Prior to your role at Navy Pier, you spent over a decade in the city’s department of Cultural Affairs and Special Events working with both former Mayor Daley and Mayor Emanuel. How did you get there?

It’s a very strange story. I’m one of those people who got really lucky at the very right time. I actually just started calling the mayor’s office and asking to speak with lots of very high-level senior staff and about nine months later they offered me a job. It doesn’t work that way anymore, you have to apply through this crazy long process so it certainly was just one of those things where I got pretty lucky. I was very determined to work there, like it was not an option for them to ultimately say no. I mean they could have! But I was desperately invested in being a part of the fabric of Chicago and I took all the avenues to do that.

One of the most memorable events was when the Blackhawks won the Stanley Cup in 2010. Were you a part of the planning for the parade?

I worked at the Mayor’s Office of Special Events for 12 years and my first job within that department was all of the city parades, which at one point there were up to 70 city parades. Every nationality; Pride Parade, Ecuadorians, Indians, everyone had a national day of celebration and they turned it into a parade. Then I became the Director of Sports Development which dealt with anything sports related that Mayor Daley saw fit. There were lots of already existing things like the Chicago Marathon and the 300 other walks and runs that go with that so I coordinated the city’s role in those but then I also interfaced with all of the sports teams, so I was responsible for the 2005 White Sox World Series parade—which was planned in 36 hours—and the Blackhawks parade, the 2016 Olympic bid rally and so on.

What is it like planning under such a time crunch?

I would have to say the key to dealing with that sort of pressure—and City Hall had its own kind of pressure—is really the level you have to perform under that pressure. There was no room for being angry, there was no room for being nasty to people. Really there is no room for that in life in general but there comes a time in the midst of a 36-hour period like that where you have to be “on” no matter what the circumstance. Whether it’s dealing with the pouring rain or how to get a jumbotron here from Texas in 12 hours, you end up thriving on that sort of energy and stress. In the events world it’s pressure and problems all of the time. Things didn’t come in, they didn’t get ordered, he didn’t show, the stagehand is missing. Being cool on your feet is really what I’d have to say is the key to the kingdom in that respect.

Have there been any cringe-worthy crisis moments that stand out from your experiences?

So many! Oh my gosh, there has been so many! The worst part of an event is that you can plan something until you’re all planned out and you can’t possibly have made any more binders, communicated any more, you have all your ducks in a row and then it all falls apart. It’s  almost inevitable that it will happen. Race to Taste was a 5K that the city does and we ran out of cups on a very hot summer day, that was a total problem. I went to dye the Daley Plaza fountain orange for the Olympic rally and it turned out pink! Everyone was calling like, “Is this for breast cancer?” But events go on! You know?

Is there anything you learned from working so closely Mayor Daley and Mayor Emanuel that outsiders wouldn’t expect?

That’s an interesting question. What am I supposed to say that’s classified or not? Mayor Daley had a wicked sense of humor. I think that didn’t get seen very much. And he was incredibly kind. I think when people saw him he was at a press conference and being grilled by the press but you didn’t get to see his true spirit. His love for Chicago was far beyond anything I would have ever imagined, it was incredible. Mayor Emanuel makes unbelievable eye contact. When he talked to you, it’s laser-focus! He’s very laser-focused in everything he does. In the way he walks, the way he talks. He is a man on a mission, which is great. They are very similar in a lot of respects. That’s an unbelievable job that comes with incredible power but incredible pressure at the same time.

What was it like behind the scenes when Oprah infamously shut down Michigan Avenue for the flash mob performance with the Black Eyed Peas? 

Michigan Avenue had never been shut down before for anything besides the Magnificent Mile Lights [Festival] but what Oprah wants, Oprah gets. She conducts herself in a way where people listen and she paid all of the city fees that it took to do that. It was an incredibly cool event for Chicago. A lot of times when we looked at peoples’ requests to do things like that they were weighed with, “How does it benefit Chicago?” I understand you are Oprah and this is a very important thing but, is this good for us? And it was. It was huge! Oh my gosh, it was broadcast and people were watching Oprah in every corner of the world. Chicago misses her I think. I know I do! It feels different without her.

Have you met her?

A couple of times. It’s weird, I’ve been in the presence of mayors and a lot of presidents but Oprah I have to say was one of the more wild people to be around. She’s exactly like you would think she’d be. I worked with them on a couple of things. She welcomed all the Olympians back from Athens and they did a big thing in Millennium Park. I was the person who oversaw the re-naming of the street on her last day. She and Mayor [Daley] retired within like two days of one another. I was an emotional wreck!

In your new role as Director of Entertainment at Navy Pier, what are you hoping to accomplish?

My mission is to get Chicagoans to want to spend time here. It’s a tourist destination, we’re never going to have to fight for that. It’s a beautiful venue and it’s lovely to be this close to the water. There’s nowhere else in the city where you can spend recreational time on Lake Michigan and to be on the East end, there is absolutely nothing like it. Navy Pier is going to be a source for tremendous nightlife in the next two or three years. This place is going to be somewhere where 25-and 35-year-old people want to come and hang out. The mission is to create a new source of entertainment down here. Getting to the roots of what Chicago is is what we’re going to do.

Favorite part of your job?

The fact that I can get an ice cream cone anytime I want, right? Garrett’s popcorn; I mean, are you kidding me? I’m just kidding. I love being around creative people. I love creating things to make people happy. To walk up and down Dock Street here and see people having fun and taking pictures of each other and sitting by the water arm and arm, that’s very fulfilling to me. I didn’t have a direct responsibility for any of that taking place but the fact that they’re here and they’re enjoying what they’re doing when they are here, I feel a part of that. And that’s big. That’s really big.

You are also the president of Special Olympics Chicago. How did you get involved with that organization?

I was a Special Olympics coach in high school. I’m an only child and I lived down the street from a family that had five children, the oldest of which was my age and she was profoundly physically and mentally challenged. I spent a lot of time with her growing up and it just became part of something that I wanted to do. I coached for Northern Illinois Special Recreation and I always kept my finger on special needs people and charities associated with that. Then when I moved into the city I saw that the Special Olympics did the Polar Plunge in March at North Avenue Beach and I’m like, “I love Special Olympics, it’s totally crazy but this sounds like something fun!” I grabbed a big group of people and we did it and I’ve done the plunge ever since. I raised $30,000 last year, you only have to raise $100. It’s a huge fun thing. Over the years I made sure to introduce myself to the people that were on the board and as every story goes it just unfolded into an invitation to become a member of their board and then six years later I’m the president. It honestly is crazy to me that I’m even there!

Favorite neighborhood restaurants?

I’ve been a huge fan of Lettuce Entertain You since the very beginning. My parents went to R.J. Grunts before I was even born, it’s that little gem of a place that I so much love. What I love about Lettuce Entertain You is they just keep reinventing themselves and they never stick to a concept for the fact of sticking to it, they’re constantly looking at how to improve themselves. It’s a little cheesy but I like to think to myself in the same way like, “Okay, so I’ve done this the same way all this time but that doesn’t mean it’s the best way. What can I do to turn this up a little bit?” I don’t feel like they don’t get the credit where credit is due, their restaurants are incredibly successful but if people knew the philosophy behind the way they train their servers and staff, it’s like working at Walt Disney World. And I’m not just saying that! It’s phenomenal. Mr. [Richard] Melman is an incredible visionary, as was Mr. Daley. There is something to be said in being around people like that who never sit back. They’re always sitting forward wondering, “Where are we going?” It’s incredibly inspiring.

Looking forward, is there anything on your career bucket list?

I want to plan the halftime of the Super Bowl. That was one of the things I’ve always wanted to do. What job is that? I don’t even know. I think at some point you become an independent contractor who does that sort of stuff and I certainly understand that the world is full of people who do that already but that’s always been on my wishlist. I don’t know, at some point I think I would love to get a lot more involved in the non-profit world. I love laughter and I love charity so if I can find the way to merge those, I don’t know what that job is but I also didn’t know what that job was when I got it at the city and I didn’t know what this job was at Navy Pier until I got in it.

If you could have a drink with anyone, who would it be? 

This kept me up the other night. I love having drinks and I love people. And I love a lot of people who like to have drinks! So I would say if there could be a morph between Amy Poehler and Eunice Shriver, they would be fun. Can I have both? That would be a fun person with a gigantic heart. The world is not the same because of Eunice Shriver. And for Amy Poehler, I would have to say the world will never be the same because of her. That is just one person who represents a lot of women in comedy for me and I think without laughter and without charity we’re in deep trouble.

KIRSTEN MICCOLI PHOTOGRAPHY