The Bear has done it again.  If you’re NOT like me... who tuned in at 9 in the morning on June 22nd and watched the whole second season in 2 days… don't worry. No spoilers here per se, more of an exploration and conversation about the feelings that the show elicits. It’s safe to keep reading!This show is Chicago.

Complicated and emotionally frustrating — ups and downs galore — but somehow so human that it’s immediately knowable and relatable to an astonishing variety of people.

I want to talk more about this idea of leaning into the complication. The more people we meet for potential events, partnerships, and content highlights, the more I am astounded by the out-of-the-box thinking and the boundary-crossing that folks in this city are doing. I am meeting with and interviewing amazing creative entrepreneurs who tell me about what they’re doing and using terms like “post post post-disciplinary” and “multi-disciplinary” and “multi-contextual design”

We’ve moved past the glorification of extreme greed and win-at-all-costs growth, gotten through the tech takedowns and the public shaming of that glorification (see: The Dropout, Super Pumped: The Battle for Uber, Wecrashed, and even the end of Succession).

Let me tell you how happy I am that I haven’t heard the sentence “We are basically the (insert tech services company here) of (insert sector here)” one time.The Bear hit at exactly the right time for a shift in the culture of our country. People want to feel inspired; people want to feel hope. They need those things, actually. Earnest and honest inspiration. Often times it’s harder to “brand” that feeling of boundary crossing, multi contextualism because it’s nuanced, it’s complicated. It is not simple. Calling people out is so much easier than calling people in. The Bear took a risk when it changed from being loud and stressful to quiet and considerate. It would have been easier to go loud. It would have been easier to lead with anxiety and fear but instead, they led with vulnerability. And they were rewarded.

There is confidence in that nuance. A confidence that is so uniquely Chicago. We are complicated. Humans are hard. And cities, especially those made up of many many different kinds of humans, are hard. It is when we confront ourselves with tension and division and hard problems and align around a common goal that we really begin to form connections. I thought that the juxtaposition between the back of house and front of house in episode 10 was particularly relevant to this point. The feeling that I, as a viewer, felt as we switched from the kitchen, where the team was in the shit, to the dining room, where the experience felt much calmer and orderly but somehow clinical, was a feeling that is quite familiar to me in Chicago. As we build Gertie, and I meet with the folks who are constantly “in the shit” building and innovating oftentimes with little resource and very little bandwidth, I feel energized. The conversations are hopeful and optimistic while still being real and considering the barriers and obstacles we face as a community and as a city — they lean into the complication and they thrive in it. When I talk to people in the Big B business community, it is a very different feeling, a different narrative; one of resistance to tension, driven by fear of the unknown. While I am aware of the differences in scale and stakeholders between these two different communities (creatives and small businesses typically don't have shareholders to answer to and aren’t constantly under the microscope with reporters waiting for them to screw up), we need to find ways to meet in the middle. We need to find ways to tolerate a negotiated amount of risk that makes us all feel like we’re “in the shit” together and driving towards a common goal — a stronger Chicago for all of us. When we negotiate, we make concessions, but those concessions are much more bearable when we understand why we’re making them and for whom. Not just for anonymized groups of people – “the business community” or “artists and the creative community” – we need to sit down and break bread together. We need to understand how policies or initiatives that we, as individuals from these different communities, put forth might affect a person in their day to day, their livelihood.

This is what we are hoping to do with a new monthly dinner series that we, at Gertie, have launched. For our first gathering, we partnered with Jeff Shapack and gathered 35 people in the Fulton Market District for food, drinks, and conversation with new and old friends alike. We had elected officials sitting next to artists, real estate developers, venture capital investors, founders of venture-backed companies, and small business owners. There was no prompt but the framing was that these were all people who we knew cared about the civic health and well-being of Chicago, and they were all curious to meet others from different spaces who felt the same. The food was provided by the amazing Taco Sublime — an incredible new, creative small business serving the best tacos and smash burgers in the city (you can quote me!). In Good Spirits provided the drinks — an amazing new nonalcoholic bottle shop and social club that just successfully raised enough capital (through crowdfunding) to open a brick-and-mortar in Chicago’s West Town neighborhood! Our next partners are Andy Dunn, founder of Pie, Alderperson Timmy Knudsen, and TXA TXA Club. This dinner focuses on exactly this idea of negotiating risk tolerance and what it means to grow vertically vs. laterally; could we let go of some of the ideas of success and scale that the finance and venture communities traditionally use to define success, and maybe siphon some of that excess growth and margin to the creative communities and small businesses who so often use any extra that they have to reinvest laterally in their community?  Can that become a common goal? One where we all roll our sleeves up and try to achieve together?There is no better way to find out than breaking bread together… Will report back soon. Until then… watch The Bear, and if you don't already, follow us on Instagram at @gertie.chicago to see what’s to come… xx Abby