For Blake and Shannon Casteel, raising six keiki on the Big Island has been filled with adventure, laughter and togetherness. But when the couple sat down with estate planning attorney Jennifer Shimada, their focus shifted from beach days and waterfall hikes to the legacy they hoped to leave behind.
Blake, originally from Oklahoma, and Shannon, from North Carolina, moved to Kona in 2011. Since then, their family has grown into what they describe as “a lot of wildness and fun,” with days spent exploring the island and nights filled with card games. With such a lively household, the couple wanted to ensure their children would be provided for, no matter what the future holds.
“We wanted to make sure our children knew we were thinking about their future,” Blake says. “We don’t want to be parents and grandparents who only think about themselves.”
The Casteels admit they were nervous before meeting Jennifer Shimada. Legal documents felt intimidating, and they worried about missing important details or facing costs beyond their means.
“Legal terms can be confusing,” Shannon shares. “We were worried we wouldn’t understand the process. But Jennifer really helped us—she made it clear and straightforward. It was actually a joy to work with her.”
Jennifer Shimada, who operates her practice on the Big Island, says that kind of hesitation is common. Most of her clients are kupuna who have survived an illness. She wishes more young families would take action sooner.
“None of us has a crystal ball where we can see how or when we will die,” she says.
Jennifer loves helping people finally take care of something that’s been bothering them for years. “Seeing the peace of mind on their faces is rewarding, and it feels like I am contributing to the community with my law degree and paperwork organization skills.”
She explains that at the heart of the process, there’s a trust, which functions like a contract between an individual and themselves as trustee, creating a legal entity to hold assets.
The benefit, she says, is avoiding probate—a lengthy, public and often contested court process required when someone dies owning property in Hawaiʻi.
“Owning property here will trigger probate upon your death,” she says. “A trust ensures a smooth, private and efficient transfer of assets to your loved ones.”
Other advantages include protecting finances in the event of incapacity, maintaining privacy and providing for pets.
“For families with young children, guardians are nominated in the will,” Jennifer assures. “That avoids custody disputes if the parents are unable to care for their children.”
With the Casteels, Jennifer began by walking them through her standard trust package and asking detailed questions about their children and assets. She then held what she calls a ‘design meeting,’ where the couple chose who would take on responsibilities if something happened to them.
“Most couples their age don’t usually come to me,” Jennifer shares. “So I was pleased to see them. It’s encouraging to see a busy family take the time to think through these things.”
The process, the Casteels say, turned out to be easier than they expected.
“Jennifer told us what we needed to bring, and she did the rest,” Blake shares. “She gave us her honest opinion, helped us make the right choices and waited patiently while we decided. That was a gift to us.” The result, according to the couple, was peace of mind.
Jennifer believes this process is about more than documents. Clear communication prevents family disputes and promotes harmony across generations.
“When things are written down, people are less likely to argue,” she says. “When families talk about these things, there’s less chance of misunderstanding.”
Looking back, Jennifer credits the people who have been around her along the way. “Without my mom, I don't know that I would have chosen this career path. I am also grateful to my mentors, who helped me shape who I am today by instilling good ethics and passing on their wisdom. Without them, I don't know that I would've been able to cultivate the foundations of running my own legal practice.”
Outside of work, Jennifer pursues health, wellness and creativity, from yoga and cold plunges to art classes at the Donkey Mill Art Center. But when it comes to her professional life, helping families like the Casteels remains at the heart of her practice. Estate planning may not be glamorous, but it’s life-changing. It gives families confidence in their future. For the Casteels, that confidence is exactly what they hoped to find.
“Our goal was to make sure our assets were in order if anything ever happened to us,” Blake admits. “Now we know our children will be taken care of, and the process will be handled the right way.”
Learn more at ShimadaEP.com.
"Without my mom, I don't know that I would have chosen this career path. I am also grateful to my mentors, who helped me shape who I am today by instilling good ethics and passing on their wisdom." —Jennifer Shimada.