Milwaukee County Executive David Crowley graduating from UWM

Going back to school with a full-time job and a family is never easy, but it did not stop Milwaukee County Executive David Crowley from re-enrolling nearly 20 years after he dropped out.

FOX6's Aaron Maybin spoke one-on-one with Crowley ahead of his upcoming graduation from the University of Wisconsin-Milwaukee on Sunday.

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"Most people have Sunday football, mine was Sunday homework," said Crowley. "I’m feeling good. I checked all of my grades."

Crowley knows how to make the grade, rising through the political ranks over the years. He was elected Milwaukee County executive in 2020, becoming the youngest person and first Black person elected to the office.

David Crowley sworn in as Milwaukee County executive

"I first became county executive, some of the first articles that were released was related to me being the third county executive without a college degree," he said.

That motivated him to re-enroll at UW-Milwaukee. He has been full-time the past three semesters. 

"I wanted to be an example for my daughters. Three young daughters – 17, 7 and 5 – knowing I have a daughter who is on her way to go to college, I thought it was important to show her the way to put in the work."

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Maybin: "How did you juggle being a father, being the county executive and coming to class, too?"
Crowley: "That was probably the greatest challenges, to be honest with you. I probably mastered the art of time management even more."

Soon, a lack of a degree will no longer stand in Crowley's way. On Dec. 15, Crowley is set to receive his bachelor's degree in community engagement and education.

Maybin: "How do you think this whole experience of going back to school, getting your degree, has shaped you into a better leader for Milwaukee County?"
Crowley: "This strengthened my ability to be in more uncomfortable situations – being comfortable being uncomfortable. But it also strengthens the way I talk to people related to how they interact with government."

The county executive won’t just be walking the stage come Sunday, he’ll be taking it – speaking to graduates and their familes as UWM's commencement speaker. 

"I was like, ‘oh boy, what am I going to talk about,’" Crowley said. "Just the experience of returning and constantly asking myself, ‘Did I make the right decision?’"

For Crowley, this is a full circle moment years in the making. Now, his achievement is a lesson for others. 

David Crowley on the University of Wisconsin-Milwaukee campus

"I would tell folks, that yes, I absolutely failed then. There is nothing wrong with failing, as long as you learn from it," he said. "My hope is that people understand that continuous learning is a life's journey, and no matter what age you are, you can be the student and the teacher."

Crowley said his degree can be used in different ways and industries. He also said he excelled in his public speaking class, while geography was the most difficult.

Editor's note: Portions of FOX6's interview with Crowley were edited for brevity and clarity.