How Jason Blake found a perfect fit for himself in Hawaii

Jason BlakeIn 1991, after two years at Georgetown University, Jason Blake left college, shelving his aspirations for a college degree.

“I had full-time employment that was paying well,” he says, “and I was a not-so-bright college kid, so I thought, Why bother?”

He worked for a while as a singer and then had a long career in restaurants, first as a waiter and then as a manager. Part of that time, he worked for celebrity chef Wolfgang Puck.

His life began taking a sharp turn in 2001, when he went on vacation with his then partner, now spouse. That sharp turn led to a new life that fit Jason perfectly—a life in which UIS played a role.

A dream vacation in Hawaii

In 2001, Jason and his spouse, Philip, took their first real vacation together on the island of Kaua’i and loved it.

“We came back four or five times,” Jason says, “and started asking ourselves, Why are we working all year to vacation here? Why don’t we live here and enjoy this all year round?”

In March, 2005, Jason and Philip moved to Kaua’i permanently.

Before moving, Jason had a thriving business in Chicago arranging mortgages for clients, but in Kaua’i he discovered a very different market, one he didn’t enjoy as much. After the market crashed, he decided he just wasn’t happy anymore in the mortgage business, so set about looking for another career.

He describes the next two or three years as a “desert,” where he was piecing together odd jobs and applying for anything he saw.

A promise he broke…

During this time, Jason began to look back on his decision to drop out of college with deep regret—

  1. Leaving college was now limiting his employment opportunities, but even more,
  2. By dropping out, he had broken a promise to himself.

“I have broken other conventions,” he says, “but this wasn’t something that bothered other people. This was a promise I had made to myself. I wasn’t going to feel really good about myself without following through on that promise to earn a college degree.”

With nothing but time on his hands, Jason began looking for a way to complete his degree. Kaua’i offered only a community college and attending the University of Hawaii would have required at least a semester on another island. “That was not feasible at all,” he says, “either financially or work-wise.”

So online became his only option. He ended up choosing UIS for four reasons:

  • He liked the symmetry of having lived in Chicago for ten years and now earning his degree from a university in Illinois.
  • The online program at UIS would most easily complete the degree path he had started at Georgetown.
  • The pricing compared favorably to other institutions.
  • The business program was highly ranked nationwide.

“There wasn’t a more perfect fit out there for me,” he says.

On a the way to a degree, a career finds Jason

Halfway through his UIS program, a friend suggested that Jason become an insurance agent, advising people who had recently become eligible for Medicare. No one on Kaua’i was providing this service, so Jason began doing it part-time until he could find something “real” for himself.

“A year later,” he says, “I looked up and realized that I was making more than a fulltime income and that I loved what I was doing. There’s a tsunami of people becoming Medicare eligible—more than 10,000 people a day, and if consumers don’t make the right choices they can end up with penalties that cause trouble every month of their lives.”

Advising people on Medicare became another perfect fit for Jason. “This is what I enjoy being a wonk about,” he says, laughing. “At any other point in my career, I would have said this sounds like the most boring thing in the whole world, but I love it, and the people I work with are awesome.”

Following through on his degree

A job he loved which also paid well didn’t stop Jason from finishing his UIS degree, however, which he did in Spring of 2015.

“I didn’t need the job for financial reasons any more, but I still loved the learning,” he says. “In every class I came away with at least one big nugget that changed my viewpoint on business.”

His course on business and the law, for example, gave him a foundation that changed his understanding about the way business worked. “Our nation has a rule of law, for better or for worse,” he says. “If you think that doesn’t affect business, you’re crazy.”

Jason even learned something important from his least favorite class—management information systems. “It was so valuable to me to see how data is mined, how markets are created, and how all the different systems and proprietary technologies need to be able to talk to each other for business to run smoothly.” He describes the current information environment as “a modern-day Tower of Babel.”

Perhaps most importantly, Jason realized again how satisfying learning can be, especially when he really studied a topic. He even enjoyed an online science class on chemistry and cooking. “It got me cooking a lot more in my life.”

Jason’s new life in Hawaii

Kaua’i, Jason says, is like a small town, and he seems to fit in perfectly. He’s president of the Kaua’i Concert Association, a classical musical society. Three times a year, he also directs a fundraiser called Kaua’i Sings in support of a local nonprofit. “Basically it’s Kaua’i’s version of American Idol,” he says. “That’s the big one for me and the dearest to my heart.”

In his spare time, Jason has also written a book that’s available on Amazon: 10 Things I Learned Living on an Island, a deceptively light-hearted exploration of life on Kaua’i—with some very thought-provoking observations on life that apply to all of us.

Today Jason says he’s very happy in his new life—and it’s easy to see from what he says that it’s true.

Like his new job, his degree program from UIS and his volunteer work, Kaua’i is definitely another great fit for him.