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

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.

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

[shanisafan]

Two things: Thanks for featuring OLDER millennials and middle range income earners. Please do more of these kinds of features. Not every Millennial is on the younger side and we are not all clearing 100k a year.

[juliorivera]

So I served in the USAF with Wilson and he is literally one of if not the coolest guy ever. Very kind hearted and very genuine. Funny as all get out and just a really awesome person to be around. He just always had this very positive vibe about him. Dude was an absolute beast too. He would run like 15 miles or some ridiculous amount after a day of training just for fun lol. Miss you brother. Hope all is well. -Rivera

[Casheverytime]

Everyone else on here brags about their money situation and this dude is out here being real with it. Props

[kiersten]

JD was a regular customer at a coffee shop I worked out. Hands down one of the friendliest, most positive people I have met!

[jrtrading]

I had Mr. Wilson my 5th grade year in his first year teaching ever. I'm now graduating high school, and I can still say with certainly he was the best teacher, man, and inspiration I've ever ran into through the school system. I'm thankful he's well and only wish the best for him.

[lindawang]

When he said he was the king of uber eats, right after he said he didn't make enough money at his teaching job, I assumed he was delivering uber eats, not spending 300 dollars a month ordering from it.

[ryanhawaiian]

Firstly, props to JD for being so transparent with both his financial situation and the lessons he’s learned along the way. You can tell this guy has the heart of a teacher. I believe many others will be able to watch this and empathize with what he’s going through, especially in enduring the challenges with his company. Mahalo JD, and best of luck 🤙🏼

[denise_abe]

Meal prepping and cooking really does help save money. Buy things in bulk and cook for lunches and dinners. Eating out costs so much.

[evakeeslar]

$1650 rent in Kailua is cheap, but still expensive for one person. I used to live next door to a house rented by a bunch of teachers. Most of the younger teachers I had growing up in Hawaii either had multiple roommates or worked 3 jobs to make ends meet.

[korrabel]

Thanks for showing us someone that is just starting to improve their financial journey

[damondominique]

and he seems more fulfilled than people making twice his salary

[ciel]

SORRY to hear about the passing of his mother, I wish him all the best

[luke]

Goes to show you don't need to have it all to still carry a positive attitude with you everyday.

[DouglasLee]

I love this! Its REAL. Not another person doing the humble brag. Its also good to learn from everyday people so that we can connect with those and learn from their mistakes.

[theexperiment]

God bless this guy’s efforts to survive and eventually thrive. May the force be with him.

[msthing]

That guy's character *is* his quality of life. On some level, I wish I was as chill and just top worrying about every dollar.

[DaechoongMama]

If you are single in Hawaii this is how to do budget eating. Go to Costco get a 10lb bag of frozen chicken thighs (around $10) and Kirkland meatballs. For the chicken thighs, defrost them the night before, fry it, stew it, there’s a million ways to eat it. Get a rice cooker. For fruit: apples from Costco. They last a long time. Always have rice on hand. Go to farmers market at windward mall for all your veggies. You can eat for $300 maybe less for the whole month as a oppose to a few meals with Uber eats!

[cheezybred]

He seems like a great guy, im worried he doesnt fully understand the financial mess hes in. Living paycheck to paycheck in hawaii, not tackling his loans and no retirement savings is a big hole. That uber eats money needs to go straight to his loans and he needs to drive uber instead of surfing. The yolo passion stuff needs to wait, Just until he gets out of the mess. Great vid!

[khangtruong]

In hawaii, teacher are under paid. Living cost is much higher and teacher's pay are lower than most states. Most teacher in hawaii moved away to find better paying jobs in the mainland.

[LifeofKairo]

Teachers are heroes.
I just wish that the school system taught us how to ACTUALLY thrive in the world rather than just be an employee.