A Tale of Two Cities: Working and Living 150 Miles Apart

By Monica O'Brien | Published: May 13, 2008

As many of you know, I live/work in Madison, WI now. Sort of. Because I actually live/attend school in Chicago. Sort of. Confused yet?

Here’s the update on my new job:

It’s going great, except when I’m not working.

When I accepted the job at Brazen Careerist, my only stipulation was that I didn’t have to move. I have nothing against Madison; in fact, I enjoy the charm of the downtown area. But I have a life in Chicago that I love, and obligations in Chicago which I can’t leave.

So we decided I could commute to Madison two or three days a week. Which turned into five, I think. And to be honest, the whole commuting thing is not going so well.

Here’s my dilemma:

The difficult part about doing the job you want is you also want to be present for it. So I want to be in Madison, working in my little office, just about every day.

But not actually. Because Chicago is my home, and it’s where my heart is. It’s where my family is. It’s where my wonderful friends are. It’s where the skyscrapers that inspire me and captivate me are. So whenever I’m in Madison, I want to be in Chicago.

Chicago. Madison. Chicago. Madison?

It’s tough having two lives that pull you in different directions, and for awhile I really thought I could reject my time in Madison as “my life.” Instead, I would come here on vacation every week, sort of like a summer home. And I didn’t need a ton of friends in Madison, because I already have a lot of friends in Chicago. And I didn’t need a real place to stay and call my own in Madison, because I already own a condo in Chicago.

Here’s the lesson learned:

I was delusional to think commuting would be easy. Yeah, really. Delusional. And everyone tried to tell me this before I took the job, but I decided not to listen.

So here’s the one thing you need to consider when starting a job in a city you don’t live in: how much you love the job. Because trust me, if you don’t really love your job, you are not going to make it.

But for what it’s worth, I’m happy I didn’t listen to the naysayers. Because if I had thought this job opportunity through a little better I would have gotten too scared to do it. And that would have been stupid.

So here’s to the bright side of my double life: I have great coworkers. I’m doing something I love. I get to spend the summer in the beautiful state of Wisconsin. I get to buy all the clothes on the sales rack at Madison’s Urban Outfitters and wear them in Chicago where they would be double the price. My parents and husband are excited for me, and supportive of my career path. The Capitol is pretty when it’s lit up at night.

And I live in Madison. And I live in Chicago. Sort of.

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  • Madison must seem pretty puny compared to Chicago. Much less to worry about as far as traffic is concerned though, and you have to admit it's a pretty beautiful place.
  • Michael, you know, I really enjoy Madison. It's just hard to "live" in two different places. But I'm starting to think of it as home all the same.
  • Monica,

    Thanks again for the in-depth run down regarding Chicago. Like I said, I only spent the weekend there, but loved it. I spent another weekend in Naperville during the winter though, and man, harsh winters up north.

    In any event, If I ever make that leap I'll try not to commute very far; however, if Brazeen came calling I suspect I'd do the same. At least give me a reason to keep my truck.
  • I know how you feel it can be strenuous, I worked in southern Iowa for six months on an internship, but my family was all in Madison (8 hours away) and my University and friends were all in River Falls (6 hours away) so it made for a lot of miles put on my truck and a sense of leading two different lives. It was nice in the summer, but wait until winter comes.
  • Commuting sucks.
  • I'm really amazed that you can make those sorts of commutes. I'm facing my first real "serious" internship this summer and I'm facing a an hour each way commute out of the city to the burbs and back - that is daunting me.

    I hope that the gas prices haven't killed you with your long commute.

    Best,
    James
  • Hi everyone, thanks for the comments.

    The commute isn't so bad, because I live in Madison half the time and Chicago half the time. So it's a once a week commute. And I take the bus, which is fun because I love taking public transportation.

    What's hard is having two separate lives. I'm not sure if I made that clear in my post. But the good thing is there are advantages to living in two places, not just one, and I'm learning to adjust to my new schedule.
  • Jay
    Thanks for this great post. I'm considering taking a job (and a lot more pay) in Madison, but I presently live in Naperville. It's about a 2.5 hour drive one way. I'd be in Madison for 4 days a week, working from home/Naperville on Fridays. Because I've got 2 kids and extended family in the Naperville area, I can't move to Madison (let alone sell my home for a decent price!)...

    My new job would pay for or subsidize the commute, my apartment in Madison, food, dry cleaning, that kind of thing. So it's tempting.

    Can you let me know how awful the commute is?

    Cheers!
  • Jay, that's pretty much my schedule - 4 days a week in Madison, Friday-Sunday in Chicago. I don't drive up here, I usually take the bus from O'Hare airport because it's close to where I live (which you would probably not be doing).

    On the occasions that I have driven, it's not a bad drive. No traffic, little construction. The bad part is the tolls - I pay about $4.20 one way. You would have to check your route to see what you might pay.

    Good luck with your decision! The first few months of commuting were hard, but I've gotten used to it and it's a comfortable routine for me now.
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