Eight days of solid work. For a startup tech conference – the largest ever – midVenturesLAUNCH – working with guys so impressive, it’s spurred me to continue to take risks with my life and to strive for more.
But also, working in Chicago, it hit me.
How the hell did I end up here?
Not because I don’t like it or I am not enjoying myself – au contraire! I love it here. It has everything one could want in a city – arts, entertainment, crazy taxi cabs, nightlife, hustle and bustle and the extreme focus and drive that it takes to survive in one. But it also has – waterfront, weather (something I missed living in LA and something I got a bit too much of in England) and nice people, beautiful neighborhoods, an international community, big deciduous trees, a subway and nice people.

The thing is – I just can’t figure it out. I can’t pigeon hole this city.
I stop, I look around, I talk to the people in it. It’s so normal, but then again, not.
And it’s in the Midwest.
I go back to my original question. How did I get here?
I can’t explain it more than that – that question has been plaguing me for the past two weeks – in a good way. Like a plague full of skittles and smiles and Modern Family tv shows.
Jock thinks it’s because I can’t fit Chicago into a neat box. Moi? Trying to compartmentalize?? Never!
Then I remember what change is like – finding a spider in your apartment. First step – coming face to face with a disgusting, 8-legged creature building a nasty, invisible web in the corner of your window. You realize it’s tiny, so much smaller than you. You smile because it doesn’t even know what’s coming to it. You feel good about yourself for recognizing how vulnerable and small it is and how much power you wield. This sucker ain’t got nothing on you.
Then – it moves. You scream and jump onto the first safe thing you can find – something familiar and up high. You underestimated its danger. You misjudged your own feelings and capabilities. There is no way in hell you can fight this vicious creature.
The spider pauses for a moment, still poised on all eight legs, ready to attack – but it gives you a moment to recollect yourself. Out of the corner of your eye, you see that this room is filled with your own stuff, your own weapons, weapons that you have been hoarding and storing your entire life – perfect weapons that will crush anything in its path, they just need to be used to the right capacity.
You reach for that shoe/folder/mental and emotional crutch. It starts to walk away, you ease up the tension in your neck, take deep breaths and begin to realize what a fool you are for getting so scared in the first place. After all, what doesn’t kill you makes you stronger.
But, The spider moves again!! This time…in your own direction and it’s MUCH bigger than you anticipated. In fact, it must be poisonous. You are definitely going to die. Thoughts of death, paralyzation and foaming from the mouth occur to you – there is no way you’ll survive and you feel so lonely. Why did you ever get yourself into this situation? In a small apartment, alone and with something so different from you encompassing the same space. You should have stayed living with your mother forever where she could kill the spiders for you.
You panic, jump up and down, reach for your phone – but then it kicks in. Survival instinct. You are a ninja – a spider-killing, change-conquering, death-defying superhero.
The spider is dead. Your hair is sticking straight up. You have goo on your shoe.
You feel elated. You spray spider-killing spray all over your apartment, you are ready for the next attack and you feel stronger than you ever have before. Nothing can take you down. Why aren’t there more spiders to kill everyday? – you think to yourself.
OK, so maybe the spider-killing metaphor went on a bit too long, but you get my point.
I’m expecting highs and lows along the way, and I’m expecting to get hit with something nasty when I least expect it, but I also know how great I will feel once it’s all conquered, my life is on a path and Chicago is where I can call home.