From Hawaii to Legacy Planning

Sharese Lee
1 day ago
4 min read

My personal journey with Life Insurance & Legacy Planning

Growing up in Hawaii, nobody talked about life insurance. It wasn't at the dinner table, it wasn't in school, and it certainly wasn't in the community. But the moment I saw what happens to families who are left without a plan, I knew I couldn't stay silent.

There's something about living in paradise that makes you feel left out. The ocean is right there. The sun is always warm. Life in Hawaii moves at its own gentle pace, and conversations about death, estate planning, and financial protection just don't seem to fit the vibe. I get it, I lived it.

But here's what I also lived: watching families fall apart losing someone they loved. Not just from grief, but from chaos, the debt, the legal battles, and the financial weight that came crashing down because their loved one didn't have a plan.

The Stories That Changed Everything

I started hearing story after story. A family loses their mother and within months, siblings who once shared holidays together are fighting over property in probate court. A husband passes unexpectantly, and his wife discovers the mortgage, the car payments, the credit card debt, and the funeral expenses are all hers to figure out, alone. A father leaves behind a will, assuming that was enough to protect his kids. It wasn't.

That realization hit me hard. A will is a starting point, but it is not a protection plan. The moment a will enters probate, the courts are involved. And once the courts are involved, the process becomes expensive, time-consuming, and emotionally exhausting for the people you love the most, at the worst possible time in their lives.

What a Will Can't Do for Your Family

So many people in Hawaii, and across the country, operate under the assumption that a will covers everything. Let me be clear about what it does not do:

The Moment I Was Sold

My perspective shifted completely when I learned how the wealthy use life insurance, it is not just a death benefit, but a living financial strategy. Permanent life insurance builds cash value over time, and that growth is tax deferred. The wealthy have quietly used this for generations as a way to grow savings without the tax burden that comes with traditional investment accounts. It's not a secret; it's just not talked about in communities like the one I grew up in.

When I learned how the rich use life insurance as a savings vehicle without getting taxed and how putting your home in a trust eliminates court costs and family division, I was completely sold.

And then there was the trust. Placing your home or any significant asset into a living trust means it passes directly to your heirs without going through probate at all.

For those of you who don't know what probate is, here's a quick breakdown.

Probate is the court process that happens after someone dies.

When a person passes away, the government doesn't just automatically hand everything they owned over to their family.

Instead, a court steps in to officially:

Verify the will — confirm it's real and valid (or decide what happens if there isn't one)
Inventory everything — identify all the assets, property, and debts the person left behind
Pay the debts — creditors and the government get paid first before family sees anything 😕 (this one got me)
Distribute what's left — only then does the remaining inheritance go to the family 😐

Why is it a problem?

It's slow — probate can take anywhere from several months to a few years to fully resolve. It's expensive! Court fees, attorney fees, and administrative costs can eat up 3–8% of the estate's total value. It's public. Anyone can look up probate records, meaning your family's financial situation becomes public information. And it's stressful! Your loved ones are grieving while simultaneously dealing with lawyers and courts.

The simple analogy:

Think of probate like a traffic jam between your death and your family receiving what you left them. A will tells everyone where the car is supposed to go — but probate is the congested highway it has to travel through to get there.

How do you avoid it?

That's exactly what a living trust solves. Assets held in a trust pass directly to your beneficiaries — no court, no delays, no public record, no extra costs. It's like taking a private road straight to the destination.

With a living trust, no court, no lawyers fighting over it. No months of waiting. Your family gets what you intended for them, the way you intended it, on a timeline that respects their grief instead of dragging them through a legal process.

That was it for me. I didn't just research it, I did it! I got life insurance. I put my home and all my possessions in a trust fund. I did it for one person, my son.

Why I got Licensed and Why I Want to Help You

Once I understood the power of what I had put in place for my family, I couldn't keep it to myself. I got my insurance license, for Hawaii, because I wanted to be the person who brings this conversation to communities that have never had it. Communities like the one I came from in Hawaii. Families who are working hard, building something, and loving the people around them, but leaving a massive gap in their protection plan because nobody ever told them this mattered.

The Peace of Mind You Deserve

I rest easy now. Not because nothing bad can ever happen, but because if it does, my son is protected. He won't have to deal with probate courts. He won't have to hire lawyers to fight for what is rightfully his. He won't face a divided family over assets. He won't be handed a pile of debt and a funeral bill while he's still grieving.

That peace...that's what I want for every family I work with. It's not about being morbid. It's about being intentional, loving, and prepared. It's about saying to the people you love: no matter what happens, I've got you.

You don't have to have everything figured out. You just have to start. I started the same way, by asking questions and being willing to learn. And it changed everything for my family.

I'm here to help you do the same.