The Big Apple: It’s so hard to Say Goodbye to Yesterday

(Part two of a three-part series)


By Charles Dion Springfield



Final day in Milwaukee apartment.

If I had a chunk of change for every time I had to explain why I was leaving Milwaukee, I probably would have had enough coins to put down on first and last month’s rent, security deposit and the broker’s fee on an apartment in the West Village.

There were some people who totally understood the need for me to move on. And some people couldn’t imagine trading in the comfort, security and ease of Milwaukee for the rat race, fast pace and attitude of New York City. As a result, I had to use my third eye to determine if the person was “Team MKE” or “Team NYC” and craft my response appropriately whenever discussing my move with someone.

Discussing the move with the “Team NYC” camp was easy. All I really had to say was I’m seeking more diversity (of thought, of cultural backgrounds, of types of people and of style approaches), different business opportunities that weren’t currently available to me and that I severely needed to open up my dating pool since I had been single the majority of my nearly 8 years in Milwaukee. During the conversation, I was greeted by a number head bobs indicating he or she understood and phrases like “Amen” or “I hear that” or “I’m so happy for you” and “you belong in New York.”

It was a total 180 degree shift when beginning the discussion with “Team MKE.” When he or she or they would ask why I wanted to move, I got into heated confrontations early when I would say or even allude to MKE just not being enough for me culturally or a place where I can date regularly or even occasionally. I was greeted with responses like “Milwaukee has so much culture…there’s a different cultural festival nearly every weekend in the summer” and “maybe you’re too picky” and “maybe you’re not hanging out with the right people.”

As the question arose more and more, I learned from my mistakes and put the onus on myself knowing I would most likely be walking on eggshells. I would immediately communicate the things I thought were great about MKE, then I would segueway into how I’ve always wanted to move to NYC and now I was finally fulfilling a life-long goal.

Some responses were smooth and others were bumpy. But I never figured out a completely articulate canned response that everyone would – or should – understand until I was having a talk with a “Team NYC” person.

For me, living in MKE was like starting a new promising relationship. It was beautiful. It was familiar because of my history there. It was memorable. It was comfortable. And it appeared to be mostly free of drama. I had a great time getting to know it better – or getting reacquainted with it after being away for about 10 years. Milwaukee had changed so much in that time, and I had tons of experiences which led me to do a lot of growing up. But like most relationships, it eventually had to come to an end. When I framed it that way, most people got the picture.

Parting is Such Bittersweet Sorrow

Walking up 5th Avenue.

New York!!!! Concrete jungle where dreams are made of/There's nothing you can't do/Now you're in New York!!! These streets will make you feel brand new/The lights will inspire you/Let's hear it for New York, New York, New York!!!!

It was so unreal. I could actually see the end of my existence in MKE. I had completed my last day of work at my advertising agency which had been my professional home for nearly the last four years. I had mostly everything packed in my apartment for storage or to take with me. And I was a few days away from getting on the plane and embarking on a new life and adventures in NYC. WTF!!!

Although I was super excited about leaving, it was definitely bitter sweet. I started my public relations/advertising career in MKE in 2003. My first group of friends were pulled from my new world and the world of servers and bartenders in the city, which the advertising/PR world also revolved around. Plus the bulk of my family lived in the city, so I was leaving A LOT of people behind.

I’ve moved around the country enough to know that proximity has a way of keeping people together and fully engaged as friends. While you say things won’t change when you leave, it’s inevitable. If you’re not in your friend’s neighborhood or can’t swing by for a chat or meet up at a party, you slowly start to drift apart. The feelings don’t necessarily change. But the power of the connection unfortunately diminishes.



Mom and me.



Knowing this, I couldn't leave without properly saying goodbye to all the wonderful people I've met while in Milwaukee by throwing myself one last party. It was one of my best parties yet. I had colleagues from 2003 to newer ones gained in 2010. I had friends stop by who moved to Chicago, traveling an hour and a half to hug me and wish me well. My party venue, a champagne bar, rolled out the red carpet for me and allowed me to co-develop a signature champagne cocktail for the occasion: The Charles/Siddity Chocolate that incorporated Champagne, chocolate and raspberry liquor and a chocolate truffle.

The whole experience was surreal and moving. It was like a scene in a movie in which seniors in high school were having one last blowout party before transitioning into their new lives. It was the absolute best thing to propel me to a new life knowing that I was loved, respected and supported. People were confident that I would take NYC by the balls. And the going away party cemented the fact, in my mind, that I was absolutely making the right direction despite it being a risky move without a steady job in a super slow economy.

So the day finally arrived. I rode to the airport with my younger brother and mother. I flew to NYC in business class, sipping on glasses of wine. I had a car service pick me up at the airport to take me to my new home on the Upper West Side of New York. And I went to bed knowing that I would wake up the next day as an official New York City resident.

TO BE CONTINUED