Uptown Girl and Where I Was in 2022

Back at home in Uptown, Chicago.

It’s been about a year. This time last year, I was about to purchase a two-flat in Logan Square. Things were all set to close; I rented out my condo in Uptown and prepped to move, but the deal fell through literally at the last minute, leaving Sam (the boyfriend), me, and our two cats with nowhere to live in the coming month.

Nothing like a quick pivot to shake up 2022. Sam and I immediately started searching for an apartment in River North. The thought of renting a high-rise in the clubbiest neighborhood in Chicago didn’t sit right with me, but I was sold by the view of our soon-to-be apartment as soon as the agent opened the door. “Can we move in next week?”

During the early part of the ’22 year, time flew by in a whirlwind. I got appendicitis (ouch!), and a few weeks after recovering from that, I started a new job at a restaurant – Gilt Bar – in addition to my full-time gig at the VC firm.

The job at Gilt Bar was my way of trying to recreate the pre-COVID delight that I enjoyed waiting tables at the northern-burb rustic Italian restaurant, Campagnola. Looking back, I really still consider January – March of 2020 the “Golden Age” in my life thus far. At that time, waiting tables during the weekends, writing and traveling as much as possible during the weekdays, and generally keeping myself active and busy only with things that interested me seemed too good to be true. I literally had that exact thought the final week before lockdown as I walked into work to prep tables for dinner service at 5 PM, “this is too good to be true and simply cannot last”. Like clockwork, COVID locked everyone down and I fell ill. Sometimes intuition has a mysterious way of foreshadowing what is around the corner.

When I walked in for the interview at Gilt Bar in early 2022 and the manager asked me why I wanted to be there given my corporate day job, I explained how table service is like theater, and it’s my job to give guests the best show possible for the evening. I meant it. Wining and dining is something that’d been a constant source of joy since childhood when I kept guests at my parent’s inn quenched and satiated with bottomless coffee and house-made breakfast delicacies.

The period of time at Gilt Bar proved to challenge me emotionally, physically, and psychologically. Long days servicing investors at the VC firm melded into last-minute “on-call” shifts at Gilt Bar, earmarked by the dreaded “$5 Happy Hour” food and drink specials until 5:30, shortage of small plates, and annoying coffee service that would take 10 minutes out of my floor time already stretched thin by an over-assignment of tables. This was not the leisurely, clockwork-like dance of Campagnola, but a fast-paced, high-stress sprint every evening to serve as many guests as possible while keeping my cool. It helped that I’d walk out with upwards of $600/shift – more than a day at work in finance. The 12:30-1 AM clock out, however, (when the shift of night workers would come in to prep donuts for Donut Vault and blast music of all sorts in the basement), was taking a toll on me. How long could this last?

Almost three months into my time at Gilt Bar, my relationship on the rocks, my physical health deteriorating, and my sanity barely keeping it together, I get a call from a recruiter proposing a new role that would eventually become my new day job. It seemed like manifestation: I needed a solid excuse to quit Gilt Bar since my conscience kept me there despite the miserable long nights, but I was getting used to the extra income. This new opportunity seemed to engulf both my day job and my side hustle.

On the same day I accepted the job position at the new firm, I drafted my resignation letter at the firm, literally copied the letter, word for word, and swapped out my previous employer with “Gilt Bar”. An extremely heavy weight evaporated off of me.

That brings us to now – kinda. I’m in the same position as June of 2022, however, Sam and I have decided that instead of inflating our lifestyles with our new jobs, we would scale back, move back to Uptown, and dream a little.

Now, instead of a $200 dinner at Gilt Bar, we get a $50 dinner at Demera. Instead of an $8 latte at Edie’s, we grab a $3 coffee at First Sip Cafe. Instead of $18 orange chicken at Panda Express, $13 Bún bò Huế at any one of the many Vietnamese places on Argyle. Music has come back into our lives again thanks to Green Mill and Aragon Ballroom, and the lakeshore, right outside our doorstep, provides us with an endless supply of trails, trees, and ponderous views through which to contemplate the next steps in our journey.

Since the pandemic ravaged our lives, never have I been more excited for what lies ahead. It feels as if I’ve passed through the 7 stages of grief throughout the last 3 years, and now a reawakening begins, ushered in by the smell of Phở and sounds of Jazz right outside our doorstep.