County Executive David Crowley was just a junior in high school when he was inspired to make a difference. It was Reggie and Sharlen Moore with Milwaukee’s Urban Underground who helped him see his potential to become a community leader and make long-needed changes in Milwaukee. But it was one thing that Moore used to say to him that stuck out.
“You have great ideas, but you’ve got one problem: you don’t finish s–t,” Moore would say.
From then on, it was all about following through for County Executive Crowley, exactly what he hopes to do with his graduation on Sunday, finishing a degree that was started over 17 years ago.
Graduating with a bachelor’s degree in Community Engagement and Education, Crowley cements his formal education on a resume that would already impress anyone. He has served as Milwaukee’s County Executive since 2020 and previously represented Milwaukee for 1 1/2 terms in the State Assembly.
He started his college career studying sociology in the fall of 2007, but dropped out after failing classes. He returned shortly after to take another stab at it but left without a degree in 2013. But by this time, his life had taken on another calling, being a community organizer and legislative aide. It was this path that led him to where he is today.
Finishing his Degree
Even after almost two decades, finishing his degree was personal.
“There was a level of imposter syndrome when I was in those seats,” Crowley said. “I knew I didn’t have my degree and so I knew I needed to shatter that glass ceiling.”
But like most students, he struggled to balance life and school, especially while managing the budget and affairs of Wisconsin’s largest county. He typically had classes all day, and meetings just after. It wasn’t until 9 p.m. each night that he would get personal time, which he said usually consisted of homework.
“It was really about mastering the art of time management,” Crowley said. “I still have responsibilities of waking my girls up, getting them ready for school, I still have work to do as county executive and a husband, but it was really about making sure every morning I do my thing.”
But for Crowley, the hard work was all worth it.
One of his fondest memories in college was his public speaking course. He impressed his classmates, setting the bar high with his public speaking skills. But it was the relationships he built through his classes that encouraged him the most.
“Many of my classmates did not know what the county executive is,” Crowley said. “Many of the students here don’t get a chance to interact with elected officials…so it was a great opportunity to give them my experience and connect them to government.”
He said he also feels that these connections will help him become a better-elected official by understanding younger generations and bridging the age gap in politics.
Community Building as a Public Official
The relationship-building he continued as a student has inspired his political journey. Whether it was creating connections across the aisle of the State Assembly or connecting with underrepresented communities in Milwaukee, Crowley has helped build relationships as Milwaukee County’s first black executive, helping him combat an issue that is deeply personal to him.
Crowley, who grew up on 23rd St. and Burleigh in Milwaukee’s infamous 53206 zip code, has deeply seen the effects of Milwaukee’s ongoing racial segregation. His experiences helped inform his campaign’s biggest platform, achieving racial equity.
“We are building this plane as we fly it, but at the end of the day, folks need to understand this plane does have a destination and it’s going to take all of us to reach our goals of desegregating this community,” Crowley said.
He said that he’s been excited about the changes he’s made as county executive toward this goal. Policies such as building affordable housing throughout the county, working with public institutions and private businesses, and “intentional inclusion,” which he said has helped make the county’s government truly representative of the community.
But he also says he’s learned a lot about equity through his degree.
“The things I learned the few semesters I was here, I absolutely contributed that to my community organizing to my staffing, and my work as an elected official,” Crowley said. “I think it’s going to continue to strengthen that because of the relationships and experiences I had the opportunity to listen to and hear while being a student.”
Moving Forward
After achieving his degree, he said he hopes to continue serving the community, but doesn’t currently plan to pursue education further.
“I don’t want to have any more dreams of papers eating me at night,” Crowley said.
But as his educational experience ends, he hopes to keep giving back to his community as a leader and spend more time with his family.
As he steps foot onto the stages of the Panther Arena and Fiserv Forum this weekend to speak at the graduations of UW-Milwaukee and MATC, he hopes to offer his best advice to graduating students – don’t be afraid to fail.
“There’s nothing wrong with failure, unless you don’t learn from it,” Crowley said. “I failed in the beginning, I will absolutely admit that, but in the midst of that, I had the opportunity to learn through my experiences.”
He said his embrace of failure has led him to where he is now, walking across the stage as a college graduate.