I was thinking lately how it feels like it’s been years since I’ve been active in my blog. Well, that’s probably because it has been literally been over a year since I’ve posted on here. Whoopsie!

This year has been insanely busy. For one, I moved away from Oklahoma at the beginning of the year after living there for 11 years. In my pre-move purge, I threw away sooooo much stuff and organized the hell out of what I decided to keep. (I cannot confirm nor deny the status of their organization as of late, but I felt pretty good about myself at that time.) I drove to my mom’s house over the week of Christmas to drop off some boxes—I sold 4 medium-sized cardboard boxes to Half Price Books for a whopping $75 and still have approximately 6 boxes in my mom’s basement—and then I made the BIG move to Chicago shortly after that. It was a pretty stressful time in general, and while it felt kind of freeing for me to sell a lot of the stuff that I had since college, it stressed my dog out. Thankfully, she got some anti-anxiety medication prescribed to her (twins!), and she calmed down even more once we hit that Ohio soil—she’s obsessed with my mom and her house that she comes to every Christmas when we visit. It helps that my mom also has a massive backyard for my dog to explore every inch of sans a leash connected to me, trailing a mere 3 feet behind her. I left the city that I’ve known for over a decade—wow, that makes me feel ancient—to move to a different city that I’ve only visited a few times in my life. Luckily, I have family here, and after living at least 12 hours from a single family member the whole time I lived in Oklahoma, having my cousin and my aunt and my uncle just a train or bus ride away could not be more welcome.

Just a week after quitting my job, I moved in with my mom and applied for jobs in Chicago like crazy. I kept an Excel spreadsheet of how many jobs I applied for, and it was over 120 at the end of February. Job-hunting is no joke, guys. Like any other human in existence, I was terrified that I made the move and quit my job prematurely, that I would never find another job, that I wouldn’t be able to find a reasonably priced apartment in a safe neighborhood, that nothing that I was hoping for would actually happen.

After I turned 30 in October, I knew that it was time for a change. I’ve wanted to live in a city for a really long time, and when people think of a big city (well, when I do), they think: NEW YORK. One of my sisters lives in New York, so I get to visit her and try out her local spots, eat really delicious food, and maybe see a concert or a movie or something. Most of all, I just like spending time with her and chatting. While it’s so cool to visit, I don’t want to live there. I thought of all the cities that I could possibly move to—LA never sounded like my cup of tea, Phoenix didn’t really call to me, I didn’t want to live in the South again, and none of the other bigger cities stuck out as a fun place for me to live. Like I said, I have family in Chicago, and the first time my family and I visited (that I actually remember) was when I was 8 or 9. I remember my mind being absolutely blown when I saw the multi-story American Girl Doll store. Why I waited in line to have a grown adult brush my doll’s hair is beyond me. Those people just work there. But, props to that whole franchise, because I was obsessed, and a large chunk of young girls were too. In order to fund my obsession, I did as many chores as humanly possible to get my hands on dolls that were supposed to be fully grown girls but also small enough to prop up on my hip and carry around as if I was saying to the world: “Yes, this is my child. She closes her eyes when you lay her down AND she has two teeth!!!” I remember being thrilled that I finally earned enough money to buy the latest addition to their franchise—twin babies. Good lord… Fast forward to my eighteenth birthday, after I long ditched the dolls, I took a bus from Cincinnati to Chicago. I was visiting that same sister who was staying with my aunt and uncle in their Oak Park home at the time. She lived there while she completed an internship in the city for interior design. On the day of my actual birthday, we walked from their house to Ernest Hemingway’s childhood home and did the whole tour and also visited his museum across the street. This was probably the nerdiest yet best way to spend my eighteenth.

I always knew that I liked Chicago, but I didn’t really think about moving there specifically until my sister and her boyfriend were chatting to me one day when I was visiting them in their place in New York. I was talking to them about how unhappy I was at that time in my life—I had great friends, I was halfway done with a master’s program, I had Harper, I recently got into painting with watercolor, I had a favorite local coffee shop that I’d spend as much time at as humanly possible, and I was finally in a different apartment, far away from my asshole neighbors. (If you’d like to read about how horrible my first ever apartment experience was, here ya go.) As I was saying, I was sitting at my sister and her boyfriend’s dining table in New York, and we got to talking about how I was doing as of late. At one point, I thought I’d eventually buy a house and set up camp in Tulsa. But, I got halfway done with my master’s in English at the University of Tulsa and most of my friends were married and/or had a kid or two, and I was starting to feel like Tulsa wasn’t my home anymore. David, my sister’s boyfriend, said, “What about Chicago?” He pointed out that it could be really nice to live near my aunt, uncle, and cousin who all lived there. I already got along with them really well, and for the past few years, they’d throw in a “Visit us whenever you like” or “We’ve just got to get you to move to Chicago!” I thought about it for a moment and replied, “Yeah, I could move there in like 2027 or something, when I graduate. I just wish my master’s program was more creative-based than literature-based.” He said simply, “What if you just moved when your lease is up and finish grad school in Chicago? I’m sure they have way more options for grad school, especially writing.” In a word, I was flabbergasted. When I have a plan about something or how it’s supposed to go, I tend not to think of any other possibilities. I had never, and I mean NEVER, thought about the possibility of moving before my program was up. I was halfway done with it at that point, so I had 18 credit hours under my belt. I could stay and graduate from the program, which would take another year and a half, or I could put it on pause and find a program that better fitted my goals. After we all brainstormed together for a bit, it hit me that it was actually possible. I could move, I could get a new job, I could go to even MORE concerts than I already do, I could get a masters in something I really enjoy, I could live close to family, and I could live in a non-Bible Belt state. Like… all of that was actually possible. I was approaching my third decade of life, and a new thing that I realized was just how important and comforting it is to have family around you, because I know how lonely it can be when they’re not. I could live in a really cool city, be super close to my aunt and uncle and cousin, drive to visit my mom every few weeks, and celebrate even the smallest holidays with family after not doing so for the past 8 or 9 years—things were looking up.

A few months prior, I started to have this feeling that my time in Oklahoma was coming to an end. I remember being at my friend’s house for a Fourth of July pool party, and I weirdly knew in my gut that this was the last holiday I would spend with them. There was a weird sense of finality to it. It didn’t feel scary or bad; it just felt right. In those 11 years living in Tulsa, I made some really special friends, and their spouses and children are freaking delights. I miss being able to just send a text in the group chat, seeing if anyone wanted to have a picnic in the park or have a potluck dinner. They—along with some trusty SSRIs and weekends spent watercoloring at Pony Coffee—kept me sane those 11 years. Sadly, Pony was only discovered the last 8 or so months before I moved, but I think that the shop and those baristas kept me more afloat than they probably knew.

It’s now July, it’s Sunday, and I am at a writing group at a coffee shop in the West Loop. I ordered a delicious iced oat milk latte with the shop’s homemade brown sugar syrup. I have a creative meet-up group directly after this, where I’ll be able to chat with people about life and our interests, all while we do our own crafts. I just finished a pet portrait of a dog named Spencer (as seen here), and I’m working on another commissioned pet portrait of my previous coworker’s cat, Miss Kitty America. I took the bus to this coffee shop, and I’m not sure which route I’ll take to get to the next place—I’m still getting used to not having to drive everywhere. I’ll probably take my pup for a walk and listen to my audiobook when I get home, clean my apartment, watch a movie, chat with my boyfriend, take a nap—I don’t really know! Even though I just recently moved to Chicago and am still considered a “newbie” at my new job, I know with every fiber of my being that this was a really good decision for me.

I don’t really know what the point of this blog post is other than an update life, but I’m writing now to say that I’m happy where I’m at. I really am loving it here so far, and even though I’m not doing what I had planned for myself literally a year ago, I’m happier than I thought I could be.

Reagan Fleming