"It's kind of emotional. I'm trying to fight back tears because it was the best time of my life," said Ed Hennessey, who is seeing his old classroom for the first time in a year.
It's where he spent 20 years of his life, teaching thousands of kids at Oviedo High School.
"Would you say you were living your dream?" WESH 2 News asked Hennessey.
"I was, other than money. I mean, it was a struggle," Hennessey said.
As a teacher, Hennessey said he never earned more than $50,000. He said he struggled to make ends meet as he worked to support two children and pay off his student loans.
Hennessey said he always had a second job, as well. He worked at Blockbuster, Old Navy, Target, Uber and then Shipt.
Hennessey became a shopper for Shipt, part-time. In 2015 he developed a system and a fan base. Two years later, he realized he could make some real money, which made him reflect on his time in the classroom.
"I don't think there is a way to turn it around unless you're going to offer more money," he explained.
So, in 2017, he made a bold life-changing decision: He took a year sabbatical from teaching to shop full time.
Currently, Hennessey is making a six-figure salary.
"I make over $100,000 a year," he said.
"Delivering groceries?" WESH 2 News asked Hennessey.
"Delivering groceries," he replied.
He said he makes double his teaching salary now. At 45 years old, last month, he officially retired from his passion.
"Leaving education is one of the scariest things, and very sad," he said.
So these days, Hennessey spends his time in his car and scouring the aisles of supermarkets.
Every day, he picks up groceries and delivers them to families in Seminole County.
WESH 2 News asked him how he became the talk of Lake Mary.
"I guess my approach, and just making sure that I'm going to grab some cereal, making sure that I know my customers and know exactly what they want," he said.
Hennessey said life is different now. He works when he wants, and mostly 50 to 60 hour weeks. He no longer gets summers off. Instead of grading tests and making lesson plans at home, he is glued to his phone -- his lifeline -- which he said he doesn't mind.
"It's so relaxing. I get to go out and I'm outside all the time. I see people and I'm my own boss. I am who I want to be," he said.
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