JD Wilson, 38, is a third grade teacher making $47,000 a year at St. Anthony's School in Kailua, Hawaii. After his events company, Lead U, was halted due to Covid, JD decided to fall back on his teaching certificate and head to Hawaii for a teaching job. In a span of 72 hours, he got the job, rented out his apartment in New Jersey, packed a bag and moved to the island.

This is an installment of CNBC Make It's Millennial Money series, which profiles people across the globe and details how they earn, spend and save their money.

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At the start of 2020, JD Wilson was earning around $75,000 a year operating his “dream” business, an events company called Lead U that hosts empowerment workshops at schools across the country.

The idea for the company sprang to mind in 2016, when Wilson was a teacher in New Jersey watching the Dribbler, a former Harlem Globetrotter, perform at an assembly for his fourth grade students. Why stick to teaching math when he could craft experiences that would teach students life lessons they would remember for years to come? Wilson thought.

He resigned from his teaching job at the end of the school year, and from 2016 to 2020, Wilson built Lead U, reveling in the energy and enthusiasm of the students he visited and empowering them to “find the leader within.” Life was good: The company was pre-booked throughout 2020 and Wilson was traveling to Canada and England to host assemblies and workshops. He felt fulfilled helping kids gain confidence.

“The money started coming in, and I loved what I was doing,” Wilson says. “I felt like I was really, really making an impact on the kids.”

Then the coronavirus pandemic hit, and Lead U lost all of its business since the company relied on in-person workshops and presentations. Like millions of others in the U.S. and across the world, Wilson’s life changed seemingly overnight.

Having lost his mother a few months earlier, and now his business, by mid-March Wilson was at his “lowest point” in years, he says. He knew he needed a change of scenery.

With a teaching degree and experience to fall back on, he began applying to schools in Hawaii, where teachers are often in high demand. In such high demand, in fact, that Wilson was offered a job teaching third grade when he cold-called a school — if he could start in three days.

Wilson packed a single bag, had a goodbye luau with his family and moved to Kailua, in Oahu, Hawaii, in July of 2020. Hawaii is significantly more expensive than New Jersey, he says, and he’s making $47,000 per year, about half as much as he used to.

But despite the drop in income, he loves the island and its energy. When he first moved, he says he was shocked that people in the community who didn’t know him took time to drop off food during his two-week quarantine. It’s helped him gain perspective on how he really wants to live his life and treat others.

“I’m learning from the culture out here. I’m learning from the people. I’m learning from my colleagues,” he says.

Still learning and growing

Wilson says he has a lot to learn, both in life and when it comes to his money.

He took a circuitous route to entrepreneurship. After graduating from high school in 2001, he attended East Stroudsburg University, graduating in 2006 with a bachelor’s degree in history and around $70,000 in student loan debt.

“It’s not the greatest thing to get after five years of schooling,” Wilson admits of his degree, noting it was difficult to find a job. From there, he joined the U.S. Air Force and was deployed to Iraq. He remained in the military until 2010.

The military “humbled me and made me realize you have to do what you want to do in life,” he says. That’s when he decided to get his post-baccalaureate in teaching at Caldwell University, which the military paid for.

Looking back, Wilson says he has made some mistakes. Perhaps the biggest was taking out so many student loans, he says. While the military paid off around $25,000, he still has around $40,000 left and pays $586 a month (he has continued to pay them each month, despite the Covid-related pause on federal student loan payments).

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Living On $47K A Year In Kailua, Hawaii | Millennial Money

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