Anniversaries for longevity have been elusive milestones in my life. Growing up, the longest I lived anywhere was two years. I stayed in my college town for six years, not because it took me that long to get two  degrees, but because I was so blinded by love that it took me a couple of years to figure out that the one thing I really wanted was to be left alone. I haven’t held a job, other than freelancing, for longer than two years. My aforementioned relationship was my longest, and it lasted just four years before ending with a lot of screaming and a partially-shattered sense of self-worth.

And when it was over, I landed in Chicago — five years ago today.

Conventional wisdom says that your early twenties are supposed to be the “best years of your life” and I guess, for me, that was no exception. I woke up two hours before my alarm, something that would have never happened in my first two years here, and watched the snowflakes dance along the Christmas lights hanging across the horseshoe curved courtyard.  It hit me that I’m just 365 days away from having more of an identity as a Chicagoan than a Kentuckian, if time were the only measure.

In celebration of my fifth anniversary, here’s part one of (at least) a two-part series of things I’ve learned from my first five years in Chicago.

Invest in good winter gear

When I arrived in Chicago, there was snow on the ground. That’s not usual for November-March, but on that particular morning in January there was just enough on the ground to argue that better footwear would be needed. My Chucks were reduced to squishy-soled water weights strapped onto my feet with fraying laces. As I carried my redneck suitcases (trash bags) full of clothes into my first city apartment my single agenda items– figure out how to get the sofa inside — was soon joined by a second: find better shoes.

The sofa was solved by using a rope to hoist it onto the balcony. I was proud of the new place, a two-bedroom that my parents were going to help me pay for until I found a roommate. I found it on my own, and it wasn’t until I moved in that I realized I committed a huge Chicago faux pas: I was renting west of Western Avenue. Now that gentrification has really picked up that carries less of a stigma, but I spent the first six months of my Chicago tenure convinced that the Norman Rockwell façade of the Northwest corner of Lincoln Square was hiding something more dangerous. Turns out, there’s just a caste system involving Chicago addresses.

In my first week in Chicago, I clocked nearly twenty miles of walking, all in boat shoes (without socks) and tennis shoes (also without socks). My feet were wet and cold, and on the first day of heavy snow and subsequent days of -30 degree weather, I caved to the importance of winter footwear. Money was something I didn’t have, so I got a pair of knock-off UGGs from the clearance rack at Macy’s. They lasted only a couple of weeks, until the snow started to melt; the faux-suede took on water like the Titanic and I sloshed around as if wearing a pair of icebergs.

One of the first things I had to do prior to starting grad school was meet a mentor for drinks at a gastro pub situated at street level of the 23-floor high-rise in which I was set to start classes at the end of the month. I still felt counterfeit when walking into the grown-up establishments catering to  cosmopolitan adults, places that often involved revolving doors and reservations, and if my own insecurities weren’t enough of a burden, as soon as I stepped on the rug my footsteps were met by gasps from the hostess, an early 20’s female, a thin stick of perfection with an orange-tinted face draped in long blonde waves (I’ll later learn we call those Trixies here), who looked at me as though I were a Great Dane whose paws were filthy. What she realized before I did was that my footwear had succumb to scientific principles; my budget boots were disgorging fluid with every step I took, water rushing out of the sides of the boots with great force, spilling onto the floor.

I shuffled to the table trying to avoid sloshing. The man across from me was pristine in a vintage gabardine jacket and rubbers over his wing-tipped oxfords. His cashmere scarf was finer than my fake one, and he sat with a stoic confidence that I assumed was gifted to individuals that had spent more than 30 days in the city. Each sip of my Sazerac and every word uttered about how grad school and the resultant change of career would revolutionize my life reminded me that I might not fit in. It was my nature to have cold feet, and on that day I did, quite literally, as my soggy boots created pools on the tile where they rested, the squid ink decay of car exhaust and other city unpleasantries deep enough for ducks to wade on the Italian tile.

The next day I took the red line to the Chicago stop. I found a place called Soupbox and ate clam chowder, my feet still suffering the same fate from the melting snow. I walked to the North Face store and charged new boots, a puffy sleeping bag coat, a hat, gloves, and a scarf to my emergency credit card. It was easily the most expensive shopping spree I’d had in all of my 23 years, but I wore the boots out of the store and threw the soggy sandbags I’d just disowned into the bin in front of the Jamba Juice.

There’s a joke that all women in this city look the same during the winter months, but it’s more about survival than conformity. Try walking two miles in fake UGGs and a wool pea coat in negative temperatures; chances are you’ll accept your fate as a Stay-Puft Marshmallow Man. Today I put on the same boots and coat I bought that day and spent 45 minutes dusting my car off from the snow that festooned its hood. There’s exactly one type of person in Chicago and I learned that quickly: We’re all masochists who would rather complain about the weather than move somewhere that’s better (and that’s because the spring and fall are amazing here).

Without a Budget, You’re not going to make it

I knew that living in a big city would be more expensive, but it’s also fair to say that I didn’t have a great concept of how exponentially more difficult my life would be financially. Prior to the big move, I’d never been reckless fiscally. Sure, I decided to fly to Los Angeles on a whim to see a concert with my best friend and probably spent more on vinyl records than necessary, but I always had a safety net. I knew that money would be tight here. I had loans for grad school with a couple thousand in residual funds to help defray the cost of housing (which it did, for roughly two months out of the year). I had a full-time job, but was earning just enough to subsist, not thrive.

When you’re strapped is when you learn the truth about your spending habits. Emergency credit cards turned into a means for paying for groceries, and each month when payments were due I played the shell game with my bank accounts and shifted money from one place to another, watching it disappear and feeling guilty over every purchase from eyeliner to toilet paper.

I had no outrageous spending habits to correct, but when you don’t have much it adds up quickly, especially when you don’t adjust your discretionary spending. I naively thought that if I avoided places like Barneys and Alinea that the money would just sort itself out, but coffee four times a week, beer three times a week, and even the cheap tacos added up. Then came the car troubles, a sick puppy, and a back injury. Bottled water taxes and the 9.25 percent the city takes on everything sent me into spending depressions (and forced me to buy one of those stainless steel water bottles).

Then came the frugal years. When I’d go out with friends, I’d surgically dissect our bill, paying for only the food I ate instead of subsidizing their drinking habits. It felt unfriendly and cold, but when every dollar mattered, it was the best I could do. I eventually stopped accepting dinner invitations and would eat Chef Boyardee before showing up for just drinks, where I’d drink club soda with lime, sometimes tipping bartenders in quarters. I got my hair cut by students who often left the ends jagged or split and the roots a different color from inexperience. I shopped at second-hand stores, bartered for tickets to baseball games, and limited my social calendar to free events.

My one oasis in an otherwise functionally poor existence was a student membership to the Art Institute. It was $50 I could have used, but on days when I felt lost, broke (which was most days), or in need of a few hours of escape, I could wander the museum for hours, rubbing elbows with Monet and French tourists. I memorized the museum; I could tell you which miniatures had dogs in them and which I wished were real so I could live in them. It was a slice of culture, one that I played like a VHS tape of Roger Rabbit when I was a kid. With afternoons of art and free fruit-water on the members-only patio, I was enriching my life since my other alternative was usually sitting at home.

My salary is now above the area median income, and yet budgets seem even more important now. There’s a tendency for young professionals here to parade about as though they are millionaires when in fact they are swimming in debt or one disaster away from bankruptcy.  I went out with someone recently who informed me that he spent over $450 on cabs last month, all because his friends like to go out in River North and he doesn’t like to take the train. I lived with someone who made a modest salary, yet went out to eat four nights a week at the city’s fanciest restaurants and often wondered aloud what had become of her savings. My father always warned me when I was a kid that “expenses would rise to meet income.” What he didn’t tell me, of course, is if you’re not careful your expenses can rise exponentially higher than your income and that you’ll have to call and beg for some emergency cash because your emergency credit card is maxed out. This leaky sieve of a city encourages commerce. I’ll spend the rest of my life confronting that, I’m afraid.

When people come to visit, let them stay with you, and give them a map.

There was a reaction that I always waited for when I told people I was moving to Chicago: the moment their eyes would light up when they realized that they might not have to pay for a hotel on their next visit. I can sympathize with that reaction, having done my fair share of sofa surfing over the years. Since I was moving to a place where I hardly knew anyone, the prospect of people coming to visit was exciting.

It’s exciting, that is, until you realize what visitors entail. You have to have the refrigerator stocked, even if they plan to eat every meal out, because if you don’t, they’re going to decide they want bagels at the house or mimosas before heading out to see Buckingham Fountain. You also have to convince them that you always have clean sheets, an organized closet, and guest towels. If it’s your parents, then you also have to hide everything that would imply that you’re doing anything but ideal, which means stashing the mail, prescription medication, text books, and condoms.

In my first year, a handful and a half of people came to stay.

Sometimes it was strictly transactional. An old coworker needed a place to stay during Lollapalooza, another on their drive up north. But the worst trips, and most of them were like this, was the Thursday-Sunday trip in which they showed up agenda-less and proclaimed, “We are here to experience ‘city-life!’” Of course what they don’t know is that once you’re living in the city, the definition of that becomes very different than it does for someone who is just passing through. My definition of “city-life” was sitting in coffee shops with free wireless, going to bars to watch college football, and going to my favorite BYOB Neapolitan pizza place that wasn’t mentioned in any of the tourism brochures. To them it meant going to the Cheesecake Factory, then ESPNZone, and then riding your bellyful of overpriced nachos and tasteless cheesecake to the top of the Sears Tower to look out upon the sprawling landscape.

After paying roughly $45 dollars to see the top of the damn skyscraper and $50 for two martinis at the Hancock, you lose your energy to argue that there are better restaurants than Weber Grill, better bars than Mothers, and accept that some people are just on a reckless quest through the tourist strip of Chicago. These people are oblivious and unsalvageable and they should be sent out on their own. Arm them with directions to Lou Malnati’s (which they’ll like better than Pequods), the Bean, the Macy’s on State, Wrigley Field, and something Ferris Bueller- or Blues Brothers-related and send them on their way. Don’t go with them and tell them to save room for dinner and take them somewhere that you like and listen to the things they saw. And when at the end of the dinner they say, “I wish we had come to more places like THIS,” do not smile. And do not, under any circumstances, say that you told them so.