Chicago: One Year

Chicago, damn. 

Delving into my photo library trying to find the first photo I ever took of Chicago, I discovered an image taken on May 3, 2010 from an airplane en route to California. As we descended into O’Hare, my window seat afforded the first glimpse of a seemingly grand city nestled along a gigantic lakefront with the immense green of Lincoln Park set on a backdrop of sprouting skyscrapers. The date stamp on the photo is significant because it would be five years later on the same date that I would relocate to Chicago from Washington, D.C.



For the inauguration of The Urban OptimistI have collected some personal highlights from my first year living in the Second City. A preview of topics include neighborhood spotlights, a dizzying recap of live music around the city, the Midwest’s blatant affinity for booze, some professional highlights, the endless mélange of good food, a lengthy stream of consciousness on architecture, and adventures with my best friend.

Four Months in Roscoe Village

After nearly 11 hours of driving from my old home in the District, Jessica and I crossed over the Chicago Skyway and the distant view of that skyline began to draw closer. She put on Frank Sinatra’s “Chicago” as traffic crawled by the Loop. We had finally arrived!

The transition into my new city had a peculiar similarity to the Washington, DC neighborhood I left behind: the same nickname. For my initial four months, I called Roscoe Village, or “The Village Within the City” home. On the second floor of a traditional Chicago rowhouse, I shared a summer abode with my awesome friend Wendy whom I met years prior in Richmond and was busy tackling laboratory work at the University of Chicago and preparing her brilliant mind for nursing school at DePaul University. Wendy’s best friend was our third roommate, a sweet white-haired Canaan named Lucy who has a loving nature like no other dog I have ever known. Roscoe Village is a mostly quiet neighborhood to the west of Lakeview and houses young families, several low-key restaurants and bars, and is accessible via the L’s Brown line. I enjoyed climbing up to the rooftop to gaze at summer storms with friends, jogging over to check out the jagged roofline of Studio Gang’s WMS Boathouse in Clark Park set along the north branch of the Chicago River, catching music at nearby dive Beat Kitchen, and discovering that my alma mater had a local headquarters for Hokie football games a few blocks away at Riverview Tavern. I linked up every morning with Lincoln Avenue bike commuters as we made our way to and from River North and the Loop for work (a preferred alternative to the slow crawling sardine box otherwise known as the Brown Line).

Although short-lived, my time in Roscoe Village was well spent and will always remind me of my first summer in Chicago. Some day I may even get back over there to retrieve a bunch of magazines and some weights I left there when I moved out. Sorry Wendy!


Within the first few days of settling in, a small group of avid photographers met at the Sheridan Red line station in Lake View for a mild afternoon of photography. We went from capturing portraits and puddlegrams under the L tracks to roaming Graceland Cemetery, rendezvousing with others for refreshments in a reserved room at Uncommon Ground and ending the evening on the 48th floor rooftop terrace of the New York Building amidst a thick layer of fog. I had known most of these talented people via Instagram and the Chitecture community for the past few months and it felt fantastic to meet many of them in person finally and share a common pastime. This was one of my first memories living in the city that showed me a fresh spirit of connection with amazing people that I would continue to unearth throughout the Midwest.

A collaborative cruise between Chitecture and Chicago’s First Lady took place in July and I expanded acquaintances with amazing photographers even more while we took in the most spectacularly vivid sunset I’ve seen so far in my time here.

Chicago’s odd weather and urban density collide for interesting and challenging shots year-round and the community has been helping me learn that it is a never-ending process of finding beautiful moments to capture, compose and share. The point is to just go shoot. One of the best outings for photos was easily Open House Chicago, an epic two-day affair every year in October where the city’s vast architectural treasures are open to the public. A highlight was gaining access to 360-degree views of the city from the 71st floor of the Aon Center.

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It’s always fun to scroll back in time through my scattered feed on Instagram (@jbhay) to see how I have sharpened my skills to capture subjects of architectural geometry, reflections, random urban elements, or travel and look forward to continuing to evolve and explore this creative outlet as far as I can.


I’ve only been here for a year, but have only seen the tip of the iceberg when it comes to the Midwest and their alcohol. When I wasn’t working, or scouting the city for that perfect photo, absorbing swaths of sound around town or at home, or pedaling through the city or by the lake, it was definitely spent exploring the city’s finest watering holes for local craft beer, a classic cocktail, or just a delicious Old Style.

In late May 2015, many of us gathered to kick off Chicago Craft Beer Week at Garfield Park Conservatory for their “Beer Under Glass” event. Underneath this glass museum sheltering multiple mini-climates of flora and in the gardens outside, Chicagoland brewers extended samples of their concoctions to avid beer fans. Many of the beers I would continue to order in bars across the city in my first year were first sampled here, including Pilsen’s Moody Tongue, Indiana’s 3 Floyds Brewing Co., Goose Island, Solemn Oath, Revolution Brewing, and Half Acre, among dozens more. I’m very excited to be in attendance again in a few weeks and when I’m not seeking a sample you can find me hunting for a bag (or ten) of Dinky Donuts.

My other go-to joints have been all over town, whether closing out Rainbo Club with a draft PBR and all of the friends, sipping on cocktails presented on Tarot cards at The Drifter after work, paying more than necessary for a beer and a view of Millennium Park at Cindy’s, a PBJ special at the Boiler Room, or hopping down below the Old Chicago Inn after Open House Chicago for an old fashioned at Room 13. A profound evening of imbibing came as a surprise gift from Jessica to congratulate me on passing the Professional Engineer exam, when she reserved a table at The Aviary in West Loop where we indulged in wildly presented and complex cocktails. Nearby establishments Estelle’s, Flat Iron, Happy Village, Gold Star, and Innertown Pub are the regulars for an affordable cold beverage and catching up with friends in a backyard patio or at the billiards table. While I long for my East Coast options in Natty Boh or Yuengling at times, an Old Style is the most perfect alternative. Last but not least and to my total and complete surprise, it was not long after I moved to Chicago where it was ME asking others if they wanted to join in a shot of Malört. Cheers!


Where to begin? Chicago is a music mecca. I used to make my first trips to this city just to spend three days soaking up sun and sonic waves among the masses with friends at Pitchfork Music Festival. (My fourth trip included a death-defying (ask me about that one next time you see me) weekend in April 2012 where I went crate digging in Lakeview at Dave’s Records and Grammaphone and saw Tortoise live at the Empty Bottle).

Living in Washington DC for five years was mind-bending for an avid music worshipper like me, as there was always someone great playing in town or a new band to check out. Chicago turns it up to eleven. There is almost too much happening at any given day of the week and I rarely get out at the magnitude that I used to (i.e., nearly every night ages 22-26). The first band I got to see in Chicago as a proper resident was Hiatus Kaiyote at Double Door as they were touring Choose Your Weapon. Some of my favorite nights have been catching my great friends in Bow & Spear, Space Blood, and Norman Toronto play at house parties, Emporium Arcade Bar, Beat Kitchen, and at Quencher’s Saloon. We were “in the round” watching my favorite band Tortoise kick off their The Catastrophist tour at Thalia Hall in January. At Lincoln Hall, long-time Japanese favorites Toe played a night of instrumental math rock to a sold out crowd. The Appleseed Cast stopped by Subterranean for the 15th anniversary of their album Mare Vitalis. We danced under Downtown Sound summer storms at the Pritzker Pavilion to Helado Negro and cumbia legends Ondatropica with Quantic. The opening of Chicago’s elevated park, The 606, included the 606 Festival along Humboldt Boulevard where we listened to a mix of soul, funk and hip-hop from the one and only DJ Spinna. A rainy Saturday in May closed Division Street steps from my house for Do Division Street Fest where Stones Throw boss Peanut Butter Wolf played an impeccable set followed by my first time seeing Murder By Death. Which brings me to festivals in Chicago.

We were lucky enough to get VIP wristbands to another amazing summer weekend at Pitchfork Music Festival and enjoyed sets by Caribou, Jamie xx, Todd Terje, Freddie Gibbs & Madlib, Sleater-Kinney, and the Montreal outfit Ought to name a few. The 3-day Riot Fest came in September and was single-handedly my favorite weekend in Chicago so far with an outstanding music festival of diverse proportions. Set in Douglas Park for the first time after a storied battle with Humboldt Park residents and business owners, the 2015 lineup included plenty of everything. All of my teenage favorites were there (Coheed & Cambria, Thrice, Less Than Jake) and the coolest highlight was getting to see Millencolin for the first time ever (Life On A Plate ftw). We partied hard with Andrew W.K. We watched Iggy Pop from a ferris wheel. The late Merle Haggard had us swooning in the Saturday sunset. Snoop Dogg showed up an hour late but still delivered and Modest Mouse closed out late into Sunday night before we all trudged home with our broken and muddy shoes wondering how we could make next year come sooner to do it all over again.

My favorite album of 2015 was easily The Epic by jazz giant Kamasi Washington and my favorite show of 2015 was when his entourage rolled through the Bottom Lounge to deliver two hours of stunning selections from his sprawling triple LP on Brainfeeder. Chicago drummer Makaya McCraven opened up the evening with cuts from his new exploratory jazz record In The Moment with Tortoise’s Jeff Parker on guitar and Justefan showing off his brilliance on the vibes. His sound had resonated with me previously on record, but his live act is such a cosmic and groovy experience. Months after that Kamasi show, we were able to send Makaya and his crew off for their Europe tour at the Hideout (probably the coolest venue in Chicago so far). It was here that the multi-instrumentalist talent of Mikel Patrick Avery and his free jazz *PLAY* project floored me; I cannot wait to see this act again. In 2016, Jessica and I fulfilled a lifelong desire to catch Buddy Guy perform at his Legends club on South Wabash for a January weeknight of blues. We had back to back Friday evenings in Hyde Park at the Promontory to catch vibraphone master Roy Ayers spread some sunshine and New Orleans trumpeter Christian Scott fill the room with the latest flavorings of his Stretch Music. I finally went across town recently to visit the Metro and watch Hamilton, ON natives Jessy Lanza and Junior Boys. After last seeing him perform in 2010 in the immense Tennessee Theater for the eclectic Big Ears Festival, Tim Hecker sold out the Empty Bottle for a late Friday evening of debuting his latest Love Streams through a thick cavalcade of fog. As of this writing, we are all thrilled to catch up with our Blacksburg friends Wild Nothing at Thalia Hall and eager for the festivals to arrive as summer begins to show signs of promise around the corner. Lastly, I can’t forget that one blurry evening I got to see Flying Lotus, a sonic hero of mine since 2010, perform in a nightclub in the basement of my office building.

Visit From Home

Growing up, my parents had a limited scope of travel plans for my sister and I and it usually involved driving through Virginia mountains or along the Outer Banks of North Carolina to escape our Tidewater region or vacationing in Gatlinburg, TN or Myrtle Beach, SC. Don’t get me wrong, each trip was rewarding at the time, but that’s about all we did. I’m positive that they both had not even been west of the Mississippi in their entire lives. That is why I was thrilled to convince them to come visit me for my birthday weekend in September. Easily one of my most memorable weekends of all my time in Chicago, I most likely drove them into the ground showing off this big and beautiful city to them. We went from O’Hare straight to exploring at Renegade Craft Fair along Division Street within the first few hours. We rode the L to the Loop and walked to Millenium Park because my Dad had always wanted to see “the Bean”. We watched music at Pritzker Pavilion and then caught a sunset cruise on Lake Michigan. We drove to Garfield Park Conservatory and even randomly out to Superdawg Drive-In at Milwaukee and Devon! We strolled along Montrose Beach and had drinks at The Dock. I showed them the South Pond Nature Boardwalk at Lincoln Park. We caught the skyline from Museum Campus. I finally had a deep dish at Lou Malnati’s. On my birthday morning, before they had to catch their flight back to Virginia, we went up to see what Chicago looked like from the Skydeck at Willis Tower and then caught a cab to Manny’s Deli for lunch. It was awesome getting both of those fine people out of their element and showing them this magnificent city by the lake.


There is no way I can either seriously exclude from this list or even begin to cover the vast amount of culinary ecstasy hiding out in so many of Chicago’s diverse neighborhoods. Much like DC’s eclectic and hyped culinary scene, but with an endless amount of land area to inhabit, Chicago eats very, very well. Aside from the essential deep dish and Chicago hot dogs that one gets to experience quickly, some of my favorite times are sitting down with a solid group of friends to share some outrageously delicious food. West Loop is a haven of delectable spots, including Publican, Green Street Smoked Meats, Little Goat Tavern, Au Cheval, and BellyQ to name just a few. Oysters in the summer at Frontier, crispy cauliflower and hot chicken at Pub Royale, the patio at Parson’s Chicken, small plates at Mott St, Singapore noodles at Bento Box, brunch at Dusek’s in Pilsen, and literally everything at Fat Rice are some of my personal happy places in the city. Corned beef sandwiches at Manny’s in South Loop, deep dish at Pequod’s in Lincoln Park, sushi at Nori or Enso or Trike, candied bacon at Honky Tonk BBQ in Pilsen, Big Star tacos in Wicker Park. For the fast food cravings, I certainly lean towards Sultan’s spicy falafel sandwiches or dropping by Picante on Division Street in the summer for a burrito. With too many to remember, list, and explore, I’m looking forward to another year of eating well in Chicago. On one of my first nights in the city, I learned about a Chicago startup with the brilliantly named smartphone app Nomwell, which I highly recommend getting to keep track and make sense of where you have eaten and where you want to dine in the future.

On a final note, I would like to delve into business owner, culinary explorer, Eater Chicago writer, and all-around amazing woman Sarah Freeman. Trading time between running the monthly Sauced Night Market, exploring the rapidly expanding culinary scene in Chicago, and writing about all things that taste good for Eater, Sarah has been a close friend and inspiration for getting things done like a boss. Sauced is a business she co-founded that operates out of venues like Emporium Arcade Bar in Logan Square or Thalia Hall in Pilsen that bring people and food together in a fun social atmosphere and highlights local chefs, craft artisans, and most importantly, community. With her experience at Sauced, Sarah collaborated with Locallective to host three nights of epic cuisine with celebrated chef Brandon Baltzley and his CRUX: WINTER IN THE RUST BELT TOUR in an arts space located in a Pilsen industrial warehouse where food enthusiasts gathered for cocktails and a five-course meal including an unforgettable grilled trout. I’m very excited to see what Sarah has in store for Chicago in 2016 and beyond.

Working in River North

After working for the Navy for nearly six years, I began an exciting endeavor in the private sector at an engineering firm in River North. I got to work with one of my absolute best friends here (who helped me not only get to Chicago in the first place, but introduced me to lifelong friends back in college when we met studying structural engineering together), met some brilliant engineers, and gained skills I had needed for years within the green building and sustainability industry. In the first few weeks, it was common for the Principal to schedule a site walk with new employees for a kind of one-on-one to gain a sense of their understanding of building systems. We met for a final systems inspection at a Lincoln Park mansion on St. James Pl, which turned out to be the future residence of billionaire Morningstar founder and Chicago philanthropist Joe Mansueto. In between reviewing dozens of building projects attempting LEED certification, I gained profound insight into mechanical ventilation, Chicago energy benchmarking, and material selection for a University of Chicago adaptive reuse project required to certify under the Living Building Challenge. For fun, we cruised on Lake Michigan for a company outing in the summer, rented out an entire Italian restaurant in River North for a holiday party, and enjoyed many interesting post-work drinks and acts at The Drifter, a small speakeasy underneath the vintage Green Door Tavern. Although not directly related to my specific experience at this firm, I flew back to Virginia to sit for the Professional Engineering exam in October 2015 and received the amazing news of a passing score in December and the Principal personally came to congratulate me and told me to expense the test on the company. An enormous professional goal had been achieved during my time at this firm and after years of education, experience, and multiple attempts at that 8-hour engineering exam.

And then came a pivotal moment at 4:45 PM on a Friday afternoon after a busy day navigating through a frustrating LEED review where the Principal called me to a conference room and succinctly told me my position had to be cut due to a necessary business decision to restructure our bleeding Sustainability Studio. My first experience whatsoever with this prospect came at a total and complete shock. I took a cab home and was pretty upset until the following Monday when I basically hit the ground running with a giant to-do list: file for unemployment, schedule a crown fitting immediately, figure out that thing called Obamacare that our country had been talking about back and forth for years, update my resume, and get active on job posting websites. I was scheduled for the LEED AP exam a week after the lay-off so I focused on making sure I passed that (which I did, 193/200!). At the time of writing, it has been 74 days since that fateful Friday and it has not turned out to be the nightmare I originally thought. While the lay-off came as a surprise and felt like a huge setback at the time, it has been one of the most positive and enriching experiences of my twenties. I had been consistently employed since June 22, 2009 with rare downtime outside of the usual paid time off, vacations and holidays. I was reminded we inevitably fail or deal with situations out of our control, but good things grow from these experiences more than we could ever imagine. I sat comfortable for years with a government job never having to think about such a scary thought (until I actually was laid off during the 2013 “sequestration” and government shutdown). 
In these past two months, I’ve had time I so desperately needed to reignite a vision of my future and take stock of my achievements and where I want to direct my life’s work. I’ve read some great entrepreneur books, made myself business cards, continued networking and attending engineering and architecture lectures, and have had some solid input and assistance from a small, but growing professional network. I’ve remained superbly positive due to the support of my girlfriend, amazing friends, and the realization that this has been a temporary blessing in disguise in order to pivot to something grander. It’s been a reinvention and startup of myself and I’m really excited about the next role I take on in Chicago and beyond, which takes me to my next sprawling subject.


I grew up in the suburbs in southeastern Virginia. I studied civil engineering in the Blue Ridge mountains at Virginia Tech. I started my career at the largest Navy base in the world. I moved to DC to be part of an outstanding team managing the design, construction and turnover of a massive military medical complex in Bethesda, Maryland. I worked for three years on the historic Washington Navy Yard further honing my skills as a young engineer and working on many challenging, yet fulfilling building projects for all sorts of Federal clients. 
In the back of my mind throughout all of this, my mind would wander and wonder what it would be like to have taken a different path, to have been given an opportunity to work somewhere else designing and building in a different role. I always wondered if I was supposed to be an Architect. Frank Lloyd Wright once said that an engineer was only a kind of frustrated architect. My personal reading focused on following trends, news, articles, and philosophy about design, urban planning, architecture, structural engineering, material science, sustainability, historic preservation and construction. Realizing my cravings for learning were on an epic scale, I strived to expand my intellect and understanding of the built environment we interact with every day. I loved talking to people about architecture and the history behind a building or the engineering challenges that presented themselves during the construction of massive civil and public projects. In the months leading up to Chicago, I devoured books on engineering and architecture, engaged with the architecture community in DC, and began to allow my photography to capture whatever it was that I was seeking: a beautiful staircase, an abundance of arches, or structural engineering insights that made architecture even possible. It was becoming clear that everything I spent time on was somehow reinforcing my goals of becoming an expert in my field. 
I failed the Civil-Structural P.E. exam three times. I thought about giving up – why bother passing this exam, I thought? The significant architecture surrounding me in DC and eventually Chicago and the history behind it and my own education and experience continued to inspire me through all of this and to achieve the professional designation I had already invested so much time towards. I watched as DC and again Chicago tore itself apart trying to remake itself and invest and build and create and expand. Cities are always growing and evolving through time and professionals have always been there to take care of this necessary business. I watched as old clashed with new both in the office and in the buildings facing each other out on the street. Over the course of three months, the Chicago Architecture Biennial was filled with fascinating lectures, ideas, and exhibits that I absorbed like a sponge, but nothing seemed to address anything supremely relevant or dire (aside from the sustainably designed Horizon lakefront kiosk from Ultramoderne and Jeanne Gang’s reimagining of the police station in communities with her Polis Station exhibit). Was it valuable to have ideas about creating a NYC-style Central Park in Chicago by shifting Lake Shore Drive further east and creating large swaths of new real estate potential as a solution to the shortsighted economic pitfalls of government? In my personal reading, I noted how it took Peter Rice, a brilliant engineer famous for his expertise on the Sydney Opera House and with renowned builder Renzo Piano on the Pompidou Center in France, until his mid-30s to discover his role and capacity as a Designer due to his extraordinary skills as an engineer and an architect. I watch as River North (and other neighborhoods with infill) erase its history in favor of mixed-use multifamily high rise construction and likened it to my time in the sterile, uninspiring blocks of the Ballston-Rosslyn corridor in Arlington, Virginia. While indeed solutions to urban growth and by no means worse than the urban-suburban sprawl that shapes every U.S. city, these neighborhoods seem characterless and bogus at times. 
There are so many stakeholders in this industry and everyone plays a significant role in evolving our built environment for the present and future habitation of people, a city’s sole reason for existence. Ove Arup once stated, “The challenge is finding out how to use the power to get the environment we would like to have, instead of one forced on us by expediency or by economic forces we fail to control.” I myself have been very focused and somewhat devoted to understanding new, exciting structural forms, building technology and sustainable development with the understanding that we sometimes forget who will inhabit these so-called masterpieces or design breakthroughs: people. At times, I feel lost thinking about where the industry is going, how technology will shape our future for the better, and whether or not I will or need to make a mark on my time in this profession. All we can continue to do for now is learn and remain focused and devoted on the central position of total design.

A resonating approach and philosophy on design that I stumbled on in reading years ago continues to inspire: Design is the first signal of human intention.  

Moving to Wicker Park 

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After four months in Roscoe Village, I packed up my room once again including my 600 or so vinyl records and loaded another moving truck for a move across town to Wicker Park. Deciding to move to Chicago was probably one of the toughest decisions I ever made as I was leaving behind what I grew to love and know in DC and a tremendous source of personal and professional growth that originated from my time there. However, the easiest decision I’ve had to make was deciding to move in with the most inspiring and hard-working individual I’ve ever met with passions and energy comfortably aligned with mine. One year after initially meeting on the banks of the Rappahannock River far away in Virginia at our friends’ wedding, we moved in together on the top floor of an incredible apartment in Wicker Park with lots of space, light and books. We began hosting friends in our second bedroom almost immediately for weekend visits. We grooved in the living room with friends or alone to our favorite music. We kept warm in the winter by binging through HBO’s The Wire or the entire James Bond anthology.

As the weather starts to get a little brighter and the days a bit longer, I’m looking forward to another solid summer with this wondrous roommate of mine, heading to the 606 or Humboldt Park for a morning run or afternoon walk, achieving VIP status at Sultan’s, spending that box of tokens we’ve been hoarding at Emporium Arcade, hosting more friends in our freshly renovated second bedroom, finding a cat or two, figuring out what to do with our growing book collection stockpiled all over the house, mapping out all of our travel goals and planning that year abroad, using her for more awesome DMC social gatherings around Chicago, pushing each other to achieve the best in life, and basically nerding out on all of the things together forever. Love you Jess! (PS: Thanks for the domain name as a Christmas present and for continuing to inspire!)





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