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Nicholas Jackson

After dropping out of Madison West High School, MATC and UW-Madison, Nicholas Jackson will finally receive his degree from UW-Madison on Saturday. On Monday, he'll start work at American Family Insurance's DreamBank.

Nicholas Jackson wanted to be a movie director when he grew up.

His own life is made up of scenes depicting struggle and triumph and all the feel-good satisfaction that comes with knowing there’s a happy ending.

More than a decade after dropping out of Madison West High School, and after a series of starts and stops in his pursuit of a college degree, Jackson, 33, will graduate from UW-Madison on Saturday.

But his story almost didn’t end that way.

Jackson came to Madison at age 15 with his older sister and single mother, Alicia, who was diagnosed with amyotrophic lateral sclerosis (ALS).

High school was hard for him, a period of his life he described as an “existential crisis.”

He watched as his mom’s ALS worsened. Before moving to Wisconsin, she needed a cane. Then a walker. In Madison, she required an electric wheelchair.

Around age 16, he negotiated with bankers to use a stamp of his mom’s signature for managing the family’s finances. She could no longer sign checks.

Jackson shielded his home life from most of his classmates and teachers. He tested well in school, but lacked the motivation to follow through on assignments and skipped classes.

Realizing in his senior year that he had too many F’s on his transcript to graduate, Jackson dropped out and took a job at Fazoli’s on the East Side.

More setbacks

With a high school equivalency diploma in hand, Jackson enrolled at Madison Area Technical College the following fall. He felt college was what he was supposed to do — but not what he necessarily wanted to pursue.

Jackson failed one course and got an incomplete in another. He formally withdrew by the end of the first semester.

“Once I dropped out, that was the end of my education for 11 years,” he said.

Two years later, Jackson’s mom died, and he coped by throwing himself into a five-year project writing, filming, editing and starring in a movie about zombie crime fighters called “The Zombie Hero.” He earned $30, but he didn’t care. He finally finished something he took pride in.

Then he began a string of odd jobs: Delivering toner cartridges around town, slicing meat at the Pick ‘n Save deli, waiting tables at Uno’s Chicago Grill and selling soaps at Lush Cosmetics. He worked those jobs to pay the bills, but along the way he picked up an interest in customer service, like how to appease the woman whose turkey was cut too thin and how to market different scents.

Jackson’s older sister, Christina, graduated from UW-Milwaukee in May 2014, about 13 years after she graduated from high school. Sitting among thousands in the U.S. Cellular Arena, he watched his sister cross the stage to get her diploma and thought to himself: “If she can do that, so can I.”

He reapplied to MATC but said officials were understandably leery of letting him back in after his first failed attempt. Jackson had to provide an extenuating circumstance for his disenrollment a decade earlier. He presented them with a copy of his mother’s death certificate and obituary.

“That was borderline groveling,” he remembered. “Like, ‘Please let me back in.’”

He earned an “A” in every single class at MATC, even calculus, and accumulated enough credits to transfer to a four-year university.

Jackson’s grades landed him an acceptance letter to UW-Madison’s School of Business. But within weeks on campus, he realized the competitive environment was a bad fit for him, so he did what he’d already done before twice in his life — he dropped out.

“It was a tough decision,” he said. “I went to MATC and didn’t even have an associate degree to show for it. But I recognized I was just not happy there.”

Hours of research on academic programs during his semester off eventually drew him to the School of Human Ecology, where he studied retailing and consumer behavior, a major that he said blended his interests in business, management and customer service at a school that emphasizes collaboration.

Nicholas Jackson

As a "dream curator" for American Family Insurance's DreamBank, Jackson says he will work with community members attending workshops to help identify their potential and realize their dreams.

Not ‘typical’

There were times in Jackson’s two years at UW-Madison where he recognized he was different.

About 2% of UW-Madison undergraduates are over the age of 25, according to the university. Nationally, the average is 21%.

Among a sea of students ages 18 to 22, Jackson sat in the front row of his classes and befriended his professors. He often wore ties to class because he went straight to his internship at American Family Insurance afterward. A few students mistook him for a teacher’s assistant.

“Living in a dorm, going out to bars — I never had that,” he said. “I feel like I missed out on the typical American college experience. But I also feel like I appreciate things a lot more because of how much harder it took to get here.”

He’s also come to find value in sharing his story and helping others recognize their own potential.

Jackson officially begins work Monday as an event planner in American Family’s marketing department. He will work as a “dream curator” at the company’s DreamBank in Madison.

He’s already considering his next step in education, a master’s degree a few years from now.

But first Jackson will do something he’s never done.

The high school dropout, the one who bypassed an associate degree to transfer to UW-Madison, has never participated in a commencement ceremony.

On Saturday, he will finally don a cap and gown.

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Kelly Meyerhofer covers higher education for the Wisconsin State Journal. She can be reached at 608-252-6106 or kmeyerhofer@madison.com.