish is wanting to leave Texas for good since it’s too hot for her here. I’m not opposed to the idea especially since Chicago would be a new experience for us and the abundance of trucking jobs is an added bonus. What do y’all think? I’ve been looking at trucking jobs in Austin and it’s slim pickings. Contrary to what some say trucking in Austin is not good financially.

 

oh I’d be hesitant to take something local that would require driving in town. It’s a zoo out there!

 

We’ve been to all those towns and there isn’t really anything Polish going on there. Btw, my wife was born and raised in Poland and has only lived on the US a few years.

You could be right but from what I’m seeing Chicago has a lot more to offer. I could probably start a new job over there each month and never run out of employers

 

Unfortunately I don’t have the experience yet to qualify for employment with an agency. I also forgot to mention that one of the reasons we’re considering Chicago is due to me being exempt from property tax in the state of Illinois. Additionally Chicago also gives us the ability to be back in Europe in less than 9 hours and has great access food, shopping, entertainment, and education. A big selling point though is the Polish connection for the Mrs. though.

South Dakota will be a tough sell for my wife. I tried to convince her to go to Florida and she would rather go home