“I feel like I am literally living the dream,” said Bobbi Lee Simpson, reflecting on her journey from Madison Metropolitan School District (MMSD) student to principal of one of its schools.
Simpson is in her first year as principal of Ada Deer Elementary, formerly Conrad A. Elvehjem Elementary. Although she graduated from MMSD, her path into education began in Minnesota, where she moved in the 1990s. There, she enrolled in a local community college’s Urban Teaching Program to become a paraprofessional, marking the start of her career in education.
“Working as a paraprofessional and being in a space where I’m encouraging students to be all they can be caused me to look at the woman in the mirror and declare that I could be more,” Simpson said.
Simpson began her career as a paraprofessional, assisting students and managing the classroom under the supervision of a licensed teacher. But she was encouraged to pursue a career in teaching. The assistant principal who hired Simpson had also started as a paraprofessional, giving her an example of how she could advance in education.
Simpson completed her Urban Teaching program and set out to earn her teaching license. She initially considered the National Institute for Teaching Excellence program, but Cambridge College was piloting a new undergraduate program that offered another path forward.
Simpson ultimately became a cross-categorical teacher — a special educator certified to instruct and support students K-12 with a variety of disabilities — back home at MMSD after she completed her program.
“Part of why I wanted to work as a cross-categorical special education teacher was that, growing up in Madison, I saw how children of color were overidentified in special education. And there are statistics to prove it,” Simpson said. “I had this thirst and desire to put myself wherever I felt like our people were, to give them the encouragement I felt like they needed.”
Simpson wanted to be someone who could be there to see themselves past the labels placed on them or circumstances in life that prevent them from chasing their dreams.
Simpson was drawn to education because there were not many people she saw growing up that looked like her. She wanted to be a source of inspiration for other students one day to know that they could be exactly like her if they wanted. The sky is the limit, Simpson said.
“Representation is important, and so I wanted to put myself in a position to be an inspiration to others, and then it’s just I always wanted to do something that made a difference that impacts others,” Simpson said.
After 15 years as a cross-categorical teacher, Simpson felt like she could pursue more. She sees herself as a lifelong learner, which she believes is hard not to be when working in the education space.
“You just find yourself pursuing more always because that’s kind of like the mantra that you’re speaking on a daily basis with students, and so I think after a while, I just naturally began to think about what more could there be for me,” Simpson said.
Simpson came across the Summer Principal Academy through Columbia University’s Teachers College in 2020.
More work remained beyond completing the program. Because it was based out of state, Simpson needed to enroll in an additional program through the Wisconsin Department of Public Instruction to earn the credentials required to become a principal in Wisconsin. She learned about another highly competitive program, the District Leadership Preparation Pipeline, which prepares educators to take on leadership roles.
“I thought, ‘Well, I’ll just throw my name in the hat and see how I shake out,’” Simpson said. “Fortunately, I was able to get into that program and completed that just last year, and that put me in the running for my ultimate position right now.”
Becoming the principal at the school district she graduated from felt surreal, Simpson said. The theme at the school this year is “living the dream,” and Simpson feels like that is exactly what she’s doing right now.
“We have this opportunity in life to be all we can be, and to imagine great things and to actually pursue them,” Simpson said. “Even this year, our teachers are taking our curriculum and the modules and trying to figure out how we make it something that is relevant outside the walls of the school. Where can we take this? How far can we dream?”








