Millennial Money

How this 38-year-old teacher earning $47,000 a year in Hawaii spends his money

How this 38-year-old teacher making $47,000 in Hawaii spends his money
How this 38-year-old teacher making $47,000 in Hawaii spends his money

This story is part of CNBC Make It's Millennial Money series, which details how people around the world earn, spend and save their money.

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."

JD Wilson, 38, is a teacher in Kailua, Hawaii.
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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, a little more than half as much as he used to.

JD Wilson leading a Lead U assembly.
Courtesy of JD Wilson

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.

JD Wilson joined the US Air Force after graduating from college.
Courtesy of JD Wilson

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).

For Wilson, the student loans are a symptom of a larger issue: He's never been good at managing his finances, he says, personal or business. At 38, he's still learning some of the basics.

JD Wilson in his classroom in Kailua, Hawaii.
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One of his main goals in Hawaii is to create and stick to a budget. He's making progress, noting that he no longer buys single-use plastic items like water bottles, which he used to do without a second thought. In fact, he's cut out virtually all discretionary spending and says that his lower salary actually motivates him to save more.

"I'm not good with money, and it is probably one of my biggest flaws and the thing I need to work on the most," he says. "But I'm learning, I'm always learning, every day."

Family ties

Wilson grew up with his parents and two older sisters, Laurie and Wendy, in Toms River, New Jersey, near the Jersey Shore. Theirs was a happy suburban household, Wilson says. His parents sent all three kids to private school and encouraged their children to pursue their dreams; Wilson says he was at the beach every day.

But there were challenges behind the scenes, Wilson says. Though his parents hid any money worries from him, finances became tighter when his mother, Diane, was diagnosed with multiple sclerosis in the late '90s; by the time he was in high school, she was confined to a wheelchair and had to quit her job as a teacher.

To pay for her medical bills, the family had to make sacrifices, including selling their home when she was diagnosed and renting different apartments over the next few years to save money. For a few months the summer before Wilson entered high school, the kids and their parents all lived with different friends because they couldn't afford to rent a place.

JD Wilson and his mother, Diane.
Courtesy of JD Wilson

Even with sacrifice, the family struggled financially. "We didn't have money to get all the amenities that would have made her life so much easier," Wilson says. "But you never would have noticed it because of her attitude ... she continued to maintain being such an amazing mom."

Wilson's mother passed away in October 2019. He credits her and his father with instilling a work ethic in all of their children and with giving him permission to put "passion over profits." If he pursued what he loved, his parents told him, the money would work itself out.

"They always, always said ... that as long as you're doing what you love, that's all that really matters at the end of the day," Wilson says. "And I believe in that 100%."

How he budgets his money

Here's a look at how Wilson spends his money as of March 2021.

JD Wilson's budget in March, 2021.
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  • Rent: $1,675 (one-bedroom apartment, including Wi-Fi and utilities)
  • Food: $650 ($350 for groceries, $300 for dining out)
  • Student loans: $586
  • Car: $194 (including gas and insurance)
  • Phone: $130
  • Gym: $85 (including separate yoga classes)

Since he moved, Wilson has kept all discretionary spending low. Life in Hawaii is expensive and after paying for rent, groceries and his student loans each month, he doesn't have much money left over. Since filming, he says he has cut his food budget significantly.

He keeps a "minimalist" lifestyle, as he describes it, sleeping on an air mattress in his sparsely furnished apartment and owning a single cup (affectionately, and appropriately, named Cup).

"There's something about having very simple things at home that helps me emotionally and mentally throughout the day," he says.

JD Wilson took up surfing in Hawaii.
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Currently, Wilson does not have retirement savings, and, because of his relatively low salary coupled with higher living expenses, he has depleted most of his pre-Covid savings. He moved to Hawaii with around $10,000, and now his savings account is down to around $1,100. "I ran through it," he says.

He doesn't plan to live this way forever. But for now, he says the situation works for him. He teaches, surfs, sleeps and eats. He doesn't need much else at the moment.

It's a drastic change from his life in New Jersey, when he was always on the move, seeing people and hosting events. He appreciates the slower pace.

"Back home, the first question people usually ask you is, 'What do you do for a living?'" he says. "Here it's, 'What are you doing today?'"

JD Wilson left New Jersey for Hawaii after the coronavirus pandemic hit the US.
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For the past few months, as the Covid-19 vaccine rollout has accelerated in the U.S. and Americans have started envisioning returning to something of a "normal" life, Wilson has been working on restarting Lead U. He's even already booked some events.

Going forward, he also hopes to create a healthier budget and establish savings for himself and for his company.

"The truth is, the biggest investment I'm making right now is in myself, and in the bet that, hopefully, Lead U comes back," he says. "You have to do what you want to do in life, and you have to make it happen on your own."

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