From High School Dropout to College Grad: Nicholas Jackson’s Story

For most of us, high school is a rite of passage. We’re raised thinking that’s the first step into adulthood, and without it, we couldn’t possibly have the future we wanted.

But what happens if that’s just not an option? How do you pave a path forward from there? That’s a question employee Nicholas Jackson had to tackle head-on in his early adult years when he made the decision to drop out of high school to care for his mother, who was terminally ill with ALS (Amyotrophic Lateral Sclerosis).

“My decision to drop out did not come lightly,” says Nicholas. “At the time, my sister and I were the primary care-givers for my mom. I was also stricken with depression and an existential crisis. I was always a good test-taker, but I couldn’t find the motivation to complete assignments outside of school, so my grades suffered and I was failing. I made the decision to cut losses and drop out. However, with a glimmer of foresight, I obtained a GED during that time. After that, I was able to work and provide some help to our household.”

For Nicholas, this was the right decision. Being there for his mother in her final years and supporting his family gave him a sense of purpose. But he always had the feeling that he wasn’t living up to his potential. So, after his mom passed and he took some years to come to terms with it, he ultimately decided to go back to school and pursue a future he knew he was capable of attaining.

“A few things came together at the right time that inspired me to go back to school,” shares Nicholas. “First, and most importantly, I met the woman who would become my wife. She helped me to see that I had more potential and that I could make a bigger impact in the world through education. She promised she’d be there to support me. Then, in 2014, I attended my sister’s graduation from UW-Milwaukee. And that event really solidified the idea that going back was possible.”

Taking small steps to explore the idea, Nicholas began his renewed journey with education by enrolling in a non-credit course that’d take the pressure off of going back to the classroom after 11 years.

“It was fun and challenging, and I seemed to thrive in that environment,” explains Nicholas. “I was approaching school with a different attitude, from a place of curiosity and gratitude, and it made all the difference.”

From there, Nicholas decided to dive in and take on about 15 credits a semester while working part time. With the support of his wife, financial aid, and their side-hustle (an online crafting business), he was able to make ends meet and pursue his degree at the same time. But while this picture might look perfect from the outside, there were no shortage of bumps along the way — he still had a lot to figure out.

“When I transferred from Madison College to the University of Wisconsin-Madison, I transferred directly into the School of Business,” shares Nicholas. “It was a great accomplishment, but it turns out it wasn’t a great fit for me. I took a semester off and tried to pivot. I needed more information, so I researched majors that I hadn’t known about or considered before. I found the School of Human Ecology and ultimately majored in Consumer Behavior, with a B.S., and also achieved a Certificate in Studio Art.”

Having taken so long to get here, he wanted to make sure his path was the right one. And taking it one step at a time was the best way to accomplish that. Now, 16 years after dropping out of high school and 5 years after starting his collegiate journey, Nicholas has graduated and taken on a full-time roll as a Dream Curator at the American Family Insurance DreamBank — a role he feels is a perfect fit for his passions and experience.

If there’s one thing we can learn from Nicholas’ inspiring story, it’s that there’s no one right journey — it’s about discovering and pursuing the journey that’s right for you. Because when it comes down to it, you can get to where you’re going if you commit to the challenge, adapt as you go and keep your future in mind.

“When I see how proud my family is of me, and how sharing my story of perseverance can give some hope to someone else, I know that I achieved what I set out to do,” says Nicholas. “I know it’s a cliché, but I’ve found it to be true: it’s never too late. I could call this a fairy-tale ending, but I think it would be more correct to call it a beginning.”


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