A few weeks ago, the American and I decided on a plan of action for the next few months: We were going to spend the rest of the summer (and perhaps a little longer) in Chicago.

“Why Chicago?” everyone asked.
“Why not?” I responded.

I’d only ever visited Chicago in a November’s descent into winter. And it was C O L D. But The American assured me that there is no better place to enjoy summer in the country (outside of the temperate and wonderfully reliable SF Bay Area), as he found on his own adventures last year. It’s the home of some of the greatest sports teams (the Bulls, Blackhawks, Cubs and White Sox), fantastic architecture (you can never have too much Frank Lloyd Wright), and a fascinating local history. And the pizza! Yes please!

Chicago is one of the largest US cities, so there’s plenty of economic and social opportunities for us. Plus, the American has both his Aunt (and her family) as well as his best mate living in the greater Chicagoland area. The best mate is his comedic partner in crime, and the banter between those boys is hilarious. So what were we waiting for?

Do something uncomfortable

I love to travel, and I love to live in new places: getting to know the local weather men, and wandering around a city on foot, ‘filling in’ my mental map of a city. It was the way we discovered so many of the gems of San Francisco, Dunedin, Galway, Dublin, Melbourne and Sydney have to offer. But I thought those days of throwing on a backpack and setting off for a new city were over (at least for a while), but staying put in one place just does not hold my interest at the moment.

I’m a walking contradiction: as much as my adventurous spirit loves uprooting and moving to (yet) another place, the practical side of me sees only red flags and insurmountable brick walls. Moving to Chicago, for me, was an exercise in doing the very thing that makes me uncomfortable, yet it has satisfied a large part of my soul that sought the adventure. Sometimes, you’ve got to take a risk.

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As Dr Brene Brown says, lean into the discomfort. I could be living an ordinary life, full of regular, uninteresting, safe days. Instead, I chose the unknown. That’s what this adventure is about for me: learning, growing, experiencing life outside of my comfort zone. And already there’s been half a dozen times I’ve wanted to throw my hands up and say, “Enough! I’m packing it in and heading back to the Bay Area!”. Particularly the days when we’ve walked more than 11 miles in the high and humid 90s, desperately seeking a suitable apartment.

Dealing with the plethora of fears

I have a boat-load of fears and anxieties about this adventure, as I do with pretty much every adventure I undertake:

What happens if we can’t find somewhere to live?
What happens if I can’t find work?
How will I make friends?
What if I hate it here?
How do these people survive winter here?
Yada, yada, yada…

They’re all normal, completely reasonable fears, yet these possess the power to paralyse me. I charted the positives and negatives in a list, a task more reminiscent of my Type-A sister. My internal dialogue was divided, but once written out on paper, these fears weren’t so daunting. And ultimately, the column entitled ‘reasons to move to Chicago’ won out. Plus, I have no idea how people do winter in this city, and perhaps it’s time that I find out by experiencing it for myself. Well, at least part of the winter.

I am chasing dreams of a completely different variety here in Chicago, and I’m still trying to write the story of an interesting life. I want to collect tales, enjoy new experiences, meet new folk. Keeping my eyes and my heart open takes plenty of courage, and some days I can’t find it within. I am really lucky to have a wonderful support network who encourages and supports me, and I am so grateful for them. They help me reshape the ‘why?’, into the ‘why not?’.

Early thoughts about Chicago

We’ve been here in Chicago for ten days already, and I can’t say I love the place instantly as I did San Francisco. Chicago is very different. For one, it’s much more gritty: the people, the environment. There’s a toughness in Chicago I’ve not experienced before. Then you venture out to the shores of Lake Michigan, just steps from the CBD, and it’s as though you’re in another world: I almost can’t believe it’s real.

I like it, but I don’t love it. Yet.

We are scheduled to move into our new apartment on the 29th. Fingers crossed that it all works out, eh?