Four seasons of Chicago

I first came to Chicago in the Fall. I came with optimism in my smile, jitters in my nerves and a brain brimming with uncertainty about the future, my future.

That made Fall the perfect season to move in. It was stunning from the very first time I saw it. I'd never seen anything like it. Crisp air off the coast of Lake Michigan. Leaves of golden yellow, bronze orange, brick red. I thought color combinations like these only existed in videogames and photography oversaturated in Photoshop.

There are just so many things to like about Chicago. Its architecture is so diverse and varies even neighborhood by neighborhood. The rivers that weave throughout parts of the city. The parks with large swaths of hills and grass. The effective, if clumsy 'L' trains.

But my absolutely favorite thing to do was one of the first: driving down Lakeshore Drive with Lake Michigan on one side and Chicago's city skyscrapers on the other, and thinking: "This, looks like it could be the perfect city I’ve always dreamed of."

I've since grown to love other cities more than Chicago, although the windy city remains my favorite in the United States.

It at once feels like home, with its generally warm and inviting people and a focus on the things that make the heart tick: family, and friends.

But at the same time, the city is about struggle, ambition and survival. Like every city in the world, particularly ones older than 50 years, it suffers every consequence of embracing a large public square housing millions of people. It embraces technology, but it’s almost as if the gravitational pull of family, friends and relationship—things that take time and can’t really be rushed—has slowed down its ability to innovate compared to the west coast. Or gives the city a far less polished, ritzy feel that one attributes to the east.

As if the city was trying for some sort of balance, of holding on to what it knew was core to a life of happiness, and simultaneously discarding those things in the name of pursuing your dreams. And cycling through the two back and forth. I was fine with that.

It is a city always changing. And for my own life, Chicago is one of the cities that changed me the most.

As a native boy of the California west coast, I hate humidity. I think most people do. The air sticks to you. The heat inhibits your breathing. It's gross.

Chicago summers are full of humidity. But no matter how bad it gets, you can't let it, or the random downpours of rain, stop you. There's too much fun, excitement and unpredictability to be had. That's what summer in America is about.

I hesitate to say that, actually.

I hate the idea of a monolithic 'America' in terms of culture. But if I had to place one city that feels distinctly "American,” with its jazz music, intense love of sports, comedy shows, glamorous barbecues, over-the-top Independence Day celebrations, diverse international immigrant communities and distinct neighborhoods, hometown feel but big city desires...Chicago would be it.

I think I like that because it’s how I sort of view myself: a hometown kid but with big city desires. That was my story too, in one Chicago summer. My crazy, you-only-live-once story of hating Washington DC and flying back to Chicago on a whim to pursue a life I say I knew I wanted but that’s a lie. I honestly thought I might be throwing my future away, and I only knew that I would be able to build some new memories with my friends and chase some interests that I had but didn’t know if they would lead me anywhere.

I'd never experienced that before and frankly I doubt I will ever again.

Where I said to hell with it. Let's do this, and see what happens. And it was the best thing I had ever done.

People say sex is living. Drinking is living. The ‘house with a white picket fence and two-point-five kids’ is living.

For me, pursuing your dream, at the cost of an uncertain future, with all the riskiness of being reckless, but trusting in your own convictions, that is living.

That's what we romanticize most about America. Or maybe just me. And Chicago summer is where I found it.

I'll never forget when the snow first melted. Humans have notoriously short-term memory. Israelites complain after escaping Egypt. People forget the convictions for their New Year’s Resolutions. I forget that lovely grass patches and fields exist beneath the surface of white powdery blankets, when it had only been three months.

But Spring doesn’t need you to remember it. It just shows up and says: “Hey, in case you forgot, look how beautiful nature is?”

Spring is when I took a class in photography, and when I fell in love with being behind a camera. I’m still not very good at it, but it taught me something important about myself: I love people watching. I love capturing random moments in life, in mine or others’, on camera or in (short-term) memory.

Spring is the best time for it too. It’s when people come back out of their shells, out of hibernation. Kids put on waterproof boots and jump in melted puddles of snow. Humans take their dogs out for races. Friends from out of town are actually willing to come visit. People play soccer and look rusty with their three-month stale skills they haven’t practiced throughout the winter.

It’s also when people seem most willing to try new things too—the “well I couldn’t do anything all winter so let’s do everything now” mentality. Food. Skills. Relationships.

I love trying new things. There’s something raw and fulfilling about being stripped of all applicable knowledge, diving in and learning as you go. Doesn’t matter if it’s making a fool of yourself and doing comedy on stage, eating something new and being unsure of how you’ll react or uprooting your life and moving somewhere new.

Those are some of the best moments. And like photography continues to teach me, moments are meant to witnessed. Sometimes that’s the whole reason they happen. For no other reason than to be noticed, and sometimes enjoyed.

Even the bad ones. The painful, heartbreaking, gut-wrenching ones. You capture them even though you want them to be gone, because they’re experiences you’ll learn from.

Otherwise, you miss them. You forget about them. Forget the lesson you were supposed to learn from having been through them. And reminders that Spring comes around again and again and there are many more moments to be had, and that many of them will in fact, be good.

I think that’s where hope comes from. Knowing that everything I know, isn’t everything that is knowable. That there’s a whole world out there to explore and understand, full of rich new experiences and moments to learn from.

Hope springs change. But change also springs trepidation. And facing trepidation requires hope.

Chicago has been a rock in my life for the past five years. Other than Hong Kong, I'm not sure any other city has had such a strong hold on my psyche or been a location for such big catalysts for life upheavals.

Winter is a painful time in Chicago. You can tell who’s from out of town by if their clothing places a silly premium on style over function. When it’s twenty below zero, Fahrenheit, nobody cares what you look like. And you don’t either.

The air chills your bones. Any piece of exposed skin feels like it’s being pricked by knives. Walking turns to sloshing and there’s no good counter to rapidly falling snow. Not the “let’s stare up at it because it’s falling gracefully and it’s romantic” kind of falling snow. More like blizzards.

Everyone rushes to be inside. And then they don't want to go out because it takes a herculean effort to put on all those layers, the scarf, the hat, the gloves, the boots. It sounds silly but it consumes ten minutes every single time. Everyone looks miserable. But when you make eye contact, people still force a smile.

That's what pain is like. You smile when you can. You smile because you try to find the beauty in freezing. It’s shivering and you want to get under the heat lamp but a flock of pigeons has taken up the space and for once gives zero f***s about you and won’t budge. The only thing to do is laugh. To pick up a snowball and toss it at someone else and say, this weather is shit, but you could never have this game without it. To say at least this spiked hot chocolate tastes better than ever.

No one wants to visit Chicago in the winter. And yet here I am, visiting in winter, and walking away from Chicago for maybe the last time.

Specifically, I mean that this is the last time I think Chicago will have the same effect on me that it has had in the past. I always feel like I left a part of my heart here. I daydreamed about moving back here, up till as recently as three months ago even. To move back to the city that won me over like few ever had.

And yet this winter reminds me, after almost five years of living in the so much smaller city of Seattle, that maybe my life is meant to be elsewhere. That maybe even the 'perfect city' isn't perfect for everyone, for all times of their life.

Yeah, I will be back. But it will be different. And like all things Chicago is known for, it goes through seasons. Life goes through phases. Maybe this is one of them. Things simply change. And as I've experienced but have never quite really learned or taken to heart, sometimes life changes too. And you should change with it.

That when pain comes around you find the snowballs and the spiked hot chocolates and other joyful things that only come around at the same time. The reasons to smile.

I hope, that the next time I come to Chicago, I might have learned that lesson on some level, and that I’ll let Chicago be different. Expect it have a different place in my life, and that I will still love the city for that.

And I guess, wouldn’t it be boring if it stayed the same forever?

Till next time, Chicago.