Now it gets trickier.
After his landslide win on Tuesday night over Joe Lhota, Bill de Blasio now has to try to morph from being a canny politician into a strong leader. He got off on the right foot yesterday by naming two seasoned veterans of the civic arena to run his transition committee, Carl Weisbrod and Jennifer Jones Austin.
After tapping Weisbrod and Austin, De Blasio is how heading off to the Somos El Futuro conference in Puerto Rico which for years has served as a working vacation for New York Democratic elected officials after Election Day. One of the biggest challenges for de Blasio will be saying no to the many shakers and movers who will want some of his valuable time away from the beach.
Long after he leaves San Juan, saying "no" will be one of the biggest challenges for a Mayor de Blasio. For most of his career, he's served as a conciliator, someone who has tried to bring people together through talk and cajoling. It's a different story in City Hall's West Wing where you will be hated and disliked by some people – no matter what you do. Often to a fault, Ed Koch, Rudy Giuliani, and Michael Bloomberg embraced the "take your medicine" approach to running the city. It will be de Blasio's challenge to strike the right balance between being a stern father and a pushover.
While de Blasio swims and networks in Puerto Rico, a group of leading foundations is building a giant tent dedicated to discussing the transition from the Bloomberg to the de Blasio administrations. It could be an interesting forum for ideas and arguments about what de Blasio needs to do next as he takes control of the city's mammoth municipal government. NY1 will be part of that conversation next week and will be bringing some of "Road to City Hall" from the tent. After a largely uninspiring general election campaign, let's hope the next eight weeks are filled with some good ideas.