The wonder of saying yes and letting go (Part 3)

My fondest memories of school had nothing to do with class. And my favorite work memories weren’t really about the work. It’s always been about the people and the stories that happened somewhere along the way.

And great stories, great memories always start with a yes.

Note: For this story, it might be helpful to start with Part 1 and Part 2

Like one time when Lainey was hosting a Women of Jellyvision night and asked the men on the sales team to consider sending flowers and chocolates. Sam called a meeting for me and Omar to discuss. “Maybe, but what if we sent some kind of singing telegram?” Yes! Did a quick Google search. Made a call. The actress went through different options available. Clown. Grim Reaper. Pink Gorilla. We looked at each other and without needing to discuss, we were already in complete agreement.

“Well, I think we’ve gotta go with the Pink Gorilla.”


But we didn’t give Lainey any sort of head’s up. So they’re gathered in the apartment, bottles of wine opened, appetizers out and they look out the window to see a fuzzy pink gorilla standing outside on the sidewalk. Doorbell buzzes.

Knock, knock. Who’s there? Pink Gorilla. Pink gorilla who–wait, what?

Lainey gives us a call and, even at that point, I don’t think we either confirmed or denied being responsible. So they cautiously buzzed in the pink gorilla assuming it was either tied to me, Sam, and Omar or they were at the beginning of a horror movie.

Pink Gorilla climbs up the stairs. She walks in, catches her breath (it was like 85 degrees outside). Starts to sing. Then maybe 10-15 minutes later, the pink gorilla exits and the Women of Jellyvision sales look at each other wondering, “What the hell just happened??”

The Beginning of Long Overdue

A little after the four-year mark at Jellyvision, I had an idea for a startup business. It didn’t have a name at the time and the picture was still pretty blurry. The general concept, though, was to help people turn their stories into books. Could be early-stage authors, could be someone retired who wants to write their first book, or could be families who just want to sit down with their parents/grandparents and record stories.

I’d spent four years in the flow, both at work and life in general, seeing ideas come together over and over again. Even something as random as the Pink Gorilla. The flow is this magical thing that drives out fear and makes anything seem possible. So even something like starting a business, it didn’t seem that scary anymore. It was a leap of faith I could meet with at least a small Yes.

But the ego or pride, whatever you want to call it, likes to believe things that happen inside the flow are it’s own. Loves to take credit, forgetting the power of the flow is about doing less. Letting go. Accomplishments are the ego’s fuel and it loves to dream about future goals and destinations. And maybe that’s necessary at first. You need the overconfident “I can do this” pep talk to make the initial leap. But without knowing it, I was beginning to exit the flow. I started to make my own plans disguised behind a leap of faith. My plan: I’ll go work at a Venture Capital firm, learn how early-stage companies get started, learn how they pitch to investors, then in 1-2 years my business idea (now called Long Overdue) will be ready to go. It was like going off to college again. I’ll keep playing basketball and study political science… 

And so I worked incredibly hard in 2019. Before work. After work. Almost every Friday night for a year, these were my Long Overdue working nights rather than going out. I was lost trying to figure out how to get started. How to build a website. Find customers. Navigate the legal and banking paperwork. The whole way, I felt like the harder I worked the more I was proving to myself that I could do this. The destination was my continual motivation. If I can just get to this point, then I’ll be happy. If only Long Overdue could only become my full-time job…

During this time, I was also taking writing classes at Second City; the original home of the “Yes And” philosophy. The idea that great improv comedy, great writing, great stories start with a Yes And. I was enjoying the classes, but I decided after Writing 3 to take a break and, as was the case with most things, the plan was to focus more on Long Overdue. A few of my friends continued in the writing program and come October they were ready to do casting for their Writing 6 graduation comedy show. My friend Lauren sent me an email about the audition.

There were plenty of reasons to say no. I’ve never been in a sketch comedy show before. The last time I was on stage was 2008. And where would I find the time? Eh, it’s too much. But, despite all these valid Nos, I said yes. Went to the audition. And a few months later, I was on the 36 bus heading to Second City for opening night.

New Year’s Revolution

Control. Planning. Outlines. These things should bring a sense of comfort. But what’s interesting about the flow is I can never plan my way into it. There’s a calm to the flow. More like sailing than hitting the gas. Yet for something so peaceful, it sure starts out with a lot of stress.

Late November, I lost my job at the VC firm. My plan didn’t work out and now I was discovering how hard the job hunt is right around the holidays. Received plenty of Nos. Add insult to injury: I spent my 30th birthday unemployed. Spent six or seven weeks without a day job. Cue the sad violin music.

But there were the Second City practices. And Long Overdue was no longer a solo endeavor. Omar, Kimberly, and Keith were on board and I was feeling like the Frodo (sometimes Gollum) to their Gandalf, Aragorn, and Sam Gamgee. Steve Lund, a friend from the Jellyvision days, sent me an article that sparked an idea for Long Overdue. Lynn, Sam, Dan Piva, David Daskal, Michele Popadich. I hate listing out names because you’re always bound to leave someone out, but so many people were helping. That final day of my 20s, Omar and I met with two of our mentors, one came up with a product idea for us, the other gave encouragement to slow down and enjoy the ride. It’s a long game.

Then, on my 30th birthday, Ashley showed me a GoFundMe page she’d created months ago for Long Overdue. I sat there in shock. Tears welling up. I scrolled through the names of family and friends feeling like George Bailey at the end of It’s a Wonderful Life. As hard as I worked in 2019, the biggest accomplishment was done right here by my wife who stuck with me, despite all the mess I’d made. The people around me carried Long Overdue further than I ever could. That night, I felt myself letting go of writing my own story. Moving back into the flow. It was kind of like that old verse in Ecclesiastes: Better one handful with tranquillity than two handfuls with toil and chasing after the wind.

Around two months later, I was sitting backstage at Second City in between sketches. It was around the halfway point of our fourth and final show. Ashley, my parents, Uncle John, Aunt Patti, my cousin Clair were out in the crowd. My in-laws had come to the second Friday. Sam and Molli, the same friends who organized the Seinfeld Mustache Day, completely surprised me by rallying a dozen current and former Jellyvision folks together for the finale. It was so cool looking out and seeing everyone in the crowd.

And sure, there were nerves before the show. Always are. Nervously bouncing up and down backstage even though we’d done this comedy show three times before. But at that moment 30 minutes in, I sat backstage in complete peace. Content. At rest. Words can’t really describe the full feeling of being in the flow. This feeling carried over to the bar afterward with friends and family, then to karaoke with the writers, then off to a midnight improv show with the cast. This calm carried over into the next day when Ashley and I joined my parents and family for dinner at Black & Caspian. And without planning it out, no outline, no idea where the idea would go, I asked the restaurant owner (Leyla), if she wanted to do an interview for a restaurant article. Why? Who knows. Just seemed like something interesting to do. And like any good story, it started with a yes.

So I entered February of 2020 feeling like this was going to be an incredible year. It was already off to a great start and, most importantly, I was back inside the flow. What could go wrong? I walked over to Black & Caspian, sat down to start the interview for the blog. I had no mask, no hand sanitizer, and no idea how different the world would be in just a matter of weeks.

This series will end up being partially a profile of the New York Bagel & Deli restaurant in Chicago, part reflections, and philosophy on how ideas come together. In case you missed Part 1, you can read that right here. And if you enjoy this type of style, you might enjoy the four-part series I did featuring Tango Sur and some Kierkegaard.

Despite the name, Medium Rare isn’t normally a food blog. But for the next several weeks, every Tuesday, I’ll be featuring great local restaurants around the Lakeview neighborhood in hopes that readers support these spots with pickup & delivery orders now and go in-person later this year. Other posts in the series include:

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